TWI716521B - A colorant compound, and a colorant material comprising the same - Google Patents

Abstract

A disclosure of the present invention includes novel colorant compounds based on triarylmethane structure, methods for preparing the same, and colorant materials comprising the same.

Description

Coloring agent compound and coloring agent material containing the compound

This application claims the priority of Korean Patent Application No. 10-2015-0187985 filed on December 28, 2015, and the entire content of the application is incorporated into this application by reference for all purposes. If the disclosures of any patents, patent applications, and publications incorporated into this application by reference conflict with the description of this application to the extent that the terminology is unclear, this description should take precedence.

The invention relates to a novel colorant compound based on a triarylmethane structure and a preparation method thereof. The present invention also relates to a coloring agent composition containing the colorant compound for a filter and a display device equipped with the filter.

Optical filters are widely used in various applications, especially in display devices, such as liquid crystal displays (LCD) and organic light emitting displays (OLED). Due to the rapid development of these display technologies, further improvements in filters are required in this field, especially in terms of brightness, contrast, and color reproducibility. surface.

When forming a filter, a color composition having a colorant material containing a pigment and/or dye is often used. Pigments generally show better stability to heat and/or the environment, but the achievable brightness is often insufficient compared to dyes. On the other hand, when dyes are used as filter colorants, satisfactory filter brightness may be achieved, but its stability, especially light stability and thermal stability, chemical resistance and/or contrast are often insufficient .

In particular, dyes with a triarylmethane structure are considered to be good candidates for this filter application. However, its stability, especially light stability and thermal stability, is not high enough to withstand one or more filter manufacturing processes. In addition, a significant amount of triarylmethane dye is often washed away during the development process (for example, eluted into the development solution) after the light irradiation process in the manufacture of the filter.

The object of the present invention is to provide a compound containing a triarylmethane structure with excellent thermal stability. Another object is to provide a coloring agent compound, especially a blue coloring agent compound, which can withstand the high temperature processing used to make filters in display applications while exhibiting sufficient brightness and/or contrast. Another object of the present invention is to provide a compound containing a triarylmethane structure, which is not significantly washed away during the development process of filter manufacturing. Another object of the present invention is to provide a compound containing a triarylmethane structure with good light resistance.

Indeed, the inventors of the present invention have unexpectedly discovered that the compounds of the present invention exhibit excellent light stability and excellent chemical resistance. It has also been found that the compounds according to the present invention can be advantageously used to form filters with excellent brightness and/or contrast. In addition, it has been found that the compound of the present invention can well withstand the development process after the light irradiation process in the manufacture of the filter.

In the present invention, "alkyl" should be understood to specifically refer to a linear, branched, or cyclic hydrocarbon group usually having from 1 to 20 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl, pentyl, neopentyl, hexyl, cyclopropyl, cyclobutyl Group, cyclopentyl, and cyclohexyl. Some or all of the hydrogen atoms of the alkyl group may or may not be replaced by other groups (such as halogen atoms, amine groups, or hydroxyl groups).

In the present invention, "alkoxy" should be understood as specifically referring to a linear, branched, or cyclic hydrocarbon group (Alk-O-) with a single bond bonded to oxygen, and the hydrocarbon group usually has from 1 to 20 Carbon atoms, preferably from 1 to 8 carbon atoms.

In the present invention, "alkylene" should be understood to specifically mean a divalent group derived from an alkyl group. Representative examples of alkylene groups include -(CH ₂ ) _j -groups (j is from 1 to 20, preferably 1 to 10), such as methylene (-CH ₂ -), ethylene (- CH ₂ -CH ₂ -) and propylene (-CH ₂ -CH ₂ -CH ₂ -).

In the present invention, "aryl" should be understood to specifically refer to any functional group or substituent derived from an aromatic ring. Specifically, the aryl group may have 6 to 20 carbon atoms (preferably 6 to 12, because it is easy to form Synthesis below), in which some or all of the hydrogen atoms of the aryl group may or may not be replaced by other groups, especially halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, thioalkoxy groups, and heterocyclic groups. , Amino or hydroxyl substitution. The aryl groups are preferably optionally substituted phenyl, naphthyl, anthryl and phenanthryl.

In the present invention, "arylene group" should be understood to specifically mean a divalent group derived from an aryl group. A representative example of the arylene group is phenylene (-C ₆ H ₄ -).

In the present invention, "heterocyclic ring" should be understood to specifically mean a cyclic compound having at least one heteroatom as a member of one or more rings. Common heteroatoms on the ring include sulfur, oxygen, and nitrogen. The heterocycles may be either saturated or unsaturated, aromatic or non-aromatic, and may be three-membered, four-membered, five-membered, six-membered, or seven-membered. These heterocyclic rings may be further fused with one or more other ring systems. Examples of such heterocyclic rings include pyrrolidine, oxolane (oxolane), thiolane (thiolane), pyrrole, furan, thiophene, piperidine, ethylene oxide, sulfide cyclopentane (thiane), pyridine, piperan , Pyrazole, imidazole and thiopyran, and their derivatives. These heterocycles can be further substituted with other groups, such as alkyl, alkoxy, aryl, thioalkoxy, amino or aryloxy as defined above.

In the present invention, "halo" should be understood to specifically mean that at least one hydrogen atom of the following chemical group has been replaced by a halogen atom, and the halogen atom is preferably selected from fluorine and chlorine, and more preferably fluorine. If all hydrogen atoms have been replaced by halogen atoms, the halogenated chemical group is fully halogenated. For example, "haloalkyl" includes (per)fluoroalkyl, such as (per)fluoromethyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary-butyl or tertiary- Butyl; and for example -CF ₃ , -C ₂ F ₅ , heptafluoroisopropyl (-CF(CF ₃ ) ₂ ), hexafluoroisopropyl (-CH(CF ₃ ) ₂ ) or -CF ₂ (CF ₂ ) ₄ CF ₃ .

