KR101747528B1 - Indole-based compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Indole-based compound, colorant composition comprising the same and resin composition comprising the same Download PDF

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KR101747528B1
KR101747528B1 KR1020150116900A KR20150116900A KR101747528B1 KR 101747528 B1 KR101747528 B1 KR 101747528B1 KR 1020150116900 A KR1020150116900 A KR 1020150116900A KR 20150116900 A KR20150116900 A KR 20150116900A KR 101747528 B1 KR101747528 B1 KR 101747528B1
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박종호
김성현
이다미
고지수
김해중
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주식회사 엘지화학
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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Abstract

In this specification, a novel indole-based compound, a coloring material composition containing the same, and a resin composition containing the same are described.

Description

INDOLE-BASED COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME,

The present invention relates to a novel indole-based compound, a coloring material composition containing the same, and a resin composition containing the same.

In recent years, LEDs, OLEDs, and QDs have been widely used as light sources for liquid crystal displays (LCDs) instead of conventional CCFLs. However, in order to manufacture thin-film displays and flexible displays, display products using a self-emission such as an LED, OLED or QD as a unit pixel have been developed and produced.

However, display using LEDs, OLEDs, and QDs as unit pixels is difficult to maximize, so even when using LEDs, OLEDs, QDs, etc., .

In order to realize a desired color, a light source and an appropriate color filter are required, and it is difficult to realize a desired color coordinate by using a currently used color material, and development of a new color material is required.

Korean Patent Publication No. 2001-0009058

In this specification, a compound having a novel structure, a colorant composition containing the same, and a resin composition containing the same are described.

One embodiment of the present disclosure provides compounds of formula 1:

Figure 112015080471246-pat00001

In Formula 1,

At least one of R 1 to R 14 is represented by the following formula 2 or 3,

Figure 112015080471246-pat00002

Figure 112015080471246-pat00003

Y 1 and Y 2 are each O or NR,

L 1 , L 3 and L 4 are the same or different and each independently a divalent linking group,

L 2 and L 5 are each a direct bond or a divalent linking group,

R 1 to R 14 groups of the non-Formula 2, R 15, R 16, R 17 and R are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted alkenyloxy group having 2 to 25 carbon atoms; A substituted or unsubstituted 8 to 50 aralkenyl group; - (L 6) m COOH; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

n is an integer of 0 to 6, m is 0 or 1,

L 6 is a direct bond or a divalent linking group,

X - is an anion,

The * in the formulas (2) and (3) are the moieties connected to the core structure of formula (1).

Another embodiment of the present invention provides a colorant composition comprising the compound represented by Formula 1 above.

Another embodiment of the present invention provides a resin composition comprising the color material composition.

The compound according to one embodiment of the present disclosure can act as a dye and therefore can be used as a color filter material. Specifically, according to one embodiment of the present invention, the resin composition containing the compound can obtain absorption and transmission spectra suitable for a desired light source, thereby achieving higher color reproducibility, high brightness, and high contrast ratio. According to one embodiment of the present invention, the resin composition containing the compound has a high degree of crosslinking and is excellent in heat resistance and / or chemical resistance. Therefore, the resin composition according to one embodiment of the present invention has less color change due to heat treatment and less elution into a solvent.

Fig. 1 shows the results of measuring the chemical resistance of the substrates prepared in Examples 1 to 10 and Comparative Example 1. Fig.

Hereinafter, the present invention will be described in detail.

An embodiment of the present invention provides a compound represented by the above formula (1). The compound of formula (1) is characterized in that at least one of the substituents is represented by formula (2). By having the substituent of the above formula (2) in the core structure of the formula (1), it can be polymerized with a substance having a polymerizable group by radicals or heat. Herein, the compound having the polymerizable group which can be polymerized with the compound of the formula (1) may be the same as or different from the compound of the formula (1).

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; Acryloyl group; Acrylate groups; Ether group; A nitrile group; A nitro group; A hydroxy group; A cyano group, and a heterocyclic group containing at least one of N, O, S, or P atoms, or has no substituent group.

 In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25.

In the present specification, the alkenyloxy group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the aralkyl group is specifically an aryl moiety having 6 to 49 carbon atoms, and the alkyl moiety has 1 to 44 carbon atoms. Specific examples include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, Group, an?,? -Methylphenylbenzyl group, a 1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzyl group, a 3,5-difluorobenzyl group, , p-methoxybenzyl group, m-methoxybenzyl group,? -phenoxybenzyl group,? -benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, But are not limited to, an ethyl group, an aminobenzyl group, a nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like.

