KR20170060579A - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by the general formula (1), a colorant composition containing the same, and a resin composition containing the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a coloring material composition, a coloring material composition containing the same, and a resin composition containing the same. BACKGROUND ART [0002]

The present application claims the benefit of Korean Patent Application No. 10-2015-0164880, filed on November 24, 2015, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound, a colorant composition containing the same, and a resin composition containing the same.

BACKGROUND ART [0002] In recent years, LEDs or OLED devices which do not drive liquid crystal but perform self-luminescence instead of conventional CCFL have been widely used as a light source of a liquid crystal display (LCD). When an LED or an OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required.

However, it is generally not easy to adjust or adjust the required color coordinates using light emitted from an LED or OLED light source. In addition, the method of improving the color purity, luminance and contrast ratio in the production of a color filter using a pigment dispersion method using already developed color materials, in particular, a pigment has reached a limit.

Development of a new color material is required to overcome such a problem and satisfy the requirement.

Korean Patent Publication No. 2001-0009058

The present invention provides a novel compound, a colorant composition containing the same, and a resin composition containing the same.

According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Y is a direct bond; Or CQ1Q2,

R1 to R14, Q1 and Q2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; Carboxy group (-COOH); -OC (= O) R "'; sulfonic acid group (-SO ₃ H); sulfonamide group; a substituted or unsubstituted alkyl ring; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted Substituted or unsubstituted aryloxy groups, substituted or unsubstituted alkylthio groups, substituted or unsubstituted arylthioxy groups, substituted or unsubstituted alkylsulfoxy groups, substituted or unsubstituted arylsulfoxy groups, substituted or unsubstituted alkenyl groups, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

R "'is a substituted or unsubstituted alkyl group.

According to another embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.

According to another embodiment of the present invention, there is provided a resin composition comprising the color material composition.

According to one embodiment of the present invention, there is provided a photosensitive material produced using the above resin composition.

According to one embodiment of the present disclosure, there is provided a color filter including the aforementioned photosensitive material.

Further, according to an embodiment of the present invention, there is provided a display device including the color filter described above.

According to one embodiment of the present invention, the colorant composition comprising the compound represented by Formula 1 has excellent color characteristics, heat resistance, light resistance, and solvent resistance, and prevents or prevents re-aggregation of the finely divided pigment and dye A higher color reproduction ratio, a higher luminance, a higher contrast ratio, and the like can be achieved.

1 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 1
Fig. 2 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 2. Fig.
3 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 3. Fig.

Hereinafter, the present specification will be described in more detail.

According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; Carboxy group (-COOH); A sulfonic acid group (-SO ₃ H); A sulfonamide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group is an alkyl ester group in which the oxygen of the ester group is substituted with a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms; A cycloalkyl ester group substituted with a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or an aryl ester group substituted with an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, the sulfonamide group is -SO ₂ NR'R "may be in the R 'and R" are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In this specification, the amine group is -NH ₂ ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the monoalkylamine group, the dialkylamine group, the N-alkylarylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 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 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And the like. However, the present invention is not limited thereto.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group in the monoarylamine group, the diarylamine group, the aryloxy group, the aryloxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group, The same as the example of the aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

In the present specification, examples of the heteroaryl group in the monoheteroarylamine group, the diheteroarylamine group, the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.

In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.

In this specification, the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.

According to one embodiment of the present invention, the formula 1 may be represented by the following formula 1-a or 1-b.

[Chemical Formula 1-a]

[Chemical Formula 1-b]

The definitions of R 1 to R 14, Q 1 and Q 2 in the general formulas (1-a) and (1-b) are the same as those in the general formula (1).

According to one embodiment of the present invention, in the above formula (1), Q1 and Q2 are hydrogen.

According to one embodiment of the present invention, in the general formula (1), R1 to R14 are the same or different from each other, and each independently hydrogen; A halogen group; A nitro group; A carboxy group; An ester group; A hydroxy group; A sulfonic acid group (-SO ₃ H), a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.

And R "'is a substituted or unsubstituted alkyl group.

And R "'is a methyl group.

