KR101757172B1 - Yellow dye composition for a color filter - Google Patents
Yellow dye composition for a color filter Download PDFInfo
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- KR101757172B1 KR101757172B1 KR1020150108226A KR20150108226A KR101757172B1 KR 101757172 B1 KR101757172 B1 KR 101757172B1 KR 1020150108226 A KR1020150108226 A KR 1020150108226A KR 20150108226 A KR20150108226 A KR 20150108226A KR 101757172 B1 KR101757172 B1 KR 101757172B1
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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Abstract
The present invention relates to a yellow dye composition for a color filter comprising a compound represented by the following formula (1) as a coloring agent, and has excellent heat resistance and solubility, and can be used for a color filter.
[Chemical Formula 1]
In the above formula (1), R 1 to R 6 are the same as described in the detailed description of the invention.
Description
The present invention relates to a yellow dye composition for a color filter, and more particularly to a yellow dye composition for a color filter having high heat resistance and solubility.
Unlike a CRT, a liquid crystal display (LCD) is a flat panel display that is widely used for a wristwatch, a computer, and the like because it has no self-luminescence and needs a backlight, but has low operating voltage and low power consumption.
The light passing through the liquid crystal of the liquid crystal display device has different polarization states due to the birefringence phenomenon of the liquid crystal, and the color is passed through the liquid crystal panel through the color filter.
In order to realize color, the color filter is provided with a color filter having three colors of red, green, and blue on a liquid crystal to adjust the ratio of light passing therethrough, thereby realizing a natural color have.
As a colorant for such a color filter, an anthraquinone pigment (for example, CI Red 177) or a diketopyrrolopyrrole pigment (for example, CI Red 254) may be used as a kind used in the red filter. Further, in the formation of the red filter, C.I. (For example, CI Green 36 or CI Green 7) can be used as the coloring agent used for the green filter, and yellow pigments such as Yellow 138, 139, 150 and 185 can be used in combination as a coloring agent. Yellow pigments such as CI Pigment Yellow 138, 139, 150 and 185 can be used in combination with these green pigments. As the coloring agent of the yellow filter, CI Yellow pigments such as Pigment Yellow 138, 139, 150 and 185 can be used.
On the other hand, electrophotographic methods such as electro deposition, printing, photo polymer pattern, and mill-base are used for the manufacture of such color filters.
In the electrodeposition method, there is a critical problem in the uniform arrangement of pixels and the enlargement of the substrate due to the irregularity of the peripheral shapes of the electrodes. In the printing method, it is difficult to align precise positions with respect to the liquid crystal cell, and the inaccurate pattern formation, There is a disadvantage that it is not suitable for enlarging the substrate. The dyeing method has advantages such as high precision of pattern formation (high resolution), high light transmittance and high color purity, but has problems in that the color of the dye is faded or the heat resistance, light resistance, .
In general, the composition of the color resist is mainly composed of an acryl copolymer, a photopolymerizable material, a photoinitiator, a crosslinking agent, a pigment, a dispersant, a solvent, and the like. In order to produce a high-quality color filter, the image quality and suitability with the post-process should be good. In order to improve the quality of the image, the transmittance and the contrast ratio must be high, and the uniformity and flatness of the film must be maintained. In addition, the color filter should have good resistance to thermal and chemical processes during the post-process, and should have reliability to operate stably even in an environment exposed to light and heat.
As a prior art relating to such a yellow dye for color filters, Korean Patent Laid-Open Publication No. 10-2014-0066545 (Apr. 2014.06.02) discloses a technique for preparing a yellow colored high-transmittance yellow dye for LCD, , A coloring composition comprising a dye dispersion, a color filter comprising a coloring composition, and a process for producing a dye, and also disclosed in Korean Patent Publication No. 10-2012-0030887 (2012.03. 29.) describes a yellow resin composition for a color filter comprising a yellow dye, a yellow pigment, an acrylic binder resin, a reactive unsaturated compound, a polymerization initiator and a solvent, and a yellow color filter made using the same.
However, in spite of the prior art including the above-mentioned prior arts, there is a continuing need to study a composition for a color filter having excellent heat resistance and solubility in a solvent by introducing a new structure or improving an existing structure have.