In the present specification, the aryl moiety of the aralkenyl group may be an explanation of the aryl moiety described below, and the alkenyl moiety may be the description of the alkenyl moiety described above.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 40 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, the fluorenyl group may have a substituent, and the substituents may combine to form a spiro structure. Examples of the fluorenyl group include

Figure 112015080471246-pat00004
.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but is preferably 2-40 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, And the like, but the present invention is not limited thereto.

In the present specification, the alkylene group means that there are two bonding sites in the alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 1 , L 3 and L 4 are the same or different and independently substituted or unsubstituted alkylene groups having 1 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 1 , L 3 and L 4 are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, L 1 , L 3 and L 4 are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms.

According to one embodiment of the present invention, L 1 , L 3 and L 4 in the general formula (2) are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 2 and L 5 are a direct bond or a substituted or unsubstituted alkylene group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 2 and L 5 are a direct bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 2 and L 5 are a direct bond or a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms.

According to one embodiment of the present invention, in the general formula (2), L 2 and L 5 are a direct bond or methylene.

According to one embodiment of the present invention, in Formula 2, L 6 is a direct bond or a substituted or unsubstituted alkylene group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 6 is a direct bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 6 is a direct bond or a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms.

According to one embodiment of the present invention, in Formula 2, L 6 is a direct bond or methylene.

According to one embodiment of the present disclosure, in Formula 2, Y 1 and Y 2 are O or NR, and R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted alkenyloxy group having 2 to 25 carbon atoms; A substituted or unsubstituted 8 to 50 aralkenyl group; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.

According to one embodiment of the present invention, in Formula 2, Y 1 and Y 2 are O or NH.

According to one embodiment of the present disclosure, in Formula 2, R 15 is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.

According to one embodiment of the present disclosure, in Formula 2, R 15 is hydrogen; Or a methyl group.

According to one embodiment of the present invention, at least one of R 1 to R 8 in Formula 1 is represented by Formula 2 or 3.

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 Is represented by the above formula (2) or (3).

According to one embodiment of the present invention, in Formula 1, one of R 5 to R 8 is represented by Formula 2 or 3.

According to one embodiment of the present invention, at least one of R 2 and R 6 in Formula 1 is represented by Formula 2 or 3.

According to one embodiment of the present invention, at least two of R 1 to R 8 in the general formula (1) are represented by the above general formula (2) or (3).

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 And at least one of R 5 to R 8 is represented by the above formula (2) or (3).

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 And one of R 5 to R 8 is represented by the above formula (2) or (3).

According to one embodiment of the present invention, in Formula 1, R 2 and R 6 are represented by Formula 2 or 3.

According to one embodiment of the present invention, in the above formula (1), a group not represented by the formula (2) or (3) among R 1 to R 8 is selected from hydrogen, an alkyl group having 1 to 25 carbon atoms, an alkoxy group having 1 to 25 carbon atoms, L 6 ) m COOH.

According to one embodiment of the present invention, in the above formula (1), the group not represented by the formula (2) or (3) among R 1 to R 8 is hydrogen, methyl, methoxy, -CH 2 COOH or COOH.

According to one embodiment of the present invention, in the general formula (1), the group not represented by the general formula (2) or (3) among R 1 to R 8 is hydrogen.

According to one embodiment of the present invention, R 2 in Formula 1 is represented by Formula 2 or 3, and R 6 is hydrogen, an alkyl group having 1 to 25 carbon atoms, an alkoxy group having 1 to 25 carbon atoms, or - (L 6 ) m COOH, and R 1 , R 3 , R 4 , R 5 , R 7 and R 8 are hydrogen.

According to an exemplary embodiment of the present specification, in the general formula 1, R 2 is represented by the chemical formula 2 or 3, R 6 is hydrogen, methyl, methoxy, and -CH 2 COOH or COOH, R 1, R 3, R 4 , R 5 , R 7 and R 8 are hydrogen.

According to one embodiment of the present invention, R 2 is represented by Chemical Formula 2 or 3, R 6 is methyl, methoxy, -CH 2 COOH or COOH, and R 1 , R 3 , R 4 , R 5 , R 7 and R 8 are hydrogen.