In the present invention, "millbase composition" should be understood to specifically refer to an intermediate composition that contains at least a part of the components to be included in the final composition for forming the filter. The final composition used to form the filter can be formulated by combining the color paste composition with other components. In the present invention, the color paste composition generally contains at least a coloring agent component to be included in the final composition for forming the optical filter.

One aspect of the present invention relates to compounds having the following formula (I):

In the present invention, X is independently an oxygen atom, -NH-, or a sulfur atom. In particular, X is preferably a sulfur atom.

In the present invention, R11 and R12 are each independently selected from the group consisting of a hydrogen atom, an alkyl group that may be substituted, an aryl group that may be substituted, and at least one unsaturated carbon-carbon double bond ( C=C) and does not include ester groups (OC(=O)-) groups. These alkyl and aryl groups can Replaced by other groups. Preferably, the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. These alkyl groups may be substituted by one or more halogen atoms (especially by fluorine atoms), or by amine groups. These aryl groups can be optionally fluorinated by one or more halogen atoms (such as fluorine atoms), optionally fluorinated alkyl groups having 1 to 4 carbon atoms, or optionally fluorinated alkyl groups having 1 to 4 carbon atoms. Oxy and hydroxy substitution. The groups containing at least one unsaturated carbon-carbon double bond (C=C) and excluding ester groups preferably have the following formula: -R13-R14 (II)

In the present invention, R14 is a group containing at least one unsaturated carbon-carbon double bond (C=C), especially vinyl (-CH=CH ₂ ) and -C(-ALK)=CH ₂ (wherein ALK is selected from alkyl groups, especially methyl groups), and R13 is a linking group that links R14 to the substituted amine group in the compound. R13 may be a linking group based on an alkyl group or an aryl group. One or more of the heteroatom groups (such as O, S, NH, and N(CH ₃ )) can be inserted between the CH ₂ -CH ₂ bond. The linking groups based on alkyl or aryl groups can be selected from the group consisting of: alkylene, halogenated alkylene, arylene, halogenated arylene, heteroatom, heterocyclic group , Halogenated heterocyclic groups, and any combination thereof. Exemplary types that may be a combination of R13 in the present invention include: -alkylene-arylene-, -alkylene-arylene-alkylene-, and -arylene-alkylene-alkylene Aryl-.

Specific examples of R13 include -CH ₂ -, -C ₂ H ₄ -, -C ₃ H ₆ -, -C ₄ H ₈ -, -C ₅ H ₁₀ -, -CH ₂ -O-, -C ₂ H ₄ O-, -C ₃ H ₆ O-, -C ₂ H ₄ NH-, -C ₃ H ₆ NH-, -C ₆ H ₄ -, and -C ₁₀ H ₆ -, but the present invention is not limited thereto.

Specific examples of formula](II)] include, but are not limited to:

(Wherein n is an integer of 1 or greater, preferably 1 to 18).

In the present invention, the groups containing at least one unsaturated carbon-carbon double bond (C=C) and not containing an ester group do not contain at least a (meth)acrylate group. The (meth)acrylate groups often react with developing solutions (such as KOH solutions), leading to hydrolysis of the (meth)acrylate structure, and therefore can be easily washed away during the development process. In addition, the thermal stability of the compound containing the (meth)acrylate groups is not as good as the one incorporated in the compound of the present invention contains at least one unsaturated carbon-carbon double bond (C=C) and does not include The ester group has good thermal stability.

In the present invention, R21 is independently selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group. These alkyl and aryl groups may be substituted by other groups. Preferably, the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. These alkyl groups may be substituted by one or more halogen atoms (especially by fluorine atoms), or by amine groups. These aryl groups can be optionally fluorinated by one or more halogen atoms (such as fluorine atoms), optionally fluorinated alkyl groups having 1 to 4 carbon atoms, or optionally fluorinated alkyl groups having 1 to 4 carbon atoms. Oxy and hydroxy substitution. Preferably, R21 is independently selected from aryl groups substituted with alkyl or halogen atoms. Specific examples of R21 include halogenated benzene (such as fluorinated benzene and chlorinated benzene), alkyl-substituted benzene, and alkoxy-substituted benzene, but the present invention is not limited thereto.

In the present invention, R31, R32, R33, R34, R35, R36, R37, and R38 are each independently selected from the group consisting of hydrogen atom, halogen atom, alkyl group, alkoxy group, cyano group, Nitro, sulfonyl, and hydroxyl. These alkyl groups and alkoxy groups may be substituted by other groups. R34 and R35 can be combined to form -O-, -NH-, -S-, or -SO ² -. It is preferable that R31 to R38 are hydrogen atoms.

In the present invention, R41, R42, R43, and R44 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and those containing at least one unsaturated carbon-carbon double bond (C =C) and does not include ester groups. These alkyl and aryl groups may be substituted by other groups. Examples thereof include optionally substituted alkyl groups having 1 to 10 carbon atoms, such as ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, pentyl, hexyl, 2-ethyl Hexyl, 2-methoxyethyl, 2-ethoxyethyl, 2-cyanoethyl, and 2,2,2-trifluoroethyl, but the present invention is not limited thereto. Fluorine-containing groups, especially alkyl or aryl groups substituted with at least one fluorine atom, can be used in the present invention. R41 and R42, or R43 and R44 may be combined together to form a ring structure. This ring structure can contain one or more heteroatoms such as nitrogen, sulfur and oxygen. Examples of the ring include the following structures, but the present invention is not limited to this:

In one embodiment of the present invention, R41 to R44 are ethyl groups. In the present invention, at least one of R41 and R42 and at least one of R43 and R44 may be selected from aryl groups that may be substituted, respectively. Specific examples of such aryl groups include phenyl groups which may be substituted with other groups. Preferably, any one of R41 and R42 is selected from a phenyl group that may be substituted, the remaining one is selected from an alkyl group, and any one of R43 and R44 is selected from a phenyl group that may be substituted, and the remaining one is selected Self-alkyl.

In formula](I)], at least one of R41, R42, R43, R44, R11, and R12 is selected from the group consisting of at least one unsaturated carbon-carbon double bond (C=C) and does not include an ester group The group.

