WO2019045364A2 - Colorant compound and coloring composition comprising same - Google Patents

Abstract

The present invention relates to a colorant and a coloring composition comprising the same. More particularly, the present invention relates to a coloring agent having a novel structure which exhibits excellent color characteristics, heat resistance and solubility and can be used for producing color filters, and a coloring composition comprising the same.

Description

 Title of the Invention

 COLORANT COMPOUNDS AND COLORING COMPOSITIONS CONTAINING SAME

 TECHNICAL FIELD

 Cross-reference with related application (s)

 This application claims priority to Korean Patent Application No. 10-2017-0112691, filed September 4, 2017,

Claims the benefit of priority based on Korean Patent Application No. 10-2018-0098142, filed on Aug. 22, 2018, the entire contents of which are incorporated herein by reference.

 The present invention relates to colorant compounds and to coloring compositions comprising them. More particularly, the present invention relates to a colorant compound having a novel structure showing excellent color characteristics, heat resistance and solubility, and a coloring composition comprising the same. BACKGROUND ART [0002]

 A color filter used for a liquid crystal display (LCD) and an organic light emitting diode (OLED) is used for realizing a color image in a display device. The color filter is coated on a basic substrate using various methods, Can be manufactured through the process of making.

 The color filter is formed by a red, green, and blue pixel portions on a transparent substrate such as a glass. Color filters used in an image display apparatus and a solid-state image pickup device are typically red (R), green And a blue (B) coloring pattern, and serves to color the passing light or to divide the light into three primary colors.

 The dyes displaying red, green and blue are composed of fine particles, that is, dyes or pigments. These dyes are used for obtaining color display characteristics of a desired area, To display red, green, and blue.

 Materials commonly used as coloring matters are required to have desirable absorption characteristics on the color reproducibility, light resistance under the conditions used, heat resistance, resistance to oxidizing gases such as ozone, and the like.

BACKGROUND ART [0002] In recent years, a technology for developing a large-screen and high-definition liquid crystal display has been developed. In such a situation, a color filter used for a liquid crystal display or the like is required to have a high color purity. A variety of pigments or colorants which can be used in the production of color filters are known, but only known color materials The method of improving the color purity, luminance and contrast ratio gradually reaches the limit. In particular, it is difficult to increase the pigment content in the photosensitive resin composition due to the pigment derivative and the dispersant added in accordance with the pigment dispersion method in the production of a color filter using the pigment dispersion method, and thus it is difficult to manufacture a thin film color filter. Therefore, development of a novel pigment for solving such a problem is required.

 [Prior Art Document]

 [Patent Literature]

 [Patent Document 0001] Korean Patent Publication No. 10-2014-01252183 [Description of the Invention]

 [Technical Problem]

 SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide a colorant compound having a novel structure which is excellent in color reproducibility, color characteristics, heat resistance and solubility and can be used as a colorant for a color filter and a colorant composition containing the same do.

[Technical Solution]

 In order to solve the above problems, an embodiment of the present invention provides a colorant compound represented by the following general formula (1).

 In Formula 1,

Each of R _x to ¾ is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, an N-alkylene-piperidine having at least one aromatic ring having 6 to 20 carbon atoms bonded thereto A piperidinedione or a N-alkylene-pyrrolidinedione;

R < ₆ >

Each of R ₇ to R ₁₀ is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms group or an alkoxy group having 1 to 30 carbon atoms;

(2)

 In the above Formulas 2 and 3,

Rn to _O each represent hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, Or an alkoxy group having 1 to 30 carbon atoms,

At least one of R ₇ to _O is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 30 carbon atoms to be. In another embodiment of the present invention, there is provided a coloring composition comprising the colorant compound.

 In another embodiment of the present invention, there is provided a color filter comprising the coloring composition.

 In another embodiment of the present invention, a display device including the color filter is provided.

 【Effects of the Invention】

 The colorant compound of the present invention is a compound of a novel structure which is not known in the prior art and contains a specific group and can exhibit stable color reproducibility and excellent heat resistance and solubility. In addition, since the solubility of the pigment derivative and the dispersant in the solvent is excellent compared to the conventional art, the amount of the pigment derivative and the dispersant can be reduced when the pigment dispersion method is used.

 Therefore, the color filter according to the present invention can provide a high-resolution color filter having high color reproduction rate and high brightness and contrast ratio due to excellent color reproducibility and heat resistance. In addition, it is possible to increase the pigment content in the coloring composition due to the excellent solubility of the novel colorant compound, thereby making it possible to manufacture a thin film color filter.

