阅读说明：本技术 着色剂化合物和包含其的着色组合物 (Colorant compound and coloring composition comprising the same ) 是由 朴锺镐 李多美 崔相雅 梁承秦 朴相均 金载骏 李在容 李修莲 郑智惠 于 2018-06-26 设计创作，主要内容包括：提供了着色剂和包含其的着色组合物。更特别地,提供了新的结构的着色剂和包含其的着色组合物,所述着色剂显示出优异的颜色特性和耐热性,从而可应用于滤色器的制造。(Provided are a colorant and a coloring composition comprising the same. More particularly, a colorant of a new structure, which exhibits excellent color characteristics and heat resistance, and thus is applicable to the manufacture of color filters, and a colored composition comprising the same are provided.)

1. A colorant compound represented by the following formula 1:

[ formula 1]

In formula 1, A is represented by the following formula 2a or formula 2b,

R¹to R⁶At least one of which is represented by the following formula 3,

at R¹To R⁶Wherein the other compounds not represented by the following formula 3 are each independently hydrogen; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or a substituted or unsubstituted C2-C30 heteroaryl;

[ formula 2a ]

[ formula 2b ]

In the formulae 2a and 2b, X¹Are identical to or different from each other and are hydrogen; a halogen atom; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or a substituted or unsubstituted C2-C30 heteroaryl;

[ formula 3]

＊-Q¹-Q²-R⁷-B

In formula 3, Q¹Is O or NH;

Q²is a direct bond or CO;

R⁷is a direct bond or C1-C12 alkylene;

b is a C6-C30 aryl group substituted with one or more hydroxyl groups; or C7-C30 alkylaryl substituted with one or more hydroxy groups.

2. The colorant compound of claim 1, wherein B of formula 3 is represented by formula 4 below:

[ formula 4]

In formula 4, R^a、R^b、R^c、R^dAnd R^eAny one or more of which is a hydroxyl (-OH) group, and each of which is independently hydrogen, a C1-C20 linear alkyl group, or a C3-C20 branched alkyl group.

3. The colorant compound of claim 2, wherein in formula 4, R^aAnd R^eEach independently is hydrogen; r^cIs hydroxyA group; r^bAnd R^dEach independently is a C3-C20 branched alkyl group.

4. The colorant compound of claim 3, wherein R of formula 4^bAnd R^dEach independently a C4 branched alkyl group.

5. The colorant compound of any of claims 2-4, wherein R of formula 1⁶Represented by formula 4.

6. The colorant compound of claim 5, wherein R of formula 1¹To R⁵Each independently hydrogen.

7. The colorant compound of claim 6, wherein the compound represented by formula 1 is any one selected from the group consisting of:

8. a coloring composition comprising the colorant compound according to any one of claims 1 to 7.

9. The coloring composition of claim 8, further comprising at least one of a dye and a pigment.

10. The coloring composition according to claim 9, wherein the dye and the pigment include one or more compounds exhibiting any one of yellow, red and green colors.

11. The coloring composition of claim 10, wherein the compound exhibiting yellow color comprises one or more compounds selected from the group consisting of: metal complex-based compounds, azo-based compounds, quinophthalone-based compounds, isoindoline-based compounds, and styryl-based compounds.

12. The coloring composition of claim 10, wherein the compound exhibiting red color comprises one or more compounds selected from the group consisting of: metal complex-based compounds, azo-based compounds, xanthene-based compounds, diketopyrrolopyrrole-based compounds, anthraquinone-based compounds and perylene-based compounds.

13. The coloring composition of claim 10, wherein the compound exhibiting green color comprises one or more compounds selected from the group consisting of: metal complex-based compounds, triarylmethane-based compounds, and anthraquinone-based compounds.

14. The coloring composition of claim 9, wherein the pigment comprises one or more selected from the group consisting of: a yellow pigment group including PY129, PY138, PY139, PY150, and PY 185; a red pigment group comprising PR48, PR48: 1, PR48: 2, PR48:3, PR48: 4, PR 177, PR 179, PR 207, PR254, PR 255, PR 264 and PR 269; and a green pigment group comprising PG 7, PG 36, PG 58, and PG 59.