According to one embodiment of the present invention, at least one of R 13 and R 14 in the general formula (1) is a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, at least one of R 13 and R 14 is a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, and the rest is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, at least one of R 13 and R 14 is an alkenyl group having 2 to 25 carbon atoms, and the rest is hydrogen; Or an alkyl group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, at least one of R 13 and R 14 in the formula (1) is an allyl group, and the remainder is a methyl group.

According to one embodiment of the present invention, in the general formula (1), R 13 and R 14 are the same or different and each independently represent a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 13 and R 14 are the same or different and each independently an alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in the general formula (1), R 13 and R 14 are allyl groups.

According to one embodiment of the present invention, in the general formula (1), R 13 and R 14 are the same or different and each independently represents hydrogen or an alkyl group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 13 and R 14 are the same or different and each independently an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, in the general formula (1), R 13 and R 14 are methyl groups.

According to an exemplary embodiment of the present specification, in the general formula 1, R 1 to R 8 of at least one of which is being represented by the formula 2 or 3, R 1 to R 8 of the at least one substituent that is not represented by the chemical formula 2 or 3, And one is a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, one of R 1 to R 8 is represented by the above formula (2) or (3) and one of R 1 to R 8 , which is not represented by formula Substituted or unsubstituted C2-C25 alkenyl group.

According to one embodiment of the present invention, in Formula 1, one of R 1 to R 8 is represented by Formula 2 or 3, and any one of R 13 and R 14 is a substituted or unsubstituted C 2-20 Lt; / RTI >

According to an exemplary embodiment of the present specification, in the general formula 1, R 1 to R 8 2 of one is represented by the formula 2 or 3, R 1 to R 8 substituents of the not represented by Formula 2 or 3 of the dog Is a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, one of R 1 to R 8 is represented by Formula 2 or 3, and R 13 and R 14 are the same or different from each other, Is an alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 And at least one of R 5 to R 8 is represented by the above formula (2) or (3), and one of the substituents not represented by the formula (2) or (3) among R 1 to R 8 is a substituted or unsubstituted C2 to C25 Alkenyl group.

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 And at least one of R 5 to R 8 is represented by the above formula 2 or 3, and any one of R 13 and R 14 is a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 Of at least one of the R 5 to R 8 and at least one being represented by the formula (2) or triple, R 1 to R 8 2 out of of the substituents that are not represented by the formula (2) is a substituted or unsubstituted C2 to 25 ring alkenyl Nylon.

According to one embodiment of the present invention, in Formula 1, R 1 to R 4 And at least one of R 5 to R 8 is represented by the formula 2 or 3, and R 13 and R 14 are the same or different and each independently a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 9 to R 12 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted alkenyloxy group having 2 to 25 carbon atoms; Or a substituted or unsubstituted 8 to 50 aralkenyl group.

According to one embodiment of the present invention, in Formula 1, R 9 to R 12 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R 9 to R 12 are the same or different from each other, and each independently hydrogen; Or a methyl group.

According to one embodiment of the present invention, in Formula 1, n is 1 or 2.

According to one embodiment of the present invention, in the above formula (1), n is 1.

According to one embodiment of the present invention, in the general formula (1), X < - > may be a monovalent or a divalent or more anion. Examples of the anion include, but are not limited to, those described in U.S. Patent Nos. 7,939,644, 2006-003080, 2006-001917, 2005-159926, 2007-7028897, Anions described in Japanese Patent Application Laid-Open No. 2005-071680, Korean Patent Application Laid-Open Nos. 2007-7000693, 2005-111696, and 2008-249663 can be applied. Specific examples of the anion include a trifluoromethanesulfonic acid anion, a bis (trifluoromethylsulfonyl) amide anion, a bistrifluoromethanesulfonimide anion, a bisperfluoroethylsulfonimide anion, a tetraphenylborate anion, a tetra Keto (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl methide, halogen groups such as fluorine, iodine and chlorine groups.

According to one embodiment of the present invention, the compound of Formula 1 may be represented by the following structural formulas.

Figure 112015080471246-pat00005

According to another embodiment of the present invention, the compound of Formula 1 may be represented by the following structural formulas.

Figure 112015080471246-pat00006

Wherein Y is O or NR, and the definition of R is as described above.

According to another embodiment of the present invention, the compound of Formula 1 may be represented by the following structural formulas.

Figure 112015080471246-pat00007

Wherein Y is O or NR, and the definition of R is as described above.