Preferably, any one of R11 and R12 is selected from the group containing at least one unsaturated carbon-carbon double bond (C=C) and does not include an ester group, and the remaining one is selected from alkyl groups which may be substituted. Group or aryl group which may be substituted. Specific examples of R11 or R12 as the remaining one include alkyl (especially ethyl and propyl), halogenated benzene (such as fluorinated benzene and chlorinated benzene), alkane Group-substituted benzene and alkoxy-substituted benzene, but the present invention is not limited thereto.

In the present invention, "a" represents the valence of the relative anion "An", and as such, is an integer of 1 or more. "A" may be an integer of 1. "A" is preferably an integer of 2 or greater, more preferably 2 or 3, and most preferably 2.

In the present invention, "m" represents the number of cationic moieties, and because of this, it is an integer of 1 or more. Between these "m" and "a", the following equation 1 is generally satisfied: m=a (Equation 1).

In the present invention, "An" represents any relative anion. The type of the relative anion is not particularly limited in the present invention, and may be an organic anion, or an inorganic anion. For examples of such relative anions, you can refer to Japanese Patent Application Publication No. JP 2014-108975 A, the disclosure of which is incorporated herein by reference in its entirety. In the present invention, An ^{a- is} preferably selected from the group consisting of halide ion, borate anion, carboxylate anion, sulfate anion, sulfonate anion, sulfonylimide anion, phosphate anion And any combination thereof. Particularly preferred in the present invention are the anionic compounds containing at least one sulfonate group, especially those containing two or more sulfonate groups. In particular, sulfoximine anions such as bis(trifluoromethane)sulfonamide anions can be used in the present invention. In a specific embodiment of the present invention, the relative anion (An) may comprise anionic dye or pigment compounds, and these compounds comprise at least one anionic functional group (such as carboxylate group, sulfate group, phosphate group, and sulfonate group) ). Examples of dyes and pigments can be found in PCT International Patent Application Publication No. WO 2012/144521 A1 and Japanese Patent Application Publication No. JP 2014-108975 A. Without wishing to be bound by any specific theory, by selecting an anionic dye or pigment compound as the relative anion (An), the thermal stability of the compound of the present invention is believed to be able to be further improved (at least partly due to an increase in its molecular weight).

Another aspect of the invention relates to methods of preparing the compounds of the invention. Such methods include reacting a compound of formula (III) with a compound of formula (IV):

In the formulas (III) and (IV), X, R11, R12, R21, R31 to R38, and R41 to R44 each have the same meaning as defined above. If necessary, a desired relative anion can be introduced.

For additional details of the method of preparing the compound, the following examples can be referred to.

The compounds of the present invention are advantageously used as blue colorants, where they can optionally be used in combination with at least one additional dye or pigment. Therefore, another aspect of the present invention provides a colorant material, the colorant material Contains a compound according to the invention, and optionally at least another dye or pigment. Examples of dyes and pigments can be found in PCT International Patent Application Publication No. WO 2012/144521 A1 and Japanese Patent Application Publication No. JP 2014-108975 A, respectively, which are incorporated herein by reference in their entireties. In particular, the compound of the present invention can be used as a colorant material in combination with blue pigments (such as ε-type copper phthalocyanine particles) or purple pigments (such as pigment violet (PV)-23), and the pigment may optionally contain at least one Sulfonate group.

The compound of the present invention can be suitably used for the formation of an optical filter. Therefore, still another aspect of the present invention relates to a composition for forming an optical filter, the composition comprising the compound or colorant material according to the present invention. The composition can optionally contain at least one component selected from the group consisting of: pigments, dyes, binders, dispersing aids or dispersants, polymerizable monomers, solvents, inhibitors, polymerization initiators, And any combination of them.

Further details of the above components, including pigments, dyes, binders, dispersing aids/dispersants, polymerizable monomers, solvents, inhibitors, and initiators, can be found, for example, in WO 2012/144521, JP 2014-108975 A, And found in the disclosure of PCT International Patent Application Publication No. WO 2013/050431, which disclosure is incorporated herein by reference in its entirety.

In the present invention, the composition for forming the filter may be a color paste composition for the filter. The colorant composition preferably includes: (A) a colorant material; (B) a solvent; and (C) a binder, wherein the colorant material (A) contains the compound of the present invention or the colorant material of the present invention material.

The present invention also relates to a filter comprising the compound or colorant material of the present invention. Such filters can be prepared by photolithography, especially by the following steps: the colorant composition according to the present invention is combined with other additional components (such as photoresist (PR) materials) to form The composition for forming the filter is applied to the substrate, dried, irradiated with light, and developed with a developing solution. During this light irradiation treatment, the unsaturated carbon-carbon double bond (C=C) in the compound of the present invention may polymerize and thus form a polymer material containing repeating units derived from the compound of the present invention. Therefore, yet another aspect of the present invention relates to a polymer material comprising at least one repeating unit derived from the compound of the present invention. Such polymer materials can be more firmly fixed on the substrate, and therefore are not easily washed off during the development process using a developing solution (for example, a KOH-based solution). These filters can be suitable for preparing display devices, such as liquid crystal display devices, light-emitting display devices, or solid-state image sensing devices, such as charge coupled devices (CCD) and the like.

The present invention therefore also relates to the use of the compound of the present invention as a colorant (preferably as a blue colorant), and to the use of the compound or colorant material of the present invention for the preparation of filters (and in particular for forming filters) The purpose of the blue part).

Yet another aspect of the present invention relates to compounds having the following formula (III):

In formula (III), X, R11, R12 and R21 each have the same meaning as defined above, and at least one of R11 and R12 is selected from those containing at least one unsaturated carbon-carbon double bond (C=C ) And does not include ester groups.

The following examples are intended to describe the invention in more detail without intending to limit it.

Instance Example 1-1: Preparation of Compound 1

KSCN (20 g, 338.35 mmol) was dissolved in 250 ml of acetone, and the temperature was cooled to 0°C. Benzyl chloride (37.3ml, 321.43mmol) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and then it was cooled to 0°C. Isopropylamine (20 g, 338.35 mmol) was added dropwise, and then, it was stirred at room temperature for 1.5 hours. The mixture was slowly added to the H ₂ O in 1500ml. The produced solid was filtered and washed with 500 ml of H ₂ O to obtain compound 1.

