KR20200136165A - Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, to a color material composition having improved heat resistance and light absorption coefficient, to a photosensitive resin composition, to a photosensitive material, to a color filter, and to a display device.

Description

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

The present specification relates to a compound, a color material composition including the same, and a photosensitive resin composition. In addition, the present specification relates to a photosensitive material manufactured by using the photosensitive resin composition, a color filter, and a display device including the same.

Recently, 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 the color filter, so that dissolution and dispersibility are inferior, and multiple scattering of light occurs due to large aggregated particles. The scattering of polarized light has been pointed out as the main factor that lowers 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 is limited in selecting a color material for realizing color coordinates for high-color purity display devices. 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, brightness, and contrast ratio by increasing color purity.

Korean Patent Publication No. 2001-0009058

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

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

[Formula 1]

In Formula 1,

R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

r11 and r12 are integers from 0 to 3,

When r11 is 2 or more, R11 is the same as or different from each other, and when r12 is 2 or more, R12 is the same or different from each other,

X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted ring,

Except when both R and R'are hydrogen,

L is a direct bond; A substituted or unsubstituted alkylene group; -CO-; Or -SO ₂ -.

An exemplary embodiment of the present specification provides a colorant composition comprising the compound.

An exemplary embodiment of the present specification, the coloring material composition; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing 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 represented by Formula 1 according to the present specification may be used as a material for a color material composition of a color filter. Compared to the conventionally known quinophthalone-based dye compound, heat resistance and extinction coefficient are improved, so that the color material composition according to the present specification has less heat deterioration and it is possible to manufacture a color filter with improved brightness.

1 is a diagram showing the extinction coefficient of compounds according to Example 1 and Comparative Example 1. FIG.

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 a case where a member is in contact with another member, but also a 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 otherwise stated.

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

[Formula 1]

In Formula 1,

R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

r11 and r12 are integers from 0 to 3,

When r11 is 2 or more, R11 is the same as or different from each other, and when r12 is 2 or more, R12 is the same or different from each other,

X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted ring,

Except when both R and R'are hydrogen,

L is a direct bond; A substituted or unsubstituted alkylene group; -CO-; Or -SO ₂ -.

The compound represented by Formula 1 may be used as a colorant composition material for a color filter. As a structure in which the chromophores of a conventionally known quinophthalone-based compound are connected in a dimer form, it is possible to improve heat resistance as well as improve the absorption coefficient of a single molecule state, thereby reducing the color material content in the color material composition. In addition, if an amine group substituted with an alkyl group or an unsubstituted amine group is connected to the quinoline skeleton, the solubility in an organic solvent increases, and there is a concern of loss during solvent filtration in the wet dispersion process, but substitution with an aryl group, arylalkyl group or heteroaryl When the amine group or the aryl or heteroaryl group is directly bonded, the solvent resistance and heat resistance may also be improved. Therefore, the colorant composition including the compound represented by Chemical Formula 1 is less deteriorated by heat, and it is possible to manufacture a color filter with improved luminance.

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; -COOH; Alkoxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heteroaryl group; Arylalkyl group; Acryloyl group; Acrylate group; Amine group; It means that it is substituted with one or more substituents selected from the group containing a heterocyclic group and an anionic group including one or more of N, O, S, or P atoms, or does not have any substituents.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the ring means an aromatic or aliphatic ring in that adjacent groups 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 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 alkyl group may be a linear or branched chain, 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 number of carbon atoms of the cycloalkyl group is 3 to 20. 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 alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkenyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkenyl has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group.

In the present specification, the cycloalkenyl 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group are preferably a cyclopentenylene group and a cyclohexenylene group, 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, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a 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 arylalkyl group may specifically have 6 to 30 carbon atoms in the aryl moiety and 1 to 30 carbon atoms in the alkyl moiety. The description of the aryl group according to the present specification may be applied to the aryl moiety, and the description of the alkyl group according to the present specification may be applied to the alkyl moiety. Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, α-methylbenzyl group, α,α-dimethylbenzyl Group, α,α-methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, α,α-ditrifluoromethylbenzyl group , p-methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyl group oxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrolel Ethyl group, aminobenzyl group, nitrobenzyl group, cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group, and the like, but are 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 the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridinyl group, bipyridinyl 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, dibenzo There are furanyl groups and the like, but are not limited thereto.

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 acryloyl group refers to a photopolymerizable unsaturated group, for example, a (meth)acryloyl group, but is not limited thereto.

In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, such as a (meth)acrylate group, but is not limited thereto.