According to another embodiment of the present invention, the compound of Formula 1 may be represented by the following structural formulas.

Figure 112015080471246-pat00008

Wherein Y is O or NR, and the definition of R is as described above.

According to another embodiment of the present invention, the compound of Formula 1 may be represented by the following structural formulas.

Figure 112015080471246-pat00009
Figure 112015080471246-pat00010

Figure 112015080471246-pat00011

The compound of formula (1) can be prepared by referring to the following Production Examples.

Another embodiment of the present disclosure provides a colorant composition comprising the compound of formula (1).

The colorant composition may further include at least one of a dye and a pigment in addition to the compound of the formula (1). For example, the colorant composition may contain only the compound of Formula 1, but may include the compound of Formula 1 and at least one dye, or may include the compound of Formula 1 and at least one pigment, , One or more dyes, and one or more pigments.

In one embodiment of the present invention, there is provided a resin composition comprising the color material composition.

In one embodiment of the present invention, the resin composition comprises a binder resin; Multifunctional monomers; Photoinitiators; And a solvent.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of a resin composition.

The binder resin may be a copolymer resin of a monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility. The binder resin may further include a binder generally used in the art.

The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the unsaturated imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.

Examples of the acid anhydride include maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.

The alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.

In one embodiment of the present invention, the acid value of the binder resin is 50 to 130 KOH mg / g, and the weight average molecular weight is 1,000 to 50,000.

The multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol tetramethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate. Species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator may be selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, It may be at least one selected.

The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.

Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.

The triazine-based compound may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] Methyl) -6- p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like .

The oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.

The solvent is selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one selected from the group consisting of citrate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.

In one embodiment of the present invention, the content of the compound of Formula 1 is 5 wt% to 60 wt% based on the total weight of the solid content of the resin composition, and the content of the binder resin is 1 wt% to 60 wt% %, The content of the initiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The standard of weight percentage based on solid content and solid content of each component can be measured by general analytical means used in the art such as liquid chromatography or gas chromatography.

In one embodiment of the present invention, the resin composition is a resin composition comprising a compound selected from the group consisting of a photo-crosslinking agent, a curing accelerator, an adhesion promoter, a surfactant, an antioxidant, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, Or two or more additives.

In one embodiment of the present invention, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of the solid content in the resin composition.

The photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide; Benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.

As the curing accelerator, curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.

Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.

Specifically, the silicone surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F- TF-1116SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1025SF, TF- , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Such as thiourea such as diaryldisulfide, dilaurylthiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; Bis (2,4-ditbutylphenyl) pentaerythritol diphosphite) or (1, 2-dibutylphenyl) pentaerythritol phosphite, , 1,1'-biphenyl) -4,4'-diylbisphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] Based secondary antioxidants such as 2,4-bis (1,1-dimethylethyl) phenyl] ester.

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone may be used. Anything that is commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.

The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.

In one embodiment of the present invention, there is provided a photosensitive material made of the resin composition.

More specifically, the resin composition of the present invention is applied onto a substrate by a suitable method to form a photosensitive material in the form of a thin film or a pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.

Examples of the light source for curing the resin composition according to the present invention include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emits light having a wavelength of 250 nm to 450 nm.

The resin composition according to the present invention can be used as a pigment dispersing type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of an organic light emitting diode or a thin film transistor liquid crystal display (TFT LCD) And can be used for a photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board and a photosensitive material for a plasma display panel (PDP) Is not specifically set.

In one embodiment of the present invention, a color filter including the photosensitive material is provided.

The color filter can be produced using a resin composition containing the compound of formula (1). The resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

The resin composition according to one embodiment of the present invention can provide a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance, have.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the kind thereof is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

In another embodiment, the color filter may further comprise an overcoat layer.

Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectivity of chrome, and environmental pollution caused by a chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.

A display device including the color filter according to the present invention is provided.

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD) A liquid crystal display (LCD), and a cathode ray tube (CRT).

Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.

< Manufacturing example  1>

Figure 112015080471246-pat00012

      1a 1b 1c

Under N 2 , 10 ml (62.80 mmol, 1 eq) of the compound 1a and 13.37 g (94.20 mmol, 1.5 eq) of the compound 1b were added to 100 ml of acetonitrile and stirred at 85 ° C for 24 hours. After cooling to room temperature, the precipitate was filtered off under reduced pressure, washed with CHCl 3 and dried to obtain 16.068 g (53.35 mmol) of the compound 1c. Yield 85%

The results of measurement using 1 H-NMR of 1c are as follows.