DISCLOSURE OF THE INVENTION In order to solve the above-mentioned problems, the present invention is to solve the problem of heat resistance and solubility in organic solvents, which is a problem of conventional coloring compositions containing yellow dyes, and is characterized in that yellow dyes excellent in heat resistance and excellent in solubility in organic solvents Composition can be provided.
The present invention provides a yellow dye composition for a color filter comprising a compound represented by the following formula (1) as a colorant.
[Chemical Formula 1]
In Formula 1,
R1 is any one selected from the group consisting of a cyano group and a carbamoyl group,
R2 is a substituent represented by the following formula (2)
(2)
- (CH 2 CH 2 O) p H
Wherein p is from 1 to 10,
R3 to R6 are the same or different and each independently an alkyl group having 1 to 18 carbon atoms,
n is 1.
The present invention also provides a color filter comprising a colored layer formed using the yellow dye composition.
The yellow dye composition of the present invention is excellent in heat resistance and excellent in solubility in a solvent, and has the advantage of reducing scattering of light and increasing the brightness of a color filter.
1 is a graph showing a TGA evaluation result of a yellow dye according to the present invention.
2 is a graph showing the color change of the yellow dye according to the present invention.
FIG. 3 is a graph illustrating the reflectance of a yellow dye according to the present invention after coloring green finish. FIG.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily carry out the present invention.
In the drawings of the present invention, the sizes and dimensions of the structures are enlarged or reduced from the actual size in order to clarify the present invention, and the known structures are omitted so as to reveal the characteristic features, and the present invention is not limited to the drawings .
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings. In the following description, well-known functions or constructions are not described in detail to avoid obscuring the subject matter of the present invention.
The present invention relates to a yellow dye composition for a color filter. In the color composition for a color filter according to the present invention, the coloring agent comprises a compound represented by the following general formula (1).
[Chemical Formula 1]
Wherein R 1 is any one selected from the group consisting of hydrogen, a halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group and a carbamoyl group, R 2 is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, Or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 18 carbon atoms, Which is selected,
(2)
- (CH 2 CH 2 O) p H
Wherein p is 1 to 10, R3 to R6 are the same or different and are independently selected from the group consisting of hydrogen, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, An arylalkyl group having 7 to 20 carbon atoms, and n is 1 or 2.
The alkyl group which is a substituent used in the compound of the present invention means a residue in which a hydrogen radical is removed from an alkane which is a hydrocarbon. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, iso-amyl, hexyl and the like.
The above-mentioned cycloalkyl is a substituent group in which the alkyl groups are linked together to form a ring, and examples thereof include cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
Also, an aryl group, which is a substituent used in the compound of the present invention, means a residue in which hydrogen radicals are removed from arene, which is an aromatic compound composed of a hydrocarbon containing at least one ring.
Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aryl group such as a phenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyl group, a crycenyl group, a naphthacenyl group, a fluoranthenyl group and the like, and the arylalkyl group means a residue in which the aryl group and the alkyl group are bonded to each other A benzyl group, a phenylethyl group, and a phenylpropyl group.
The compound represented by Formula 1 corresponds to an organic salt having a sulfonic acid anion group having an azo group on the left side and a tetraalkylammonium cation group on the right side as shown in FIG.
[Figure 1]
Wherein the substituent R 1 is any one selected from the group consisting of cyano and carbamoyl, and R 2 may be a substituent represented by the general formula (2).
That is, the substituent R2 in the yellow dye composition of the present invention, there is interaction with the solvent in the case with the ethylene group (-CH 2 CH 2 O-), as indicated in the above formula (2) as repeating units it can be effectively , The solubility of the dye in an organic solvent can be improved. In this case, the degree of polymerization (p) of the ethyleneoxy group in the above formula (2) may be 1 to 10.
Further, the substituents R3 to R6 may be an alkyl group having 1 to 18 carbon atoms, and the number (n) of sulfonic acid cations in the general formula (1) is preferably 1 Lt; / RTI > In this case, it can have high heat resistance and high solubility in an organic solvent, and can be suitably used as a coloring composition for a color filter.
On the other hand, the compound represented by the formula (1) can be obtained by reacting the sulfonated compound represented by the formula (A-1) with the tetraalkylammonium salt represented by the formula (B-1) .
