KR20210039113A - Compound, photosensitive resin composition comprising same, photosensitive material, color filter, display device - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, a photosensitive resin composition comprising the same, a photosensitive material, a color filter, and a display device. The compound according to an exemplary embodiment of the present specification can be applied in the field of color filters and can reduce the content of a yellow colorant for supplementing a green colorant.

Description

Compound, photosensitive resin composition containing the same, photosensitive material, color filter, display device {COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING SAME, PHOTOSENSITIVE MATERIAL, COLOR FILTER, DISPLAY DEVICE}

The present specification relates to a compound, and a photosensitive resin composition comprising the same. It also relates to a photosensitive material, a color filter, and a display device.

In recent years, a color filter is required to have high luminance and high contrast ratio. In addition, one of the main objectives of the development of a display device is to differentiate display device performance through improved color purity and to improve productivity in a manufacturing process.

Conventionally, since the pigment type used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, they are aggregated in a color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to large aggregated particles. This scattering of polarized light has been pointed out as a major factor in lowering the contrast ratio. Efforts have been made to improve brightness and contrast ratio through ultra-fine pigmentation and dispersion stabilization, but the degree of freedom in selecting a color material for realizing color coordinates for a high-color-purity display device is limited. In addition, the already developed color material, particularly the pigment dispersion method using a pigment, has reached its limit in improving the color purity, brightness, and contrast ratio of a color filter using the same.

Accordingly, there is a need to develop a new color material capable of improving color reproduction, luminance, and contrast ratio by increasing color purity.

Korean Patent Publication No. 2001-0009058

The present specification is to provide a compound, a photosensitive resin composition including the same, a photosensitive material, a color filter, and a display device including the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X is CH,

R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

r1 is an integer from 0 to 4, and when r1 is 2 or more, R1 is the same as or different from each other,

r2 is an integer from 0 to 6, and when r2 is 2 or more, R2 is the same as or different from each other.

An exemplary embodiment of the present specification, the above-described compound; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising at least one selected from the group consisting of a solvent.

An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.

An exemplary embodiment of the present specification provides a color filter including the photosensitive material.

An exemplary embodiment of the present specification provides a display device including the color filter.

The compound according to an exemplary embodiment of the present specification may be applied in the field of color filters, and by effectively absorbing the maximum absorption wavelength range of 420 nm to 460 nm than the existing yellow color material, the content of the yellow color material for supplementing the green color material is reduced. Can be reduced.

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

In the present specification, when a member is positioned “on” another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X is CH,

R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

r1 is an integer from 0 to 4, and when r1 is 2 or more, R1 is the same as or different from each other,

r2 is an integer from 0 to 6, and when r2 is 2 or more, R2 is the same as or different from each other.

Since the compound according to the present specification contains 4-Methylfuro[3,4-c]quinoline-1,3-dione, the conjugation can be extended to a longer wavelength than that of phthalic anhydride. The part introduces a substituted or unsubstituted aromatic ring with a strong electron donating ability at the 8th position of the quinoline, resulting in an additional long wavelength of the maximum absorption wavelength. Additionally, heat resistance may be improved through 4-phenylfuro[3,4-c]quinoline-1,3-dione.

The compound according to the present specification has a core structure in which conjugation is extended to a phthalic anhydride structure, and thus has excellent heat resistance and excellent absorbance. In addition, it is possible to effectively absorb 420 nm to 460 nm, which is a wavelength region of a yellow color material to complement the green color material.

Examples of the substituents of the compound represented by Formula 1 are described below, but are not limited thereto.

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

Means a site bonded to another substituent or a bonding portion.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Alkoxy group; Ester group; Alkyl group; Cycloalkyl group; Aryl group; Heteroaryl group; It means that it is substituted with one or more substituents selected from the group containing a heterocyclic group containing one or more of N, O, S, or P atoms, or does not have any substituents.

In the present specification, the "adjacent" substituent refers to a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. can do. For example, two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" substituents.

In the present specification, the ring means an aromatic or aliphatic ring in that adjacent substituents can be bonded to form a “ring”. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The aryl group and the heteroaryl group may be described below. In addition, the ring may be an aliphatic ring, and the aliphatic ring may be a cycloalkyl group. The description below may be applied to the cycloalkyl group.

