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Title:
A COLORANT COMPOUND, AND A COLORANT MATERIAL COMPRISING THE SAME
Document Type and Number:
WIPO Patent Application WO/2017/114742
Kind Code:
A1
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.

Inventors:
HAN SANGMIN (KR)
CHOI ILJO (KR)
JEONG EUNHA (KR)
LEE SEUNGHWAN (KR)
Application Number:
PCT/EP2016/082338
Publication Date:
July 06, 2017
Filing Date:
December 22, 2016
Export Citation:
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Assignee:
IRIDOS LTD (KR)
SOLVAY (BE)
International Classes:
C09B11/02; C09B69/10
Domestic Patent References:
WO2015115282A12015-08-06
WO2015093501A12015-06-25
Foreign References:
DE2602403A11976-07-29
Other References:
DATABASE WPI Week 201554, Derwent World Patents Index; AN 2015-38065D, XP002767759
Attorney, Agent or Firm:
MROSS, Stefan et al. (FR)
Download PDF:
Claims:
C L A I M S

1. A compound having the formula (I) below:

wherein

X is independently oxygen atom, -NH-, or sulfur atom; each Rl 1 and R12 are independently selected from the group consisting of hydrogen atom, alkyl groups which may be substituted, aryl groups which may be substituted, and groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group;

R21 is independently selected from the group consisting of hydrogen atom, alkyl groups which may be substituted, and aryl groups which may be substituted; each R31, R32, R33, R34, R35, R36, R37, and R38 are independently selected from the group consisting of hydrogen atom, halogen atom, alkyl groups which may be substituted, alkoxy groups which may be substituted, cyano group, nitro group, sulfonyl group, and hydroxyl group; each R41, R42, R43, and R44 are independently selected from the group consisting of hydrogen atom, alkyl groups which may be substituted, aryl groups which may be substituted, and groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group, in which each R41 and R42, or R43 and R44 may be bound together to form a ring structure; provided at least one of R41, R42, R43, R44, Rl 1 and R12 is selected from the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group;

An is a counter- anion; and m is an integer of 1 or more; and a is an integer of 1 or more; provided the following equation is met: m = a (Equation 1) 2. The compound according to claim 1, wherein at least one of Rl 1 and

R12 comprises the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group.

3. The compound according to claim 1 or 2, wherein the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group complies with at least one of the following structures:

wherein n is an integer of 1 or more.

4. The compound according to any one of claims 1 to 3, 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.

5. The compound according to any one of claims 1 to 4, wherein X is sulfur atom.

6. The compound according to any one of claims 1 to 5, wherein R21 is aryl group which may be substituted.

7. The compound according to any one of claims 1 to 6, wherein Ana" is selected from the group consisting of halides, borate anions, carboxylate anions, sulfate anions, sulfonate anions, sulfonimide anions, phosphate anions, and any combination thereof.

8. The compound according to any one of claims 1 to 7, wherein Ana" is an anionic compound comprising at least one sulfonate group.

9. A method for preparing the compound according to any one of claims 1 to 8, comprising reacting the compound of formula (III) and the compound of formula (IV) below: wherein each X, Rl 1, R12, R21, R31 to R38, and R41 to R44 have the same meaning as in claim 1.

10. A polymeric material comprising at least one recurring unit derived from the compound according to any one of claims 1 to 8.

11. A colorant material comprising the compound according to any one of claims 1 to 8 or the polymeric material according to claim 10, and optionally at least another dye or pigment.

12. A composition for forming color filter, comprising the compound according to any one of claims 1 to 8 or the colorant material according to claim 11, and optionally at least one component selected from the group consisting of a pigment, a dye, a binder, a dispersion aid or dispersant, a polymerizable monomer, a solvent, an inhibitor, a polymerization initiator, and any

combination thereof.

13. A millbase composition for color filter, comprising (A) a colorant material; (B) a solvent; and (C) a binder, wherein the colorant material (A) comprises the compound according to any one of claims 1 to 8 or the colorant material according to claim 11.

14. Use of the compound according to any one of claims 1 to 8 or the colorant material according to claim 11 for the preparation of color filter for display device.

15. A compound of formula (III) below:

wherein each X, Rl 1, R12 and R21 have the same meaning as in claim 1, and at least one of Rl 1 and R12 is selected from the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group.

Description:
A colorant compound, and a colorant material comprising the same

This application claims priority to a Korean patent application No. 10- 2015-0187985 filed on December 28, 2015, the whole content of this application being incorporated herein by reference for all purposes. Should the disclosure of any patents, patent applications, and publications which are incorporated herein by reference conflict with the description of the present application to the extent that it may render a term unclear, the present description shall take precedence.

TECHNICAL FIELD

The present invention relates to novel colorant compounds based on triarylmethane structure, and methods for preparing the same. The present invention also concerns colorant compositions for color filter comprising the colorant compound, and display devices equipped with such color filter.

BACKGROUND OF THE INVENTION

Color filters are widely used in various applications, particularly used in display devices, such as liquid crystal display (LCD) and organic light-emitting display (OLED) and the like. Due to rapid progression of the display

technologies, further improvement of the color filter, especially in terms of brightness, contrast ratio, and color reproduciability, is required in the art.

When forming the color filter, a color composition having a colorant material comprising a pigment and/or a dye is often used. Pigment usually shows better stability against heat and/or environment, but an achievable brightness is often insufficient compared with dye. On the other hand, when dye is used as the color filter colorant, satisfactory brightness of the color filter may be attained, but its stability, especially light stability and thermal stability, chemical resistance and/or contrast ratio are often insufficient.

Particularly, a dyestuff having a triarylmethane structure is believed to be a good candidate for the color filter application. However, its stability, especially light stability and thermal stability, is not high enough to endure color filter fabrication process(es). Also, substantial amount of the triarylmethane dyes are often washed off during a development process after photo-irradiation process in color filter fabrication (e.g. elution into a developer solution).