[Reaction Scheme A]
[Formula A-1] [Formula B-1]
R 1 and R 2 in the formula A-1 and R 3 to R 6 in the formula B-1 are the same as defined in the formula 1, X in the formula B-1 is halogen, BF 4 - , PF 6 - , ClO 4 - Which one is chosen.
The preparation of the compound represented by the formula (1) described in Reaction Scheme A is carried out by allowing the anion portion in the compound having a sulfonic acid group in the formula (A-1) and the cation portion of the compound having a quaternary ammonium group in the formula (B- As a reaction, HX can be removed as a by-product.
In this case, the compound of formula (1) may be prepared in a basic atmosphere and may be washed with water or alcohol to purify the compound.
The yellow dye composition for a yellow color filter may further comprise a resin and a polymerizable monomer and / or a polymerization initiator to prepare a yellow dye composition for a yellow color filter.
The resin may be a thermoplastic resin or a thermosetting resin, and preferably an acrylic resin may be used. At this time, the acrylic resin may be a copolymer of a first unsaturated monomer and a second unsaturated monomer.
The first unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specifically may be selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.
Examples of the second unsaturated monomer include an alkenyl aromatic monomer, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound And a combination thereof. Representative examples of the alkenyl aromatic monomer include styrene,? -Methylstyrene, vinyltoluene, vinylbenzyl methyl ether, and the like; Representative examples of the above unsaturated carboxylic acid ester compound include monomers such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2- Benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl methacrylate, And the like; Representative examples of the unsaturated carboxylic acid aminoalkyl ester compound include 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate and the like; Typical examples of the carboxylic acid vinyl ester compound include vinyl acetate and vinyl benzoate; Representative examples of the unsaturated carboxylic acid glycidyl ester compound include glycidyl acrylate, glycidyl methacrylate and the like; Representative examples of the vinyl cyanide compound include acrylonitrile, methacrylonitrile and the like; Representative examples of the unsaturated amide compound include, but are not limited to, acrylamide, methacrylamide, and the like. These unsaturated secondary unsaturated monomers may be used singly or in combination of two or more thereof.
Specific examples of the acrylic binder resin including the first unsaturated monomer and the second unsaturated monomer include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / Benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like, but not limited thereto, These may be used alone or in combination of two or more.
The resin is a methacrylic acid / benzyl methacrylate copolymer, and its copolymerization molar ratio may be in the range of 20:80 to 50:50 as methacrylic acid: benzyl methacrylate.
The polymerizable monomer may be selected from the group consisting of a thermosetting monomer, a photopolymerizable monomer, an oligomer, and a combination thereof.
Examples of the polymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di Acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, 1,6- (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol penta (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (Meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A di (Meth) acrylate, trimethylolpropane tri (meth) acrylate, novolak epoxy (meth) acrylate, dipentaerythritol penta (meth) acrylate derivatives having a carboxyl group, ethylene oxideated glycerin trimethylolpropane tri Acrylate, propylene oxide-grafted glycerin tri (meth) acrylate, and the like.
Examples of the polymerizable oligomer include epoxy (meth) acrylate, urethane (meth) acrylate, and polyester (meth) acrylate oligomer.
Since the polymerizable monomers tend to react with the cyclic ether to improve the solvent resistance, it is preferable to include a monomer or oligomer having a carboxyl group. Examples of the monomer or oligomer having a carboxyl group include esters of a (meth) acrylate containing an ester hydroxyl group with a hydroxyl group-containing (meth) acrylate and a polyvalent carboxylic acid and a polyvalent carboxylic acid anhydride, .
As the polymerization initiator, a material selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof may be used.
Examples of the thermal polymerization initiator include organic peroxides and azo compounds, and the following materials may be used alone or in combination of two or more.
Examples of the organic peroxide include organic peroxides such as isobutyl peroxide, 2,4-dichlorobenzoyl peroxide,? -Methylbenzoyl peroxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, 2,5-dimethyl-2,5-di (tert-butylperoxy) hexane, 1,3-bis (tert- butylperoxyisopropyl) Benzene, dicumyl peroxide, di-tert-butyl peroxide, parramentane hydroperoxide, tert-butylcumylperoxide, di-tert-hexyl peroxide, tert-butyl peroxyacetate, 2,4,4- Butylperoxybenzoate, 2,2-di- (tert-butylperoxy) butane, di-tert-methoxybutylperoxydicarbonate, di-2-ethylhexylperoxy Diisopropyl peroxydicarbonate, and the like, and examples of the azo compound include 1,1 Azobis-cyclohexane-1-carbonitrile, 2,2'-azobis- (2,4-dimethylvaleronitrile), 2,2'-azobis- (4-methoxy- Azobis- (valeronitrile), 2,2'-azobis- (methylisobutylate), 2,2'-azobis- (isobutyronitrile), 4,4'- ) And the like.