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

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, the ester group may be represented by -COOR100, and R100 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. In the ester group, oxygen of the ester group may be substituted with a C 1 to C 25 linear, branched or cyclic chain alkyl group or a C 6 to C 30 aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-oxy And the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited to these. The heterocyclic group may be aromatic or aliphatic.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the alkylene group means that the alkane has two bonding sites. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, and more specifically 1 to 10 carbon atoms.

In the present specification, the heteroalkylene group means that there are two bonding positions in an alkane containing O, N or S as a hetero atom. The heteroalkylene group may be linear, branched or cyclic. The number of carbon atoms of the heteroalkylene group is not particularly limited, but, for example, has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 1-1 below.

[Formula 1-1]

In Formula 1-1, the definition of the substituent is the same as that in Formula 1.

In an exemplary embodiment of the present specification, X is CH.

When X is N, since tautomerism of the core structure represented by Chemical Formula 1 is impossible, hydrogen bonding in the molecule is impossible, heat resistance is lowered, and planarity is relatively reduced, so that a long wavelength cannot be achieved. Accordingly, when X is N, it exhibits different material properties than when X in Formula 1 is CH according to the present specification.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted C 3 to C 20 heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 1 to 12 carbon atoms; Or a substituted or unsubstituted C 3 to C 10 heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 1 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group.

In the exemplary embodiment of the present specification, R is a halogen group, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group with a substituted or unsubstituted alkoxy group.

In the exemplary embodiment of the present specification, R is a fluorine, chlorine, hydroxy group, nitro group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group with a substituted or unsubstituted methoxy group. .

In the exemplary embodiment of the present specification, R is a phenyl group unsubstituted or substituted with fluorine, chlorine, hydroxy group, nitro group, methyl group, trifluoromethyl group, ethyl group, or methoxy group.

In an exemplary embodiment of the present specification, R is a phenyl group.

In an exemplary embodiment of the present specification, R is a methyl group.

In an exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group having 3 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R is a substituted or unsubstituted furanyl group.

In an exemplary embodiment of the present specification, R is a furanyl group.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic ring having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic ring having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic ring having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted methyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms, or adjacent substituents are bonded to each other to form a substituted or unsubstituted benzene ring; A substituted or unsubstituted pyridine ring; It forms a substituted or unsubstituted cyclohexane ring.

In an exemplary embodiment of the present specification, R1 is hydrogen; Methoxy group; Methyl group; Trifluoromethyl group; Or an n-propyl group, or adjacent R 1 is bonded to each other to form a benzene ring or a cyclohexane ring. In an exemplary embodiment of the present specification, R1 is hydrogen.

In an exemplary embodiment of the present specification, R2 is hydrogen; Naphthyl group; A phenyl group substituted with an ester group or a trifluoromethyl group; Or a naphthyl group, or adjacent R2 combine with each other to form a pyridine ring substituted with a methyl group.

The phenyl group substituted with the ester group may be represented by the following structure.

는 상기 화학식 1에 연결되는 부분을 의미한다. In the above structure,

Means a moiety connected to Formula 1 above.

In an exemplary embodiment of the present specification, R2 is a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, R2 is a naphthyl group.

In an exemplary embodiment of the present specification, R2 may be represented by the following Formula A.

[Formula A]

In Formula A,

는 상기 화학식 1에 연결되는 부분을 의미하고,

Means a moiety connected to Formula 1,

Ra is hydrogen; Or a substituted or unsubstituted aryl group,

ra is an integer of 1 to 5, and when ra is 2 or more, Ra is the same as or different from each other.

In the exemplary embodiment of the present specification, Ra is hydrogen; Or a substituted or unsubstituted aryl group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ra is hydrogen; Or a substituted or unsubstituted aryl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ra is hydrogen; Or a substituted or unsubstituted aryl group having 1 to 12 carbon atoms.

In an exemplary embodiment of the present specification, Formula A may be represented by the following Formula A-1.

[Formula A-1]

In the exemplary embodiment of the present specification, the compound represented by Formula 1 has a maximum absorption wavelength between 420 nm and 460 nm.

Preferably, the compound represented by Formula 1 may have a maximum absorption wavelength between 420 nm and 453 nm, and more preferably, may have a maximum absorption wavelength between 424 nm and 451 nm.

The maximum absorption wavelength may be measured using a solution obtained by dissolving the compound represented by Chemical Formula 1 in N-Methyl-2-pyrrolidone (NMP) and diluted with toluene.