DESCRIPTION OF THE INVENTION The purpose of the present invention is to provide a compound comprising triarylmethane structure with an excellent thermal stability. Another purpose is to provide a colorant compound, especially a blue colorant compound, which endures high-temperature process of color filter fabrication in display application as well as exhibits sufficient brightness and/or contrast ratio. Further purpose of the invention is to provide a compound comprising triarylmethane structure which is not substantially washed off during the development process of color filter fabrication. Still another purpose of the present invention is to provide a compound comprising triarylmethane structure with a good light resistance.

Indeed, it has been surprisingly found by the present inventors that the compounds of the present invention show outstanding light stability and excellent chemical resistance. It has also been found that the compounds according to the present invention can be advantageously used for the formation of color filter having excellent brightness and/or contrast ratio. Further, it has been found that the compound of the present invention can well endure the development process after photo-irradiation process of color filter fabrication.

In the present invention, "alkyl groups" is understood to denote in particular a straight chain, branched chain, or cyclic hydrocarbon groups usually having from 1 to 20 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, iert-butyl, pentyl, neopentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Some or all of the hydrogen atoms of the alkyl group may or may not be substituted with other groups, such as halogen atom, amino groups or hydroxyl groups.

In the present invention, "alkoxy groups" is understood to denote in particular a straight chain, branched chain, or cyclic hydrocarbon group usually having from 1 to 20 carbon atoms, preferably from 1 to 8 carbon atoms, singularly bonded to oxygen (Alk-O-).

In the present invention, "alkylene groups" is understood to denote in particular divalent radicals derived from alkyl group. Representative examples of alkylene groups include -(CH 2 ) j - group (j is from 1 to 20, preferably 1 to 10), such as methylene group (-CH 2 -), ethylene group (-CH 2 -CH 2 -), and propylene group (-CH 2 -CH 2 -CH 2 -).

In the present invention, "aryl groups" is understood to denote in particular any functional group or substituent derived from an aromatic ring. In particular, the aryl groups can have 6 to 20 carbon atoms (preferably 6 to 12 due to its easiness of synthesis at a low cost) in which some or all of the hydrogen atoms of the aryl group may or may not be substituted with other groups, especially halogen atom, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, thioalkoxy groups, heterocycles, amino groups or hydroxyl groups. The aryl groups are preferably optionally substituted phenyl groups, naphthyl groups, anthryl group and phenanthryl group.

In the present invention, "arylene groups" is understood to denote in particular divalent radicals derived from aryl group. Representative example of arylene groups is phenylene group (-C 6 H 4 -).

In the present invention, "heterocycles" is understood to denote in particular a cyclic compound, which has at least one heteroatom as a member of its one or more rings. Frequent heteroatoms within the ring include sulfur, oxygen and nitrogen. The heterocycles can be either saturated or unsaturated, aromatic or non-aromatic, and may be 3-membered, 4-membered, 5-membered, 6-membered or 7-membered ring. The heterocycles can be further fused with other one or more ring systems. Examples of the heterocycles include pyrrolidines, oxolanes, thiolanes, pyrroles, furans, thiophenes, piperidines, oxanes, thianes, pyridines, pyrans, pyrazoles, imidazoles, and thiopyrans, and their derivatives. The heterocycles can further be substituted by other groups, such as alkyl groups, alkoxy groups, aryl groups, thioalkoxy groups, amino groups or aryloxy groups as defined above.

In the present invention, "halogenated" is understood to denote in particular at least one of the hydrogen atoms of the following chemical group has been replaced by a halogen atom, preferably selected from fluorine and chlorine, more preferably fluorine. If all of the hydrogen atoms have been replaced by halogen atoms, the halogenated chemical group is perhalogenated. For instance, "halogenated alkyl groups" include (per)fluorinated alkyl groups such as (per)fluorinated methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or iert-butyl; and for instance -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" is understood to denote in particular an intermediate composition which comprises at least a part of components to be included in a final composition for forming a color filter. The final composition for forming a color filter can be formulated by combining the millbase composition with other components. In the present invention, the millbase composition often comprises at least colorant components to be included in the final composition for forming a color filter. One aspect of the present invention concerns a compound having the formula (I) below:

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

In the present invention, each Rl 1 and R12 are independently selected from the group consisting of hydrogen atom, alkyl groups which may be substituted, aryl groups which may be substituted, and groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group (-0-C(=0)-). The alkyl groups and aryl groups may be substituted with other groups. It is preferred that the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The alkyl groups may be substituted with one or more halogen atoms, in particular with fluorine atom, or with amino group. The aryl groups may be substituted with one or more halogen atoms, such as fluorine atom, optionally fluorinated alkyl groups having 1 to 4 carbon atoms, optionally fluorinated alkoxy groups having 1 to 4 carbon atoms, and hydroxyl group. The groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group preferably have the following formula:

-R13-R14 (II)

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

- alkylene- arylene- ,

-alkylene-arylene-alkylene-, and

-arylene-alkylene-arylene-.

Particular examples of R13 include -CH 2 -, -C 2 H 4 -, -C 3 H 6 -, -C 4 H 8 -, -C 5 H 10 -, - CH 2 -0-, -C 2 H 4 0-, -C 3 H 6 0-, -C 2 H 4 NH-, -C 3 H 6 NH-, -C 6 H 4 -, and -Ci 0 H 6 -, but the present invention is not limited thereto.

Particular examples of the formula (II) include, but not limited to:

(wherein n is an integer of 1 or more, preferably 1 to 18)

In the present invention, the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group at least do not comprise (meth)acrylate groups. The (meth)acrylate groups often react with the developer solution, such as KOH solution, resulting in hydrolysis of the (meth)acrylate structure, and therefore, can be easily washed off during the development process. Also, thermal stability of the compound containing the (meth)acrylate groups is not as good as that is attainable by incorporating the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group in the compound of the present invention.

