KR20200136163A - 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 capable of improving color purity, heat resistance, and contrast ratio by using the compound as a material, 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 a 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,

Y is a direct bond; Or CQ1Q2,

R1 to R9, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)R; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or X1 and X2 are bonded to each other to form a substituted or unsubstituted ring,

When any one of X1 and X2 is hydrogen, the rest other than hydrogen is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group, the substituted or unsubstituted heteroaryl group is not a substituted or unsubstituted triazine group.

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.

When the compound represented by Formula 1 according to the present specification is used as a material for the color material composition of a color filter, color purity, heat resistance, and contrast ratio may be improved.

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,

Y is a direct bond; Or CQ1Q2,

R1 to R9, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)R; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or X1 and X2 are bonded to each other to form a substituted or unsubstituted ring,

When any one of X1 and X2 is hydrogen, the rest other than hydrogen is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

When at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group, the substituted or unsubstituted heteroaryl group is not a substituted or unsubstituted triazine group.

The compound of Formula 1 according to the present specification may be used as a material for a color material composition of a color filter. By introducing an amine group in which one or more aryl or heteroaryl groups are substituted at the 8th position of the quinophthalone-based compound known in the prior art, it is possible to increase the absorption spectrum by increasing the electron density of the quinoline skeleton. .

For this reason, when the compound according to the present specification is used together with a phthalocyanine-based green dye, absorption in a short wavelength region may increase, thereby improving the color purity of green. The improvement of color purity makes it easier to implement a high-color display. In addition, compared to an unsubstituted amine (-NH ₂ ), an alkyl group or an alkoxy group-bonded quinophthalone-based compound, as in the compound according to the present specification, when an amine having an aromatic ring group substituted on the quinoline skeleton is substituted, it improves heat resistance. It works. Accordingly, solubility in a general organic solvent is reduced, so that loss of the solvent in the wet dispersion process can be minimized, and thus, yield and stability can be improved in the micronization process including the water washing process. This makes it possible to manufacture a color filter with improved heat resistance and contrast ratio.

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; Carbonyl group; Ester group; Carboxy; Imide group; Amide group; Anionic groups; Alkoxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Sulfonate group; Amine group; Aryl group; Heteroaryl group; Silyl group; Alkyl sulfoxy group; Arylsulfoxy group; Boron group; Acryloyl group; Acrylate group; Ether 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 carbonyl group may be represented by -COR100, 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. The number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be represented by -COOR101, and R101 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 number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the anionic group has a chemical bond with the structure of Formula 1, and the anionic group is not particularly limited, and for example, U.S. Patent No. 7,939,644, Japanese Patent Application No. 2006-003080, Japanese Patent Application No. 2006-001917, Japanese Patent Application Publication No. 2005-159926, Japanese Patent Application Publication No. 2007-7028897, Japanese Patent Application Publication No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Application Publication No. 2005-111696, Japanese Patent Application Publication No. 2008-249663, Japan Anions described in Japanese Patent Application Publication No. 2014-199436 may be applied. Specific examples of the anionic group include trifluoromethanesulfonic acid anion, bis(trifluoromethylsulfonyl)amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethane sulfonyl nilme suited _{^{to, SO 3 -, CO 2 -}} , SO 2 N - SO 2 CF 3, SO 2 N ^- SO ₂ CF ₂ CF _3, but include a halogen group such as fluorine group, an iodo group, a chlorine group, it is not limited thereto.

In the present specification, the anionic group may itself have an anion, or may exist in the form of a complex compound with other cations. Therefore, depending on the number of substituted anionic groups, the sum of the total charges of the compound molecules of the present invention may vary. Since the compound of the present invention has a cation in one amine group, the sum of the total charges in the molecule may have a value from anion to 0 as much as the number of substituted anionic groups minus one.

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 alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group are preferably an alkenyl group substituted with an aryl group such as a stylbenyl group and a styrenyl group, but are not limited thereto.

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 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, pyridyl group, bipyridyl group, pyrimidinyl group, triazine group, acridyl group , Pyridazine group, quinolinyl group, quinazolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group , A benzofuranyl group, a dibenzofuran group, 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 silyl group may be represented by the formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited to this.

In the present specification, the alkyl sulfoxy group includes a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and a butyl sulfoxy group, but is not limited thereto. The alkyl group in the alkyl sulfoxy group may be described above for the alkyl group.