15. The coloring composition according to claim 8, further comprising a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

16. A color filter comprising the colored composition according to claim 8.

17. A display device comprising the color filter according to claim 16.

Technical Field

Cross Reference to Related Applications

This application claims priority based on korean patent application No. 10-2017-0100549, dated 8/2017 and korean patent application No. 10-2018-0071074, dated 20/2018, dated 6/8, all of which are included as part of this specification.

The present invention relates to a colorant compound and a coloring composition containing the same. More particularly, the present invention relates to a colorant compound having a novel structure with excellent color characteristics and heat resistance and a coloring composition comprising the same.

Background

The color filter includes respective unit pixels displaying red (R), green (G), and blue (B) colors, which are formed on a transparent substrate, e.g., glass, and are used to realize color images in display devices such as liquid crystal display devices (LCDs), Organic Light Emitting Diodes (OLEDs), and the like.

The Coloring matter (Coloring) applied to the corresponding unit pixel of such a color filter includes fine particles in the form of a pigment or a dye. In many cases, instead of using respective single coloring matters exhibiting red, green and blue, red, green and blue colors are generated by appropriately mixing coloring materials exhibiting colors different from each other, such as coloring matters or colorants.

Recently, in the field of liquid crystal displays, the demand for large screens and high definition has rapidly increased, and thus extensive research has been conducted to realize high-performance color filters satisfying the demand.

However, the conventionally known pigment-type coloring materials show poor solubility and dispersibility in the composition due to structural limitations thereof. In addition, particles that have dissolved in the composition may re-agglomerate to form coarse particles and other foreign matter.

Therefore, it is difficult for a color filter made of a pigment-type coloring material generally known to exhibit characteristics such as color purity, color reproducibility, brightness, contrast, and the like at a level satisfying the demand for a large screen and high definition.

Meanwhile, the basic required properties of the color filter are heat resistance, light resistance, and the like. However, the conventionally known pigment-type coloring materials also have limitations in improvement of heat resistance and light resistance due to structural limitations thereof.

Disclosure of Invention

Technical problem

To overcome the above limitations, the present invention provides embodiments regarding colorant compounds having a generally unknown structure and coloring compositions comprising the same.

Technical scheme

One embodiment of the present invention provides a colorant compound represented by the following formula 1:

[ formula 1]

In the formula 1, the first and second groups,

a is represented by the following formula 2a or 2b,

R¹to R⁶At least one of which is represented by the following formula 3,

at R¹To R⁶Wherein the others not represented by the following formula 3 are each independently hydrogen; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or a substituted or unsubstituted C2-C30 heteroaryl;

[ formula 2a ]

[ formula 2b ]

In the formulae 2a and 2b,

X¹are identical to or different from each other and are hydrogen; a halogen atom; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or a substituted or unsubstituted C2-C30 heteroaryl;

[ formula 3]

＊-Q¹-Q²-R⁷-B

In the formula 3, the first and second groups,

Q¹is O or NH;

Q²is a direct bond or CO;

R⁷is a direct bond or C1-C12 alkylene;

b is a C6-C30 aryl group substituted with one or more hydroxyl groups; or C7-C30 alkylaryl substituted with one or more hydroxy groups.

Further, another embodiment of the present invention provides a coloring composition comprising a colorant compound, a binder resin, a polymerizable compound, and a photoinitiator.

Advantageous effects

Since the colorant compound provided in one embodiment of the present invention has a structure including a specific moiety, unlike a generally known compound, it can exhibit characteristics such as color purity, color reproducibility, luminance, contrast, and the like at a level satisfying the demand for a large screen and high definition, and can also exhibit excellent basic properties such as heat resistance, light resistance, and the like.

A coloring composition provided in another embodiment of the present invention comprises the above colorant compound, and when a color filter is manufactured using the coloring composition, a high-resolution, large-area color filter excellent in color characteristics (e.g., color reproducibility, etc.), heat resistance, light resistance, etc. can be manufactured.

Detailed Description

The present invention is embodied in colorant compounds and coloring compositions comprising the same. The advantages and features of the embodiments and methods of accomplishing the same will become apparent with reference to the following detailed examples. However, the present invention is not limited to the examples disclosed below, and may be embodied in various forms. These examples are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art to which the invention pertains. The invention is defined by the scope of the claims.

In the following, before describing embodiments of the present invention in detail, expressions and terms commonly used herein are defined.

First, as used herein, a-means a bond to another substituent.