In the present invention, R21 is independently selected from the group consisting of hydrogen atom, alkyl groups, and aryl groups. The alkyl groups and aryl groups may be substituted with other groups. It is preferred that the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The alkyl groups may be substituted with one or more halogen atoms, in particular with fluorine atom, or with amino group. The aryl groups may be substituted with one or more halogen atoms, such as fluorine atom, optionally fluorinated alkyl groups having 1 to 4 carbon atoms, optionally fluorinated alkoxy groups having 1 to 4 carbon atoms, and hydroxyl group. Preferably, R21 is independently selected from the aryl groups substituted with alkyl group or halogen atom. Particular examples of R21 include halogenated benzenes, such as fluorinated benzenes and chlorinated benzenes, alkyl-substituted benzenes, and alkoxy- substituted benzenes, but the present invention is not limited thereto.

In the present invention, each R31, R32, R33, R34, R35, R36, R37, and R38 is independently selected from the group consisting of hydrogen atom, halogen atom, alkyl groups, alkoxy groups, cyano group, nitro group, sulfonyl group, and hydroxyl group. The alkyl groups and alkoxy groups may be substituted with other groups. R34 and R35 may be bound together to form -0-, -NH-, -S-, or -SO -. It is preferred that R31 to R38 are hydrogen atom.

In the present invention, each R41, R42, R43, and R44 is independently selected from the group consisting of hydrogen atom, alkyl groups, aryl groups, and the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group. The alkyl groups and aryl groups may be substituted with other groups. Examples thereof include optionally substituted alkyl groups having 1 to 10 carbon atoms, such as ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, hexyl group, 2-ethylhexyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, and 2,2,2-trifluoroethyl group, but the present invention is not limited thereto. A fluorine-containing groups, in particular an alkyl group or an aryl group substituted by at least one fluorine atom, may be used in the present invention. Each R41 and R42, or R43 and R44 may be bound together to form a ring structure. Such ring structure may comprise one or more heteroatoms, such as nitrogen, sulfur and oxygen. Examples of the ring comprise the following structure, but the present invention is not limited thereto:

In one embodiment of the present invention, R41 to R44 are ethyl group. In the present invention, at least one of R41 and R42 and at least one of R43 and R44 can be respectively selected from aryl groups which may be substituted.

Particular examples of the aryl groups include benzene groups which may be substituted with other groups. Preferably, either one of R41 and R42 is selected from benzene groups which may be substituted, remaining one being selected from alkyl groups, and either one of R43 and R44 is selected from benzene groups which may be substituted, remaining one being selected from alkyl groups.

In the formula (I), at least one of R41, R42, R43, R44, Rl 1 and R12 is selected from the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group.

Preferably, either one of Rl 1 and R12 is selected from the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group, and remaining one is selected from alkyl groups which may be substituted or aryl groups which may be substituted. Particular examples of the Rl 1 or R12 as the remaining one include alkyl groups, in particular ethyl group and propyl group, halogenated benzenes, such as fluorinated benzenes and chlorinated benzenes, alkyl- substituted benzenes, and alkoxy- substituted benzenes, but the present invention is not limited thereto.

In the present invention, "a" stands for the valency of the counter-anion "An," and thus, is an integer of 1 or more, "a" may be an integer of 1. "a" is preferably an integer of 2 or more, more preferably 2 or 3, most preferably 2.

In the present invention, "m" stands for the number of cationic part, and as such, is an integer of 1 or more. Between the "m" and "a", the following Equation 1 is generally met: m = a (Equation 1)

In the present invention, "An" denotes any counter-anion. Type of the counter-anion is not particularly limited in the present invention, and can be organic anions, or inorganic anions. For the examples of such counter-anion, reference can be made to Japanese patent application publication No. JP 2014- 108975 A, of which disclosure is incorporated herein by reference in its entirety. In the present invention, An a" is preferably selected from the group consisting of halides, borate anions, carboxylate anions, sulfate anions, sulfonate anions, sulfonimide anions, phosphate anions, and any combination thereof. The anionic compounds comprising at least one sulfonate group, especially those comprising two or more sulfonate groups, are particularly preferred in the present invention. In particular, sulfonimide anions, such as bis(trifluoromethane)sulfonamide anion, may be used in the present invention. In a particular embodiment of the present invention, the counter-anion (An) may comprise anionic dye or pigment compounds which comprise at least one anionic functional group, such as carboxylate group, sulfate group, phosphate group, and sulfonate group.

Examples of the dyes and the pigments can be found in PCT international patent application publication No. WO 2012/144521 Al and Japanese patent application publication No. JP 2014-108975 A. Without wishing to be bound by any particular theory, by the selection of the anionic dye or pigment compounds as the counter-anion (An), thermal stability of the compound of the present invention is believed to be able to be further improved at least partially due to the increase of its molecular weight.

Another aspect of the present invention concerns a method of preparing the compound of the present invention. Such a method includes reacting the compound of formula (III) and the compound of formula (IV) below:

In the formulae (III) and (IV), each X, Rl l, R12, R21, R31 to R38, and R41 to R44 has the same meaning as defined in the above. The desired counter- anion may be introduced as necessary.

For further details of the method of preparing the compound, reference can be made to the following Examples.

The compound of the present invention is advantageously used as a blue colorant, of which use can be optionally combined with at least one further dye or pigment. Therefore, further aspect of the present invention provides a colorant material comprising the compound according to the invention, and optionally at least another dye or pigment. Examples of the dyes and of the pigments can be found in PCT international patent application publication No. WO 2012/144521 Al and Japanese patent application publication No. JP 2014- 108975 A, respectively, both 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 a blue pigment, such as ε-type copper phthalocyanine particles or a violet pigment such as pigment violent(PV)-23, the pigment optionally containing at least one sulfonate group.