 Best Mode for Carrying Out the Invention

 While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are shown by way of example in the drawings and will herein be described in detail. It should be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

 Hereinafter, the colorant compound of the present invention and the coloring composition containing the colorant compound will be described in more detail. Colorant compound

The colorant compound according to one embodiment of the present invention is represented by the following formula (1). [Chemical Formula 1]

 In Formula 1,

R 1 to R ₅ are independently selected from the group consisting of hydrogen halide, an aliphatic group having 1 to 10 carbon atoms, an N-alkylene-piperidine dione having at least one aromatic ring having 6 to 20 carbon atoms bonded thereto, Pyrrolidinedione; < / RTI >

R < ₆ >

Each of R ₇ to R ₁₀ is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms group) or an alkoxy group having 1 to 30 carbon atoms;

(3)

상기 화학식 2 및 3에서 ,

In the above Formulas 2 and 3,

Rn to _O each represent hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, Or an alkoxy group having 1 to 30 carbon atoms,

는 다른 치환기에 연결되는 결합을 의미한다. 본 발명의 또 다른 일실시예에 따른 착색제 화합물은 상기 화학식 1 의 착색제 화합물로서， R_{2 >} 및 R₅는 각각 수소 또는 할로겐이고; 상기 ¾은 하기 화학식 4의 작용기 또는 하기 화학식 5의 작용기일 수 있다. At least one of R ₇ to _O is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 30 carbon atoms. In the present specification,

Quot; means a bond connected to another substituent. A colorant compound according to another embodiment of the present invention is a colorant compound of the above formula (1), wherein R ₂ > and R ₅ are each hydrogen or halogen; The above-mentioned group may be a functional group of the following formula (4) or a functional group of the following formula (5).

 [Chemical Formula 4]

In the general formulas (4) and (5), R ₂₁ , R ₂₂ and ₃ are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C1 to C20 hydroxyalkyl group, a substituted or unsubstituted C6 to C30 aryl group; The substituted or unsubstituted carbon number An arylalkyl group having 7 to 30 carbon atoms; A substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms; Wherein n, r, and n ₂ may be an _{^{integer, 0≤ η ≤4, 0 <ηι}} <3, 0 <n 2 <3. In the present specification, n, n1 and n2 are to be interpreted to mean the number of functional groups substituted for the corresponding benzene rings. The term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, " the substituent group in which at least two of the substituents are bonded may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. The alkyl group may be a straight chain or branched chain 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 include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, n-butyl, n-butyl, 1-methylpentyl, N-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, Propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.

The alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-octoxy, isobutoxy, tert- , Isopentyloxy, n-propyloxy, 3,3-dimethylbutyloxy, n-octyloxy, n-nonyloxy, n- Benzyloxy, p-methylbenzyloxy, and the like, but are not limited thereto.

 The aryl group may be a monocyclic aryl group or a polycyclic aryl group having 6 to 30 carbon atoms, or 6 to 20 carbon atoms, or 6 to 12 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

The aryl group in the arylalkyl group and the alkylaryl group is the same as the aforementioned aryl group. The alkyl group in the arylalkyl group and the alkylaryl group is the same as the alkyl group described above. The colorant compound according to another embodiment of the present invention is a colorant compound of Formula 1 wherein at least one of R ₇ to R ₁₀ is a cyclic or straight chain alkyl thio group having 1 to 30 carbon atoms, An aryl thio group having 1 to 30 carbon atoms, and each of R _u to R ₂₀ is hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms.

The colorant compound according to another embodiment of the present invention is the colorant compound of Formula 1, wherein R ₇ to R ₁₀ are each hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, and at least one of Ru to R ₁₄ , Or at least one of R ₁₅ to _O may be a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms or an aryl thio group having 1 to 30 carbon atoms. In the above formula (1), at least one of R ₇ to ¾ ₀ represents a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms Or an alkoxy group having 1 to 30 carbon atoms, and more specifically, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms.

상술한 바와 같이， 상기 화학식 1 의 착색제 화합물은 퀴노프탈온 (duinaphthalone)계 유도체 화합물의 특정 위치에 하나 이상의 탄소수 1 내지 30 의 고리 또는 직쇄형 알킬 싸이오 그룹 (alkyl thio group) , 탄소수 1 내지 30 의 아릴 싸이오 그룹 (aryl thio group) 또는 탄소수 1 내지 30 의 알콕시 그룹이 치환된 구조를 가질 수 있고， 보다 상세하게는 탄소수 1 내지 30 의 고리 또는 직쇄형 알킬 싸이오 그룹 (alkyl thio group) 또는 탄소수 1 내지 30 의 아릴 싸이오 그룹 (aryl thio group)이 치환된 구조를 가질 수 있다. According to an embodiment of the present invention, at least one of the valencies R ₇ to R ₂₀ may be a ring or a straight-chain alkyl thio group having 3 to 6 carbon atoms, Butylthio group.