According to one embodiment of the present invention, in the general formula (1), R1 to R14 are the same or different from each other, and each independently hydrogen; Fluorine; Goat; bromine; iodine; A nitro group; A carboxy group; Alkyl ester groups; Cycloalkyl ester groups; Aryl ester groups; A hydroxy group; -OC (= O) CH _3; A sulfonic acid group (-SO ₃ H); Methyl group; t-butyl group; Methoxy group; Or a phenyl group.

According to one embodiment of the present invention, in the general formula (1), R6 to R9 are the same or different from each other, and each independently hydrogen; A halogen group; A nitro group; A carboxy group; An ester group; A hydroxy group; A sulfonic acid group (-SO ₃ H), a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in the general formula (1), R6 to R9 are the same or different from each other, and each independently hydrogen; Fluorine; Goat; bromine; iodine; A nitro group; A carboxy group; Alkyl ester groups; Cycloalkyl ester groups; Aryl ester groups; A hydroxy group; -OC (= O) CH _3; A sulfonic acid group (-SO ₃ H); Methyl group; t-butyl group; Methoxy group; Or a phenyl group.

According to one embodiment of the present invention, at least one of Q1, Q2, and R6 to R14 in Formula 1 is bonded to adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, at least one of Q1, Q2, and R6 to R14 is bonded to an adjacent group to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, at least one of Q1, Q2 and R6 to R14 is a benzene ring substituted with an adjacent group to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to an exemplary embodiment of the present specification, in the formula (1), at least one of Q1, Q2 and R6 to R14 may be bonded to each other adjacent group a nitro group, or a sulfonic acid group (-SO ₃ H) as a substituted or unsubstituted benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, in Formula 1, R6 and R7 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in the above formula (1), R6 and R7 are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, in the above formula (1), R 6 and R 7 combine with each other to form a benzene ring

According to one embodiment of the present invention, R 7 and R 8 in the formula (1) are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, R 7 and R 8 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, R 7 and R 8 in the general formula (1) are bonded to each other to form a benzene ring substituted or unsubstituted with a nitro group or a sulfonic acid group (-SO ₃ H); Or a naphthalene ring.

According to one embodiment of the present invention, in Formula 1, Q1 and R6 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in Formula 1, Q1 and R6 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, in Formula 1, Q1 and R6 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, in Formula 1, Q2 and R6 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in Formula 1, Q2 and R6 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, in the general formula (1), Q2 and R6 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, in Formula 1, R10 and R11 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in Formula 1, R10 and R11 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, R10 and R11 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, in Formula 1, R11 and R12 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in Formula 1, R11 and R12 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, R 1 and R 12 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, R12 and R13 in the formula (1) are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, R12 and R13 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, R12 and R13 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, R13 and R14 in the formula (1) are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, R13 and R14 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

According to one embodiment of the present invention, R13 and R14 are bonded to each other to form a benzene ring; Or a naphthalene ring.

According to one embodiment of the present invention, the formula 1 is represented by any one of the following formulas 1-c to 1-n.

[Chemical Formula 1-c]

[Chemical formula 1-d]

[Formula 1-e]

[Chemical Formula 1-f]

[Formula 1-g]

[Chemical Formula 1-h]

[Chemical Formula 1-i]

[Chemical Formula 1-j]

[Chemical Formula 1-k]

[Chemical Formula 1-l]

[Formula 1-m]

[Chemical Formula 1-n]

In the above formulas (1-c) to (1-n)

The definitions of R6 to R9, Q1 and Q2 are the same as those of the above formula (1).

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (1-1) to (1-37).

In Formula 1-25,

R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment of the present invention, in Formula 1-25, R is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

According to another embodiment of the present invention, in Formula 1-25, R is an alkyl group having 1 to 12 carbon atoms; A cycloalkyl group having 3 to 12 carbon atoms; Or an aryl group having 6 to 12 carbon atoms.

According to one embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.

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

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.

According to 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, One selected from the group consisting of trimethylolpropane trimethacrylate, trimethylolpropane trimethacrylate, trimethylolpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate Or a mixture of two or more.

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 is selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound Or more.

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 1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (O-acetyloxime) (CJ-i-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.