The compound of the present invention can be suitably used for the formation of color filter. Accordingly, still further aspect of the present invention concerns a composition for forming color filter, comprising the compound or the colorant material according to the invention. The composition may optionally comprise at least one component selected from the group consisting of a pigment, a dye, a binder, a dispersion aid or dispersant, a polymerizable monomer, a solvent, an inhibitor, a polymerization initiator, and any combination thereof.

Further details of the above-mentioned components, including pigment, dye, binder, dispersion aid/dispersant, polymerizable monomer, solvent, inhibitor, and initiator, can be found for instance in the disclosures of WO 2012/144521, JP 2014-108975 A, and PCT international patent application publication No. WO 2013/050431, of which disclosure is incorporated herein by reference in its entirety.

In the present invention, the composition for forming color filter may be a millbase composition for color filter. The millbase composition preferably comprises (A) a colorant material; (B) a solvent; and (C) a binder, wherein the colorant material (A) comprises the compound of the invention or the colorant material of the present invention. The present invention also relates to a color filter comprising the compound or the colorant material of the present invention. Such color filters may be prepared by lithographic methods, especially through the following steps: combining the millbase composition according to the present invention with other additional components, such as photoresist (PR) material, to form a composition for forming color filter, applying the composition for forming color filter on a substrate, drying, light irradiation and developing with developer solution. During the light irradiation process, the unsaturated carbon-carbon double bond (C=C) in the compound of the present invention may polymerize and thus form a polymeric material comprising the recurring unit derived from the compound of the present invention. Thus, still another aspect of the present invention concerns polymeric materials comprising at least one recurring unit derived from the compound of the present invention. Such polymeric materials may be fixed more firmly on the substrate and therefore are not easily washed off during the developing process using developer solution (e.g. solution based on KOH). The color filters are applicable for preparation of display devices, such as a liquid crystal display device, a light-emitting display device, or a solid-state image sensing device such as a charge coupled device (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 of the colorant material of the present invention for preparation of color filters, and in particular for forming the blue portion of color filters.

Still further aspect of the present invention concerns the compound having the formula (III) below :

In the formula (III), each X, Rl 1, R12, and R21 has the same meaning as defined in the above, and at least one of Rl 1 and R12 is selected from the groups comprising at least one unsaturated carbon-carbon double bond (C=C) and which does not include ester group.

The following examples are intended to describe the invention in further detail without the intention to limit it. Example

Example 1-1: Preparation of Compound 1

Compound 1

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

Example 1-2: Preparation of Compound 2

Compound 1 Compound 2

The Compound 1 (30 g, 134.94 mmol) was dissolved in 500 ml of 2N NaOH and refluxed for 15 hours. After completion of the reaction, it was filtered and washed with 500 ml of H 2 0 to obtain the Compound 2.

Example 1-3: Preparation of Compound 3

Compound 2 Compound 3 The Compound 2 (9 g, 76.14 mmol), 2-chloroacetophenone (12.94 g, 83.75 mmol), and NaHC0 3 (12.97 g, 152.28 mmol) were dissolved 250 ml of acetonitrile (ACN), and the solution was stirred for 2 hours at 60 °C. After completion of the reaction, the temperature was cooled down to room

temperature. 200 ml of DCM and 200 ml of H 2 0 were added, and extraction was conducted twice. The organic layer was dried with MgS0 4 , and filtered. The Compound 3 was obtained after the concentration under reduced pressure.

Example 1-4: Preparation of Compound 4

Compound 3

Compound 4 The Compound 3 (10.3 g, 47.17 mmol) was dissolved in 100 ml of DMF, and the temperature was cooled down to 0 °C. NaH (2.07 g, 52.89 mmol), divided by several portions, was slowly added. The mixture was stirred for 30 minutes at room temperature and the temperature was cooled down again to 0 °C. 4-vinylbenzyl chloride (6.65 ml, 47.17 mmol) was slowly added drop-wise. The mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was cooled down to 0 °C, and 100 ml of H 2 0 was slowly added drop-wise to quench the reaction. 300 ml of EA and 300 ml of H 2 0 were added and extraction was conducted twice. The organic layer was washed with 300 ml of H 2 0 for three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=20: l) to obtain the Compound 4.

Example 1-5: Preparation of Compound 5

Compound 5

The Compound 4 (10.7 g, 31.98 mmol), and 4,4'- bis(diethylamino)benzophenone (11.41 g, 35.18 mmol) were dissolved in 250 ml of toluene (anhydride), and POCl 3 (9 ml, 95.94 mmol) was added. After increasing the temperature to 100 °C, it was stirred for 15 hours. After completion of the reaction, the temperature was cooled down to room

temperature. The temperature was then cooled down to 4 °C in ice bath, and 100 ml of IPA was slowly added drop- wise for quenching. 200 ml of H 2 0 was added to the mixture, and 300 ml of DCM was added to extract three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment

(DCM:EA:MeOH=5:5: l) to obtain the Compound 5.

Example 1-6: Preparation of Compound 6

Compound 5 Compound 6 The Compound 5 (17.4 g, 25.68 mmol), and bis(trifluoromethane) sulfonamide lithium salt (11.05 g, 38.52 mmol) were dissolved in 250 ml of MeOH, and stirred for 2 hours at room temperature. The mixture was was slowly added drop-wise to 500 ml of H 2 0 under stirring. 300 ml of DCM was added and extraction was conducted. The organic layer was dried with MgS0 4 and filtered. The Compound 6 was obtained after concentration under reduced pressure.