As described above, the colorant compound of the formula (1) is a compound having at least one ring or straight-chain alkyl thio group having 1 to 30 carbon atoms in a specific position of a quinophthalone derivative compound, an alkyl thio group having 1 to 30 carbon atoms An aryl thio group or an alkoxy group having 1 to 30 carbon atoms, and more specifically a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, or And an aryl thio group having 1 to 30 carbon atoms may be substituted.

 Specifically, by introducing one or more alkylthio groups into the colorant compound of formula (1) as described above, it is possible to reduce the planarity of molecules and reduce the π - π interaction between molecules. As a result, the solubility of the colorant compound in the organic solvent may be increased as the molecules are easily solitated in the organic solvent.

 Accordingly, since the solubility of the colorant compound in an organic solvent (for example, DMF) is remarkably improved, the amount of the pigment derivative and dispersant required when the coloring composition containing the colorant composition is prepared by the pigment dispersion method is remarkably reduced. Therefore, it is possible to increase the colorant compound or the pigment content in the coloring composition by the above ratio, thereby facilitating the production of the thin film color filter. Specific examples of the above-described colorant compound include the compounds represented by the following formulas (6) to (47), but the present invention is not limited thereto.

[Chemical Formula 6]

10

[화학식 15]

[Chemical Formula 15]

[화학식 20]

[Chemical Formula 20]

[화학식 26]

(26)

[화학식 29]

[Chemical Formula 29]

[화학식 35]

(35)

(37)

[Chemical Formula 39]

(41)

(43)

[Chemical Formula 45]

상기 화학식 1 의 착색제 화합물의 합성방법에는 통상적으로 알려진 합성방법 및 합성장치를 큰 제한없이 사용할 수 있다. 예를 들어， 화학식 1 의 착색제 화합물은 먼저 피그먼트 옐로우에 프탈이미드(1)111:131^1(16) 또는 1，8- 나프탈이미드 (1,8-Naphthalimide)를 선택적으로 도입한 다음， 여기에 알킬티올 (alkylthiol), 예를 들어 1-부탄티올 (1-butanthiol )을 반웅시켜 제조할 수도 있다. 착색 조성물

The method of synthesizing the colorant compound of the above formula (1) can be widely used without any limitations. For example, the colorant compound of Formula 1 can be prepared by first introducing phthalimide (1) 111: 131 ^ 1 (16) or 1,8-naphthalimide into Pigment Yellow It is also possible to prepare an alkylthiol, for example 1-butanthiol, by reacting with it. Coloring composition

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

 According to an embodiment of the present invention, the coloring composition may further include at least one of a dye (Dye) and a pigment (Pigment), wherein the dye and the pigment may be any one selected from yellow, red and green May be one containing at least one compound which exhibits color.

 According to an embodiment of the present invention, the yellow-emitting compound may be a metal-complex compound, an azo compound, a quinophthalone compound, An isoindoline-based compound, a styryl-based compound, and the like.

 According to another embodiment of the present invention, the red-emitting compound may be a metal-complex compound, an azo compound, a xanthene compound, diketopyrrolopyrrole ) Type compound, anthraquinone (&lang; 1 ^ 301110101) type compound, and perylene type compound.

According to another embodiment of the invention, the compounds representative of the green, the metal-composite _(me t _a l- _com pl _e x) based compounds, triarylmethane (triarylmethane) series compound, an anthraquinone (anthraquinone) series A compound of the present invention may include one or more compounds selected from the group including compounds.

Meanwhile, according to one embodiment of the present invention, the pigment includes a yellow pigment group including PY129, PY138, PY139, PY150, and PY185; PR 48, PR 48: 1, PR 48: 2, A red pigment group including PR 48: 3, PR 48: 4, PR 177, PR 179, PR 207, PR 254, PR 255, PR 264 and PR 269; And green pigment groups including PG 7, PG 36, PG 58, and PG 59; And the like. The coloring composition according to one embodiment of the present invention may further contain, in addition to the colorant compound, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The detailed description and specific examples of the colorant compound are as described above, and the colorant compound may be contained in the colorant composition in an amount of 20 parts by weight or more, specifically 25 parts by weight or more, based on 100 parts by weight of the colorant composition , 50 parts by weight or less, specifically, 40 parts by weight or less.