The maximum absorption wavelength can be measured using a UV/Vis Spectrophotometer (PerkinElmer's LAMBDA 365).

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may have a molar absorption coefficient ^{of 16,600 M -1} cm ^-1 to 33,200 M ^-1 cm ^-1.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may have a molar absorption coefficient ^{of 22,900 M -1} cm ^-1 to 33,200 M ^-1 cm ^-1.

Specifically, the molar absorption coefficient may be 22,990 M ^-1 cm ^-1 to about 33,100 M ^-1 cm ^-1.

When the compound represented by Formula 1 satisfies the molar extinction coefficient in the above range, there is an advantage that the content of the colorant to be introduced can be relatively reduced when the colorant for color filters is combined.

The molar extinction coefficient can be measured using a solution obtained by dissolving the compound represented by Formula 1 in N-Methyl-2-pyrrolidone (NMP) and diluted with toluene.

The molar extinction coefficient can be measured using a UV/Vis Spectrophotometer (PerkinElmer's LAMBDA 365).

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas, but is not limited thereto.

An exemplary embodiment of the present specification is the compound; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising at least one selected from the group consisting of a solvent.

An exemplary embodiment of the present specification is the compound; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.

In the exemplary embodiment of the present specification, the photosensitive resin composition may further include at least one of a dye and a pigment in addition to the compound of Formula 1 above. For example, the photosensitive resin composition may include only the compound of Formula 1, but includes the compound of Formula 1 and at least one dye, the compound of Formula 1 and at least one pigment, or It may also contain compounds, one or more dyes and one or more pigments.

In one embodiment of the present specification, the dye and the pigment are metal-complex (metal-complex)-based compound; Azo-based compounds; Metal azo-based compounds; Quinophthalone-based compounds; Isoindoine-based compounds; Methine-based compounds; Phthalocyanine-based compounds; Metal phthalocyanine-based compounds; Porphyrin-based compounds; Metal porphyrin-based compounds; Tetra aza porphyrin-based compounds; Metal tetra aza porphyrin series compounds; Cyanine-based compounds; Xanthene-based compounds; Metal dipyrromethane series compounds; Boron dipyrromethane series compounds; Metal dipyrromethane series compounds; Anthraquinone-based compounds; Diketopyrrolopyrrole-based compounds; Triarylmethane series compounds; And one or more is selected from the group consisting of perylene-based compounds.

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 the photosensitive resin composition.

The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength of the film and a monomer imparting alkali solubility, and may further include a binder generally used in the art.

Polyfunctional monomers that impart mechanical strength of the film include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.

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 (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofurpril (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, acyloctyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) )Acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) Acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.

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

The monomer imparting alkali solubility is not particularly limited as long as it includes an acid group, and for example, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono- 1 selected from the group consisting of 2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, and ω-carboxy polycaprolactone mono(meth)acrylate It is preferable to use more than one species, but is not limited thereto.

According to an exemplary embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg/g, and the weight average molecular weight is 1,000 g/mol to 50,000 g/mol.

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and specifically, 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, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more.

The photoinitiator is not particularly limited as long as it is an initiator that generates a radical by light to trigger crosslinking, but is, for example, selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. It may be one or more.

The acetophenone compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like, but is not limited thereto.

As the biimidazole-based compound, 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , Is not limited thereto.

The triazine compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -Bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionamide, 2,4-bis(trichloro Methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s -Triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.

The oxime compound is 1,2-octadione-1-(4-phenylthio)phenyl-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii 124), ethanone-1-(9-ethyl) -6-(2-methylbenzoyl-3-yl)-1-(O-acetyloxime) (CGI 242), N-1919 (Adeca), and the like, but are not limited thereto.

The solvent is 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, dimethylformamide (DMF). Chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclo Hexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol Methyl ether acetate, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol mono It may be one or more selected from the group consisting of methyl ether, but is not limited thereto.

In an exemplary embodiment of the present specification, based on 100 parts by weight of the photosensitive resin composition, the compound is 0.1 to 60 parts by weight, the binder resin is 1 to 85 parts by weight, and the polyfunctional monomer is 5 to 30 parts by weight, , The photoinitiator is 0.5 to 10 parts by weight, and the solvent provides a photosensitive resin composition that is 10 to 60 parts by weight.