In the present specification, the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is not limited thereto. The aryl group in the arylsulfoxy group may be described above for the aryl group.

In the present specification, the boron group may be represented by the formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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 ether group may be represented by -COR102. R102 is a substituted or unsubstituted alkyl group. The description of the alkyl group described above may be applied to the alkyl group.

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 an exemplary embodiment of the present specification, Y is a direct bond; Or CQ1Q2.

In an exemplary embodiment of the present specification, Y is a direct bond.

In an exemplary embodiment of the present specification, Y is CQ1Q2.

In an exemplary embodiment of the present specification, R1 to R9, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)R; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Or a substituted or unsubstituted alkyl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted aromatic ring.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted aromatic ring having 3 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted aromatic ring having 3 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted aromatic ring having 3 to 12 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; Goat; Fluorine; Nitro group; Or a substituted or unsubstituted butyl group, or adjacent substituents combine with each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Or tert-butyl group, or adjacent substituents are bonded to each other to form a benzene ring.

In an exemplary embodiment of the present specification, R1 to R5 are hydrogen.

In an exemplary embodiment of the present specification, R6 to R9 are the same as or different from each other, and each independently hydrogen; Goat; Fluorine; Nitro group; It is a tert-butyl group or adjacent substituents combine with each other to form a benzene ring.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted aromatic ring.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted aromatic ring having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted aromatic ring having 3 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted aromatic ring having 3 to 12 carbon atoms.

In the exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, Q1 and Q2 are combined with R6 to form a benzene ring.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group 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 a substituted or unsubstituted alkyl group 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 a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or when X1 and X2 are bonded to each other to form a ring, and any one of X1 and X2 is hydrogen, the rest other than hydrogen is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and when at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group, the substituted or unsubstituted heteroaryl group is not a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, X1 and X2 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; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or when X1 and X2 are bonded to each other to form a substituted or unsubstituted ring, and any one of X1 and X2 is hydrogen, the rest other than hydrogen Is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and when at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, the substituted or unsubstituted carbon number 3 to 30 The heteroaryl group of is not a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, X1 and X2 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; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or when X1 and X2 are bonded to each other to form a substituted or unsubstituted ring, and any one of X1 and X2 is hydrogen, the rest other than hydrogen Is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and when at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, the substituted or unsubstituted carbon number 3 to 20 The heteroaryl group of is not a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, X1 and X2 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; Or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or when X1 and X2 are bonded to each other to form a substituted or unsubstituted ring, and any one of X1 and X2 is hydrogen, the rest other than hydrogen Is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and when at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, the substituted or unsubstituted C3-12 The heteroaryl group of is not a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazolinyl group; Or a substituted or unsubstituted pyrimidinyl group, or X1 and X2 are bonded to each other to form a substituted or unsubstituted carbazole group, and when any one of X1 and X2 is hydrogen, the rest other than hydrogen is substituted or unsubstituted A cyclic phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazolinyl group; Or a substituted or unsubstituted pyrimidinyl group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with chlorine; Biphenyl group; A naphthyl group unsubstituted or substituted with a hydroxy group; Quinolinyl group; Quinazolinyl group; Or a pyrimidinyl group, or when X1 and X2 are bonded to each other to form a carbazole group, and when any one of X1 and X2 is hydrogen, the rest other than hydrogen is a phenyl group unsubstituted or substituted with chlorine; Biphenyl group; A naphthyl group unsubstituted or substituted with a hydroxy group; Quinolinyl group; Quinazolinyl group; Or a pyrimidinyl group.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of R1 to R9, Q1, Q2, X1, and X2 are the same as in Chemical Formula 1.

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

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

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

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

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

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with chlorine; Biphenyl group; Or a naphthyl group unsubstituted or substituted with a hydroxy group.

In the exemplary embodiment of the present specification, X1 and X2 are bonded to each other to form a substituted or unsubstituted carbazole group.

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.

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

The phthalocyanine-based compound may be represented by the following Formula P-1 or P-2.

[Chemical Formula P-1]

[Formula P-2]

In Formulas P-1 and P-2, R1 to R16 are the same as or identical to each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

A1 and A2 are the same as or identical to each other, and each independently hydrogen; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or -OA3,

A3 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In Formulas P-1 and P-2, R1 and R2 may be bonded to each other to form a substituted or unsubstituted ring.