 When the content of the colorant compound is less than the above range, it is difficult to realize a deep color. If the content of the colorant compound exceeds the above range, the curing reaction of the resin composition may not be performed properly.

 On the other hand, 100 parts by weight of the coloring composition may be 100 parts by weight of the total of the colorant compound, the binder resin, the polyfunctional monomer and the photoinitiator contained in the coloring composition. When a solvent is additionally included, Sol id contents

100 parts by weight. Meanwhile, in the coloring composition according to one embodiment of the present invention, the colorant compound of Formula 1 may be used alone or in a mixture of two or more kinds thereof. In addition, the coloring composition according to one embodiment of the present invention may optionally include other known coloring agents in addition to the coloring agent compound of the above-mentioned formula (1).

On the other hand, when the coloring composition is mixed with a known coloring agent, it is possible to further prevent the reoccurrence of pigments or to prevent foreign matters from being formed. Thus, an additional effect of improving the contrast ratio Lt; / RTI &gt; The binder resin is not particularly limited, and the binder resin Those generally used in the technical field can be used, and resins which are preferably alkali-soluble can be used.

 Specifically, a (meth) acrylic resin, an acrylamide resin, a novolac resin, or the like can be used as the alkali-soluble resin, and preferably has a weight average molecular weight (Mw) of 3,000 to 150,000 g / But the present invention is not limited thereto. On the other hand, the weight average molecular weight is measured by GPC X Geel Permeation Chromatography using polystyrene as a standard material.

 The binder resin may be contained in the coloring composition in an amount of 3 parts by weight or more, specifically 5 parts by weight or more, more specifically 10 parts by weight or more, and 30 parts by weight or less with respect to 100 parts by weight of the coloring composition , Specifically 20 parts by weight or less, more specifically 15 parts by weight or less. The multifunctional monomer is not particularly limited and those generally used in the technical field to which the present invention belongs can be used. The multifunctional monomer is a monomer having a role of forming a photoresist image by light, and specifically includes propylene glycol Methacrylate, dipentaerythritol triacrylate, dipentaerythritol triacrylate, neopentyl glycol diacrylate, 6-nucleic acid diacrylate, 1,6-nucleic acid diol acrylate tetraethylene glycol methacrylate , Bisphenoxy ethyl alcohol diacrylate, trishydroxy ethyl isocyanurate trimethacrylate, trimethyl propane trimethacrylate, diphenyl pentaerythritol triacrylate, pentaerythritol trimethacrylate , Pentaerythritol tetramethacrylate and dipenta And erythrides may be one or more species selected from the group consisting of nuclear methacrylates.

The multifunctional monomer may be contained in the coloring composition in an amount of 30 parts by weight or more, specifically 40 parts by weight or more, more specifically 50 parts by weight or more, and 80 parts by weight or less, Specifically not more than 70 parts by weight, more specifically not more than 60 parts by weight. The photoinitiator may be selected from the group consisting of 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-methoxystyryl) , 4-trichloromethyl- (phenylon) 6-triazine, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2- hydroxy) propyl ketone, benzophenone, 2,4,6-trimethylaminobenzophenone, and the like can be used, but the present invention is not limited thereto.

 The photopolymerization initiator may be contained in the coloring composition in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the coloring composition. Meanwhile, the coloring composition according to one embodiment of the present invention may further include a solvent for improving the applicability and workability.

 According to an embodiment of the present invention, the solvent may include methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene Diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxypropanol, 2-mexyl propanol, 3-methoxybutane, 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, or dipropylene glycol monomethyl ether

One or more compounds may be used, but are not limited thereto.

 The content of the solvent is not particularly limited as it is adjustable in consideration of coating properties and workability. For example, the solvent may be contained in an amount of 50 to 500 parts by weight based on 100 parts by weight of the coloring composition. According to one embodiment of the present invention, the coloring composition may further comprise, in addition to the components described above, a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, an ultraviolet absorber, a leveling agent, a photosensitizer, a plasticizer, And an additive that can be included in the conventional coloring composition for a color filter such as a surfactant.

Examples of the curing accelerator include 2-mercaptobenzoimidazole, 2- Mercapto benzothiazole, 2-mercaptobenzooxazole, 2,5-dimer, and 3-mercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, (Mercapto propionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate) Trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), and trimethylolethane tris And the like. However, the present invention is not limited thereto, and may include those generally known in the art to which the present invention belongs.

 On the other hand, the coloring composition according to one embodiment of the present invention can be used for producing a color filter by a method generally known in the technical field of the present invention, for example, a printing method or a photolithography method.