In one embodiment of the present specification, based on 100 parts by weight of the photosensitive resin composition, the compound is 0.1 to 60 parts by weight, the binder resin is 1 to 85 parts by weight, and the solvent is 10 to 60 parts by weight. It provides a resin composition.

In one embodiment of the present specification, the photosensitive resin composition may further include a leveling agent and an adhesive agent.

In the exemplary embodiment of the present specification, the photosensitive resin composition may further include 0.01 to 10 parts by weight of the leveling agent and 0.01 to 10 parts by weight of the adhesive agent based on 100 parts by weight of the photosensitive resin composition.

The total weight of the solid content refers to the sum of the total weight of components excluding the solvent in the photosensitive resin composition. The basis of the solid content and the weight percent based on the solid content of each component can be measured by a general analysis means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the photosensitive resin composition further comprises one or two or more additives selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and a dispersant. Includes.

According to an exemplary embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.

The photo-crosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds, such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone 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-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. 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 compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

The curing accelerator is used to increase curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropio) Nate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane- At least one selected from the group consisting of tris (3-mercaptopropionate) may be used.

The adhesion promoter used in the present specification includes methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxysilane One or more of methacryloyl silane coupling agents such as may be selected and used, and one or more of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. as an alkyl trimethoxy silane. You can choose and use it.

The surfactant is a silicone surfactant or a fluorine surfactant, and specifically, the silicone surfactant is BYK-Chemie's 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-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but are not limited thereto.

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-based thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy Benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethylester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-di- t-butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol Hindered phenol-based primary antioxidants such as ester); Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine Based secondary antioxidants; Thio such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane (Thio)-based secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1 ,1'-biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester ((1,1'-Biphenyl)-4,4 And phosphite-based secondary antioxidants such as'-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, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy. Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology in the art It may include those generally known in the field.

The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants, and the like can be used. These may be used individually or in combination of two or more.

Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylate, There may be at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but not limited thereto, all those commonly used in the art may be used. Specifically, F-554 can be applied.

The adhesive agent is not particularly limited, and all those generally used in the art may be used. Specifically, KBM-503 can be applied.

An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.

The photosensitive material including the photosensitive resin composition may mean that the photosensitive resin composition of the present specification is applied and cured on a substrate by an appropriate method to form a photosensitive material in the form of a thin film or pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. In addition, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

Light sources for curing the photosensitive resin composition according to the present specification include, for example, mercury vapor arcs, carbon arcs, Xe arcs, etc. that emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.

The photosensitive resin composition according to the present specification is a pigment dispersion 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 a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode. , Photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.

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

The color filter may be manufactured by using a photosensitive resin composition including the compound represented by Chemical Formula 1. A color filter may be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.

The photosensitive resin composition according to an exemplary embodiment of the present specification has excellent heat resistance and has little change in color due to heat treatment, so that it is possible to provide a color filter having high color reproducibility and high luminance and contrast ratio even by a curing process when manufacturing a color filter. I can.

The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type 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 exemplary embodiment, the color filter may further include an overcoat layer.

A grid-shaped black pattern called a black matrix may be disposed between the color pixels of the color filter for the purpose of improving contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching treatment may be used. However, in consideration of the high cost of the process, high reflectance of chromium, and environmental pollution due to chromium waste, a resin black matrix using a pigment dispersion method capable of fine processing can be used.

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material is relatively increased. There is an advantage that does not work.

An exemplary embodiment of the present specification provides a display device including a color filter.

The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be one of a thin film transistor (LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

<Example>

[Production Example 1: Preparation of Compound A]

In a 500ml beaker, add isatin (7.36g, 50mmol, 1.0eq) and 150ml of 25% NaOH aqueous solution. After stirring at room temperature for 1 hour, methyl acetoacetate (11.6g, 100mol, 2.0eq) was added and stirred for 12 hours. A white solid was then formed. When the reaction was completed, 175 ml of a 10% HCl aqueous solution was slowly added, stirred, and filtered. After washing with a little water and drying in a vacuum oven (oven) at 60 ℃ compound [A] (10.6g, 45.8mmol, 91.6%) was obtained.