As used herein, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and a heterocyclic group containing one or more of N, O and S atoms, or means a substituent obtained by connecting two or more of the substituents shown above, or unsubstituted. For example, the "substituent obtained by connecting two or more substituents" may be a biphenyl group. In other words, biphenyl group may be interpreted as an aryl group, or as a substituent obtained by linking two phenyl groups.

In the present disclosure, "aryl" may be a monocyclic aryl or polycyclic aryl having 6 to 30 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. The monocyclic aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,

A phenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present disclosure, the alkyl group may be a linear or branched alkyl group having 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present disclosure, the aryl group in the arylalkyl group and the alkylaryl group is the same as the examples of the aryl group described above. In the present disclosure, the alkyl groups in the arylalkyl and alkylaryl groups are the same as the examples of alkyl groups described above.

Hereinafter, embodiments of the present invention will be described in detail based on the expressions and terms defined above.

Colorant compound

Structure of colorant compound and its advantages

The colorant compound according to one embodiment of the present invention may have a novel structure in which the compound is based on 1) a quinophthalone or a derivative compound thereof, and 2) a specific substituent is introduced into the basic skeleton.

Specifically, the colorant compound according to an embodiment of the present invention is represented by the following formula 1:

[ formula 1]

1) In formula 1, A is represented by the following formula 2a or 2b,

it is shown that the colorant compound according to one embodiment of the present invention is based on quinophthalone or a derivative compound thereof, thereby exhibiting yellow color:

[ formula 2a ]

[ formula 2b ]

In formulae 2a and 2b, X¹Equal to or different from each other, is hydrogen; a halogen atom; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or substituted or unsubstituted C2-C30 heteroaryl.

Hereinafter, for convenience, the "quinophthalone or derivative compound thereof" will be referred to as a "quinophthalone-based compound".

2) Meanwhile, in formula 1, R¹To R⁶Is represented by the following formula 3, and in R¹To R⁶Wherein the others not represented by the following formula 3 are each independently hydrogen; substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C1-C20 hydroxyalkyl; a substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C7-C30 arylalkyl; substituted or unsubstituted C7-C30 alkylaryl; or a substituted or unsubstituted C2-C30 heteroaryl group,

it is shown that the colorant compound according to one embodiment of the present invention is a compound in which a substituent represented by the following formula 3 is introduced into at least one position of a quinophthalone-based compound:

[ formula 3]

＊-Q¹-Q²-R⁷-B

In formula 3, Q¹Is O or NH; q²Is a direct bond or CO; r⁷Is a direct bond or C1-C12 alkylene; b is a C6-C30 aryl group substituted with one or more hydroxyl groups, or a C7-C30 alkylaryl group substituted with one or more hydroxyl groups.

In this connection, there is incorporated therein a hydrophilic Q) having i) at the same time¹And Q²The portions (in the case of CO) and B and ii) the colorant compound according to one embodiment of the present invention having a substituent (formula 3) of high molecular weight may have improved characteristics such as solubility, heat resistance, and the like, compared to a compound in which the substituent is not introduced.

i) Specifically, during the preparation of a composition for a color filter, additives such as a dispersant and the like are generally added to improve the dispersibility of the colorant compound in the composition.

However, in the colorant compound according to an embodiment of the present invention, a colorant compound containing hydrophilic Q is introduced¹And Q²In part (in the case of CO)Under the same conditions) and B (formula 3), and thus, its dispersibility in a composition may be improved as compared to a compound in which the substituent is not introduced. When a hydrophilic solvent is contained in the composition, the effect can be more excellently achieved.

Therefore, unlike the general case, in preparing a composition containing the colorant compound according to an embodiment of the present invention, additives such as a dispersant and the like may be used in a small amount or may not be used, and the re-aggregation between the colorant compounds or the generation of other foreign substances may be suppressed.

In addition, a color filter realized based on the above composition can exhibit excellent characteristics such as color purity, brightness, contrast, and the like, by appropriately combining the absorption spectrum and the transmission spectrum of the color filter with the spectrum of the light source.

ii) meanwhile, in the colorant compound according to one embodiment of the present invention, a substituent (formula 3) comprising a C6-C30 aryl group or a C7-C30 alkylaryl group is introduced, and thus, the molecular weight thereof can be increased as compared to a compound in which such a substituent is not introduced.