In the present specification, "(meth)acryloyl" refers to at least one selected from the group consisting of acryloyl and methacryloyl. The notation of'(meth)acrylate' has the same meaning.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine 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 group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are not limited thereto.

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, specifically 1 to 20, 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 straight chain, branched chain or cyclic chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but, for example, 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, a heteroarylene group refers to a heteroaryl group having 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 the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R12 are hydrogen.

In the exemplary embodiment of the present specification, r11 and r12 are integers of 0 to 3,

When r11 is 2 or more, R11 is the same or different from each other, and when r12 is 2 or more, R12 is the same or different from each other.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroaryl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 3 to C 20 heteroaryl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted C 3 to C 12 heteroaryl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted pyridinyl group; Or a substituted or unsubstituted dibenzofuranyl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A phenyl group unsubstituted or substituted with chlorine, -COOH, -CF ₃ , or -SO ₃ H; A naphthyl group unsubstituted or substituted with a hydroxy group; Pyridinyl group; Or a dibenzofuranyl group.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted aromatic ring having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C3 to C20 heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted aromatic ring having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; A substituted or unsubstituted C3-C12 heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted aromatic ring having 1 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted benzyl group, or R and R'combine with each other to form a substituted or unsubstituted carbazole group.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; Biphenyl group; A phenyl group unsubstituted or substituted with chlorine or -SO ₃ H; Or a benzyl group, or R and R'combine with each other to form a carbazole group.

In the exemplary embodiment of the present specification, the case where both R and R'are hydrogen is excluded.

In the exemplary embodiment of the present specification, the case where R and R'are both hydrogen is excluded. When R is hydrogen, R'is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or when R'is hydrogen, R is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted ring.

When both R and R'are hydrogen, dispersibility decreases compared to the compound represented by Formula 1 according to the present specification, thereby lowering the brightness of the dispersion composition, and low stability against heat. On the other hand, in the case of the compound represented by Formula 1 according to the present specification, dispersibility increases, luminance increases, and stability against heat is high.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted alkylene group; -CO-; Or -SO ₂ -.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; -CO-; Or -SO ₂ -.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted C1-C20 alkylene group; -CO-; Or -SO ₂ -.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted C 1 to C 10 alkylene group; -CO-; Or -SO ₂ -.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted alkylene group; -CO-; Or -SO ₂ -.

In an exemplary embodiment of the present specification, L is a direct bond; A methylene group unsubstituted or substituted with a methyl group or -CF ₃ ; -CO-; Or -SO ₂ -.

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

[Formula 1-1]

In Formula 1-1,

The definitions of R1 to R12, r11, r12 and L are the same as in Formula 1,

Y1 to Y4 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, Y1 and Y2 or Y3 and Y4 are bonded to each other to form a substituted or unsubstituted ring,

Except when both Y1 and Y2 are hydrogen or both Y3 and Y4 are hydrogen.

In the exemplary embodiment of the present specification, Y1 and Y3 are based on the above-described definition of R, and the definitions of Y2 and Y4 are based on the above-described definition of R'.

In the exemplary embodiment of the present specification, Y1 and Y3 are based on the above-described definition of R', and the definitions of Y2 and Y4 are based on the above-described definition of R.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroaryl group,

R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, or R and R'are bonded to each other to form a substituted or unsubstituted ring,

Except when both R and R'are hydrogen. According to another exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following formulas, but is not limited thereto.

An exemplary embodiment of the present specification provides a colorant composition comprising the compound.

The color material composition may include only the compound.

In one embodiment of the present specification, the colorant composition further includes a phthalocyanine-based compound.

The phthalocyanine-based compound may specifically use a phthalocyanine-based green pigment, but is not limited thereto. The phthalocyanine-based green pigment may be, for example, Pigment Green 58 (DIC), Pigment Green 59, or Pigment Green 63 (TOYO), but is not limited thereto.

In another exemplary embodiment, the colorant 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 color material 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 the compound of Formula 1 , One or more dyes and one or more pigments may be included.

In the exemplary embodiment of the present specification, the dye and the pigment are metal-complex (metal-complex)-based compounds; Azo-based compounds; Metal azo-based compounds; Quinophthalone-based compounds; Isoindoine-based compounds; Methine-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.

In an exemplary embodiment of the present specification, the colorant composition may be a dispersion containing the compound.

Specifically, the color material composition is the compound; Dispersant; Binder resin; menstruum; And it may be a dispersion of a composition comprising zirconia beads.