Example 2-1: Preparation of Compound 7

Compound 7

4,4'-dichlorobenzophenone (10 g, 39.82 mmol), N-ethylaniline (12.52 ml, 99.55 mmol), bis(dibenzylideneacetone)palladium(0) (2.29 g, 3.98 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (2.3 g, 3.98 mmol), and potassium iert-butoxide (13.28 g, 119.46 mmol) were dissolved in 150 ml of toluene (anhydride), and stirred at 100 °C. After completion of the reaction, the temperature was cooled down to room temperature. The mixture was filter with Celite filter. The filtered organics were added to 200 ml of DCM and 200 ml of H 2 0 to extract the organic layer. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=9: 1) to obtain the Compound 7.

Example 2-2: Preparation of Compound 8

Compound 4 Compound 7

Compound 8

The Compound 4 (3.29 g, 11.17 mmol), and the Compound 7 (4.7 g, 11.17 mmol) were dissolved in 250 ml of toluene (anhydride), and POCl 3 (3.12 ml, 33.51 mmol) was added. After increasing the temperature to 100 °C, it was stirred for 15 hours. After completion of the reaction, the temperature was cooled down to room temperature. The temperature was then cooled down to 4 °C in ice bath, and 10 ml of IPA was slowly added drop- wise for quenching. 50 ml of H 2 0 was added to the mixture, and 50 ml of DCM was added to extract three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (DCM:EA:MeOH=5:5: 1) to obtain the Compound 8.

Example 2-3: Preparation of Compound 9

Compound 8 Compound 9

The Compound 8 (2.3 g, 3.13 mmol), and bis(trifluoromethane) sulfonamide lithium salt (1.35 g, 4.7 mmol) were dissolved in 30 ml of MeOH, and stirred for 2 hours at room temperature. The mixture was slowly added drop-wise to 200 ml of H 2 0 under stirring. The produced solid was filtered. The filtered solid was dissolved in 50 ml of DCM, and extracted with 50 ml of H 2 0. The organic layer was dried with MgS0 4 and filtered. The Compound 9 was obtained after concentration under reduced pressure.

Example 3-1: Preparation of Compound 10

Compound 10

Benzophenone (15g, 59.7 mmol), N-ethylaniline (20.25ml, 119.4 mmol), Pd(OAc) 2 (1 mol ), Ligand (1 mol ), and KOtBu (20g, 179.1 mmol) were dissolved in 150 ml of toluene (anhydrous) and the mixture was stirred for 2 hours at 110°C After completion of the reaction, the temperature was cooled down to room temperature. Extraction was conducted with 50 ml of H 2 0 and 100 ml of DCM. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=7: l to 5: 1) to obtain the Compound 10. Example 3-2: Preparation of Compound 11

KSCN (60g, 615.95 mmol) was dissolved in 1000 ml of acetone and the temperature was cooled to 0°C Benzoly chloride (65ml, 559.96 mmol) was added drop-wise. The mixture was stirred for 1.5 hours at room temperature and the temperature was cooled down again to 0°C. o-Toluidine (69.52ml, 559.96 mmol) was added drop-wise and the mixture was stirred for 1.5 hours at room temperature. The mixture was slowly added to 3000 ml of H 2 0. The resulting solid was filtered and washed with 1000 ml of H 2 0 to obtain the Compound 11.

Example 3-3: Preparation of Compound 12

Compound 11 Compound 12

Compound 11 (151.38g, 559.96 mmol) was dissolved in 1000 ml of NaOH (4N) and stirred for 2 hours at 90°C After the completion of reaction, the temperature was cooled down to room temperature. The Compound 12 was obtained by filtration and washing with 1000 ml of H 2 0.

Example 3-4: Preparation of Compound 13

Compound 12 Compound 13

Compound 12 (63.3g, 380.77 mmol), 2-chloroacetophenone (58.86g, 380.77 mmol) and NaHC0 3 (79.97g, 951.92 mmol) were dissolved in 1000 ml of ACN and the mixtures was stirred for 2 hours at 60°C After the completion of reaction, the temperature was cooled down to room temperature. Extraction was conducted twice with 500 ml of H 2 0 and 500 ml of DCM. The organic layer was dried with MgS0 4 and filtered. The Compound 13 was obtained after concentration under reduced pressure.

Example 3-5: Preparation of Compound 14

Compound 13 Compound 14

Compound 13 (lOOg, 375.43 mmol) was dissolved in 500 ml of DMF and the temperature was cooled down to 0°C. NaH (60%) (22.52g, 563.14 mmol), divided by several portions, was slowly added. The mixture was stirred for 1 hour at room temperature and the temperature was cooled down to 0°C. 4- vinylbenzyl chloride (52.9 ml, 375.43 mmol) was slowly added. The mixture was stirred at room temperature. After completion of the reaction, the

temperature of 300 ml of H 2 0 was cooled down to 0°C, and the mixture was slowly added to 300 ml of H 2 0 to quench the reaction. 300 ml of EA was added and extraction was conducted three times. The organic layer was washed with 100 ml of H 2 0 three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=40: l) to obtain the Compound 14.

Example 3-6: Preparation of Compound 15

Compound 10 (Intermediate) Compound 14

Compound 15 Compound 14 (19.61g, 51.27 mmol) and Compound 10 (Intermediate) (20g, 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 completion of reaction, the temperature was cooled down to room temperature. The temperature was further cooled down to 4°C under ice bath and 100 ml of IPA was slowly added drop- wise for quenching. 200 ml of H 2 0 was slowly added to the mixture and extraction was conducted three times with 300 ml of DCM. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to three Si0 2 column treatments (1 st treatment:

DCM:MeOH=10: l; 2 nd treatment: DCM:EA:MeOH=5:5: l to 3:3: 1; 3 rd treatment: DCM:MeOH=15:l to 10:1 to 7: 1) to obtain the Compound 15.