Ionization mode: APCI +:m/z = 232 [M+H]+, Exact Mass: 231.05

[Production Example 2: Preparation of Compound A-1]

5ml of acetic anhydride was added to a 100ml 2-neck round bottom flask, and [A] (1.23g, 5.3mmol, 1.0eq) was dispersed under a nitrogen atmosphere and heated at 140°C. 5ml pyridine was added and reacted at 60°C for 2 hours. After that, beige crystals precipitated. After sufficiently cooling, the precipitate was filtered and washed with anhydrous hexane. It dried under a nitrogen atmosphere to obtain a compound [A-1] (0.9g, 4.2mmol, 79.4%).

[Production Example 3: Preparation of Compound A-2]

Isatin (7.36g, 50.0mmol, 1.0eq), 25% NaOH aqueous solution 150ml, ethyl benzoylacetate (17.79g, 92.5mmol, 1.85eq), 10% HCl aqueous solution 175ml in the same manner as the synthesis method of Compound A of Preparation Example 1 Proceeding, [A-2] (10.5g, 35.8mmol, 71.6%) was obtained.

Ionization mode: APCI +:m/z = 294 [M+H]+, Exact Mass: 293.07

[Production Example 4: Preparation of Compound A-3]

[A-2] (10.0g, 34.1mmol, 1.0eq), acetic anhydride 35ml, pyridine 35ml proceed in the same manner as the synthesis method of Compound A-1 of Preparation Example 2 [A-3] (3.6 g, 13.0mmol, 38.4%) was obtained.

[Production Example 5: Preparation of Compound B]

In a 100ml 2-neck round bottom flask, quinaldine (0.55g, 3.84mmol, 1eq), [A-1] (0.90g, 4.22mmol, 1.1eq) and benzoic acid (4.0g, 32.8mmol, 8.5eq) methyl benzoate ( 6.0ml, 6.48g) was added. It reacts at 180~200℃ for 2 hours. After completion of the reaction, the mixture was cooled for 30 minutes, methyl alcohol was added, and sufficiently stirred. Filtered and dried to give a dark brown [B] (0.75g, 2.2mmol, 57.7%).

Ionization mode: APCI +:m/z = 338 [M+H]+, Exact Mass: 338.11

[Production Example 6: Preparation of Compound B-1]

In a 100ml 2-neck round bottom flask, quinaldine (0.15g, 1.05mmol, 1.0eq), [A-3] (0.32g, 1.15mmol, 1.1eq) and benzoic acid (1.05g, 8.6mmol, 8.2eq) methyl benzoate (1.57ml, 1.70g) was added. It was reacted for 5 hours at 180 ~ 200 ℃. After the reaction was completed, it was cooled for 30 minutes, methyl alcohol was added, and sufficiently stirred. Filtered and dried to obtain a yellowish brown [B-1] (0.10g, 0.25mmol, 23.8%).

Ionization Mode: APCI +:m/z = 401 [M+H]+, Exact Mass: 400.12

[Production Example 7: Preparation of Compound C]

Add 300ml of acetonitrile to a 1L 3-neck round bottom flask and add 2-methyl-8-quinolinol (29.5g, 0.186mol, 1.0eq), perfluoro-1-butanesulfonyl fluoride (50.0ml, 84.1g, 0.278mol, 1.5eq). Melted. Potassium carbonate (77.1g, 0.558mol, 3.0eq) was slowly dissolved in 75ml of distilled water, put into a flask, and stirred at 40℃ for 16 hours. Upon completion of the reaction, the solvent was removed, extracted with ethyl acetate and distilled water, and then water was removed and recrystallized with hexane. After filtration, the mixture was dried with nitrogen to obtain a white compound [C] (47.2g, 0.107mmol, 57.7%).

[Production Example 8: Preparation of Compound C-1]

[C] (20.0g, 45.3mmol, 1.0eq) and naphthalene-1-boronic acid (7.8g, 45.3mmol, 1.0eq) were added to a 500mL 2-neck round bottom flask and dissolved in 100ml of dioxane. Potassium carbonate (12.5g, 90.6mmol, 2.0eq) and tetrakis (triphenylphosphine) palladium (0) (524mg, 1.0 mol%) dissolved in 30 ml of distilled water were added and refluxed for 1 hour. When the reaction was over, the solvent was removed, only organic matter was extracted with chloroform and distilled water, and water was removed with magnesium sulfate. Recrystallized, filtered and washed. After drying, beige [C-1] (5.0g, 18.5mmol, 41.0%) was obtained.

