KR20180115585A - Compound and photo-sensitive resin composition comprising the same - Google Patents

Abstract

The present invention relates to a novel compound, a photosensitive resin composition comprising the same, a photosensitive material, a color filter, and a display device manufactured using the same. The compound is represented by chemical formula 1. In chemical formula 1, Y1 and Y2 are the same or different from each other, and each independently is a direct bond or -CQ1Q2-.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound, and a photosensitive resin composition containing the same. BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

The present invention relates to a compound, a photosensitive resin composition containing the same, and a photosensitive material, a color filter, and a display device manufactured using the photosensitive resin composition. More particularly, the present invention relates to a compound having excellent color characteristics, heat resistance, and solvent resistance, a photosensitive resin composition using the same, and a photosensitive material, a color filter, and a display device manufactured using the same.

Recently, color filters are required to have high brightness and high contrast ratio. One of the main goals of the display device development is to differentiate display device performance by improving color purity and to improve productivity in a manufacturing process.

Conventionally, a pigment type used as a coloring material of a color filter is present in a color photoresist in a particle dispersion state, and thus it has been difficult to control the luminance and contrast ratio according to the size and distribution of the pigment particles. In the case of pigment particles, multiplescattering of light occurs due to the large particles that are aggregated in the color filter and are poorly soluble and dispersible and aggregated. The scattering of the polarized light is regarded as a main factor for lowering the contrast ratio.

Efforts have been made to improve brightness and contrast ratio through ultrafiltration and dispersion stabilization of pigments, but the degree of freedom is limited in selecting a color material for implementing color coordinates for a high color purity display device.

In addition, the pigment dispersion method using the color materials, especially the pigments, already developed has reached a limit to improve the color purity, brightness and contrast ratio of the color filter using the pigment dispersion.

Accordingly, development of a new color material capable of improving color purity, luminance, and contrast ratio has been demanded.

The present invention is to provide a compound having excellent color characteristics, heat resistance and solvent resistance.

The present invention also provides a photosensitive resin composition containing the compound.

The present invention also provides a photosensitive material, a color filter, and a display element manufactured using the above compound or photosensitive resin composition.

In this specification, a compound represented by the formula (1) is provided.

Also provided herein is a colorant composition comprising the compound.

The present invention also provides a photosensitive resin composition comprising the above-described compound or a colorant composition.

The present invention also provides a photosensitive material manufactured using the photosensitive resin composition, and a color filter or a display device using the same.

BEST MODE FOR CARRYING OUT THE INVENTION The compounds according to specific embodiments of the present invention and photosensitive resin compositions containing them will now be described in more detail.

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.

In the present specification, examples of substituents are described below, but are not limited thereto.

In the present specification, the term "substituted" means that a functional group is substituted for a hydrogen atom in the compound, and the position to be substituted is not limited as far as the position where the hydrogen atom is substituted, , 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; Cyano; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; An amino group; A carboxy group; Sulfonic acid group; A sulfonamide group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, "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, or may be interpreted as a substituent in which two phenyl groups are connected.

, 또는

는 다른 치환기에 연결되는 결합을 의미하고, 단일 결합은 L 로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In the present specification,

, or

Means a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L. [

In the present specification, examples of the halogen group include 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 may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. 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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

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, iso N-pentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, , But is not limited thereto.

In the present specification, the amine group may be selected from the group consisting of -NH ₂ , a monoalkylamine group, a dialkylamine group, a N-alkylarylamine group, a monoarylamine group, a diarylamine group, an N-arylheteroarylamine group, An arylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and 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-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, An N-phenylphenylenamineamine group, an N-phenylphenylamine group, an N-phenylphenanthrenylamine group, an N-phenylphenanthrenylamine group, A phenanthrenyl fluorenylamine group, an N-biphenylfluorenylamine group, and the like, 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-arylalkylamine 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 straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

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 arylthio 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 heterocyclic group is a hetero ring group containing at least one of O, N, Se and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 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 pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but 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 60 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, A phenanthroline group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazyl group, an aziridyl group, an azaindolyl group, A heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, phthyridine, tert-pyridyl, phenazinyl, imidazopyridyl, pyripyridyl, azepin, pyrazolyl and dibenzofuranyl groups, but the present invention is not limited thereto.

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 may be selected from the examples of the above-mentioned heteroaryl group have.