Example 3-7: Preparation of Compound 16

Compound 15

Compound 16 Compound 15 (17g, 20.01 mmol) and bis(trifluoromethane)sulfonamide lithium salt (8.61g, 30.01 mmol) were dissolved in 150 ml of MeOH and the mixture was stirred for 2 hours at room temperature. 1000 ml of H 2 0 was slowly added drop- wise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. Extraction was conducted twice with 200 ml of H 2 0. 200 ml of H 2 0 was added to the organic layer for washing. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the Compound 16 was obtained. Example 4-1: Preparation of Compound 17

Compound 17 Benzophenone (lOOg, 398.23 mmol), o-toluidine (95.7 ml, 796.46 mmol),

Pd(OAc) 2 (1 mol%), Ligand (1 mol%), and KOtBu (114.8g, 1194.69 mmol) were dissolved in 1000 ml of toluene (anhydrous) and the mixture was stirred for 2 hours at 110°C. After completion of the reaction, the temperature was cooled down to room temperature. Extraction was conducted with 500 ml of H 2 0 and 500 ml of DCM. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=5: l to 2: 1) to obtain the Compound 17.

Exam le 4-2: Preparation of Compound 18 (Intermediate)

Compound 17 Compound 18 (Intermediate) Compound 17 (80g, 203.82 mmol) was dissolved in 500 ml of DMF and the temperature was cooled down to 0°C NaH (60%) (20.38g, 509.56 mmol), divided by several portions, was slowly added. The mixture was stirred for 1 hour at room temperature and the temperature was cooled down again to 0°C. Iodomethane (31.72ml, 509.56 mmol) was slowly added. The mixture was stirred at room temperature. After completion of the reaction, the temperature of 300 ml of H 2 0 was cooled down to 0 °C, and the mixture was slowly added to 300 ml of H 2 0 to quench the reaction. The resulting solid was filtered to obtain the Compound 18 (Intermediate).

Example 4-3: Preparation of Compound 19

KSCN (60g, 615.95 mmol) was dissolved in 1000 ml of acetone and the temperature was cooled to 0°C Benzoly chloride (65ml, 559.96 mmol) was added drop-wise. The mixture was stirred for 1.5 hours at room temperature and the temperature was cooled down again to 0°C. o-Toluidine (69.52ml, 559.96 mmol) was added drop-wise and the mixture was stirred for 1.5 hours at room temperature. The mixture was slowly added to 3000 ml of H 2 0. The resulting solid was filtered and washed with 1000 ml of H 2 0 to obtain the Compound 19.

Example 4-4: Preparation of Compound 20

Compound 19 Compound 20

Compound 19 (151.38g, 559.96 mmol) was dissolved in 1000 ml of NaOH (4N) and stirred for 2 hours at 90°C After the completion of reaction, the temperature was cooled down to room temperature. The Compound 20 was obtained by filtration and washing with 1000 ml of H 2 0.

Example 4-5: Preparation of Compound 21

Compound 20 Compound 21

Compound 20 (63.3g, 380.77 mmol), 2-chloroacetophenone (58.86g, 380.77 mmol), and NaHC0 3 (79.97g, 951.92 mmol) were dissolved in 1000 ml of ACN and stirred for 2 hours at 60°C. After the completion of reaction, the temperature was cooled down to room temperature. 500 ml of DCM and 500 ml of H 2 0 were added and extraction was conducted twice. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the Compound 21 was obtained.

Example 4-6: Preparation of Compound 22

Compound 21 Compound 22

Compound 21 (400g, 375.43 mmol) was dissolved in 500 ml of DMF and the temperature was cooled down to 0°C. NaH (60%) (22.52g, 563.14 mmol), divided by several portions, was slowly added. The mixture was stirred for 1 hour at room temperature and the temperature was cooled down again to 0°C. 4- vinylbenzyl chloride (52.9ml, 375.43 mmol) was slowly added. The mixture was stirred at room temperature. After the completion of reaction, the temperature of 300 ml of H 2 0 was cooled down to 0°Q and the mixture was slowly added to 300 ml of H 2 0 to quench the reaction. 300 ml of EA was added and extraction was conducted three times. The organic layer was washed with 100 ml of H 2 0 three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=40: l) to obtain the Compound 22.

Example 4-7: Preparation of Compound 23

Compound 18 (Intermediate) Compound 22

Compound 23

Compound 22 ( 19.61 g, 51.27 mmol) and Compound 18 (Intermediate) (20g, 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 completion of reaction, the temperature was cooled down to room temperature. The temperature was further cooled down to 4°C under ice bath and 100 ml of IPA was slowly added drop- wise for quenching. 200 ml of H 2 0 was slowly added and extraction was conducted three times with 300 ml of DCM. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to three Si0 2 column treatments (1 st treatment: DCM:MeOH=10: l; 2 nd treatment: DCM:EA:MeOH=5:5: l to 3:3:1; 3 rd treatment: DCM:MeOH=15: l to 10: 1 to 7: 1) to obtain the Compound 23. Example 4-8: Preparation of Compound 24

Compound 23 Compound 24

Compound 23 (17g, 20.01 mmol) and bis(trifluoromethane)sulfonamide lithium salt (8.61g, 30.01 mmol) were dissolved in 150 ml of MeOH and the mixture was stirred for 2 hours at room temperature. 1000 ml of H 2 0 was slowly added drop- wise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. Extraction was conducted twice with 200 ml of H 2 0. The organic layer was washed with 200 ml of H 2 0. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the Compound 24 was obtained.

Example 5-1: Preparation of Compound 25

Compound 25

4,4'-dichlorobenzophenone (15g, 59.23 mmol), 2,6-dimethylaniline (14.7ml, 119.46 mmol), Pd(OAc) 2 (1 mol%), Ligand (1 mol%), and KOtBu (17.2g, 179.19 mmol) were dissolved in 200 ml of toluene (anhydrous) and stirred for 10 hours at 110°C After completion of the reaction, the temperature was cooled down to room temperature. Extraction was conducted with 500 ml of H 2 0 and 500 ml of DCM. The organic layer was dried with MgS0 4 and filtered. The Compound 25 was obtained after concentration under reduced pressure and recrystallization with DCM and Hex.