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

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

The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength 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 are 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 examples include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ω-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more, but is not limited to these.

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 to 50,000 g/mol.

The acid value of the binder resin can be measured by titration with a 0.1N concentration of potassium hydroxide (KOH) methanol solution.

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 an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. 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.

The biimidazole-based compound is 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, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, 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-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.

According to an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the colorant compound is 2% to 50% by weight, and the content of the binder resin is 1% to 60% by weight And, the content of the photoinitiator is 0.1% to 10% by weight, and the content of the multifunctional monomer is 0.1% to 50% by weight.

When the photosensitive resin composition satisfies the above content, a color filter having excellent coloring power may be manufactured.

The total weight of the solid content means 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 is 1 or 2 selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, an anti-thermal polymerization agent, an ultraviolet absorber, a dispersant, an adhesion aid, and a leveling agent. It further contains the above additives.

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 photocrosslinking 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 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, and 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 this specification is methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents such as may be selected and used, and as an alkyl trimethoxy silane, one or more types of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can choose and use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based 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, and as a fluorine-based surfactant, DIC (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, and the like 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, trimethylphosphate, or triethylphosphate; 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-g, 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 Secondary antioxidants; Thio such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane 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 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. Compound type, nonionic, anionic or cationic dispersants can be used as the dispersant, 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, sulfonic acid salt, 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 is not limited thereto, all those generally used in the art may be used.

The adhesive agent may be KBM-503, for example, but is not limited thereto, and all those generally used in the art may be used.

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 forming a photosensitive material in the form of a thin film or pattern by applying and curing the photosensitive resin composition of the present specification on a substrate by an appropriate method.

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. Further, 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, a mercury vapor arc, a carbon arc, and an Xe arc 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 a color material composition containing the compound represented by Formula 1 above. 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 the 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 reproduction rate 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-like 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 process cost, high reflectance of chromium, and environmental pollution due to chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing may 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 increases. 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 any one of a liquid crystal display (Thin Film Transistor- Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

FIG. 1 shows that compound P-2 represented by Formula 1 according to Example 1 has an improved extinction coefficient for the same mass compared to compound P-5, which is a quinophthalone dye compound according to Comparative Example 1. .

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>

In the following examples, the structure of the compound was confirmed by MS analysis.

<Synthesis Example 1>

(Synthesis of Compound A-1)

Compound 8-Hydroxyquinaldine (TCI) 10 g, perfluorobutanesulfonyl fluoride 13.2 g, K ₂ CO ₃ 26 g Acetonitrile and water were cooled to reflux using a solvent. After the reaction was completed, the organic layer was separated through an extraction process, and dried under reduced pressure to obtain 25 parts by weight of a pale yellow solid.

20 g of the light yellow solid, 6 g of phenyl Boronic acid, 12 g of K ₂ CO ₃ , and 0.05 g of Pd catalyst were used, and a cooling reflux device was installed using tetrahydrofuran (THF) and water as solvents. The reactor was heated to 80°C and reacted for 4 hours. When the reaction was completed, an organic solvent was added to extract the organic layer, and then recrystallized using hexane to obtain a precipitated solid compound A-1.

[Compound A-1]

(Synthesis of Compound P-1)

Compound A-1 (2-methyl-8-phenylquinoline, 11 g, 1.1 eq) and the following compound B-1 (4.65 g, 0.5 eq) were added to a 250 ml round bottom flask (RB Flask), and benzoic acid 7 g, 100 g of methyl benzoate was added and dissolved to obtain a solution. The solution was heated to 130-200° C. and cooled to reflux for 12 hours. When the reaction was completed, methanol was slowly added while stirring while cooling, followed by stirring for an additional 30 minutes to precipitate a solid. The precipitated solid was suction filtered and washed with methanol. The obtained solid was recrystallized using dichlorobenzene or N-methyl-2pyrrolidone, and then dried under reduced pressure to obtain a yellow solid. The yield is 68%, and the MS measurement results of Compound P-1 thus obtained are as follows.

Ionization mode=: APCI +: m/z=697.2[M+H]+, Exact Mass: 696.2

[Compound P-1]

[Compound B-1]

-

-

<Synthesis Example 2>

(Synthesis of Compound P-2)

Compound P-2 was prepared in the same manner as in Synthesis Example 1 using 2-methyl-8-(2-(trifluoromethyl)phenyl)quinolone) instead of compound A-1. The yield was 53% and a yellow solid was obtained. The MS measurement results of Compound P-2 thus obtained are as follows.