Example 1-2: Preparation of Compound 2

Compound 1 (30 g, 134.94 mmol) was dissolved in 500 ml of 2N NaOH, and refluxing continued for 15 hours. After the reaction was completed, it was filtered and washed with 500 ml of H ₂ O to obtain compound 2.

Example 1-3: Preparation of Compound 3

Compound 2 (9g, 76.14mmol), 2-chloroacetophenone (12.94g, 83.75mmol), and NaHCO ₃ (12.97g, 152.28mmol) were dissolved in 250ml of acetonitrile (ACN) and heated at 60°C The solution was stirred for 2 hours. After the reaction was completed, the temperature was cooled to room temperature. Add 200 ml of DCM and 200 ml of H ₂ O, and perform extraction twice. The organic layer was dried with MgSO ₄ and filtered. Compound 3 was obtained after concentration under reduced pressure.

Example 1-4: Preparation of Compound 4

Compound 3 (10.3 g, 47.17 mmol) was dissolved in 100 ml of DMF, and the temperature was cooled to 0°C. NaH (2.07 g, 52.89 mmol) in portions was added slowly. The mixture was stirred for 30 minutes at room temperature, and the temperature was again cooled to 0°C. Slowly add 4-vinylbenzyl chloride (6.65 ml, 47.17 mmol) dropwise. The mixture was stirred for 2 hours at room temperature. After the reaction was completed, the mixture was cooled to 0°C, and 100 ml of H ₂ O was slowly added dropwise to quench the reaction. Add 300 ml of EA and 300 ml of H ₂ O and perform extraction twice. The organic layer was washed three times with 300 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=20:1) to obtain compound 4.

Example 1-5: Preparation of Compound 5

Compound 4 (10.7g, 31.98mmol) and 4,4'-bis(diethylamino)benzophenone (11.41g, 35.18mmol) were dissolved in 250ml of toluene (anhydrous), and POCl ₃ (9ml, 95.94mmol). After raising the temperature to 100°C, it was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. Then the temperature was cooled to 4°C in an ice bath, and 100 ml of IPA was slowly added dropwise for quenching. 200 ml of H ₂ O was added to the mixture, and 300 ml of DCM was added to extract three times. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (DCM:EA:MeOH=5:5:1) to obtain compound 5.

Example 1-6: Preparation of Compound 6

Compound 5 (17.4g, 25.68mmol) and bis(trifluoromethane)sulfonamide lithium salt (11.05g, 38.52mmol) were dissolved in 250ml of MeOH, and stirred at room temperature for 2 hours. The mixture was slowly added dropwise to 500 ml of H ₂ O with stirring. Add 300 ml of DCM and perform extraction. The organic layer was dried with MgSO ₄ and filtered. Compound 6 was obtained after concentration under reduced pressure.

Example 2-1: Preparation of Compound 7

(2.3g，3.98mmol)、以及三級丁醇鉀(13.28g，119.46mmol)溶解於150ml甲苯(無水的)中，並且在100℃下攪拌。在該反應完成之後，將溫度冷卻至室溫。用矽 藻土過濾器過濾該混合物。將過濾的有機物添加至200ml的DCM和200ml的H₂O中以萃取該有機層。將有機層用MgSO₄乾燥並且過濾。在減壓下濃縮之後，使該殘餘物經受SiO₂柱處理(Hex：EA=9：1)以獲得化合物7。 The 4,4'-dichlorobenzophenone (10g, 39.82mmol), N-ethylaniline (12.52ml, 99.55mmol), bis(benzylideneacetone)palladium(0) (2.29g, 3.98) mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl

(2.3g, 3.98mmol) and potassium tertiary butoxide (13.28g, 119.46mmol) were dissolved in 150ml of toluene (anhydrous) and stirred at 100°C. After the reaction was completed, the temperature was cooled to room temperature. The mixture was filtered through a Celite filter. The filtered organics were added to 200 ml of DCM and 200 ml of H ₂ O to extract the organic layer. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=9:1) to obtain compound 7.

Example 2-2: Preparation of Compound 8

Compound 4 (3.29 g, 11.17 mmol) and compound 7 (4.7 g, 11.17 mmol) were dissolved in 250 ml of toluene (anhydrous), and POCl ₃ (3.12 ml, 33.51 mmol) was added. After raising the temperature to 100°C, it was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. The temperature was then cooled to 4°C in an ice bath, and 10 ml of IPA was slowly added dropwise for quenching. 50 ml of H ₂ O was added to the mixture, and 50 ml of DCM was added to extract three times. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (DCM:EA:MeOH=5:5:1) to obtain compound 8.

Example 2-3: Preparation of Compound 9

Compound 8 (2.3 g, 3.13 mmol) and lithium bis(trifluoromethane)sulfonamide salt (1.35 g, 4.7 mmol) were dissolved in 30 ml of MeOH, and stirred at room temperature for 2 hours. The mixture was slowly added dropwise to 200 ml of H ₂ O with stirring. Filter the resulting solids. The filtered solid was dissolved in 50ml of DCM, and extracted with 50ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. Compound 9 was obtained after concentration under reduced pressure.

Example 3-1: Preparation of Compound 10

Benzophenone (15g, 59.7mmol), N-ethylaniline (20.25ml, 119.4mmol), Pd(OAc) ₂ (1mol%), ligand (1mol%), and KOtBu (20g, 179.1mmol) ) Was dissolved in 150 ml of toluene (anhydrous), and the mixture was stirred at 110°C for 2 hours. After the reaction was completed, the temperature was cooled to room temperature. It was extracted with 50 ml of H ₂ O and 100 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex: EA=7:1 to 5:1) to obtain compound 10.