In the present specification, the alkylene group is a divalent functional group derived from an alkane, for example, a linear, branched or cyclic alkylene group, an ethylene group, a propylene group, an isobutylene group, a sec- A butylene group, a tert-butylene group, a pentylene group, a hexylene group and the like.

In the present specification, the haloalkylene group means a functional group in which the above-mentioned alkylene group is substituted with a halogen group, for example, perfluoropropane-2,2-diyl, etc. .

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

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 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.

In the present specification, the term "direct bond" means that no atom or atomic group exists at the corresponding position and is connected to the bond line.

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

[Chemical Formula 1]

In Formula 1,

Y1 and Y2 are the same or different and are each independently a direct bond or -CQ1Q2-,

A is a direct bond; Ether group; Carbonyl group; Ester group; Diester group; Peroxy group; An amino group; Imino; Imide; Azo group; An amide group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; A heteroalkylene group having 1 to 10 carbon atoms; A haloalkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 3 to 20 carbon atoms,

R1 to R26, Q1 and Q2 are the same or different from each other 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.

As shown in the above formula (1), the solubility of a compound in a solvent is increased by a sulfonate group contained in the molecular structure, so that it is possible to prevent re-aggregation of the compound, It is confirmed through experiments that the color purity, luminance and contrast ratio can be improved when applied, and the invention is completed.

In particular, in the compound of one embodiment, two sulfonate groups are introduced into the molecular structure due to dimer formation, the solubility enhancement effect by the sulfonate group can be further enhanced, and the spectrum emitted from the light source and the absorption and transmission spectra of the color filter It is possible to improve the color reproducibility and the brightness and the contrast ratio by increasing the color purity by increasing the color purity, and the heat resistance is improved due to the increase of the molecular weight, so that the color purity, brightness and contrast ratio change rapidly even after the heat treatment process And stable display performance can be achieved.

In addition, the compound of one embodiment can achieve the effect of improving the heat resistance property by using an aromatic functional group bonded to the sulfonate group terminal, for example, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms have.

In Formula 1, Y1 and Y2 are the same or different from each other and are each independently a direct bond or -CQ1Q2-, wherein -CQ1Q2- is C and Q1 and Q2 are each independently bonded to carbon Functional group. Therefore, if Y1 or Y2 is a direct bond, five rings of pentagonal ring are formed. When Y1 or Y2 is -CQ1Q2-, a hexagonal ring having six carbon atoms may be formed.

In formula (1), A represents a direct bond; Ether group; Carbonyl group; Ester group; Diester group; Peroxy group; An amino group; Imino; Imide; Azo group; An amide group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; A heteroalkylene group having 1 to 10 carbon atoms; A haloalkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 3 to 20 carbon atoms.

More preferably, in Formula 1, A is a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms can be used.

The diastereomer group may include a functional group containing two ester functional groups, for example, a functional group represented by the following general formula (2).

(2)

In Formula 2, X is an alkylene group having 1 to 10 carbon atoms; A heteroalkylene group having 1 to 10 carbon atoms; A haloalkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 3 to 20 carbon atoms. Preferably, X is an alkylene group having 1 to 5 carbon atoms such as a methylene group, an ethylene group, and a propylene group.

The haloalkylene group having 1 to 10 carbon atoms means a functional group in which an alkylene group having 1 to 10 carbon atoms is substituted with a halogen group, for example, perfluoropropane-2,2-diyl ) And the like.

In the general formula (1), R1 to R26 are the same or different from each other and each independently represents hydrogen; A halogen group; A nitro group; A carboxy group; An ester group; A hydroxy group; -OC (= O) R "'; sulfonic acid group (-SO ₃ H); a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy ring; a substituted or unsubstituted aryl group, Or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

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

And R "'is a methyl group.

In the general formula (1), R1 to R26 are the same or different from each other and each independently represents hydrogen; Fluorine; Goat; bromine; iodine; A nitro group; A carboxy group; Alkyl ester groups; Cycloalkyl ester groups; Arylalkyl ester groups; A hydroxy group; -OC (= O) CH _3; A sulfonic acid group (-SO ₃ H); Methyl group; t-butyl group; Methoxy group; A phenyl group; Or a naphthyl group.

In Formula 1, at least one of Q1, Q2, and R17 to R26 may be bonded to adjacent functional groups to form a substituted or unsubstituted aromatic ring.