The content of the phthalocyanine compound and the compound represented by Formula 1 is preferably in the range of 5 to 800 parts by weight of the compound represented by Formula 1 with respect to 100 parts by weight of the phthalocyanine compound.

When the compound represented by Formula 1 satisfies the range by weight, the compound represented by Formula 1 may exhibit an effect of improving luminance, and a photosensitive resin composition having good heat resistance and light resistance may be prepared.

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 g/mol 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 Selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate. It may be one 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., Shijii124), ethanol,-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 may further include an antioxidant.

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

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 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 reproduction rate and high luminance and contrast ratio even by the 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).

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.

<Production Example>

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

<Production Example 1>

[Synthesis of Compound 1-1]

In the flask, 5 g of 2-methylquinolin-8-amine and 1.2 equivalents of 4-iodo-1,1-biphenyl were added to xylene, and 3 equivalents of tribasic potassium phosphate were added to the reaction solution, followed by stirring. 0.15 equivalents of bis(dibenzylideneacetone)palladium and xantphos were added, refluxed, and when the reaction was complete, extraction was performed using water and chloroform. The organic layer was dried using sodium sulfate. After distillation under reduced pressure to remove the organic solvent, it was recrystallized with ethyl acetate and ethanol to obtain compound 1-1 (6.2 g, yield 63%).

MS measurement results of Compound 1-1 are as follows.

Ionization mode=: APCI +: m/z=311.2[M+H]+, Exact Mass: 310.2

[Synthesis of Compound 1]

5 g of the compound 1-1 and 1.2 equivalents of tetrachlorophthalic anhydride were added to 5 g of benzoic acid and 20 g of methylbenzoate, followed by heating and stirring at 200°C. After the reaction was completed, it was cooled to room temperature, 30 equivalents of methanol was added, and stirred for about an hour to precipitate a solid. After filtering the precipitated solid, it was recrystallized with dichlorobenzene and ethanol to obtain compound 1 (7.2 g, yield 75%).

The MS measurement results of Compound 1 are as follows.

Ionization Mode=: APCI +: m/z=577[M+H]+, Exact Mass: 576

<Production Example 2>

[Synthesis of Compound 2]

In the synthesis of compound 1, except for using phthalic anhydride instead of tetrachlorophthalic anhydride, it was synthesized in the same manner to obtain compound 2 (5.1g, yield 72%).

The MS measurement results of Compound 2 are as follows.

Ionization Mode=: APCI +: m/z=441.2[M+H]+, Exact Mass: 440.2

<Production Example 3>

[Synthesis of Compound 3-1]

To a flask, 2.4 equivalents of 5 g of bromobenzene was added to toluene, and 3 equivalents of sodium tert-butoxide was added to the reaction solution, followed by stirring. 1.0 equivalent of tetrakis triphenylphosphine palladium) palladium was added, refluxed, and when the reaction was complete, extraction was performed using water and chloroform. The organic layer was dried using sodium sulfate. The organic solvent was removed by distillation under reduced pressure to obtain compound 3-1 (5.5 g, yield 56%).

MS measurement results of Compound 3-1 are as follows.

Ionization mode=: APCI +: m/z=311.2[M+H]+, Exact Mass: 310.2

[Synthesis of compound 3]

In the synthesis of compound 1, it was synthesized in the same manner, except that compound 3-1 was used instead of compound 1-1. Through this, it was possible to obtain compound 3 (6.3g, yield 68%). The MS measurement results of Compound 3 are as follows. Ionization Mode=: APCI +: m/z=577[M+H]+, Exact Mass: 576

<Production Example 4>

[Synthesis of compound 4]

In the synthesis of compound 3, except that phthalic anhydride was used instead of tetrachlorophthalic anhydride, it was synthesized in the same manner. Through this, it was possible to obtain compound 4 (5.7g, yield 80%). MS measurement results of Compound 4 are as follows. Ionization Mode=: APCI +: m/z=441.2[M+H]+, Exact Mass: 440.2

<Production Example 5>

[Synthesis of compound 5]