Ionization mode=: APCI +: m/z=833.2[M+H]+, Exact Mass: 832.2

[Compound P-2]

<Synthesis Example 3>

(Synthesis of Compound A-2)

8-Aminoquinaldine 5g, Bromobenzene 11.9g, K ₂ CO ₃ 9.4g, Pd catalyst 0.16g was used, and toluene was used as a solvent to install a cooling reflux device. The reactor was heated to 120° C. and reacted for 24 hours. When the reaction was completed, an organic solvent was added to extract the organic layer, and then recrystallized using ethyl acetate and ethanol (EtOH) to obtain a precipitated solid compound A-2.

[Compound A-2]

(Synthesis of Compound P-3)

Compound P-3 was prepared in the same manner as in Synthesis Example 1 using Compound A-2 instead of Compound A-1. The yield was 41% and a yellow solid was obtained. The MS measurement results of Compound P-3 thus obtained are as follows.

Ionization Mode=: APCI +: m/z=879.3[M+H]+, Exact Mass: 878.3

[Compound P-3]

<Synthesis Example 4>

(Synthesis of Compound P-4)

Compound P in the same manner as in Synthesis Example 2 using the following compound B-2 (5,5'-(perfluoropropane-2,2-diyl)bis(isobenzofuran-1,3-dione)) instead of the compound B-1 -4 was prepared. A yellow solid was obtained with a yield of 64%. MS measurement results of the compound P-4 are as follows.

Ionization mode=: APCI +: m/z=983.2[M+H]+, Exact Mass: 982.2

[Compound B-2]

[Compound P-4]

<Synthesis Example 5>

(Synthesis of Compound P-5)

Compound P-5 was prepared in the same manner as in Synthesis Example 1, except that phthalic anhydride was used instead of Compound B-1. A yellow solid with a yield of 50% was obtained. The MS measurement results of Compound P-5 are as follows.

Ionization mode=: APCI +: m/z=418.2[M+H]+, Exact Mass: 417.1

[Compound P-5]

<Synthesis Example 6>

(Synthesis of Compound P-6)

Compound P-6 was prepared with reference to Example 1 described in Prior Document KR 10-2018-0115585 A. The yield was 65% yellow solid. MS measurement results of Compound P-6 are as follows.

Ionization mode=: APCI +: m/z=873.1[M+H]+, Exact Mass: 872.1

[Compound P-6]

<Synthesis Example 7>

(Synthesis of Compound P-7)

Compound P-7 was prepared in the same manner as in Synthesis Example 1, except that 8-aminoquinaldine was used instead of Compound A-1. A yellow solid was obtained with a yield of 63%. The MS measurement results of Compound P-7 are as follows. Ionization Mode=: APCI +: m/z=575.2[M+H]+, Exact Mass: 574.2

[Compound P-7]

[Preparation of photosensitive resin composition Example 1]

<Dispersion solution preparation>

Based on a total of 100 parts by weight of the final dispersion, 7 parts by weight of the compound P-2, 8.75 parts by weight of the dispersant LPN-22102 (BYK), and 14.25 parts by weight of the binder resin, the solvent propylene glycol monomethyl ether acetate 28.00 parts by weight, zirconia beads 200 The composition was prepared in parts by weight. After the composition was milled in a paint shaker, dilution was performed with 42 parts by weight of propylene glycol monomethyl ether acetate, and beads were filtered to prepare a final dispersion.

<Preparation of photosensitive resin composition Example 1>

Based on 100 parts by weight of the total weight of the photosensitive resin composition, 11 parts by weight of the dispersion of the compound P-2, 22 parts by weight of the Pigment Green 63 dispersion composition of TOYO, 15.05 parts by weight of the binder resin, the polyfunctional monomer dipentaerythritol hexaacrylate 13.28 Photosensitive resin composition Example 1 was prepared by mixing parts by weight, 0.6 parts by weight of leveling agent F-554, 0.15 parts by weight of adhesive aid KBM-503, 0.72 parts by weight of photoinitiator SPI-03, and 37.20 parts by weight of solvent propylene glycol monomethyl ether acetate. .

The binder resins used in Examples and Comparative Examples are all the same binder resin, and are copolymers in which the contents of methacrylic acid, benzyl methacrylic acid, and styrene are 29% by weight, 52% by weight, and 19% by weight, respectively, based on the total weight.