Accordingly, the colorant compound according to one embodiment of the present invention can be prepared into a composition having improved heat resistance based on the increased molecular weight of the colorant compound.

In addition, the color filter realized based on the composition may exhibit stable display properties because color purity, brightness, contrast, etc. do not rapidly change during heat treatment for realization.

Briefly, a colorant compound according to one embodiment of the invention may: i) exhibits yellow color because the compound is a quinophthalone-based compound, and may ii) have improved solubility because a substituent represented by the following formula 3 is introduced thereto, thereby exhibiting superior characteristics such as color purity, color reproducibility, contrast, heat resistance, and the like, compared to a compound in which the substituent is not introduced.

These advantages and features, and the methods of accomplishing the same, will become apparent with reference to the following detailed examples.

Examples of colorant Compounds

Hereinafter, the colorant compound according to one embodiment of the present invention will be briefly described based on the examples described in detail below. However, the following description is for illustrative purposes only, and the scope of the present invention is defined by the claims as set forth above.

Generally, compounds contained in pigments have no large substituent, and therefore, most of them are insoluble in a solvent. Therefore, the pigment is generally dispersed in a particle state without dissolving in a solvent, and therefore, the pigment absorbs a wide spectral region including a new absorption spectrum generated by an attractive force between compound molecules and an intrinsic absorption spectrum of the compound molecules.

To solve this problem, in one embodiment of the present invention, a large substituent is introduced into the colorant compound of formula 1.

Specifically, according to one embodiment of the present invention, in formulae 2a and 2b, X¹May be identical to each other, are hydrogen. Further, according to an embodiment of the present invention, B of formula 3 may be represented by formula 4 below:

[ formula 4]

In formula 4, R^a、R^b、R^c、R^dAnd R^eAny one or more of which is a hydroxyl (-OH) group and each of the others is independently hydrogen, a C1-C20 linear alkyl group, or a C3-C20 branched alkyl group.

When a large substituent of formula 4 is introduced into the colorant compound of formula 1, the solubility thereof in a solvent can be improved as compared with a compound in which a large substituent is not introduced.

Here, the increased solubility may contribute to improvement of color purity, color reproducibility, brightness, contrast, etc. by reducing generation of a new absorption spectrum due to attractive force between molecules of the colorant compound of formula 1.

In addition, the increased solubility may facilitate injection of other materials required to improve the processability of a color pattern by significantly reducing the amount of materials (e.g., a dispersant, etc.) required to disperse the colorant compound of formula 1.

In particular, when the bulky substituent of formula 4 has a hindered structure in which a hydroxyl group is located between two different branched alkyl groups, a radical and singlet oxygen involved in molecular degradation may react with the hindered structure, thereby improving the stability of the chromophore compared to a compound in which the hindered structure is not introduced.

Specifically, according to one embodiment of the present invention, in formula 4, R^cMay be a hydroxyl group; r^aAnd R^eMay each independently be hydrogen. R^bAnd R^dMay each independently be a C3-C20 branched alkyl group, specifically a C3-C10 branched alkyl group, and more specifically a C3-C6 branched alkyl group.

More specifically, R of formula 4^bAnd R^dMay each independently be a C4 branched alkyl group, and in such cases, formula 4 may be located at R of formula 1⁶And R of formula 1¹To R⁵May each independently be hydrogen.

As an example of this case, the compound represented by formula 1 may be any one selected from the following compounds, but is not limited thereto:

the colorant compound of formula 1 can be prepared by various methods generally known in the art, including the preparation examples described below. Therefore, the method for preparing the colorant compound of formula 1 is not particularly limited.

Coloring composition

According to another embodiment of the present invention, there is provided a coloring composition comprising the colorant compound of formula 1.

Here, the detailed description and specific examples of the colorant compound of formula 1 are the same as those described above. Hereinafter, the composition including the colorant compound of formula 1 will be described in detail, but any description overlapping with the foregoing description will be omitted.

The colorant compound may be included in an amount of about 10 wt% or more, or about 15 wt% or more, or about 20 wt% or more and about 50 wt% or less, or about 40 wt%, or about 30 wt% or less, relative to 100 wt% solids content included in the coloring composition. If the content of the colorant compound is too low, the color purity may be lowered, and if the content is too high, the curing reaction of the resin composition may not occur properly. From this viewpoint, the colorant compound is preferably contained within the above range.