Ionization mode: APCI +:m/z = 270 [M+H]+, Exact Mass: 269.12

[Production Example 9: Preparation of Compound C-2]

[C-1] (0.87g, 3.2mmol, 1.0eq), [A-3] (0.98g, 3.5mmol, 1.1eq) and benzoic acid (3.2g, 26.2mmol, 8.2) in a 100ml 2-neck round bottom flask. eq) methyl benzoate (4.8ml, 5.2g) was added. It was reacted for 4 hours at 180 ~ 200 ℃. After completion of the reaction, methyl alcohol was added, heated, stirred sufficiently, and filtered. Organic matter was extracted with chloroform and distilled water, the solvent was removed, purified with MeOH, filtered and dried to obtain [C-2] (1.3g, 2.4mmol, 76.4%) as a yellow solid.

Ionization mode: APCI +:m/z = 527 [M+H]+, Exact Mass: 526.17

Compound of Comparative Example 1

[Production Example 10: Preparation of Comparative Example Compound]

In a 250ml 2-neck round bottom flask, add 8-aminoquinaldine (5g, 31.6mmol, 1.0eq), tetrachlorophthalic anhydride (19.8g, 69.5mmol, 2.2eq), zinc chloride (1.29, 9.5mmol, 0.3eq) and 1-chloronaphthalene. The reaction was carried out at 220° C. for 4 hours. Cool to 180℃, add N-Methyl-2-pyrrolidone (NMP), and heat at 200℃ for 1 hour. After completion of the reaction, the product was filtered, washed and dried to obtain [Comparative Example] (18.0g, 25.9mmol, 82.1%).

Ionization Mode: APCI +:m/z = 694 [M+H]+, Exact Mass: 693.94

<Preparation of photosensitive resin composition of Example>

Example 1

Based on 100 parts by weight of the total weight of the photosensitive resin composition, 0.4 parts by weight of the compound B, 78.18 parts by weight of the binder resin A, 0.6 parts by weight of leveling agent F-554, 0.08 parts by weight of adhesive aid KBM-503, solvent (DMF, Dimethylformamide) A photosensitive resin composition Example 1 was prepared by mixing 20.74 parts by weight.

The binder resin A is a copolymer having a mass ratio of benzyl methacrylate; N-phenylmaleimide; styrene; methacrylic acid = 55:9:11:25.

Examples 2 and 3

Photosensitive resin compositions 2 and 3, respectively, were prepared in the same manner as in Example 1 of the photosensitive resin composition, except that Compound B in Example 1 was changed to the compound of Table 1 below.

<Preparation of photosensitive resin composition of Comparative Example 1>

Photosensitive resin composition Comparative Example 1 was prepared in the same manner as in Example 1 of the photosensitive resin composition, except that the compound of Example 1 was changed to the compound of Comparative Example.

Comparative Example 1 Example 1 Example 2 Example 3 compound Comparative example B B-1 C-2

<Experimental Example>

Board fabrication

The photosensitive resin compositions prepared according to Examples 1 to 3 and Comparative Example 1 were spin-coated on glass (5cm X 5cm) and pre-heat treatment (Prebake) was performed at 100° C. for 100 seconds to form a film. After the pre-heat treatment, post bake was performed at 230° C. for 20 minutes to prepare a substrate.

Heat resistance evaluation

An absorption spectrum in a wavelength range of 380 nm to 780 nm was obtained using a spectrometer (MCPD, Otsuka Co., Ltd.) for the post-heat treatment (post bake one time) prepared by the substrate manufacturing method.

In addition, the prepared post-heat treatment substrate (one post bake) was additionally treated at 230° C. for 40 minutes to obtain a transmittance spectrum in the same measurement range with the same equipment.

Using the values L*, a*, and b* obtained from the absorption spectrum obtained using the C light source as a backlight, the heat resistance (ΔEab) was calculated by the following formula 1 and shown in Table 2 below.

[Calculation 1]

△Eab(L*, a*, b*) = {(△L*) ² +(△a*) ² +(△b*) ² } ^1/2

A small ΔEab value indicates that the color change is small, indicating excellent heat resistance.