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

Compound 25 Compound 26 (Intermediate)

Compound 25 (25g, 59.44 mmol) was dissolved in 200 ml of DMF and the temperature was cooled down to 0°C. NaH (60%) (5.94g, 148.61 mmol), divided by several portions, was slowly added. The mixture was stirred for 1 hour at room temperature and the temperature was cooled down again to 0°C.

Bromoethane (11.1ml, 148.61 mmol) was slowly added. The mixture was stirred at room temperature. After completion of the reaction, the mixture was cooled down to 0°C, and 300 ml of H 2 0 was slowly added to the mixture to quench the reaction. 300 ml of EA was added and extraction was conducted three times. The organic layer was washed with 300 ml of H 2 0 three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=10: l) to obtain the Compound 26.

Example 5-3: Preparation of Compound 27

Compound 27

KSCN (8.8 lg, 90.77 mmol) was dissolved in 100 ml of acetone and the temperature was cooled to 0°C Benzolychloride (9.57ml, 82.52 mmol) was added drop-wise. The mixture was stirred for 1.5 hours at room temperature and the temperature was cooled down again to 0°C. 2,6-Dimethylaniline (10.16ml, 82.52 mmol) was added drop-wise and the mixture was stirred for 1.5 hours at room temperature. 500 ml of H 2 0 was slowly added to the mixture. The resulting solid was filtered and washed with 1000 ml of H 2 0 to obtain the Compound 27.

Example 5-4: Preparation of Compound 28

Compound 27 Compound 28 Compound 27 (23.46g, 82.49 mmol) was suspended in 200 ml of NaOH

(4N) and the mixture was stirred at 80°C After the completion of reaction, the temperature was cooled down to room temperature. The Compound 28 was obtained by filtration and washing with 500 ml of H 2 0. Example 5-5: Preparation of Compound 29

Compound 28 Compound 29

Compound 28 (lOg, 54.91 mmol), 2-chloroacetophenone (8.48g, 54.91 mmol), and NaHC0 3 (11.53g, 137.27 mmol) were dissolved in 100 ml of ACN and the mixture stirred for 2 hours at 60°C After the completion of reaction, the temperature was cooled down to room temperature. 200 ml of DCM and 200 ml of H 2 0 were added and extraction was conducted twice. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the Compound 29 was obtained. Exam le 5-6: Preparation of Compound 30

Compound 29 Compound 30 Compound 29 (4.6g, 16.4 mmol) was dissolved in 100 ml of DMF and the temperature was cooled down to 0°C. NaH (60%) (0.72g, 18.04 mmol), divided by several portions, was slowly added. The mixture was stirred for 1 hour at room temperature and the temperature was cooled down again to 0°C. 4- vinylbenzyl chloride (2.31ml, 16.4 mmol) was slowly added. The mixture was stirred at room temperature. After the completion of reaction, the temperature of 100 ml of H 2 0 was cooled down to 0°C, and the mixture was slowly added to 100 ml of H 2 0 to quench the reaction. 200 ml of EA was added and extraction was conducted three times. The organic layer was washed with 100 ml of H 2 0 three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=40: l) to obtain the Compound 30. Example 5-7: Preparation of Compound 31

Compound 26 (Intermediate) Compound 30

Compound 31 Compound 30 (6g, 15.05 mmol) and Compound 26 (Intermediate) (7.17g,

15.05 mmol) were dissolved in 100 ml of toluene (anhydrous) and POCl 3 (4.2ml, 45.15 mmol) was added. The temperature was increased to 100°Cand the mixture was stirred for 15 hours. After the completion of reaction, the

temperature was cooled down to room temperature. The temperature was further cooled down to 4°C under ice bath and 10 ml of IPA was slowly added drop-wise for quenching. 200 ml of H 2 0 was slowly added to the mixture and extraction was conducted three times with 300 ml of DCM. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to three Si0 2 column treatments (1 st treatment:

DCM:MeOH=10: l; 2 nd treatment: DCM:EA:MeOH=5:5: l to 3:3: 1; 3 rd treatment: DCM:MeOH=15:l to 10:1 to 7: 1) to obtain the Compound 31.

Example 5-8: Preparation of Compound 32

Compound 31 Compound 32

Compound 31 (l lg, 12.33 mmol) and bis(trifluoromethane)sulfonamide lithium salt (10.62g, 37.01 mmol) were dissolved in 150 ml of MeOH and the mixture was stirred for 2 hours at room temperature. 1000 ml of H 2 0 was slowly added drop- wise to the mixture under stirring. The resulting solid was filtered and dissolved in 200 ml of DCM. Extraction was conducted twice with 200 ml of H 2 0. The organic layer was washed with 200 ml of H 2 0. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the Compound 32 was obtained.

Example 6 (Comparative): Preparation of the compound (A-I-l)

The following compound (A-I-l) was prepared in accordance with the Example 1 of Korean patent application publication No. 10-2014-0026284. Example 7 (Comparative): Preparation of the compound comprising

methacrylate group

Example 7-1: Preparation of Compound 33

Compound 33 2-hydroxyethyl methacrylate (9.32 ml, 76.84 mmol) was dissolved in 100 ml of ACN, and TEA (32.13 ml, 230. 52 mmol) was added. p-TsCl (21.98 g, 115.26 mmol) was 30 ml of ACN, and added to the solution. The mixture was stirred for 3 hours at room temperature. After completion of the reaction, 200 ml of H 2 0 and 200 ml of DCM were added to extract. The organic layer was washed with IN HC1. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment (Hex:EA=5: l to 3: 1) to obtain the Compound 33.