1 H NMR (500 MHz, DMSO , ppm): 7.92-7.91 (1H, s, ArH), 7.84-7.82 (1H, d, ArH), 7.63-7.61 (2H, t, ArH), 3.98 (3H, s , N-CH 3), 2.78 (3H, s, CH 3), 1.53 (6H, s, CH 3 × 2)

Figure 112015080471246-pat00013

    1c 1d 1e

4 g (13.28 mol) of the compound 1c was added to 320 ml of diethyl ether: 2M NaOH = 1: 3 and stirred for 30 minutes. The organic layer was passed through a MgSO 4 and the solvent removed under reduced pressure. 3 g (17.32 mmol, 1 eq) of the compound 1d was dissolved in 30 ml of MC and a solution of 2.5 g (1.953 mol, 1.13 eq) of (chlorethylene) dimethyliminium chloride dissolved in 35 ml of MC was slowly added Respectively. Stir for 15 minutes and slowly add 75 ml of a 10% aqueous NaOH solution in an ice bath. The mixture was stirred for 1 hour and 30 minutes, and the organic layer was separated, washed with brine, and passed through MgSO 4 . The solvent was removed under reduced pressure and used in the next reaction without further separation.

Figure 112015080471246-pat00014

   2a 2b 2c

Under N 2 , 7 g (46.007 mmol, 1 eq) of the compound 2a and 4.755 g (55.209 mmol, 1.2 eq) of the compound 2b were added to 100 g of glacial acetic acid and stirred at 125 ° C for 12 hours. After cooling to room temperature, the solvent was removed under reduced pressure. 2000 ml of water was added to the reaction product, and the mixture was extracted with 800 ml of MC. The extracted organic layer was passed through MgSO 4 and the solvent was removed under reduced pressure. 7.052 g (34.698 mmol) of the compound 2c was obtained. The yield is 75.4%.

The measurement results of the compound 2c using 1 H-NMR are as follows.

1 H NMR (500 MHz, CDCl 3 , ppm): 8.13-8.11 (IH, dd, ArH), 8.03-8.02

ArH), 7.64-7.62 (1H, d , ArH), 2.35 (3H, s, N = C-CH3), 1.34 (6H, s, CH 3 × 2)

Figure 112015080471246-pat00015

      2c 1b 2d

Under N 2 , 7 g (34.44 mmol, 1 eq) of the compound 2c and 9.777 g (68.88 mmol, 2 eq) of the compound 1b were added to 80 ml of toluene and 40 ml of acetonitrile and stirred at 111 ° C for 12 hours. The mixture was cooled to room temperature, and the precipitate was filtered under reduced pressure. (washed with n-hexane). 6.7 g (19.410 mmol) of the compound 2d was obtained. Yield 56%

1 H NMR (500 MHz, DMSO , ppm): 8.40 (1H, s, ArH), 8.20-8.18 (1H, d, ArH), 8.03-8.00 (1H, d, ArH), 3.99 (3H, s, N -CH 3), 2.80 (3H, s, C-CH 3), 1.56 (6H, s, C- (CH 3) 2

Figure 112015080471246-pat00016

     1e 2d 3a

10.23 g (50.830 mmol, 1.01 eq) of the compound 1e and 17.37 g (50.322 mmol, 1 eq) of the compound 2d were placed in 200 g of acetic anhydride under N 2 and reacted at 145 ° C for 24 hours. It was cooled to room temperature and precipitated in 2000 ml of diethyl ether. Filtered and dried under reduced pressure. The residue was purified by column (MC / MeOH = 18/1) to obtain 21.292 g (40.30 mmol) of the compound 3a. Yield 80%

The results of measurement of the compound 3a by 1 H-NMR are as follows.