According to one embodiment of the present invention, the content of the colorant composition is 0.1 wt% to 60 wt%, the content of the binder resin is 1 wt% to 60 wt% based on the total weight of the solid content in the resin composition , 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%.

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.

According to one embodiment of the present invention, the resin composition is one or more than one selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, Further comprising an additive.

According to 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; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -Diylbisphosphonous acid tetrakis [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.

According to one embodiment of the present invention, there is provided a photosensitive material produced using 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.

According to an embodiment of the present invention, there is provided a color filter including the photosensitive material.

The color filter can be produced by using the resin composition containing the color material composition. 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.

According to another embodiment, the color filter may further include 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.

Production Example 1. Preparation of Formula 1-1

1) Preparation of intermediate 3

25 g (157.041 mmol, 1 eq) of Intermediate 1 was placed in 200 g of methylene chloride (Preparation: Daejung) and stirred. An ice-bath was installed to adjust the reaction solution to 0 ° C, and 19.07 g (188.454 mmol, 1.2 eq) of triethylamine was slowly added dropwise to the reaction solution. 30.787 g (174.321 mmol, 1.11 eq) of Intermediate 2 was then slowly added dropwise to the reaction solution. The reaction was carried out at 0 ° C for 30 minutes and then stirred at room temperature for 24 hours. 300 g of distilled water (DI-Water) was added to the reaction solution, stirred for 30 minutes, and then the organic layer and the water layer were separated. 200 ml of MC was added to the separated water layer and further extracted. The organic layer was mixed with 200 ml of a 5% K ₂ CO ₃ solution and stirred, followed by separation of the organic layer. Distilled water (DI-Water) was added to the organic layer and extraction was repeated until neutralization occurred. The solvent was removed from the organic layer under reduced pressure. The precipitate was added with 500 ml of ethyl acetate (EA): n-hexane (n-Hex) = 1: 3 and stirred. The mixture was filtered under reduced pressure and the precipitate was dried at 80 ° C overnight to obtain 45.736 g (152.79 mmol) (Yield: 97%).

_{1H NMR (500MHz, CDCl 3)} : 8.00 ~ 7.97 (t, 3H), 7.70 ~ 7.68 (d, 1H), 7.66 ~ 7.65 (d, 1H), 7.59 ~ 7.55 (t, 1H), 7.47 ~ 7.42 (q , 3H), 7.21-7.20 (d, IH), 2.51 (s, 3H)

2) Preparation of formula 1-1

Intermediate 3 Intermediate A-1 Compound 1-1

Under nitrogen, 1.32 g (4.41 mmol) of Intermediate 3, 0.65 g (4.41 mmol) of Intermediate A-14, 10 g of Benzoic acid and 10 g of methyl benzoate were added to a 2-neck-round bottom flask and stirred. The reaction was carried out at 150 ° C for 5 hours. The reaction solution was slowly added dropwise to 200 ml of methanol and stirred for 1 hour. The precipitate was filtered off under reduced pressure, washed with methanol, and dried at 80 ° C overnight to obtain 1.14 g (2.56 mmol) of the compound of Formula 1-1 (yield: 58.1%).

Ionization mode =: APCI +: m / z = 430 [M + H] ⁺ , Exact Mass: 429

Production Example 2. Preparation of Formulas 1-2

2) In the same manner as in Production Example 1, except that Intermediate A-2 was used in place of Intermediate A-1 in the preparation of Formula 1-1.

Production Example 3. Preparation of Formulas 1-3

2) In the same manner as in Production Example 1, except that Intermediate A-3 was used in place of Intermediate A-1 in the preparation of Formula 1-1.

Production Example 4. Preparation of Formulas 1-4

2) In the same manner as in Production Example 1, except that Intermediate A-4 was used instead of Intermediate A-1 in the preparation of Formula 1-1.

Preparation Example 5. Preparation of Formulas 1-5

2) In the same manner as in Production Example 1, except that Intermediate A-5 was used in place of Intermediate A-1 in the preparation of Formula 1-1.

Production Example 6. Preparation of Formulas 1-6

2) In the same manner as in Production Example 1, except that Intermediate A-6 was used in place of Intermediate A-1 in the preparation of Intermediate 1-1.