Example 7-2: Preparation of Compound 34

Compound 3 Compound 33

Compound 34

NaH (60%) (1.37 g, 34.35 mmol) was dissolved in 50 ml of DMF, and temperature was cooled down to 0 °C. The Compound 3 (5 g, 22.90 mmol) was added slowly, and stirred for 30 minutes at room temperature. The mixture was cooled down to 0°C, and the Compound 33 (9.76 g, 34.35 mmol) was slowly added and stirred at room temperature. After completion of the reaction, the mixture was cooled down to 0°C, and 100 ml of H 2 0 was slowly added drop- wise to quench the reaction. 100 ml of E.A. was added and extraction was conducted twice. The organic layer was washed with 100 ml of H 2 0. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to Si0 2 column treatment

(Hex:EA=18: l) to obtain the Compound 34.

Example 7-3: Preparation of Compound 35

o

Compound 34

Compound 35 The Compound 34 (1.2 g, 3.63 mmol), and 4,4'-bis(diethylamino) benzophenone (1.76 g, 5.44 mmol) were dissolved in 30 ml of toluene

(anhydride), and POCl 3 (1.7 ml, 18.15 mmol) and 2.5-di-iert-butylhydroquinone (DTBHQ) (80 mg, 0.363 mmol) were added. After increasing the temperature to 100 °C, it was stirred for 15 hours. After completion of the reaction, the temperature was cooled down to room temperature. The temperature was then cooled down to 4 °C in ice bath, and 10 ml of IPA was slowly added drop- wise for quenching. 100 ml of H 2 0 was slowly added to the mixture, and 100 ml of DCM was added to extract three times. The organic layer was dried with MgS0 4 and filtered. After concentration under reduced pressure, the residue was subjected to 1 st Si0 2 column treatment (DCM:MeOH=10: l) and to 2 nd Si0 2 column treatment (DCM:EA:MeOH=5:5: l to 3:3: 1) to obtain the Compound 35. Example 7-4: Preparation of Compound 36

Compound 35 Compound 36

The 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 for 2 hours at room temperature. The mixture was slowly added drop- wise to 100 ml of H 2 0 under stirring. The produced solid was filtered and dissolved in 50 ml of DCM, and 50 ml of H 2 0 was added to extract twice. The organic layer was added to 50 ml of H 2 0 and washed. The organic layer was dried with MgS0 4 and filtered. The Compound 36 was obtained after

concentration under reduced pressure. Example 8: Preparation of blue colorant composition 1 1.5 g of the Compound 6 obtained from Example 1, and 13.5 g of ε-type copper phthalocyanine particles kneaded in mixer were introduced to bead mill together with 6.75 g of DISPERBYK-2000 (available from BYK CHEMIE), 7.5 g of dipentaerythritol hexaacrylate, and 120.75 g of propyleneglycol monomethylether acetate (PGMEA), and ground for 6 to 8 hours at 40 °C using zirconia bead (size: 0.05-2 mm) to obtain the blue colorant millbase. The blue colorant millbase was mixed with photoresist (PR) material (millbase:PR = 30 wt :70 wt%) 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 for using the Compound 9 obtained in Example 2 instead of the

Compound 6.

Example 10: Preparation of blue colorant composition 3

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

Example 11: Preparation of blue colorant composition 4

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

Example 12: Preparation of blue colorant composition 5 The blue colorant composition 5 was obtained by repeating Example 8, except for using the Compound 32 obtained in Example 5 instead of the Compound 6.

Example 13 (Comparative): Preparation of blue colorant composition 6 The blue colorant composition 6 was obtained by repeating Example 5, except for using the compound (A-I-l) obtained in Example 6 instead of the Compound 6.

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

The blue colorant composition 7 was obtained by repeating Example 5, except for using the compound comprising methacrylate group (the Compound 36) obtained in Example 7 instead of the Compound 6.

Performance tests

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

(2) Light resistance evaluation: The film prepared according to (1) above was further subjected to light irradiation (UV irradiation) for 20 hours with an intensity of 400 W/m .Spectroscopy was then performed on the film by using Otsuka Photal MCPD 3000 colorimeter to obtain x and y color coordinates (x, y) and brightness (Y). ΔΥ, Δχ, Ay, and Δ E*ab were measured by comparing the respective value before and after the light irradiation for 20 hours. The results are provided in Table 1.

[Table 1 : Results of light resistance test]

Example ΔΥ Δχ Δ Υ AE*ab

8 (Inventive) 49.785 0.142 0.1713 79.162

9 (Inventive) -0.382 0.011 0.0229 13.994

10 (Inventive) 5.005 0.028 0.057 33.83

11 (Inventive) 2.28 0.022 0.045 26.021

12 (Inventive) 5.005 0.029 0.057 33.83

13 (Comparative) 86.338 0.177 0.2322 118.32 (3) Chemical resistance evaluation: Examples 8-12 and Comparative Example 13 were evaluated regarding stability against an organic solvent by using N-methyl-2-pyrrolidone (NMP). The film prepared according to (1) above was further soaked in NMP for 15 minutes. The chemical resistance against NMP was evaluated by Δ E*ab. The results are provided in Table 2.

[Table 2: Results of chemical resistance test]

(4) Elution test: The color of the film was observed before and after the development with KOH solution. The color of the films prepared from the blue colorant compositions 3 and 4 was changed from deep blue to light blue after the development with KOH solution (washed off), while the deep blue color of the films prepared from the blue colorant compositions 1 and 2 was not substantially changed or was only slightly changed.

As shown in the above, the Compounds 6, 9, 16, 24, and 32 according to the present invention, corresponding to Examples 8-12, respectively, exhibit greatly improved light stability (AE*ab) and excellent chemical resistance over the compound (A-I-1). Moreover, the Compounds 6, 9, 16, 24, and 32 according to the present invention were not substantially washed off during the

development process as opposed to the fact that substantial amount of the compound (A-I-1) and the Compound 36 were washed off.