The photopolymerization initiator is a photopolymerization initiator generally used in a photosensitive resin composition. For example, the photopolymerization initiator is at least one compound selected from the group consisting of a triazine compound, an acetophenone compound, a nonimidazole compound, an active radical generator, But the present invention is not limited thereto.
Wherein the active radical generator generates an active radical by irradiating light. Examples of the active radical generator include benzoin-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and oxime-based compounds.
As the polymerization initiator, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound or the like may be used in addition to the compounds listed above.
Specific examples of the photopolymerization initiator used in the present invention include 1-hydroxy-cyclohexyl-pentyl-ketone (Irgacure 907), 2-methyl-1- [4- (methylthio) (Irgacure 500), Irgacure 20wt% mixed with 50wt% benzophenone, Irgacure 184C, 2-hydroxy-2-methyl-1-phenyl- (Irgacure 1000), 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methyl-1-propanone (Irgacure 2959) mixed with 80% by weight of Darocur 1173, Alpha-D-methoxy-alpha-phenylacetophenone (Irgacure 651), 2-benzyl-2- (dimethylamino) -1- [4- (4-morpholinyl) phenyl] (Irgacure 1300) mixed with 1-butanone (Irgacure 369), Irgacure 36930wt% and Irgacure 651 70wt%, diphenyl (2,4,6-trimethylbenzoyl) -phosphine oxide (Darocur TPO) 50 wt% and Multiacure 1173 50 wt% mixed initiator (Darocur 4265), phosphine oxide, An initiator (Irgacure 2005) in which phenylbis (2,4,6-trimethylbenzoyl) (Irgacure 819), Irgacure 8195wt% and Darocur 1173 95wt% were mixed, Irgacure 819 10wt% and Darocur 1173 90wt% (Irgacure 2020) mixed with Irgacure 819 20wt% and Darocur 1173 80wt%, bis (eta 5-2,4, -cyclopentadien-1-yl) bis [2,6-difluoro- - (1H-pyrrol-1-yl) phenyl] titanium (Irgacure 784), and a benzophenone-containing mixed initiator (HSP 188).
In the present invention, the yellow dye composition for a yellow color filter may further contain other coloring agents to prepare a coloring composition, and the other coloring agents may be used alone or in combination of two or more.
The other coloring agent is not particularly limited and, for example, a specific yellow dye may be used together with a red coloring agent to form a coloring composition for forming a red pixel, and a green coloring agent may be used to form a green pixel The coloring composition can be used.
As other colorants, any of pigments, dyes and natural pigments can be used, and organic pigments and organic dyes are preferred in the sense of obtaining pixels with high luminance and color purity.
More specifically, the organic dyes are selected from the group consisting of anthraquinone dyes, anilino azo dyes, triphenylmethane dyes, pyrazole dyes, pyridonazo dyes, atrapyridone dyes, oxolin dyes, , And xanthene dyes to prepare a coloring composition for a color filter.
In addition, the present invention can provide a color filter comprising a colored layer formed using the yellow dye composition.
Hereinafter, examples for producing the yellow resin composition for a color filter according to the present invention will be described. However, it should be understood that the present invention is not limited thereto.
≪ Example 1: Preparation of yellow dye >
1) Synthesis of pyridone intermediate
Methyl acetoacetate and ethyl cyanoacetate were placed in a three-necked flask together with an aliphatic amine. The mixture was cooled from the outside, and triethylamine was added at about 0 ° C. , Heated to 90 ° C, and then stirred for 12 hours to complete the reaction.
After confirming the reaction with TCL, the reaction product is lowered to pH 1 with concentrated hydrochloric acid (HCl), and the obtained product is filtered, washed with 2N HCl and dried to synthesize a pyridone intermediate.