Specifically, in Formula 1, at least one of Q1, Q2, and R17 to R26 may be bonded to adjacent functional groups to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

In the above formula (1), Y1 and Y2 may each independently be a direct bond.

The compound of one embodiment may be represented by the following general formula (1-1).

[Formula 1-1]

In Formula 1-1,

A is a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms, and R27 and R28 are the same or different and are each independently a phenyl group or a naphthyl group.

The compounds of this embodiment may be represented by the following general formulas (1-2) or (1-2).

[Formula 1-2]

[Formula 1-3]

In the above formulas (1-2) or (1-3), A represents a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms, and R28 to R31 are the same or different from each other and are each independently a phenyl group or a naphthyl group.

The compound of one embodiment may be represented by any one of the following formulas (1-4) to (1-15).

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

Meanwhile, according to another embodiment of the present invention, a colorant composition comprising the compound of one embodiment may be provided.

The content of the above-mentioned compounds includes the above-mentioned contents in relation to the above embodiment.

The colorant composition may further include at least one of a dye and a pigment. For example, the colorant composition may include only the compound of one embodiment, but it may include the compound of one embodiment and one or more dyes, or may include the compound of one embodiment and one or more pigments, One or more dyes, and one or more pigments.

The specific kind of the dye (Dye) or the pigment (Pigment) used herein is not particularly limited, and various materials widely used in the field of color filters or displays can be used without limitation.

According to another embodiment of the present invention, the colorant composition of the compound of one embodiment or the colorant composition of the another embodiment; Binder resin; Multifunctional monomers; Photoinitiators; And a solvent can be provided.

The content of the above-mentioned compound includes the above-mentioned contents in relation to the above embodiment, and the content of the coloring material composition includes the above-mentioned contents regarding the other embodiments.

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, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate. 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 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 at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Ethyl) -6- (2-methylbenzoyl-3-yl) -1- (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.

The content of the compound may be 5% by weight to 60% by weight based on the total weight of the solid content in the photosensitive resin composition. The content of the binder resin may be 1 wt% to 60 wt%, the content of the photoinitiator may be 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer may be 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.

Further, the photosensitive resin composition may further include an antioxidant. The content of the antioxidant is 0.1% by weight to 20% by weight based on the total weight of the solid components in the photosensitive resin composition.

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).

The photosensitive resin composition may further comprise one or two or more additives selected from the group consisting of a photo-crosslinking agent, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant and a leveling agent. The content of the additive is 0.1% by weight to 20% by weight based on the total weight of the solid components in the photosensitive 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.

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.

The photosensitive resin composition may be a pigment dispersed type photosensitive material for forming a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode, And can be used for a photosensitive material for forming a photosensitive layer, a photosensitive material for forming a column spacer, a photosensitive layer, a photocurable ink, 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) I do not.

According to another embodiment of the present invention, a photosensitive material prepared using the photosensitive resin composition of the embodiment may be provided.

The content of the photosensitive resin composition includes the above-mentioned contents in relation to the other embodiments.

Specifically, the photosensitive resin composition of the embodiment can be applied on a substrate 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 photosensitive resin composition include, but are not limited to, mercury vapor arc, carbon arc, and Xe arc, which emits light having a wavelength of 250 nm to 450 nm.

According to another embodiment of the present invention, a color filter including the photosensitive material of the embodiment may be provided.

The content of the photosensitive material includes the above-mentioned contents in relation to the other embodiments.

The color filter can be produced using a photosensitive resin composition containing the compound of one embodiment. The photosensitive resin composition is coated on a substrate to form a coating film, and the color filter can be formed by exposing, developing and curing the coating film.

The photosensitive resin composition is excellent in heat resistance, has less change in color due to heat treatment, and can provide a color filter having a high color reproducibility and a high luminance and contrast ratio even in a curing process in the production of a color filter.

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.

According to another embodiment of the present invention, a display device including the color filter of the above embodiment may be provided.

The content of the color filter includes the above-described contents of the other embodiments.

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).

According to the present invention, a compound having excellent color characteristics, heat resistance, and solvent resistance, a photosensitive resin composition using the same, and a photosensitive material, a color filter, and a display device manufactured using the same can be provided.

The invention will be described in more detail in the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

≪ Preparation Examples 1 to 2 &

Production Example 1

Compound A-1 was synthesized through the reaction shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

25 g (157.041 mmol, 1 eq) of Compound 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 占 폚, and 19.07 g (188.454 mmol, 1.2 eq) of triethylamine (TEA) was slowly added dropwise to the reaction solution.