Production Example 7. Preparation of Formulas 1-7

Intermediate 3 Intermediate A-7 Compound 1-7

Under nitrogen, a solution of 1.32 g (4.41 mmol) of Intermediate 3, 0.851 g (4.41 mmol) of Intermediate A-7 and 10 g of Benzoic acid were added to a 2-neck-round bottom flask and stirred. And the reaction was carried out at 190 ° C to 200 ° C for 5 hours. The reaction solution was slowly added dropwise to 200 ml of methanol and stirred for 1 hour. The precipitate was filtered off under reduced pressure, washed with methanol, and then dried at 80 ° C overnight to obtain 0.802 g (1.690 mmol) of a compound of formula (1-7) (Yield: 38.3%).

Ionization mode =: APCI +: m / z = 475 [M + H] ⁺ , Exact Mass: 474

Preparation Example 8. Preparation of Formulas 1-8

Was prepared in the same manner as in Preparation Example 7, except that Intermediate A-8 was used instead of Intermediate A-7.

Preparation Example 9. Preparation of Formulas 1-9

In the same manner as in Production Example 7 except that Intermediate A-9 was used in place of Intermediate A-7.

Production Example 10. Preparation of Formulas 1-10

Was prepared in the same manner as in Preparation Example 7, except that Intermediate A-10 was used instead of Intermediate A-7.

Preparation Example 11. Preparation of Formula 1-11

In the same manner as in Production Example 7 except that Intermediate A-11 was used instead of Intermediate A-7.

Production Example 12. Preparation of Formulas 1-12

Was prepared in the same manner except that Intermediate A-12 was used in place of Intermediate A-7 in Preparation Example 7.

Preparation Example 13. Preparation of Formula 1-13

Was prepared in the same manner as in Preparation Example 7, except that Intermediate A-13 was used instead of Intermediate A-7.

Preparation Example 14. Preparation of Formula 1-14

Was prepared in the same manner except that Intermediate A-14 was used in place of Intermediate A-7 in Preparation Example 7.

Production Example 15. Preparation of Formulas 1-15

In the same manner as in Preparation Example 7, except that Intermediate A-15 was used in place of Intermediate A-7.

Preparation 16. Preparation of Formulas 1-16

Was prepared in the same manner as in Preparation Example 7, except that Intermediate A-16 was used instead of Intermediate A-7.

Production Example 17. Preparation of Formulas 1-17

Was prepared in the same manner except that Intermediate A-17 was used in place of Intermediate A-7 in Preparation Example 7.

Preparation 18. Preparation of Formulas 1-18

Was prepared in the same manner except that Intermediate A-18 was used in place of Intermediate A-7 in Production Example 7.

Preparation 19. Preparation of Formulas 1-19

In the same manner as in Preparation Example 7 except that Intermediate A-19 was used in place of Intermediate A-7.

Preparation 20. Preparation of 1-20

Intermediate 3 Intermediate A-20 Compound 1-20

Under nitrogen, a solution of 1.32 g (4.41 mmol) of Intermediate 3, 0.874 g (4.41 mmol) of Intermediate A-20, 10 g of Benzoic acid and 10 mL of methyl benzoate were added to a 2-neck-round bottom flask and stirred. And the reaction was carried out at 190 ° C to 200 ° C for 5 hours. The reaction solution was slowly added dropwise to 200 ml of methanol and stirred for 1 hour. The precipitate was filtered under reduced pressure, washed with methanol, and then dried at 80 ° C overnight to obtain 0.602 g (1.350 mmol) of a compound of formula 1-20 (yield: 30.6%).

Ionization mode =: APCI +: m / z = 480 [M + H] +, Exact Mass: 479

Preparation 21. Preparation of the compound of the formula 1-21

In the same manner as in Production Example 20 except that Intermediate A-21 was used instead of Intermediate A-20.

Preparation 22. Preparation of Formulas 1-22

In the same manner as in Production Example 20 except that Intermediate A-22 was used instead of Intermediate A-20.

Preparation 23. Preparation of Formulas 1-23

In the same manner as in Production Example 20 except that Intermediate A-23 was used instead of Intermediate A-20.