Example 3-2: Preparation of Compound 11

KSCN (60 g, 615.95 mmol) was dissolved in 1000 ml of acetone, and the temperature was cooled to 0°C. Benzyl chloride (65ml, 559.96mmol) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and the temperature was cooled to 0°C again. O-toluidine (69.52 ml, 559.96 mmol) was added dropwise, and the mixture was stirred at room temperature for 1.5 hours. The mixture was slowly added to the H ₂ O in 3000ml. The obtained solid was filtered and washed with 1000 ml of H ₂ O to obtain compound 11.

Example 3-3: Preparation of Compound 12

Compound 11 (151.38 g, 559.96 mmol) was dissolved in 1000 ml of NaOH (4N) and stirred at 90°C for 2 hours. After the reaction was completed, the temperature was cooled to room temperature. Compound 12 was obtained by filtration and washing with 1000 ml of H ₂ O.

Example 3-4: Preparation of Compound 13

Compound 12 (63.3 g, 380.77 mmol), 2-chloroacetophenone (58.86 g, 380.77 mmol) and NaHCO ₃ (79.97 g, 951.92 mmol) were dissolved in 1000 ml of ACN, and the mixture was stirred at 60°C Lasts 2 hours. After the reaction was completed, the temperature was cooled to room temperature. Extraction was performed twice with 500 ml of H ₂ O and 500 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. Compound 13 was obtained after concentration under reduced pressure.

Example 3-5: Preparation of Compound 14

Compound 13 (100 g, 375.43 mmol) was dissolved in 500 ml of DMF and the temperature was cooled to 0°C. Slowly add portions of NaH (60%) (22.52 g, 563.14 mmol). The mixture was stirred at room temperature for 1 hour, and the temperature was cooled to 0°C. Slowly add 4-vinylbenzyl chloride (52.9 ml, 375.43 mmol). The mixture was stirred at room temperature. After the reaction was completed, the temperature of 300 ml of H ₂ O was cooled to 0° C., and the mixture was slowly added to 300 ml of H ₂ O to quench the reaction. Add 300 ml of EA and perform extraction three times. The organic layer was washed three times with 100 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=40:1) to obtain compound 14.

Example 3-6: Preparation of Compound 15

Compound 14 (19.61 g, 51.27 mmol) and compound 10 (intermediate) (20 g, 51.27 mmol) were dissolved in 500 ml of toluene (anhydrous), and POCl ₃ (14.33 ml, 153.81 mmol) was added. The temperature was increased to 100°C and the mixture was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. The temperature was further cooled to 4°C in an ice bath and 100 ml of IPA was slowly added dropwise for quenching. 200 ml of H ₂ O was slowly added to the mixture and extraction was performed three times with 300 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to three SiO ₂ column treatments (first treatment: DCM:MeOH=10:1; second treatment: DCM:EA:MeOH=5:5:1 to 3: 3:1; third treatment: DCM:MeOH=15:1 to 10:1 to 7:1) to obtain compound 15.

Example 3-7: Preparation of compound 16

Compound 15 (17 g, 20.01 mmol) and lithium bis(trifluoromethane)sulfonamide salt (8.61 g, 30.01 mmol) were dissolved in 150 ml of MeOH, and the mixture was stirred at room temperature for 2 hours. 1000 ml of H ₂ O was slowly added dropwise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. The extraction was carried out twice with 200 ml of H ₂ O. 200 ml of H ₂ O was added to the organic layer for washing. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, compound 16 was obtained.

Example 4-1: Preparation of Compound 17

Combine benzophenone (100g, 398.23mmol), o-toluidine (95.7ml, 796.46mmol), Pd(OAc) ₂ (1mol%), ligand (1mol%), and KOtBu (114.8g, 1194.69mmol) Dissolved in 1000 ml of toluene (anhydrous), and the mixture was stirred at 110°C for 2 hours. After the reaction was completed, the temperature was cooled to room temperature. It was extracted with 500 ml of H ₂ O and 500 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=5:1 to 2:1) to obtain compound 17.

Example 4-2: Preparation of Compound 18 (Intermediate)

Compound 17 (80 g, 203.82 mmol) was dissolved in 500 ml of DMF and the temperature was cooled to 0°C. Slowly add portions of NaH (60%) (20.38 g, 509.56 mmol). The mixture was stirred at room temperature for 1 hour, and the temperature was cooled to 0°C again. Slowly add methyl iodide (31.72ml, 509.56mmol). The mixture was stirred at room temperature. After the reaction was completed, the temperature of 300 ml of H ₂ O was cooled to 0° C., and the mixture was slowly added to 300 ml of H ₂ O to quench the reaction. The resulting solid was filtered to obtain compound 18 (intermediate).

Example 4-3: Preparation of Compound 19

KSCN (60 g, 615.95 mmol) was dissolved in 1000 ml of acetone, and the temperature was cooled to 0°C. Benzyl chloride (65ml, 559.96mmol) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and the temperature was cooled to 0°C again. O-toluidine (69.52 ml, 559.96 mmol) was added dropwise, and the mixture was stirred at room temperature for 1.5 hours. The mixture was slowly added to the H ₂ O in 3000ml. The obtained solid was filtered and washed with 1000 ml of H ₂ O to obtain compound 19.

Example 4-4: Preparation of Compound 20

Compound 19 (151.38 g, 559.96 mmol) was dissolved in 1000 ml of NaOH (4N) and stirred at 90°C for 2 hours. After the reaction was completed, the temperature was cooled to room temperature. Compound 20 was obtained by filtration and washing with 1000 ml of H ₂ O.

Example 4-5: Preparation of Compound 21

Compound 20 (63.3g, 380.77mmol), 2-chloroacetophenone (58.86g, 380.77mmol) and NaHCO ₃ (79.97g, 951.92mmol) were dissolved in 1000ml of ACN, and stirred at 60°C for 2 hours . After the reaction was completed, the temperature was cooled to room temperature. 500 ml of DCM and 500 ml of H ₂ O were added, and extraction was performed twice. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, compound 21 was obtained.