Then, 30.787 g (174.321 mmol, 1.11 eq) of Compound 2 was 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 the organic layer and the water layer were separated. The separated water layer was further extracted with 200 ml of MC. 200 ml of a 5% K ₂ CO ₃ solution was added to the organic layer and stirred, followed by separation of the organic layer. Distilled 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 to 500 ml of a solution of ethyl acetate (EA) n-hexane (n-Hexane) 1: 3 and stirred, filtered under reduced pressure and the precipitate was dried at 80 ° C for one day to obtain Compound A- 1 (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)

Production Example 2

Compound A-2 was synthesized in the same manner as in Preparation Example 1, except that 39.339 g (174.321 mmol, 1.11 eq) of Compound 3 was used instead of Compound 2 as shown in Reaction Scheme 2 below.

 [Reaction Scheme 2]

≪ Examples 1 to 12: Preparation of compound, photosensitive resin composition and photosensitive material &

Example 1

(1) Preparation of Compound

Compound C-1 was synthesized through the reaction shown in Reaction Scheme 3 below.

[Reaction Scheme 3]

1 g (3.399 mmol) of A-1, 0.518 g (1.670 mmol) of B-1, 1 g of Benzoic acid and 10 ml of methyl benzoate were placed in a 2-neck round bottom flask and stirred at 180 ° C for 5 hours. Then, 100 ml of methanol was added, and the precipitated substance was filtered under reduced pressure and then dried in an oven. As a result, 1.05 g (1.2024 mmol) of the compound C-1 was obtained. (Yield: 72%)

The results of the MS measurement of the compound C-1 are shown below.

Ionization mode =: APCI +: m / z = 873 [M + H] +, Exact Mass: 872

(2) Preparation of Photosensitive Resin Composition

5.554 g of the compound C-1 synthesized above, a binder resin [a copolymer of benzyl methacrylate and methacrylic acid (having a molar ratio of 70:30, an acid value of 113 KOH mg / g, a weight average molecular weight of 20,000 g / mol as measured by GPC (I-369, BASF), 1.016 g of an additive (F-475, manufactured by DIC), 10.376 g of a photopolymerizable compound , 12.443 g of Dipentaerythritol hexaacrylate (DPHA), and 68.593 g of a solvent (Propylene Glycol Monomethyl Ether Acetate, PGMEA) were mixed to prepare a photosensitive resin composition.

(3) Manufacture of photosensitive material

The above photosensitive resin composition was spin-coated on glass (5 cm X 5 cm) and pre-baked at 100 ° C for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 250 μm, and the entire substrate was irradiated with an exposure dose of 40 mJ / cm 2 using an exposure machine. Thereafter, 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.

Example 2

(1) Preparation of Compound

(1.051 mmol) of Compound C-2 was synthesized in the same manner as in Example 1, except that 0.493 g (1.590 mmol) of B-2 was used instead of Compound B-1 as shown in Reaction Scheme 4 below. (Yield: 66%).

The results of the MS measurement of the compound C-2 are shown below.

Ionization mode =: APCI +: m / z = 857 [M + H] +, Exact Mass: 856

[Reaction Scheme 4]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-2 was used instead of the compound C-1.

Example 3

(1) Preparation of Compound

1.1 g (1.284 mmol) of Compound C-3 was synthesized in the same manner as in Example 1, except that 0.493 g (1.590 mmol) of B-3 was used instead of Compound B-1 as shown in Reaction Scheme 5 below. (Yield: 81%).

The results of MS measurement of the compound C-3 are shown below.

Ionization mode =: APCI +: m / z = 857 [M + H] +, Exact Mass: 856

[Reaction Scheme 5]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-3 was used in place of the compound C-1.

Example 4

(1) Preparation of Compound

(1.343 mmol) of Compound C-4 was synthesized in the same manner as in Example 1, except that 0.512 g (1.590 mmol) of B-4 was used instead of Compound B-1 as shown in Reaction Scheme 6 below. (Yield: 85%).

The results of MS measurement of the compound C-4 are shown below.

Ionization mode =: APCI +: m / z = 884 [M + H] +, Exact Mass: 885

[Reaction Scheme 6]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-4 was used instead of the compound C-1.