Preparation 24. Preparation of Formulas 1-24

In the same manner as in Production Example 20 except that Intermediate A-24 was used instead of Intermediate A-20.

Preparation 25. Preparation of Formulas 1-26

In the same manner as in Production Example 20 except that Intermediate A-26 was used instead of Intermediate A-20.

Examples. Preparation of resin composition

The resin compositions of Examples 1 to 4 were prepared in the amounts shown in Table 1 below.

Intermediates 1, 2 and A-1 to A-23 used in the above Preparation Example were obtained from Sigma Aldrich.

Example 1 Example 2 Example 3 Example 4 (1-1) 5.554 g - - - 1-9 - 5.554 g - - 1-20 - - 5.554 g - 1-23 - - - 5.554 g Binder resin (g) 10.376 Photoinitiator (g) 2.018 Additive (g) 1.013 The multifunctional monomer (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)
Multifunctional monomer: dipentaerythritol hexaacrylate (DPHA)
Additive: DIC F-475
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)

Board Fabrication

The resin compositions prepared in Examples 1 to 4 were spin-coated on glass (5 × 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 at 250 mu m and the entire surface of the substrate was irradiated with an exposure dose of 40 mJ / cm < ² >

Subsequently, 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 prepare a substrate.

Heat resistance evaluation

After the substrate was fabricated under the above conditions, the substrate was subjected to heat treatment (post bake 1 time (PB 1 time)) to obtain an absorption spectrum in a visible light range of 380 nm to 780 nm using a spectrometer (MCPD Otsuka). Also, the prebake (prBake) substrate was further subjected to post bake (PB) at 230 ° C for 20 minutes to obtain the transmittance spectrum in the same equipment and measurement range.

Using the obtained absorption spectrum and the C light source backlight, Eab was calculated using the obtained value E (L *, a *, b *) and shown in Table 2 below.

? E (L *, a *, b *) = {(? L *) 2+ (? A *) 2+

The smaller ΔE value means that the color heat resistance is excellent.

If ΔE <3, it can be used as a color filter for a color filter.

The results of the heat resistance measurement are shown in Table 2. As shown in Table 2, it was confirmed that the color change (? Eab) 3 of the compound applied to Examples 1 to 3 was smaller than that.

1 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 1,

Fig. 2 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 2,

3 shows an absorption spectrum of a visible light region of a substrate made of the resin composition of Example 3. Fig.

△ Eab (post heat treatment - pre heat treatment) Example 1 2.84 Example 2 0.87 Example 3 0.26

Claims (12)

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

In Formula 1,
Y is a direct bond; Or CQ1Q2,
R1 to R14, Q1 and Q2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; Carboxy group (-COOH); -OC (= O) R "'; sulfonic acid group (-SO ₃ H); sulfonamide group; a substituted or unsubstituted alkyl ring; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted Substituted or unsubstituted aryloxy groups, substituted or unsubstituted alkylthio groups, substituted or unsubstituted arylthioxy groups, substituted or unsubstituted alkylsulfoxy groups, substituted or unsubstituted arylsulfoxy groups, substituted or unsubstituted alkenyl groups, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,
R "'is a substituted or unsubstituted alkyl group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-a or 1-b:
[Chemical Formula 1-a]

[Chemical Formula 1-b]

The definitions of R 1 to R 14, Q 1 and Q 2 in the general formulas (1-a) and (1-b) are the same as those in the general formula (1). The compound according to claim 1, wherein R1 to R14 are the same or different from each other and each independently hydrogen; A halogen group; A nitro group; A carboxy group; An ester group; A hydroxy group; A sulfonic acid group (-SO ₃ H), a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group,
And R "'is a substituted or unsubstituted alkyl group. 2. The compound according to claim 1, wherein at least one of Q1, Q2 and R6 to R14 is bonded to adjacent groups to form a substituted or unsubstituted aromatic ring. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (1-1) to (1-37):

In Formula 1-25,
R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group. A colorant composition comprising a compound according to any one of claims 1 to 5. The colorant composition according to claim 6, further comprising at least one of a dye and a pigment. A compound according to any one of claims 1 to 5; 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 represented by the formula (1) is 0.1 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 according to claim 10. A display device comprising a color filter according to claim 11.

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