 For example, according to the photolithography method, the colored composition is applied onto a transparent substrate by a method such as spray coating, spin coating, slit coating, roll coating, or dipping. An exposure process is selectively performed on the coating film through a mask having a predetermined pattern. Meanwhile, the pre-exposure baking and / or post-baking may be further performed. After exposure, the coloring composition is developed to form the desired photoresist pattern. The developed substrate is washed and dried to obtain a color filter in which a desired type of photoresist pattern is formed. On the other hand, the obtained color filter can be utilized in a display device or the like. As described above, the colorant compound of the present invention is a compound of a novel structure which is not known in the prior art and contains a specific group, and can exhibit stable color reproducibility and excellent heat resistance and solubility. In addition, since the solubility of the pigment derivative and the dispersant in the solvent is excellent compared to the conventional art, the amount of the pigment derivative and the dispersant can be reduced when the pigment dispersion method is used.

Therefore, the color filter according to the present invention can provide a high-resolution color filter having high color reproduction rate and high brightness and contrast ratio due to excellent color reproducibility and heat resistance. Further, due to the excellent solubility of the novel colorant compound, It becomes possible to increase the pigment content in the composition, thereby making it possible to manufacture a thin film color filter.

DETAILED DESCRIPTION OF THE INVENTION

 Best Mode for Carrying Out the Invention Hereinafter, the operation and effects of the present invention will be described in more detail through specific examples of the present invention. It is to be understood, however, that these embodiments are merely illustrative of the invention and are not intended to limit the scope of the invention. Production Example 1: Synthesis of Compound 1

 PY138 Compound (A) Compound 1

Compound A was obtained by the method described in U.S. Patent No. 6,849,116 B2. Specifically, 25.5 g of phthalimide and 7.4 g of paraformaldehyde were stirred and added to 560 g of fuming sulfuric acid at 3.6% by weight at 25 ^° C. The mixture was heated to 50 ^° C and stirred for 30 minutes.

To this was added 100 g of Pigment Yellow 138 (BASF) and the mixture was heated with lOCrC and stirred for 3 hours. The scum was then added to 3500 grams of water and stirred at 60 ^° C for 30 minutes. The thus precipitated product was filtered, washed with water to neutrality, and then dried at 90 ^° C in a vacuum drying rack to obtain a compound (A).

Next, 3 g (3.417 mmol) of the compound (A), 0.52 g (7.033 mmol) of 1-butanthiol and 1.94 g (14.06 mmol) of K ₂ CO ₃ were added to 500 ml of 1-neck RBF and heated at 60 ^° C. for 24 hours Lt; / RTI &gt; The solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure and the residue was purified by column to obtain Compound 1. As a result of APCI negat ive MS analysis, the molecular weight 907 of Compound 1 was confirmed.

 Compound (B) Compound 2 Compound B was obtained in the same manner as in Production Example 1 except that 1, 8-naphthalimide was used instead of phthalimide according to the method described in U.S. Patent No. 6,849,116 B2.

Next, 3 g (3.32 mmol) of the compound (B), 0.49 g (6.65 mmol) of 1-butanthiol and 1.83 g (13.28 mmol) of K ₂ CO ₃ were added to a 500 ml 1-neck RBF and heated at 60 ^° C. for 24 hours Lt; / RTI &gt; The solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the residue was purified by column to obtain Compound (2). As a result of APCI negat ive MS analysis, the molecular weight 957 of Compound 2 was confirmed.

 Compound (C) Compound (D) Compound 3 Compound C was obtained according to the synthesis method described in Korean Laid-Open Patent Publication No. 2013-0137028, and Compound D was obtained by the method described in US Pat. No. 6,849,116 B2.

Next, the compound (D) in 500ml 1-neck RBF 3g (3.92mmol ), 1- Butanthiol 0.58g (7.84mmol), K 2 C0 3 2. Put 17g (15.69mmol), at 60 ^° C Stir for 24 hours. The solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure and the residue was purified by column to obtain the above compound 3. As a result of APCI negat ive MS analysis, the molecular weight 819 of Compound 3 was confirmed.

 Compound (C) Compound (E) Compound 4 Compound C was obtained according to the synthesis method described in Korean Laid-Open Patent Publication No. 2013-0137028, and the compound described in US Pat. No. 6,849,116 B2 was used instead of phthalimide. 8-naphthalimide was used to obtain the compound E. ·

 Next, 3 g (3.6anmol) of the above compound (E), 1-norbornene-

Butanthiol 0.54g (7.36隱ol), K 2 C0 3 2.03 put (14.72瞧() 1), at 60 ^° C

Stir for 24 hours. The reaction solution was cooled in an upper atmosphere, and then filtered under reduced pressure. The solvent was removed under reduced pressure and the residue was purified by column to obtain the above compound 4. As a result of APCI negat ive MS analysis, the molecular weight 869 of Compound 4 was confirmed.