Example 4-6: Preparation of Compound 22

Compound 21 (400 g, 375.43 mmol) was dissolved in 500 ml of DMF and the temperature was cooled to 0°C. Slowly add portions of NaH (60%) (22.52 g, 563.14 mmol). The mixture was stirred at room temperature for 1 hour, and the temperature was cooled to 0°C again. Slowly add 4-vinylbenzyl chloride (52.9 ml, 375.43 mmol). The mixture was stirred at room temperature. After the reaction was completed, the temperature of 300 ml of H ₂ O was cooled to 0° C., and the mixture was slowly added to 300 ml of H ₂ O to quench the reaction. Add 300 ml of EA and perform extraction three times. The organic layer was washed three times with 100 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=40:1) to obtain compound 22.

Example 4-7: Preparation of Compound 23

Compound 22 (19.61 g, 51.27 mmol) and compound 18 (intermediate) (20 g, 51.27 mmol) were dissolved in 500 ml of toluene (anhydrous), and POCl ₃ (14.33 ml, 153.81 mmol) was added. The temperature was increased to 100°C and the mixture was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. The temperature was further cooled to 4°C in an ice bath and 100 ml of IPA was slowly added dropwise for quenching. 200 ml of H ₂ O was added slowly and extraction was performed three times with 300 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to three SiO ₂ column treatments (first treatment: DCM:MeOH=10:1; second treatment: DCM:EA:MeOH=5:5:1 to 3: 3:1; third treatment: DCM:MeOH=15:1 to 10:1 to 7:1) to obtain compound 23.

Example 4-8: Preparation of compound 24

Compound 23 (17 g, 20.01 mmol) and lithium bis(trifluoromethane)sulfonamide salt (8.61 g, 30.01 mmol) were dissolved in 150 ml of MeOH, and the mixture was stirred at room temperature for 2 hours. 1000 ml of H ₂ O was slowly added dropwise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. The extraction was carried out twice with 200 ml of H ₂ O. The organic layer was washed with 200 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, compound 24 was obtained.

Example 5-1: Preparation of Compound 25

Combine 4,4'-dichlorobenzophenone (15g, 59.23mmol), 2,6-dimethylaniline (14.7ml, 119.46mmol), Pd(OAc) ₂ (1mol%), ligand (1mol %), and KOtBu (17.2g, 179.19mmol) were dissolved in 200ml of toluene (anhydrous) and stirred at 110°C for 10 hours. After the reaction was completed, the temperature was cooled to room temperature. It was extracted with 500 ml of H ₂ O and 500 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure and recrystallization with DCM and Hex, compound 25 was obtained.

Example 5-2: Preparation of Compound 26 (Intermediate)

Compound 25 (25 g, 59.44 mmol) was dissolved in 200 ml of DMF and the temperature was cooled to 0°C. Slowly add portions of NaH (60%) (5.94 g, 148.61 mmol). The mixture was stirred at room temperature for 1 hour, and the temperature was cooled to 0°C again. Bromoethane (11.1 ml, 148.61 mmol) was added slowly. The mixture was stirred at room temperature. After the reaction was completed, the mixture was cooled to 0°C, and 300 ml of H ₂ O was slowly added to the mixture to quench the reaction. Add 300 ml of EA and perform extraction three times. The organic layer was washed three times with 300 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex: EA=10:1) to obtain compound 26.

Example 5-3: Preparation of Compound 27

KSCN (8.81 g, 90.77 mmol) was dissolved in 100 ml of acetone, and the temperature was cooled to 0°C. Benzyl chloride (9.57 ml, 82.52 mmol) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and the temperature was cooled to 0°C again. 2,6-Dimethylaniline (10.16 ml, 82.52 mmol) was added dropwise, and the mixture was stirred at room temperature for 1.5 hours. 500 ml of H ₂ O was slowly added to the mixture. The obtained solid was filtered and washed with 1000 ml of H ₂ O to obtain compound 27.

Example 5-4: Preparation of Compound 28

Compound 27 (23.46 g, 82.49 mmol) was suspended in 200 ml of NaOH (4N) and the mixture was stirred at 80°C. After the reaction was completed, the temperature was cooled to room temperature. Compound 28 was obtained by filtration and washing with 500 ml of H ₂ O.

Example 5-5: Preparation of Compound 29

Compound 28 (10g, 54.91mmol), 2-chloroacetophenone (8.48g, 54.91mmol) and NaHCO ₃ (11.53g, 137.27mmol) were dissolved in 100ml of ACN, and the mixture was stirred at 60°C for continuous 2 hours. After the reaction was completed, the temperature was cooled to room temperature. Add 200 ml of DCM and 200 ml of H ₂ O, and perform extraction twice. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, compound 29 was obtained.

Example 5-6: Preparation of Compound 30

Compound 29 (4.6 g, 16.4 mmol) was dissolved in 100 ml of DMF and the temperature was cooled to 0°C. Slowly add portions of NaH (60%) (0.72 g, 18.04 mmol). The mixture was stirred at room temperature for 1 hour, and the temperature was cooled to 0°C again. Slowly add 4-vinylbenzyl chloride (2.31 ml, 16.4 mmol). The mixture was stirred at room temperature. After the reaction was completed, the temperature of 100 ml of H ₂ O was cooled to 0° C., and the mixture was slowly added to 100 ml of H ₂ O to quench the reaction. Add 200 ml of EA and perform extraction three times. The organic layer was washed three times with 100 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=40:1) to obtain compound 30.

Example 5-7: Preparation of compound 31

Compound 30 (6 g, 15.05 mmol) and compound 26 (intermediate) (7.17 g, 15.05 mmol) were dissolved in 100 ml of toluene (anhydrous), and POCl ₃ (4.2 ml, 45.15 mmol) was added. The temperature was increased to 100°C and the mixture was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. The temperature was further cooled to 4°C in an ice bath and 10 ml of IPA was slowly added dropwise for quenching. 200 ml of H ₂ O was slowly added to the mixture and extraction was performed three times with 300 ml of DCM. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to three SiO ₂ column treatments (first treatment: DCM:MeOH=10:1; second treatment: DCM:EA:MeOH=5:5:1 to 3: 3:1; third treatment: DCM:MeOH=15:1 to 10:1 to 7:1) to obtain compound 31.