In preparing the coloring composition according to one embodiment of the present invention, the colorant compound of formula 1 may be used alone or in a combination of two or more thereof.

Further, the coloring composition of the present invention may further comprise any other known colorant compound, as needed, in addition to the colorant compound of formula 1.

For example, the coloring composition of the present invention may further include at least one of a dye and a pigment in addition to the colorant compound of formula 1. Specifically, the dye and the pigment may include one or more compounds exhibiting any one of yellow, red and green colors, respectively.

More specifically, the compound exhibiting yellow color may include one or more compounds selected from the group consisting of: metal complex-based compounds, azo-based compounds, quinophthalone-based compounds, isoindoline-based compounds, and styryl-based compounds.

The compound exhibiting red color may include one or more compounds selected from the group consisting of: metal complex-based compounds, azo-based compounds, xanthene-based compounds, diketopyrrolopyrrole-based compounds, anthraquinone-based compounds and perylene-based compounds.

The compound exhibiting green color may include one or more compounds selected from the group consisting of: metal complex-based compounds, triarylmethane-based compounds, and anthraquinone-based compounds.

The pigment may comprise one or more selected from: a yellow pigment group including PY129, PY138, PY139, PY150, and PY 185; a red pigment group comprising PR48, PR48: 1, PR48: 2, PR48:3, PR48: 4, PR 177, PR 179, PR 207, PR254, PR 255, PR 264 and PR 269; and a green pigment group comprising PG 7, PG 36, PG 58, and PG 59.

In addition, the coloring composition according to one embodiment of the present invention may further include a binder resin, a polymerizable compound, and a photoinitiator.

The polymer resin is not particularly limited, and those generally used in the art to which the present invention pertains may be used. For example, an alkali-soluble resin may be used.

Specific examples of the alkali soluble resin may include (meth) acrylic resins, acrylamide resins, novolac resins, etc., and for example, resins having a weight average molecular weight (Mw) of 3,000 to 150,000g/mol may be used, but the present invention is not limited thereto.

The polymer resin may be included in an amount of about 3 wt% or more, or about 5 wt% or more, or about 10 wt% or more and about 30 wt% or less, or about 20 wt%, or about 15 wt% or less, with respect to 100 wt% of the solid content included in the coloring composition, but the present invention is not limited thereto.

The polymerizable compound is not particularly limited, and those generally used in the art to which the present invention pertains may be used. For example, photopolymerizable compounds having ethylenically unsaturated groups can be used. The compound having an ethylenically unsaturated group may be an acrylate-based compound.

More specific examples thereof may include one or more compounds selected from the group consisting of: pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ethylene glycol di (meth) acrylate, and polyethylene glycol di (meth) acrylate, but the present invention is not limited thereto.

The polymerizable compound may be included in an amount of about 30% by weight or more, or about 40% by weight or more, or about 50% by weight or more and about 80% by weight or less, or about 70% by weight, or about 60% by weight or less, with respect to 100% by weight of the solid content included in the coloring composition, but the present invention is not limited thereto.

The photoinitiator (i.e., photopolymerization initiator) is not particularly limited, and those generally used in the art to which the present invention pertains may be used. For example, the photoinitiator may include one or more compounds selected from the group consisting of: 2, 4-trichloromethyl- (4 '-methoxyphenyl) -6-triazine, 2, 4-trichloromethyl- (4' -methoxystyryl) -6-triazine, 2, 4-trichloromethyl- (fipronil) 6-triazine, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy) propyl ketone, benzophenone, and 2,4, 6-trimethylaminobenzophenone, but are not limited thereto.

The photoinitiator may be included in an amount of about 0.1 wt% to about 10 wt% with respect to 100 wt% of a solid content included in the coloring composition, but the present invention is not limited thereto.

The coloring composition of the present invention may further comprise a solvent in order to increase coating characteristics and workability.

For example, the solvent may comprise one or more compounds selected from the group consisting of: methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, and dipropylene glycol monomethyl ether, but are not limited thereto.

The content of the solvent may be controlled in consideration of coating characteristics and workability, and thus is not particularly limited, but the solvent may be included in an amount of about 50 parts by weight to about 500 parts by weight with respect to 100 parts by weight of the solid content included in the coloring composition.