Example 5

(1) Preparation of Compound

0.82 g (0.843 mmol) of Compound C-5 was synthesized in the same manner as in Example 1, except that 0.652 g (1.590 mmol) of B-5 was used instead of Compound B-1 as shown in Reaction Scheme 7 below. (Yield: 53%).

The results of the MS measurement of the compound C-5 are shown below.

Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948

[Reaction Scheme 7]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-5 was used in place of the compound C-1.

Example 6

(1) Preparation of Compound

1.3 g (1.288 mmol) of Compound C-6 was synthesized in the same manner as in Example 1, except that 0.706 g (1.590 mmol) of B-6 was used instead of Compound B-1 as shown in the following Reaction Scheme 8 (Yield: 81%).

The results of the MS measurement of the compound C-6 are shown below.

Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948

[Reaction Scheme 8]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1, except that the compound C-6 was used in place of the compound C-1.

Example 7

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used in place of the compound A-1 and 0.444 g (1.431 mmol) of the compound B-1 was used as in the following Reaction Scheme 9 1 g (1.030 mmol) of Compound C-7 was synthesized (Yield: 71.9%).

The results of the MS measurement of the compound C-7 are shown below.

Ionization mode =: APCI +: m / z = 973 [M + H] +, Exact Mass: 972

[Reaction Scheme 9]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1, except that the compound C-7 was used instead of the compound C-1.

Example 8

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used in place of the compound A-1 and 0.421 g (1.431 mmol) of the compound B-2 was used as in the following reaction scheme 10 0.9 g (0.941 mmol) of Compound C-8 was synthesized (Yield: 65.8%).

The results of MS measurement of the compound C-8 are shown below.

Ionization mode =: APCI +: m / z = 957 [M + H] +, Exact Mass: 956

[Reaction Scheme 10]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-8 was used instead of the compound C-1.

Example 9

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used instead of the compound A-1 and 0.421 g (1.431 mmol) of the compound B-3 was used as in the following Reaction Scheme 11 0.9 g (0.941 mmol) of Compound C-9 was synthesized (Yield: 65.8%).

The results of the MS measurement of the compound C-9 are shown below.

Ionization mode =: APCI +: m / z = 957 [M + H] +, Exact Mass: 956

[Reaction Scheme 11]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1, except that the compound C-9 was used instead of the compound C-1.

Example 10

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used instead of the compound A-1 and 0.461 g (1.431 mmol) of the compound B-4 was used as in the following Reaction Scheme 12 1 g (1.015 mmol) of Compound C-10 was synthesized (Yield: 71%).

The results of MS measurement of the compound C-10 are shown below.

Ionization mode =: APCI +: m / z = 985 [M + H] +, Exact Mass: 984

[Reaction Scheme 12]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-10 was used instead of the compound C-1.

Example 11

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used in place of the compound A-1 and 0.586 g (1.431 mmol) of the compound B-5 was used as in the following Reaction Scheme 13 0.78 g (0.730 mmol) of Compound C-11 was synthesized (Yield: 51%).

The results of MS measurement of the compound C-11 are shown below.

Ionization mode =: APCI +: m / z = 1073 [M + H] +, Exact Mass: 1072

[Reaction Scheme 13]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-11 was used in place of the compound C-1.

Example 12

(1) Preparation of Compound

Except that 1 g (2.862 mmol) of A-2 was used instead of the compound A-1 and 0.636 g (1.431 mmol) of the compound B-6 was used as in the following reaction scheme 14 1.16 g (1.045 mmol) of the compound C-12 was synthesized. (Yield: 73%)

The results of the MS measurement of the compound C-12 are shown below.

Ionization mode =: APCI +: m / z = 1107 [M + H] +, Exact Mass: 1106

[Reaction Scheme 14]

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1 except that the compound C-12 was used in place of the compound C-1.

≪ Comparative Example: Preparation of Compound, Photosensitive Resin Composition and Photosensitive Material >

Comparative Example 1

(1) Preparation of Compound

PY138 pigment having the following chemical structure was used.

(2) Preparation of Photosensitive Resin Composition and Photosensitive Material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in Example 1, except that the PY138 pigment was used in place of the compound C-1.

<Experimental Example: Measurement of Physical Properties of Compound, Photosensitive Resin Composition, and Photosensitive Material>

The physical properties of the photosensitive resin composition or photosensitive material obtained in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Tables 1 to 3.