1 H NMR (500 MHz, DMSO , ppm): 8.36-8.31 (1H, t, -CH = CH-CH =), 8.00 (1H, s, ArH), 7.94-7.92 (1H, d, ArH), 7.62 (1H, d, ArH), 7.44-7.42 (2H, m, ArH), 7.32-7.31 (1H, d, ArH), 7.29-7.26 , -CH = CH-CH =) , 3.65 (3H, s, N-CH 3), 3.62 (3H, s, N-CH 3), 1.69-1.68 (12H, d, C (CH 3) 2 × 2 )

Figure 112015080471246-pat00017

3a 3b 3c

2 g (3.785 mmol, 1 eq) of the compound 3a was dissolved in 100 g of acetonitrile, and the temperature was adjusted to 0 to 4 ° C. 0.871 g (4.542 mmol, 1.2 eq) of EDC-HCl and 0.093 g (0.7569 mmol, 0.2 eq) of DMAP were added and stirred for 10 minutes. 0.739 g (5.677 mmol, 1.5 eq) of the compound 3b was added, and the mixture was reacted at 0 to 4 ° C for 2 hours. After 24 hours at room temperature, the solvent was removed under reduced pressure. The residue was purified by column (MC / MeOH = 17/1 to 15/1) to obtain 1.97 g (3.075 mmol) of the compound 3c. Yield 81%

Figure 112015080471246-pat00018

        3c 3d Compound A

1.97 g (3.075 mmol) of the above compound 3c was completely dissolved in acetone and MeOH, and then 1.324 g (4.613 mmol, 1.5 eq) of the above compound 3d dissolved in MeOH was slowly added to the reaction solution. The reaction was carried out at room temperature for 24 hours, and the solvent was removed under reduced pressure. To the reaction was added 100 ml of water and extracted with 100 ml of MC. The extracted organic layer was passed through MgSO 4 to remove water, and the solvent was removed under reduced pressure. 2.38 g (3 mmol) of the above compound A was obtained. Yield 97%.

MS analysis of the compound A:

m / z 513.3 [Dye-anion] + (Exact Mass: 513.27)

m / z 279.9 [anionic] - (Exact Mass: 279.92)

< Manufacturing example  2>

Figure 112015080471246-pat00019

     2d 4a 4b

10 g (28.97 mmol, 1 eq) of the compound 2d was dissolved in 120 ml of pyridine. 4.293 g (28.97 mmol, 1 eq) of the compound 4a was added and reacted at 120 ° C for 14 hours. It was cooled to room temperature and precipitated in 1300 ml of diethyl ether. The precipitate was filtered off under reduced pressure and dried. The residue was purified by column (MC: MeOH = 10: 1 to 1: 1) to obtain 7.42 g (12.962 mmol) of the compound 4b. The yield was 89%

1 H NMR (500 MHz, DMSO , ppm): 8.36-8.31 (1H, t, = CH-CH = CH-), 8.00 (2H, s, ArH), 7.93-7.91 (2H, d, ArH), 7.30 -7.29 (2H, d, ArH) , 6.41-6.39 (2H, d, = CH-CH = CH-), 3.63 (6H, s, N- (CH 3) × 2), 1.69 (12H, s, C (CH 3) 2 × 2)

Figure 112015080471246-pat00020

         4b 3b 4c

Compound 4c was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00021

        Compound 4c

Compound B was synthesized in the same manner as Compound A above.

MS analysis of the compound B:

m / z 557.26 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  3>

Figure 112015080471246-pat00022

        4b 3b 4d

Compound 4d was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00023

            4f 3d Compound C

Compound C was synthesized in the same manner as Compound A above.

MS analysis of the compound C:

m / z 669.32 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  4>

Figure 112015080471246-pat00024

    5a 2d 5b

Figure 112015080471246-pat00025

                   5c Compound D

Compound 5a was synthesized in the same manner as Compound 1e.

Compound 5b was synthesized in the same manner as Compound 3a above.

Compound 5c was synthesized in the same manner as Compound 3c.

Compound D was synthesized in the same manner as Compound A above.

MS analysis of the compound D:

m / z 527.29 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  5>

Figure 112015080471246-pat00026

       6a Compound E

Compound 6a was used instead of Compound 5a, and Compound E was synthesized in the same manner as Compound D.

MS analysis of the compound E:

m / z 543.29 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  6>

Figure 112015080471246-pat00027

  7a 7b 2b 7c 1b 7d

5 g (33.1 mmol) of the above compound 7a was added to 43 ml of 1M NaOH, and the mixture was stirred. An ice bath was set to 0-4 ° C, and 60 ml of HCl (35%) was gradually added dropwise. 2.3 g (33.34 mmol) of NaNO 2 were dissolved in 20 ml of water and then slowly added dropwise to the stirring solution. After stirring at 0 to 4 ° C for 40 minutes, 35.8 g (158.8 mmol) of SnCl 2 .2H 2 O was dissolved in 72 ml of water and slowly dropped into the stirring solution, followed by overnight reaction at 0 to 4 ° C. The precipitate was filtered under reduced pressure, washed with 100 ml of ether and dried to obtain 8.6 g (29.61 mmol) of the compound 7b, and the yield was 89%.