Heat resistance (△Eab) Comparative Example 1 1.42 Example 1 3.18 Example 2 1.20 Example 3 0.49

According to Table 2, compared to Comparative Example 1, ΔEab values of Examples 2 and 3 were small, and it was confirmed that the heat resistance of Examples 2 and 3 was excellent.

<Preparation of solution for measuring absorbance in Example>

Example 1

A 0.0001M solution was prepared by dissolving 0.005mmol of the compound B in 50 ml of N-Methyl-2-pyrrolidone (NMP), and 1 ml of the solution was aliquoted and diluted with 9 ml of toluene to prepare a 0.00001M solution Example 1.

Examples 2 and 3

The absorbance measurement solutions 2 and 3 were prepared in the same manner as in Example 1, except that the compound B in Example 1 was changed to the compound of Table 1 above.

<Preparation of a solution for measuring absorbance of a comparative example>

Absorbance measurement solution Comparative Example 1 was prepared in the same manner as in the absorbance measurement solution Example 1, except that the compound of Example 1 was changed to the compound of Comparative Example.

<Experimental Example>

Absorbance measurement

The absorbance measurement solution prepared under the above-described conditions was measured for the maximum absorption wavelength and the molar absorption coefficient using a UV/Vis Spectrophotometer (LAMBDA 365, manufactured by PerkinElmer), and are shown in Table 3 below.

Absorption wavelength (nm) Molar absorption coefficient (M ^-1 cm ^-1 ) Comparative Example 1 429, 454 21300, 22500 Example 1 426, 451 16600, 17500 Example 2 424, 443 33100, 22990 Example 3 431, 451 26000, 23900

According to Table 3, it was confirmed that the molar absorption coefficients of Examples 2 and 3 were greater than the molar absorption coefficients of Comparative Example 1.

This is because the embodiment according to the present specification has excellent absorbance and at the same time satisfies the maximum absorption wavelength range, so that when applied to the green or red color filter of interest in the present specification, the wavelength range of 420 nm to 453 nm is effectively achieved. It was confirmed that it can sufficiently play the role of a complementary colorant that can be absorbed.

Specifically, the fact that the molar extinction coefficients of Examples 2 and 3 are larger than that of Comparative Example 1 means that when the color material for color filters is combined, there is an advantage that the content of the input color material can be relatively reduced.

In addition, it can be seen that Examples 2 and 3 can be used as a color material to compensate for insufficient absorption in the short wavelength region due to more effective absorption of the short wavelength region as well as the long wavelength region in the absorption wavelength range of 420 nm to 460 nm compared to Comparative Example 1. there was.

When an electron donating unit such as an aromatic group is present in the compound represented by Formula 1, specifically, a phenyl group is present at the substituent R position, the maximum absorption wavelength is shortened, the molar absorption coefficient is increased, and the short wavelength region There was an increase in absorption of In addition, it was confirmed that when an electron donating unit is present at the position of the substituent R2, the maximum absorption wavelength becomes longer. As a result, if an aromatic group, which is an electron donating unit, exists at the positions of the substituents R and R2 of Formula 1, effective absorption in a short wavelength region and an increase in the molar absorption coefficient can be expected.

Claims (11)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X is CH,
R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
r1 is an integer from 0 to 4, and when r1 is 2 or more, R1 is the same as or different from each other,
r2 is an integer from 0 to 6, and when r2 is 2 or more, R2 is the same as or different from each other The compound of claim 1, wherein R is a substituted or unsubstituted aryl group. The compound of claim 1, wherein R is a substituted or unsubstituted phenyl group. The compound of claim 1, wherein R2 is a substituted or unsubstituted naphthyl group. The compound of claim 1, wherein the compound represented by Formula 1 has a maximum absorption wavelength between 420 nm and 460 nm. The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following formulas:

A compound according to any one of claims 1 to 6; Binder resin; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition comprising at least one selected from the group consisting of a solvent. The method according to claim 7, wherein in the exemplary embodiment of the present specification, based on 100 parts by weight of the photosensitive resin composition, the compound is 0.1 to 60 parts by weight, the binder resin is 1 to 85 parts by weight, and the polyfunctional monomer is 5 To 30 parts by weight, the photoinitiator is 0.5 to 10 parts by weight, and the solvent is 10 to 60 parts by weight. A photosensitive material comprising the photosensitive resin composition according to claim 7. A color filter comprising the photosensitive material according to claim 9. A display device comprising the color filter according to claim 10.