1. Solvent resistance

The solubility of each of the compounds obtained in the above Examples and Comparative Examples in an organic solvent of dimethylformamide (DMF) was measured, and the solvent resistance was evaluated according to the following criteria, and the results are shown in Table 1.

○: solubility of 1% or more

X: less than 1% solubility

Results of Experimental Example 1 division Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Comparative Example 1
Solvent resistance ○ ○ ○ ○ ○ ○ ○ ○ ○ ○ ○ ○ X

As shown in Table 1, the compounds of the Examples had improved solubility in an organic solvent as compared with Comparative Examples. The increase in solubility appears to be due to the SO ₃ functionality contained in the compounds of the above examples.

Accordingly, unlike common pigments which require dispersion through a derivative, a dispersant, or the like, when dissolving an organic solvent, the compound of the above Examples does not require a derivative or a dispersant when dissolved in an organic solvent, and can be easily applied commercially.

2. Evaluation of heat resistance

The transmittance spectrum of the visible light region in the range of 380 nm to 780 nm was obtained by using a spectroscope (MCPD-Otsuka Co., Ltd.) for the prebake substrate obtained in the above example.

Thereafter, the prebake substrate was further subjected to post bake at 230 ° C for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

Eab calculation was performed using the obtained transmittance spectrum and the value E (L *, a *, b *) obtained using the C light source backlight, and it is shown in Table 2 below.

ΔE (L *, a *, b *) = {(ΔL *) 2 + (Δa *) 2 + (Δb *) 2} 1/2

 (L *, a *, b *) after the post heat treatment, and Eb = (DELTA E

The small ΔEab value means that the color heat resistance is excellent. In the case of the color filter material, when the ΔEab value is less than 3, it is recognized as an excellent material.

Results of Experimental Example 2 division Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12  Eab 2.85 0.47 0.81 2.11 0.70 0.40 0.71 1.53 0.34 0.11 0.34 0.85

As shown in Table 2, the photosensitizer of the examples had an Eab value of less than 3, indicating excellent color heat resistance.

Claims (15)

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

In Formula 1,
Y1 and Y2 are the same or different and are each independently a direct bond or -CQ1Q2-,
A is a direct bond; Ether group; Carbonyl group; Ester group; Diester group; Peroxy group; An amino group; Imino; Imide; Azo group; An amide group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; A heteroalkylene group having 1 to 10 carbon atoms; A haloalkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 3 to 20 carbon atoms,
R1 to R26, Q1 and Q2 are the same or different from each other 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 method according to claim 1,
A is a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms.
3. The method of claim 2,
Wherein said diastere group comprises a functional group represented by the following formula:
(2)

In Formula 2, X is an alkylene group having 1 to 10 carbon atoms; A heteroalkylene group having 1 to 10 carbon atoms; A haloalkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 20 carbon atoms; Or a heteroarylene group having 3 to 20 carbon atoms.
The method according to claim 1,
At least one of Q1, Q2, R17 to R26 is bonded to adjacent functional groups to form a substituted or unsubstituted aromatic ring.
The method according to claim 1,
And Y1 and Y2 are each a direct bond.
The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 1-1:
[Formula 1-1]

In Formula 1-1,
A is a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms,
R27 and R28 are the same or different and are each independently a phenyl group or a naphthyl group.
The method according to claim 1,
(1) is represented by the following general formula (1-2) or (1-2): Compound
[Formula 1-2]

[Formula 1-3]

In the above formulas (1-2) or (1-3)
A is a direct bond; Ether group; Carbonyl group; Diester group; Sulfone group; An alkylene group having 1 to 10 carbon atoms; Or a haloalkylene group having 1 to 10 carbon atoms,
R28 to R31 are the same or different and are each independently a phenyl group or a naphthyl group.
The method according to claim 1,
Wherein the formula 1 is represented by any one of the following formulas 1-4 to 1-15:
[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

A colorant composition comprising the compound of claim 1.
10. The method of claim 9,
At least one of a dye and a pigment.
A colorant composition according to claim 1 or a colorant composition according to claim 9; Binder resin; Multifunctional monomers; Photoinitiators; And a solvent.
12. The method of claim 11,
Wherein the content of the compound is 5 wt% to 60 wt% based on the total weight of the solid content in the photosensitive resin composition.
A photosensitive material comprising the photosensitive resin composition of claim 11.
A color filter comprising the photosensitive material of claim 13.
A display device comprising the color filter of claim 14.