The results of the measurement of Compound 7b using 1 H-NMR are as follows.

1 H NMR (500 MHz, DMSO , ppm): 10.29 (1H, b, COOH), 8.23 (1H, s, NH), 7.16-7.14 (2H, d, ArH), 6.95-6.93 (2H, d, ArH ), 3.48 (2H, s, Ar-CH2-COOH), 3.60 (2H, s, NH 2)

Under N 2 , 1.5 g (7.44 mmol, 1 eq) of the compound 7b and 0.956 g (11.10 mmol) of the compound 2b were added to 30 g of glacial acetic acid and stirred at 120 ° C for 19 hours. After cooling to room temperature, 800 ml of water was added and neutralized with 3% NaOH solution. The reaction mixture was quenched with 500 ml of MC, the organic layer was passed through MgSO4, and the solvent was removed under reduced pressure to obtain Compound 7c.

Under N 2 , 2.1 g (14.795 mmol) of the above compound 7c and 1b were added to 30 ml of acetonitrile, and the mixture was stirred at 85 ° C for 8 hours, and then the solvent was removed under reduced pressure. A small amount of acetone was added, followed by filtration under reduced pressure and drying. 0.472 g (19.410 mmol) of the compound 7d was obtained. The yield was 17.7%

The results of the measurement of Compound 7d using 1 H-NMR are as follows.

1 H NMR (500 MHz, DMSO , ppm): 12.45 (1H, broad, COOH), 7.84-7.83 (1H, d, ArH), 7.69 (1H, s, ArH), 7.52-7.50 (1H, dd, ArH (3H, s, N-CH3), 3.74 (2H, s, Ar-CH2-COOH)

Figure 112015080471246-pat00028

Compound 7e was synthesized in the same manner as Compound 4b.

Figure 112015080471246-pat00029

Compound 7f was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00030

Compound 7g was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00031

Compound F was synthesized in the same manner as Compound A above.

MS analysis of the compound F:

m / z 585.30 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  7>

Figure 112015080471246-pat00032

Compound G was synthesized in the same manner as Compound A above.

MS analysis of the compound G:

m / z 697.35 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  8>

Figure 112015080471246-pat00033

Compound 7h was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00034

Compound H was synthesized in the same manner as Compound A above.

MS analysis of the compound H:

m / z 611.31 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  9>

Figure 112015080471246-pat00035

Compound 7i was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00036

Compound I was synthesized in the same manner as Compound A above.

MS analysis of the compound I:

m / z 625.33 [Dye-anion] +

m / z 279.92 [anion] -

< Manufacturing example  10>

Figure 112015080471246-pat00037

Compound 7j was synthesized in the same manner as Compound 3c.

Figure 112015080471246-pat00038

Compound J was synthesized in the same manner as Compound A above.

MS analysis of the compound J:

m / z 641.32 [Dye-anion] +

m / z 279.92 [anion] -

Example  1 to 7

A photosensitive resin composition having the composition shown in Table 1 below was prepared.

practice
Example 1 practice
Example 2 practice
Example 3 practice
Example 4 practice
Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Comparative Example 1 Compound A 5.554 - - - - - - - - - - Compound B - 5.554 - - - - - - - - - Compound C - - 5.554 - - - - - - - - Compound D - - - 5.554 - - - - - - - Compound E - - - - 5.554 - - - - - Compound F - - - - - 5.554 - - - - - Compound G - - - - - - 5.554 - - - - compound
H - - - - - - 5.554 - - - compound
I - - - - - - - - 5.554 - - compound
J - - - - - - - - - 5.554 - Comparative compound - - - - - - - - - - 5.554 Binder resin (g) 10.376 Photoinitiator (g) 2.018 Additive (g) 1.016 The photopolymerizable compound (g) 12.443 Solvent (g) 68.593 Total content (g) 100 Binder resin: Copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 as measured by GPC, molecular weight distribution (PDI) 2.0, solids content 25% , Solvent PGMEA)
Photoinitiator: I-369 (BASF)
Photopolymerizable compound: DPHA (Japanese explosive)
Additive: DIC F-475
Solvent: PGMEA (Propylene Glycol Monomethyl Ether Acetate)

Comparative compound:

Figure 112015080471246-pat00039

Using the photosensitive resin compositions prepared in Examples 1 to 10, substrates were prepared as described below, and physical properties were measured.