Example 5-8: Preparation of Compound 32

Compound 31 (11 g, 12.33 mmol) and bis(trifluoromethane)sulfonamide lithium salt (10.62 g, 37.01 mmol) were dissolved in 150 ml of MeOH, and the mixture was stirred at room temperature for 2 hours. 1000 ml of H ₂ O was slowly added dropwise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. The extraction was carried out twice with 200 ml of H ₂ O. The organic layer was washed with 200 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, compound 32 was obtained.

Example 6 (comparison): Preparation of compound (A-I-1)

The following compound (A-I-1) was prepared according to Example 1 of Korean Patent Application Publication No. 10-2014-0026284.

Example 7 (comparative): Preparation of compound containing methacrylate group Example 7-1: Preparation of compound 33

2-Hydroxyethyl methacrylate (9.32ml, 76.84mmol) was dissolved in 100ml of ACN, and TEA (32.13ml, 230.52mmol) was added. P-TsCl (21.98 g, 115.26 mmol) was added to 30 ml of ACN, and added to the solution. The mixture was stirred at room temperature for 3 hours. After the reaction was completed, 200 ml of H ₂ O and 200 ml of DCM were added for extraction. The organic layer was washed with 1N HCl. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex: EA=5:1 to 3:1) to obtain compound 33.

Example 7-2: Preparation of Compound 34

NaH (60%) (1.37 g, 34.35 mmol) was dissolved in 50 ml of DMF, and the temperature was cooled to 0°C. Compound 3 (5 g, 22.90 mmol) was added slowly, and stirring was continued for 30 minutes at room temperature. The mixture was cooled to 0°C, and mixture 33 (9.76 g, 34.35 mmol) was slowly added and stirred at room temperature. After the reaction was completed, the mixture was cooled to 0°C, and 100 ml of H ₂ O was slowly added dropwise to quench the reaction. Add 100 ml of EA and perform extraction twice. The organic layer was washed with 100 ml of H ₂ O. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to SiO ₂ column treatment (Hex:EA=18:1) to obtain compound 34.

Example 7-3: Preparation of Compound 35

Compound 34 (1.2g, 3.63mmol) and 4,4'-bis(diethylamino)benzophenone (1.76g, 5.44mmol) were dissolved in 30ml of toluene (anhydrous), and POCl ₃ (1.7ml , 18.15 mmol) and 2.5-di-tertiary butyl hydroquinone (DTBHQ) (80 mg, 0.363 mmol). After raising the temperature to 100°C, it was stirred for 15 hours. After the reaction was completed, the temperature was cooled to room temperature. The temperature was then cooled to 4°C in an ice bath, and 10 ml of IPA was slowly added dropwise for quenching. 100 ml of H ₂ O was slowly added to the mixture, and 100 ml of DCM was added to extract three times. The organic layer was dried with MgSO ₄ and filtered. After concentration under reduced pressure, the residue was subjected to the first SiO ₂ column treatment (DCM:MeOH=10:1) and the second SiO ₂ column treatment (DCM:EA:MeOH=5:5:1 to 3 : 3: 1) to obtain compound 35.

Example 7-4: Preparation of Compound 36

Compound 35 (3.16 g, 4.69 mmol) and bis(trifluoromethane) sulfonamide lithium salt (2.02 g, 7.03 mmol) were dissolved in 50 ml of MeOH and stirred at room temperature for 2 hours. The mixture was slowly added dropwise to 100 ml of H ₂ O with stirring. The produced solid was filtered and dissolved in 50 ml of DCM, and 50 ml of H ₂ O was added to extract twice. The organic layer was added to 50 ml of H ₂ O and washed. The organic layer was dried with MgSO ₄ and filtered. Compound 36 was obtained after concentration under reduced pressure.

Example 8: Preparation of blue colorant composition 1

1.5 g of compound 6 obtained in Example 1, and 13.5 g of ε-type copper phthalocyanine particles kneaded in a mixer, 6.75 g of DISPERBYK-2000 (obtained from BYK CHEMIE), 7.5 g of dipentaerythritol The hexaacrylate and 120.75 g of propylene glycol monomethyl ether acetate (PGMEA) were introduced into a bead mill, and were ground with zirconia beads (size: 0.05-2mm) at 40°C for 6 to 8 hours to The blue colorant paste is obtained. Make the blue colorant paste and photoresist (PR) material (color paste: PR=30wt%: 70wt%) was mixed to prepare the blue colorant composition 1.

Example 9: Preparation of blue colorant composition 2

The blue colorant composition 2 was obtained by repeating Example 8, except that Compound 9 obtained in Example 2 was used instead of Compound 6.

Example 10: Preparation of blue colorant composition 3

The blue colorant composition 3 was obtained by repeating Example 8, except that Compound 16 obtained in Example 3 was used instead of Compound 6.

Example 11: Preparation of blue colorant composition 4

The blue colorant composition 4 was obtained by repeating Example 8, except that Compound 24 obtained in Example 4 was used instead of Compound 6.

Example 12: Preparation of blue colorant composition 5

The blue colorant composition 5 was obtained by repeating Example 8, except that Compound 32 obtained in Example 5 was used instead of Compound 6.

Example 13 (comparative): Preparation of blue colorant composition 6

The blue colorant composition 6 was obtained by repeating Example 5, except that Compound (A-I-1) obtained in Example 6 was used instead of Compound 6.

Example 14 (comparative): Preparation of blue colorant composition 7

The blue colorant composition 7 was obtained by repeating Example 5. Except that the compound containing a methacrylate group (Compound 36) obtained in Example 7 was used instead of Compound 6.

Performance Testing

(1) Preparation of film: The blue colorant composition was coated on a glass substrate (EAGLE-XG fused glass, available from Corning) by spin coating (200-300 rpm, 15 seconds), To form a film with a thickness of approximately 2 microns and pre-baked at 90°C for 90 seconds. Then, the film was exposed to light irradiation (UV irradiation) having an intensity of 40 mJ/cm ² for 2 seconds, and then developed with a KOH solution. Thereafter, the film was subjected to post-baking at 230°C for 20 minutes.