Meanwhile, the coloring composition may further include additives such as a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, an ultraviolet absorber, a leveling agent, a photosensitizer, a plasticizer, an adhesion promoter, a filler, a surfactant, and the like, which may be included in known coloring compositions for color filters.

Examples of the curing accelerator may include one or more selected from the group consisting of: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenz

Oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), and trimethylolethane tris (3-mercaptopropionate), but are not limited thereto, and the curing accelerator may include those generally known in the art.

Color filter

The colorant compound represented by formula 1 may be used to manufacture a color filter by a method generally known in the art to which the present invention pertains (e.g., by printing or photolithography).

In this regard, still another embodiment of the present invention provides a color filter comprising the colorant compound.

For example, according to the photolithography method, a transparent substrate is coated with the coloring composition by spray coating, spin coating, slit coating, roll coating, dipping, or the like. The coated substrate is selectively subjected to an exposure process through a mask having a predetermined pattern. Meanwhile, a pre-baking process and/or a post-baking process may also be performed. After exposure, the coloring composition is developed to form a desired photoresist pattern. Upon washing and drying the developed substrate, a color filter having a desired photoresist pattern formed thereon can be obtained.

As described above, the color filter manufactured by using the colorant composition may exhibit excellent characteristics such as color purity, color reproducibility, contrast, heat resistance, etc., because the colorant composition (formula 1) i) exhibits yellow based on the quinophthalone-based compound and has improved solubility of ii) by introducing a large substituent (formula 3) thereto, compared to a compound in which no substituent is introduced.

In particular, when a large substituent has a hindered structure in which a hydroxyl group is located between two different branched alkyl groups, a radical and singlet oxygen participating in molecular degradation may react with the hindered structure, and thus the stability of the chromophore may be improved as compared to a compound in which the hindered structure is not introduced.

Therefore, when the coloring composition of the present invention is used, a color filter having high reliability and high resolution can be manufactured.

EMBODIMENTS FOR CARRYING OUT THE INVENTION

Hereinafter, the action and effect of the present invention will be described in more detail with reference to specific examples thereof. However, these examples are for illustrative purposes only, and the scope of the present invention is not intended to be limited by these examples.

< example for synthesizing colorant Compound >

Preparation example 1 Synthesis of intermediate A

30g (188.45mmol) of intermediate 1, 27.93g (188.45mmol) of intermediate 1-A, 60g of benzoic acid and 200g of methyl benzoate were placed in a 500ml one-neck round bottom flask (1-neck RBF) and stirred at 180 ℃ for 10 hours. Thereafter, the solution was cooled to room temperature, and 2000ml of MeOH was added thereto, followed by stirring. The precipitate produced during this process was filtered under reduced pressure, washed with MeOH, and dried in a vacuum oven at 80 ℃ for 24 hours to obtain intermediate a. In this connection, the molecular weight of the intermediate A obtained was confirmed by MS analysis to be 289 g/mol.

Preparation example 2 Synthesis of Compound 1

30ml of nitrobenzene and 3.89g (15.56mmol) of intermediate 1-B were placed in a 100ml two-necked round-bottomed flask (2-necked RBF) and then stirred. Thereafter, 5.55g (46.67mmol) of SOCl were slowly added dropwise₂And allowed to react at 95 ℃ for 2 hours. Then, nitrogen gas was injected for 30 minutes to remove residual SOCl₂And HCl. Thereafter, the solution was cooled to room temperature, and then 3g (10.37mmol) of intermediate A and 3.15g (31.11mmol) of triethylamine were added and allowed to react at 90 ℃ for 3 hours. Then, the solution was added to diethyl ether, followed by stirring. The precipitate generated during this process was filtered under reduced pressure, washed with diethyl ether, and separated and purified by column chromatography to obtain compound 1. In this regard, the molecular weight of Compound 1 was confirmed by MS analysis to be 521 g/mol.

Preparation example 3 Synthesis of Compound 2

Compound 2 was prepared in the same manner as in preparation example 2, except that intermediate 1-C was used instead of intermediate 1-B.

Preparation example 4 Synthesis of intermediate B

Intermediate B was prepared in the same manner as in preparation example 1, except that intermediate 1-D was used instead of intermediate 1-a.