화합물 (F) 화합물 (G) 상기 제조예 1 에서 PY138 대신 화합물 F를 이용하였고， 화합물 A 대신 화합물 G를 이용하여 화합물 5를 합성하였다.

Compound (F) Compound (G) Compound F was used instead of PY138 in Preparation Example 1, and Compound 5 was synthesized using Compound G instead of Compound A.

 As a result of APCI negat ive MS analysis, the molecular weight 753 of Compound 5 was confirmed.

 Compound (I) Compound (6) was synthesized by using Compound (H) instead of Compound (A) instead of PY138 in Synthesis Example 1.

 As a result of APCI negat ive MS analysis, the molecular weight 803 of Compound 6 was confirmed.

Compound (7) Compound (7) Compound (7) was synthesized by using Compound (J) instead of Compound (7) in place of Compound (A) As a result of APCI negative MS analysis, the molecular weight 803 of Compound 7 was confirmed.

 Compound g (L) Compound g (M) Compound 8 Compound 8 was synthesized by using Compound L instead of PΠ38 and Compound M instead of Compound A in Preparation Example 1 above.

 As a result of APCI negative MS analysis, the molecular weight 853 of Compound 7 was confirmed.

Compound H (N) Compound g (O) Compound 9 Compound 0 was synthesized by using Compound N instead of PY138 in Preparation Example 1 above. Then, the compound (0) 2.231 (3.68 glu01) and 0.814 g (1-thiophenol) (7.36 g K2C032.03 14.72 g01) were added to 500 ml 1-neck RBF and stirred at 60 ^° C for 24 hours . The solution was cooled to room temperature,

Filtered. The solvent was removed under reduced pressure and the residue was purified by column to obtain Compound 9. As a result of APCI negative MS analysis, the molecular weight 735 of Compound 9 was confirmed.

 Compound 10 was synthesized by using cyclopentyl thiol instead of thiophenol in Synthesis Example 9 to prepare Compound 10. As a result of APCI negat ive MS analysis, the molecular weight 722 of Compound 10 was confirmed.

 Compound 11 Compound 11 Compound 11 was synthesized by using Compound 9 in place of thiophenol in Synthesis Example 9. As a result of APCI negat ive MS analysis, the molecular weight 749 of Compound 11 was confirmed. Comparative Manufacturing Example

Generally, Pigment Yellow 138 (BASF) used as a coloring material in the photosensitive resin composition was prepared.

PY138

Experiment 1: Solubility evaluation

 The compounds according to Preparation Examples 1 to 11 and Comparative Preparation Examples were prepared and their solubility in 100 g of dimethylformamide (DMF) was measured. The results are shown in Table 1 below. Concretely, when the solubility is 1% or more, it is 0, and when the solubility is less than 1%, it is indicated by X.

[Table 11

Example 1

5.554 g of the compound 1 synthesized according to Preparation Example 1, a copolymer of benzyl methacrylate and methacrylic acid (having a molar ratio of 70:30, an acid value of 113 KOH mg / g as a binder resin, a weight average molecular weight of 20,000 10.376 g of a solvent PGMEA), 2.018 g of 1-369 (BASF) as a photoinitiator, 12.443 g of a DPHA (Japanese explosive) as a photopolymerizable compound, 0.5 g of a solvent 68.593 g of PGMEA (polypropylene glycol monomethyl ether acetate) and 1.016 g of DIC F-475 as an additive were mixed to prepare a photosensitive resin composition. Example 2 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 2 synthesized according to Preparation Example 2 was used. Example 3

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 3 synthesized in accordance with Preparation Example 3 was used. Example 4

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 4 synthesized in accordance with the preparation example 4 was used. Example 5

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 5 synthesized in accordance with Preparation Example 5 was used. Example 6

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 6 synthesized in accordance with Preparation Example 6 was used. Example 7

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 7 synthesized in accordance with Preparation Example 7 was used. Example 8

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 8 synthesized in accordance with the preparation of Example 8 was used. Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 9 synthesized in accordance with the ninth preparation was used. Example 10

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 10 synthesized according to Preparation Example 10 was used. Example 11

 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 11 synthesized according to Preparation Example 11 was used. Comparative Example 1

 A photosensitive resin composition was prepared in the same manner as in Example 1, except that the above-prepared compound was used. Board Fabrication

The photosensitive resin compositions according to Examples 1 to 11 and Comparative Example 1 were used for the substrate production, respectively. Specifically, the photosensitive resin compositions according to the Examples and Comparative Examples were spin-coated on glass (5 x 5 cm) and pre-baked at 100 ^° C for 100 seconds to form a film.