[Reaction Scheme 1]
2) Yellow dye synthesis
As shown in the following Reaction Scheme 2, a diazo compound diazotized with sulfanilic acid was coupled to the synthesized pyridone coupler to synthesize a yellow dye. The KCl is added thereto by 10 to 15% of the volume of the reaction solution, and the resultant yellow dye is filtered and dried.
The fully dried yellow dye is well milled in a mortar and then supersaturated in hot dimethylformamide (DMF) solution. The insoluble dye is removed using a filter paper, the dimethylformamide solution is poured into a large amount of ethyl acetate to crystallize the dye, followed by filtration and drying to synthesize a yellow dye.
[Reaction Scheme 2]
3) Ammonium salt substitution
In order to improve the solubility in an organic solvent, a yellow dye for a color filter of the present invention is prepared by replacing the yellow dye synthesized as shown in the following Reaction Scheme 3 with tetraethylammonium, organic ammonium.
[Reaction Scheme 3]
≪ Example 2: Preparation of yellow dye >
A yellow dye was prepared under the same conditions as in Example 1 except that the substituent R2 had three ethyleneoxy groups.
< Comparative Example One: Sulfonic acid group and Quaternary ammonium group Manufacture of yellow dyestuffs not containing>
1) Synthesis of intermediate
Pyridone intermediates were prepared using the same procedure as for the preparation of the previously prepared pyridone intermediates.
2) Dye Synthesis
In order to prepare a dye containing an organic alkyl group without introducing a sulfonate salt, a dye is prepared according to the reaction shown in the following reaction formula (4).
First, 4-butylaniline was dissolved in water using hydrochloric acid (HCl), and then ice was added. Then, sodium nitrite (NaNO 2) was dissolved in water and slowly dropped into an aqueous solution of 4-butyl aniline Knock it off. The temperature is maintained at 5 占 폚. When the reaction is complete, the excess nitrite ion is removed with sulfamic acid.
The coupler obtained in the above step 1) is dispersed in water, and the pH is neutralized with 15% Na 2 CO 3 aqueous solution to dissolve it. Then, the solution is gradually dropped into the diazo solution. The temperature is maintained at 5 캜 or lower.
When the addition is completed, the pH is adjusted to 7 with 15% Na 2 CO 3 aqueous solution, and the coupling is completed.
After confirming with TLC, the dye is washed by adding 10 to 15% of the volume of potassium chloride (KCl) to the reaction solution, followed by filtration and drying.
The dry-cake is well milled in a mortar and then dissolved in hot dimethylformamide (DMF) solution at a saturation concentration or higher and then filtered to remove insoluble dyes.
DMF solution is added to a large amount of ethyl acetate and then stored at 10 ° C or below in a refrigerator. The resulting dye crystals are filtered and dried.
[Reaction Scheme 4]
≪ Comparative Example 2: Preparation of yellow dye not containing ammonium salt >
A yellow dye obtained in Reaction Scheme 2 was prepared in the same manner as in Example 1 except that the sulfonic acid group was not substituted with an ammonium salt.
In order to evaluate the physical properties of the obtained dyes, the solubility was evaluated using the yellow dyes prepared in Examples 1, 2, and 1 and Comparative Example 2. To evaluate the heat resistance, a color filter .
<Property evaluation 1: Solubility>
The solubilities of the dyes according to the Examples and Comparative Examples prepared above were measured for the maximum solubilities of organic solvents PGMEA, PGME, and CHN for each dye, and the solubilities of the dyes were evaluated.
As shown in Table 1, the yellow dye according to the present invention does not dissolve more than 2% in the PGMEA in the dye itself, but when the organic ammonium group is introduced into the sulfonic acid group, the solubility can be increased. It can be confirmed that the solubility of the yellow dye according to Example 1 and Example 2 is dissolved in PGMEA by 3% or more, and can be applied to a color filter using the same.
(%)
* Solubility assessment: O: recording, X: not melting
≪ Property evaluation 2: Heat resistance >
1) TGA evaluation
The TGA evaluation was carried out at a rate of 10 ° C / min from 30 ° C to 400 ° C, and the TGA was evaluated at a mass reduction rate (%) at 200 ° C for 30 minutes in the isothermal section.