Preparation example 5 Synthesis of Compound 3

Compound 3 was prepared in the same manner as in preparation example 2, except that intermediate B was used instead of intermediate a.

Preparation example 6 Synthesis of Compound 4

Compound 4 was prepared in the same manner as in preparation example 3, except that intermediate B was used instead of intermediate a.

Preparation example 7 Synthesis of intermediate C

Intermediate C was prepared in the same manner as in preparation example 1, except that intermediate 1-E was used instead of intermediate 1-a.

Preparation example 8 Synthesis of Compound 4

Compound 5 was prepared in the same manner as in preparation example 2, except that intermediate C was used instead of intermediate a.

Preparation example 9 Synthesis of Compound 5

Compound 6 was prepared in the same manner as in preparation example 3, except that intermediate C was used instead of intermediate a.

Preparation example 10 Synthesis of intermediate D

250ml of methylene chloride and 30g (189.63mmol) of intermediate 2 were placed in a 500ml two-necked round-bottomed flask (2-necked RBF), followed by stirring. Thereafter, 57.567g (568.90mmol) of triethylamine was slowly added dropwise thereto, and stirred at room temperature for 30 minutes. 50.97g (189.63mmol) of intermediate 1-F were then slowly added dropwise and allowed to react at 45 ℃ for 3 hours. 500ml of deionized water was added thereto and MgSO₄The organic layer formed by phase separation was dried. The solvent was removed under reduced pressure, and isolated and purified by column chromatography to obtain intermediate D. In this connection, the molecular weight of the intermediate D obtained was confirmed by MS analysis to be 390 g/mol.

Preparation example 11 Synthesis of intermediate E

Intermediate E was prepared in the same manner as in preparation example 10, except that intermediates 1-G were used instead of intermediates 1-F.

Preparation example 12 Synthesis of Compound 7

3g (7.66mmol) of intermediate D and 1.15g (7.74mmol) of intermediate 1-A were added to 5g of benzoic acid and 20ml of methyl benzoate in a 100ml one-neck round-bottom flask (1-neck RBF), followed by stirring. The solution was allowed to react at 180 ℃ for 10 hours and then cooled to room temperature. Thereafter, the solution was added to 200ml MeOH, followed by stirring. The precipitate generated during this process was filtered under reduced pressure, and isolated and purified by column chromatography to obtain compound 7. In this connection, the molecular weight of Compound 7 obtained was confirmed by MS analysis to be 520 g/mol.

Preparation example 13 Synthesis of Compound 8

Compound 8 was prepared in the same manner as in preparation example 12, except that the following intermediate E was used instead of intermediate D.

Preparation example 14 Synthesis of Compound 9

Compound 9 was prepared in the same manner as in preparation example 12, except that the following intermediate 1-D was used instead of intermediate 1-a.

Preparation example 15 Synthesis of Compound 10

Compound 10 was prepared in the same manner as in preparation example 13, except that the following intermediate 1-D was used instead of intermediate 1-A.

Preparation example 16 Synthesis of Compound 11

Compound 11 was prepared in the same manner as in preparation example 12, except that intermediate 1-E was used instead of intermediate 1-A.

Preparation example 17 Synthesis of Compound 12

Compound 12 was prepared in the same manner as in preparation example 13, except that intermediate 1-D was used instead of intermediate 1-A.

Preparation example 18 Synthesis of intermediate F of Compound

Intermediate F was prepared in the same manner as in preparation example 10, except that intermediate 1 and intermediate 1-H were used instead of intermediate 2 and intermediate 1-F, respectively. In this respect, the molecular weight of the intermediate F obtained was confirmed by MS analysis to be 377 g/mol.

Preparation example 19 Synthesis of Compound 13

Compound 13 was prepared in the same manner as in preparation example 12, except that intermediate F was used instead of intermediate D. In this connection, the molecular weight of the obtained compound 13 was confirmed by MS analysis to be 507 g/mol.

Preparation example 20 Synthesis of Compound 14

Compound 14 was prepared in the same manner as in preparation example 12, except that intermediate F and intermediate 1-D were used instead of intermediate D and intermediate 1-a, respectively. In this connection, the molecular weight of Compound 14 obtained was confirmed by MS analysis to be 557 g/mol.

Comparative example Compound 1

Using the PY138 (BASF,

yellow L0960 HD) as comparative compound 1.

< example for producing coloring composition >