The distance between the substrate on which the film was formed and the photo mask was set to 250 mu m, and an exposure dose of 40 mJ / cm &lt; ² &gt; was irradiated onto the entire substrate using an exposure machine. Then, the exposed substrate was developed in a developer (K0H, 0.05%) for 60 seconds and post baked at 230 ^° C for 20 minutes to prepare a substrate. Experiment 2: Evaluation of heat resistance

The substrate prepared according to the above-described substrate-aiding method was used to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm using a spectroscope (MCPD-Otsuka). Also, the prebake substrate was further postbaked at 230 ^° C for 20 minutes, and the transmittance spectrum was obtained in the same equipment and measurement range. The color change (hereinafter referred to as A Eab) was calculated using the obtained transmittance spectrum and the C light source backlight using the obtained value E (L *, a *, b *) and shown in Table 2 below. Specifically, the equation for calculating the AEab is as follows.

 AE (L *, a *, b *) = {(AL *) 2 + (ᅀ a *) 2 + (ᅀ b *) 2} l / 2 The fact that the ΔE value is small indicates that the color heat resistance is excellent , And when it has a value of AEab <3 in general, it can be said that it is a coloring material excellent in heat resistance.

[Table 2]

In Table 2, it is confirmed that the colorant compound of Comparative Example 1 is a commercial material whose color change (AEab) is as small as 0.29. In addition, the respective coloring agent compounds applied to Examples 1 to 11 were also excellent in color heat resistance so that the color change (AEab) was smaller than 3 and could reach a similar level to that of the coloring agent compound of Comparative Example 1, It is confirmed that it can be used as a pigment. Experiment 3: Contrast evaluation

 The photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 were prepared by coinciding with the constituent components and composition ratios (unit: g) shown in Table 3 below. Using the photosensitive resin composition thus prepared, a substrate was prepared according to the above-described substrate manufacturing method.

Using the contrast meter (Tsubosaka), the thus prepared substrate was measured for brightness parallel to and orthogonal to the polarizing plate on the top and bottom of the substrate, and the contrast ratio was calculated by the following equation. Contrast ratio (CR) = Brightness when the polarizer is parallel to the top and bottom of the substrate / Brightness when the top and bottom polarizers of the substrate are orthogonal Number

 [^ Cover 3] Examples in the Examples EXAMPLES Examples EXAMPLES Examples EXAMPLES Examples EXAMPLES Examples EXAMPLES COMPARATIVE EXAMPLES

12 13 14 15 16 17 18 19 20 21 22

G58 3.650 .372! .774! .660 I.660 .660; .660 3.660 3.660 3.660 .660 3.06

Y138 0.485 0.574 0.50 0.621 0.621 0.621 0.621 0.621 0.621 0.621 0.621 2.04 Compound

 0.965

 1 compound

 1.154 Compound

 0.826 HY

 0.819

 4 compound

 0.819 Compound

 0.819

 6

compound

 0.819 Compound

 0.819

 8 compound

 0.819

 9

Unity-

0.819

 10 Compound

 0.819

17.84 17.84 17.84 17.84 17.84 17.84 17.84 17.84 17.84 17.84 17.84 17.84 109 109 109 109 109 109 109 109 109 109 109 109 Optical initiation

 1.19 1.19 1.19 1.19 1.19 1.19 1.19 1.19 1.19 1.19 1.19 1.19

 0.003 0.003 0.003 0.003 0.003 0.003 0.003 0.003 0.003 0.003 0.003 Additives

91 91 91 91 91 91 91 91 91 91 91 91 Light curing 5.865 5.865; .865 5.865 5.865 5.865; 865 5.865 5.865 .865 .865 .865 compound

 Solvent 70 70 70 70 70 70 70 70 70 70 70 70 Total content 100 100 100 100 100 100 100 100 100 100 100 100 Copolymer of benzyl methacrylate metachloric acid (molar ratio 70:30, acid value (DPC) was used as an additive, and a photo-initiator was used as a photo-initiator. The results are shown in Table 1 below. F-475 as a photopolymerizable compound, DPHA (Japanese explosive) as a photopolymerizable compound, PGMEA (polypropylene glycol monomethyl ether acetate) as a solvent,

The contrast ratios of the substrates made of the photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 are shown in Table 4 below.