(2) Light resistance evaluation: The film prepared according to the above (1) was further subjected to light irradiation (UV irradiation) with an intensity of 400 W/m ² for 20 hours. Then, spectrometry was performed on the film by using an Otsuka Photal MCPD 3000 colorimeter to obtain the x and y color coordinates (x, y) and brightness (Y). ΔY, Δx, Δy, and ΔE*ab were measured by comparing the corresponding values before and after 20 hours of light irradiation. The results are provided in Table 1.

(3) Chemical resistance evaluation: Regarding stability against organic solvents The properties were evaluated in Examples 8-12 and Comparative Example 13 by using N-methyl-2-pyrrolidone (NMP). The film prepared according to (1) above was further immersed in NMP for 15 minutes. The chemical resistance to NMP was evaluated by △E*ab. The results are provided in Table 2.

(4) Elution test: Observe the color of the film before and after development with KOH solution. After development (rinsing off) with KOH solution, the color of the film prepared from blue colorant compositions 3 and 4 changed from dark blue to light blue, while the color of the film prepared from blue colorant compositions 1 and 2 was dark blue The color does not change significantly or only slightly.

As shown above, the compounds 6, 9, 16, 24, and 32 (corresponding to Examples 8-12) according to the present invention respectively exhibit greatly improved photostability (△E) over the compound (AI-1) *ab) and excellent chemical resistance. In addition, contrary to the fact that significant amounts of compound (A-I-1) and compound 36 were washed away, the compounds 6, 9, 16, 24, and 32 according to the present invention were not significantly washed away during the development process.

Claims (15)

A compound having the following formula (I):

Wherein X is independently an oxygen atom, -NH-, or a sulfur atom; R11 and R12 are each independently selected from the group consisting of: a hydrogen atom, an alkyl group which may be substituted by one or more halogen atoms, An aryl group substituted with one or more halogen atoms, and a group containing at least one unsaturated carbon-carbon double bond (C=C) and excluding an ester group; R21 is independently selected from hydrogen atoms, and may be one or more A group consisting of an alkyl group substituted with a halogen atom or an amino group, and an aryl group substituted with one or more halogen atoms or a hydroxyl group; R31, R32, R33, R34, R35, R36, R37, and R38 are each independently selected Free from the group consisting of: hydrogen atom, halogen atom, alkyl which may be substituted, alkoxy which may be substituted, cyano, nitro, sulfonyl, and hydroxyl, wherein the alkyl and the alkane The oxy group may be substituted with a cyano group, a nitro group, a sulfonyl group or a hydroxyl group; R41, R42, R43, and R44 are each independently selected from the group consisting of: a hydrogen atom, an alkane which may be substituted by at least one fluorine atom Groups, aryl groups that may be substituted by at least one fluorine atom, and groups containing at least one unsaturated carbon-carbon double bond (C=C) and excluding ester groups, wherein R41 and R42, or R43 and R44 may each be combined Together to form a ring structure; the conditions are that at least one of R41, R42, R43, R44, R11, and R12 is selected from those containing at least one unsaturated carbon-carbon double bond (C=C) and not including an ester group Group; An is a relative anion; and m is an integer of 1 or more; and a is an integer of 1 or more; its condition is to satisfy the following equation: m=a (Equation 1). Such as the compound of item 1 in the scope of the patent application, wherein at least one of R11 and R12 contains the groups containing at least one unsaturated carbon-carbon double bond (C=C) and excluding ester groups. For example, the compound of item 1 or 2 of the scope of patent application, wherein the groups containing at least one unsaturated carbon-carbon double bond (C=C) and excluding ester groups meet at least one of the following structures:

Where n is an integer of 1 or greater. Such as the compound of item 1 or 2 in the scope of patent application, wherein at least one of R41 and R42 and at least one of R43 and R44 are respectively selected from aryl groups which may be substituted by at least one fluorine atom. For example, the compound of item 1 or 2 in the scope of patent application, wherein X is a sulfur atom. For example, the compound of item 1 or 2 in the scope of patent application, wherein R21 is an aryl group substituted by one or more halogen atoms or hydroxyl groups. For example, the compound of item 1 or 2 in the scope of patent application, where An ^{a- is} selected from the group consisting of halide ion, borate anion, carboxylate anion, sulfate anion, sulfonate anion, sulfoximine anion , Phosphate anion and any combination thereof. Such as the compound of item 1 or 2 in the scope of patent application, wherein An ^a- is an anionic compound containing at least one sulfonate group. A method for preparing a compound according to any one of items 1 to 8 in the scope of the patent application, the method comprising reacting a compound of formula (III) with a compound of formula (IV):

Wherein X, R11, R12, R21, R31 to R38, and R41 to R44 each have the same meaning as described in item 1 of the scope of the patent application. A polymer material comprising at least one repeating unit derived from any one of the compounds in the scope of the patent application from 1 to 8. A coloring agent material, the coloring agent material contains the compound of any one of the scope of patent application 1 to 8 or the polymer material of the scope of patent application 10, and optionally at least another dye or pigment. A composition for forming a filter, the composition comprising the compound of any one of the scope of the patent application from 1 to 8 or the coloring agent material of the scope of the application 11, and at least one optional Components of the group consisting of: pigments, dyes, binders, dispersing aids or dispersants, polymerizable monomers, solvents, inhibitors, polymerization initiators, and any combination thereof. A color paste composition for an optical filter, the color paste composition comprising: (A) a colorant material; (B) a solvent; and (C) a binder, wherein the colorant material (A) contains as patented The compound of any one of items 1 to 8 or the coloring agent material of item 11 of the scope of patent application. A use of the compound of any one of items 1 to 8 of the scope of patent application or the use of the coloring agent material of item 11 of the scope of patent application is used to prepare a filter of a display device. A compound having the following formula (III):

Wherein X, R11, R12 and R21 each have the same meaning as described in item 1 of the scope of patent application, and at least one of R11 and R12 is selected from those containing at least one unsaturated carbon-carbon double bond (C=C ) And does not include ester groups.