Substrate fabrication conditions

The photosensitive resin composition was spin-coated on glass (5 x 5 cm) and pre-baked at 100 ° C for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 300 mu m and the entire surface of the substrate was irradiated with an exposure dose of 40 mJ / cm &lt; 2 &gt;

The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post baked at 230 캜 for 20 minutes to obtain a color pattern.

Chemical resistance measurement conditions

The substrate prepared in the above conditions was immersed in 16 ml of NMP (N-methyl-2-pyrrolidone) 2ea cut into 1 cm x 5 cm and placed in an oven at 80 ° C for 40 minutes. Then, the absorbance (A) of the NMP solution was measured using a UV-Vis spectrophotometer.

If the absorption (A) is large, it means that the coloring material (dye or pigment) elutes from the film and the chemical resistance is poor.

As a result of measuring the chemical resistance of the substrate prepared using the compositions of Examples 1 to 10 and Comparative Example 1, it was confirmed that the absorbency of Comparative Example 1 was significantly higher than those of Examples 1 to 10. The results of chemical resistance measurement for Examples 1 to 10 and Comparative Example 1 are shown in Fig.

Claims (12)

A compound of formula
[Chemical Formula 1]
Figure 112017039280947-pat00040

In Formula 1,
At least one of R 1 to R 8 is represented by the following formula 2 or 3,
(2)
Figure 112017039280947-pat00041

(3)
Figure 112017039280947-pat00042

Y 1 and Y 2 are O,
L 1 , L 3 and L 4 are the same or different and each independently represents an alkylene group having 1 to 25 carbon atoms,
L 2 and L 5 are each a direct bond; Or an alkylene group having 1 to 25 carbon atoms,
R 1 to R 8 groups of the non-Formula 2 or 3, R 9 to R 14, R 15, R 16 and R 17 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted alkenyloxy group having 2 to 25 carbon atoms; A substituted or unsubstituted 8 to 50 aralkenyl group; - (L 6) m COOH; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
n is an integer of 0 to 6, m is 0 or 1,
L 6 is a direct bond; Or an alkylene group having 1 to 25 carbon atoms,
X - is an anion,
The * in the formulas (2) and (3) are the moieties connected to the core structure of formula (1). delete delete The method according to claim 1, R 13 and R 14 at least one of a substituted or unsubstituted alkenyl group to a ring carbon number of 2 to 25 compounds. The compound according to claim 1, wherein R 9 to R 12 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms. A colorant composition comprising a compound of formula (1) according to any one of claims 1, 4 and 5. The colorant composition according to claim 6, further comprising at least one of a dye and a pigment. A compound of formula (I) according to any one of claims 1, 4 and 5, a binder resin; Multifunctional monomers; Photoinitiators; And a solvent. The method of claim 8,
Based on the total weight of the solid content in the resin composition
The content of the compound of Formula 1 is 5 wt% to 60 wt%
The content of the binder resin is 1 wt% to 60 wt%
The content of the photoinitiator is 0.1 wt% to 20 wt%
And the content of the polyfunctional monomer is 0.1 wt% to 50 wt%. A photosensitive material produced by using the resin composition according to claim 8. A color filter comprising the photosensitive material of claim 10. A display device comprising the color filter of claim 11.
KR1020150116900A 2014-08-19 2015-08-19 Indole-based compound, colorant composition comprising the same and resin composition comprising the same KR101747528B1 (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003076002A (en) 2001-09-07 2003-03-14 Fuji Photo Film Co Ltd Recording material
JP2003076003A (en) 2001-09-07 2003-03-14 Fuji Photo Film Co Ltd Recording material
JP2013173850A (en) * 2012-02-24 2013-09-05 Adeka Corp Novel compound and colored alkali developable photosensitive composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010009058A (en) 1999-07-07 2001-02-05 성재갑 Photosensitive resin composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003076002A (en) 2001-09-07 2003-03-14 Fuji Photo Film Co Ltd Recording material
JP2003076003A (en) 2001-09-07 2003-03-14 Fuji Photo Film Co Ltd Recording material
JP2013173850A (en) * 2012-02-24 2013-09-05 Adeka Corp Novel compound and colored alkali developable photosensitive composition

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