[Table 4]

Referring to the results shown in Table 4, the substrate using the photosensitive resin composition according to Examples 12 to 22 of the present invention is a substrate using a photosensitive resin composition containing a pigment (PY 138) having a low solubility in an organic solvent 2) Contrast ratio was improved by reducing light scattering.

Claims

 Claims:  [Claim 1]  A colorant compound represented by the following formula (1):  [Chemical Formula 1]

 In Formula 1,  R 1 to R 4 each represent a hydrogen atom, a halogen atom, an aliphatic group having 1 to 10 carbon atoms, an N-alkylene-piperidine dione or an N-alkylene-piperidine dione having at least one aromatic ring having 6 to 20 carbon atoms bonded thereto, A pyrrolidinedione; R &lt; ₆ &gt; Each of R ₇ to R ₁₀ is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms group) or an alkoxy group having 1 to 30 carbon atoms; (2)

 In the above Formulas 2 and 3, Rn to R ₂₀ are each hydrogen, halogen, C 1 -C 10 aliphatic group, a cyclic or straight-chain alkylthio group having 1 to 30 (alkyl thio group), an arylthio group having a carbon number of 1 to 30 (aryl thio group of ) Or an alkoxy group having 1 to 30 carbon atoms; At least one of R ₇ to _O is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 30 carbon atoms .  [Claim 2]  The method according to claim 1, R ₂ , R 4 and 1 ¾ in the above formula (1) are each hydrogen or halogen;  The colorant compound represented by the general formula (4) or the functional group represented by the following formula (5)

[Chemical Formula 5]

 In the above formulas (4) and (5) ¾i, R ₂₂ and ₃ each independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted hydroxyalkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms; A substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms; Wherein n, m, and n ₂ is an integer, 0 <n≤4, 0 <m <3, 0≤n 2 <3.  [Claim 3]  The method according to claim 1, At least one of R ₇ to R ₁₀ is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms or an aryl thio group having 1 to 30 carbon atoms, Wherein each of R _u to R ₂₀ is hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms.  [Claim 4]  In Item 1, R ₇ to _O each represent hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, At least one of Ru to ₄ , or at least one of R ₁₅ to R ₂₀ is a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms or an aryl thio group having 1 to 30 carbon atoms ).  [Claim 5] The method according to claim 1, Wherein at least one of R ₇ to R ₂₀ is a cyclic or straight-chain alkyl thio group having 3 to 6 carbon atoms.  [Claim 6]  The method according to claim 1,  Wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by Chemical Formulas 6 to 47:

[Chemical Formula 8]

48

[Chemical Formula 29]

(34)

(43)

[Chemical Formula 45]

7.  A coloring composition comprising the colorant compound of any one of claims 1-6.  8.  8. The method of claim 7,  Wherein the coloring composition further comprises at least one of a dye (Dye) and a pigment (Pigment).  [Claim 9]  9. The method of claim 8,  Wherein the dye (Dye) and the pigment (Pigment) each contain at least one compound exhibiting any one of hues selected from among yellow, red and green.  Claim 10  10. The method of claim 9,  The yellow compound may be a metal-complex compound, an azo compound, a quinophthalone compound, an i-soindolin compound, and a Styryl compound. Wherein the coloring composition comprises at least one compound selected from the group consisting of a colorant and a colorant.  [Claim 11]  10. The method of claim 9,  The red coloring compound may be a metal-complex compound, an azo compound, a xanthene compound, a diketopyrrolopyrrole compound, anthraquinone (311 (1 And at least one compound selected from the group consisting of perylene-based compounds.  Claim 12  10. The method of claim 9, Compounds representative of the green, the metal-composite (metal-complex) series compound, a triarylmethane (tri arylmethane) based compounds, anthraquinone (1; 1 ^ 3 ⁽¹ ^ 1101) is selected from the group comprising a series compound A coloring composition comprising at least one compound. [13]  10. The method of claim 9,  Wherein the pigment is selected from the group consisting of yellow pigments comprising PY129, PY138, PY139, PY150, and PY185; A red pigment group including PR 48, PR 48: 1, PR 48: 2, PR 48: 3, PR 48: 4, PR 177, PR 179, PR 207 PR 254, PR 255, PR 264 and PR 269; And green pigment groups including PG 7, PG 36, PG 58, and PG 59; &Lt; / RTI &gt;  14.  8. The method of claim 7,  A binder resin, a polyfunctional monomer, a photoinitiator and a solvent.  15.  A color filter comprising the coloring composition of claim 7.  Claim 16  A display device comprising the color filter of claim 15.