The TGA evaluation of the yellow dye according to Example 1 according to the present invention is shown in FIG. 1, showing a reduction in mass of less than 2.5% up to about 250 ° C, indicating good heat resistance.
2) Evaluation of heat resistance (color change)
35 parts by weight of a methacrylic acid / benzyl methacrylate copolymer having a number average molecular weight of 13,500 (methacrylic acid: benzyl methacrylate = 40: 60) as a colorant were added to 10 parts by weight of each of the above colorants, 15 parts by weight of acrylate, 8 parts by weight of Irgacure 651 as a polymerization initiator, and 250 parts by weight of PGMEA as a solvent were spin-coated and photopolymerized to prepare a colored composition for a color filter, which was then pre- Heat resistance was evaluated by color change between post-baking at 200 ° C.
FIG. 2 is a graph showing the change in hue of yellow dye in Example 1 obtained by the present invention (red line: before Post baking of Example 1, blue line: after Post Baking of Example 1) From the results, it can be seen that there is no significant difference between the post-baking before and after reflectance graphs of the yellow dye according to the present invention.
The color changes after post-baking in Example 1 and Comparative Example 1 are shown in Tables 2 and 3.
As shown in Tables 2 and 3, it can be confirmed that the color change of Example 1 produced by the present invention has excellent characteristics as compared with Comparative Examples.
In FIG. 3, graphs of reflectance are shown (red line: before post baking, blue line: after post baking) with the green pigment of Green 58 in the yellow dye of Example 1 according to the present invention.
According to the results shown in FIG. 3, it can be seen that the yellow dye of the present invention shows no significant change in reflectance value even after post-baking even when mixed with a green pigment, and can be used alone or in combination for a color filter .
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.
Claims (7)
[Chemical Formula 1]
In Formula 1,
R1 is any one selected from the group consisting of a cyano group and a carbamoyl group,
R2 is a substituent represented by the following formula (2)
(2)
- (CH 2 CH 2 O) p H
Wherein p is from 1 to 10,
R3 to R6 are the same or different and each independently an alkyl group having 1 to 18 carbon atoms,
n is 1.
A yellow dye composition for a color filter, which further comprises a resin, a polymerizable monomer and / or a polymerization initiator.
Wherein said resin is a methacrylic acid / benzyl methacrylate copolymer, and its copolymerization molar ratio is methacrylic acid: benzyl methacrylate in the range of 20:80 to 50:50.
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020150108226A KR101757172B1 (en) | 2015-07-30 | 2015-07-30 | Yellow dye composition for a color filter |
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| KR1020150108226A KR101757172B1 (en) | 2015-07-30 | 2015-07-30 | Yellow dye composition for a color filter |
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| Publication Number | Publication Date |
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| KR20170014583A KR20170014583A (en) | 2017-02-08 |
| KR101757172B1 true KR101757172B1 (en) | 2017-07-12 |
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| KR1020150108226A KR101757172B1 (en) | 2015-07-30 | 2015-07-30 | Yellow dye composition for a color filter |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012042896A (en) | 2010-08-23 | 2012-03-01 | Nippon Shokubai Co Ltd | Colorant composition for color filter |
| JP2012194200A (en) * | 2011-03-14 | 2012-10-11 | Jsr Corp | Coloring composition for color filter, color filter, and color liquid crystal display element |
| KR101486559B1 (en) * | 2010-09-20 | 2015-01-26 | 제일모직 주식회사 | Yellow color resin composition for color filter and yellow color filter using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102051911B1 (en) | 2012-11-23 | 2019-12-04 | 엘지디스플레이 주식회사 | High transmissional yellow dye for lcd and synthetic method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012042896A (en) | 2010-08-23 | 2012-03-01 | Nippon Shokubai Co Ltd | Colorant composition for color filter |
| KR101486559B1 (en) * | 2010-09-20 | 2015-01-26 | 제일모직 주식회사 | Yellow color resin composition for color filter and yellow color filter using same |
| JP2012194200A (en) * | 2011-03-14 | 2012-10-11 | Jsr Corp | Coloring composition for color filter, color filter, and color liquid crystal display element |
Non-Patent Citations (1)
| Title |
|---|
| Dyes and Pigmenfs 9 (1988) pp. 357-369 |
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| KR20170014583A (en) | 2017-02-08 |
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