[Production of photosensitive resin composition Examples 2 and 3, and Comparative Examples 1 to 3]

Photosensitive resin composition Examples 2 and 3 and Comparative Examples 1 to 3 in the same manner as in the photosensitive resin composition Example 1, except that the compound P-2 of Example 1 was each applied with the compound shown in Table 1 below. A photosensitive resin composition was prepared.

Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Type of compound P-2 P-3 P-4 P-5 P-6 P-7

<Experimental Example>

[Method of fabricating color filter substrates and evaluating heat resistance]

The photosensitive resin composition prepared in Examples and Comparative Examples was applied to a glass (5 cm X 5 cm) by spin coating, and then a pre-heat treatment (PreBake) was performed in which the residual solvent was evaporated by applying heat.

The resulting veneer was patterned through a photomask process, developed with an aqueous KOH alkali solution, and washed with distilled water.

The finally made veneer was subjected to a post-heat treatment (PostBake) of 20 minutes in an oven at 230°C, and an additional heat treatment process of 20 minutes (a total of 40 minutes). At this time, the absorption spectrum of the color pattern varied according to the additional heat treatment process and the color index (x, y, Y, L*, a*, b*) of the C light source were measured. Through this, an optical difference value of ΔEab was calculated according to Equation 1 below.

[Equation 1]

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

In Equation 1, △Eab means the difference between the value of △E(L*, a*, b*) after additional heat treatment and △E(L*, a*, b*) after one post heat treatment, and L *, a*, b* refer to values obtained by converting luminance and coordinates in the CIE 1976 L*a*b* color space as a cubic function.

Specifically, L* is a value representing the brightness and has a value between 0 and 100, and a* represents a degree that is close among red and green, and may have a positive/negative value. b* means the nearest degree between yellow and blue, and has a positive/negative value.

A small ΔEab value means that the stability of the color pattern according to the additional heat treatment is high, indicating that the prepared photosensitive resin composition has excellent heat resistance. In addition, the luminance (Y) value represents the value of the post-heat-treated veneer. Evaluation of the heat resistance and luminance of the photosensitive resin compositions of Examples and Comparative Examples are shown in Tables 2 and 3 below.

Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 △Eab
(Heat resistance) 5.45 3.58 4.39 2.76 2.60 1.98

Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 Luminance (Y) 52.2 55.5 54.3 56.1 55.7 58.7

According to Tables 2 and 3, it can be seen that the ΔEab (heat resistance) value of Examples 1 to 3 is smaller and the luminance (Y) value is higher than that of Comparative Examples 1 to 3. Accordingly, it was confirmed that by using the compound according to an exemplary embodiment of the present specification, a photosensitive resin composition and a color filter having less heat deterioration and excellent luminance can be manufactured .

Claims (12)

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

In Formula 1,
R1 to R12 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
r11 and r12 are integers from 0 to 3,
When r11 is 2 or more, R11 is the same as or different from each other, and when r12 is 2 or more, R12 is the same or different from each other,
X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, or R and R'are bonded to each other to form a substituted or unsubstituted ring,
Except when both R and R'are hydrogen,
L is a direct bond; A substituted or unsubstituted alkylene group; -CO-; Or -SO ₂ -. The compound of claim 1, wherein the formula 1 is represented by the following formula 1-1:
[Formula 1-1]

In Formula 1-1,
The definitions of R1 to R12, r11, r12 and L are the same as in Formula 1,
Y1 to Y4 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group, Y1 and Y2 or Y3 and Y4 are bonded to each other to form a substituted or unsubstituted ring,
Except when both Y1 and Y2 are hydrogen or both Y3 and Y4 are hydrogen. The method according to claim 1, X1 and X2 are the same as or different from each other, and each independently NRR'; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroaryl group,
R and R'are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, or R and R'are bonded to each other to form a substituted or unsubstituted ring,
A compound that is excluded when both R and R'are hydrogen. The method according to claim 1, L is a direct bond; A substituted or unsubstituted C 1 to C 10 alkylene group; -CO-; Or -SO ₂ -. 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 color material composition comprising the compound according to any one of claims 1 to 5. The colorant composition according to claim 6, further comprising a phthalocyanine-based compound. The color material composition according to claim 6; Binder resin; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition containing a solvent. The method according to claim 8, based on the total weight of the solid content in the photosensitive resin composition, the content of the colorant compound is 2% by weight to 50% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1% to 10% by weight,
The content of the polyfunctional monomer is 0.1% by weight to 50% by weight of the photosensitive resin composition. A photosensitive material comprising the photosensitive resin composition according to claim 8. A color filter comprising the photosensitive material according to claim 10. A display device comprising the color filter according to claim 11.

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