In the synthesis of Compound 3, it was synthesized in the same manner, except that 2,3-naphthalenedicarboxylic anhydride was used instead of tetrachlorophthalic anhydride. Through this, it was possible to obtain compound 5 (5.5g, yield 70%). The MS measurement results of Compound 5 are as follows. Ionization Mode=: APCI +: m/z=491.2[M+H]+, Exact Mass: 490.2

<Production Example 6>

[Synthesis of Compound 6]

In the synthesis of compound 3, it was synthesized in the same manner except that 1,8-naphthalic anhydride was used instead of tetrachlorophthalic anhydride. Through this, it was possible to obtain compound 6 (5.8g, yield 73%). The MS measurement results of Compound 6 are as follows. Ionization Mode=: APCI +: m/z=491.2[M+H]+, Exact Mass: 490.2

<Comparative Example 1>

[Comparative Example Compound 1]

Comparative Example Compound 1 was prepared with reference to Prior Document Publication No. 2008-094986 A compound (I) intermediate. 10 g of commercialized C.I. Pigment Yellow 138 and 10 g of potassium hydroxide were added to 100 ml of water, and the temperature was raised to 90°C, followed by stirring for 12 hours. After the reaction was completed, after cooling to room temperature, 500 ml of 35% HCl was added dropwise. After washing with water using acetone and ethyl acetate, Comparative Example Compound 1 (6.9g, yield 90%) as a yellow compound was obtained.

MS measurement results of the Comparative Example Compound 1 are as follows.

Ionization Mode=: APCI +: m/z=424.9[M+H]+, Exact Mass: 423.9

<Comparative Example 2>

[Comparative Example Compound 2]

Comparative Example Compound 2 was prepared with reference to Prior Document Publication No. 2017-197640 A Compound A-1. After adding 10 g of 2-methylquinolin-8-amine and 2.2 equivalents of phthalic anhydride, 10 g of benzoic acid and 30 g of methyl benzoate were added, followed by heating at 180°C. After the reaction was completed, after cooling to room temperature, 200 ml of methanol was added and stirred for 1 hour. 100 g of isobutanol and 14.9 g of dimethylpropyl amine were added to the solid washed with methanol and ethyl acetate, heated to 100° C., and stirred for 6 hours while evaporating off methanol. After cooling to room temperature, the intermediate A (82%) was obtained by washing with methanol.

10 g of cyanuric chloride and 100 ml of acetone were added, and the mixture was stirred while cooling. 15 g of intermediate A was dissolved therein in 100 ml of N-methyl pyrrolidone and added dropwise to a solution of cyanuric chloride for 1 hour. After stirring at 10°C or lower for 3 hours, 20 g of sulfanylic acid was added thereto, followed by stirring at 90°C for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, and 500 ml of water was added to the reaction mixture to precipitate crystals. Through this, a yellow compound, Comparative Example compound 2 (16.7g, yield 41.4%) was obtained.

<Example>

Preparation of photosensitive resin composition Example 1

[Compound 1 dispersion preparation]

Based on a total of 100 parts by weight of the final dispersion, 7 parts by weight of Compound 1, 8.75 parts by weight of dispersant LPN-22102 (BYK), 14.26 parts by weight of binder resin, 28.00 parts by weight of propylene glycol monomethyl ether acetate, 200 parts by weight of zirconia beads The composition was prepared. The composition was subjected to a milling process in a paint shaker, diluted with 42 parts by weight of propylene glycol monomethyl ether acetate, and the beads were filtered by 6 μm to prepare a final dispersion of compound 1.

[Preparation of photosensitive resin composition Example 1]

A photosensitive resin composition Example 1 was prepared by mixing with the components shown in Table 1 below.

The dispersion of Compound 1 was stirred in propylene glycol methyl ether acetate for 1 hour at room temperature using a shaker (Jeio Tech SK-600). Thereafter, a pigment dispersion, a binder resin (alkali-soluble resin), a polyfunctional monomer (photopolymerizable compound), and a photoinitiator were added and further stirred at room temperature for 1 hour. After removing impurities with a 6 μm filter, a photosensitive resin composition Example 1 was prepared.

ingredient Content (% by weight) Color material Compound dispersion Compound 1 14.95 Pigment dispersion Pigment Green 63
Pigment dispersion 17.55 Binder resin (alkali-soluble resin) 12.5 Polyfunctional monomer (photopolymerizable compound) 6 Photoinitiator 1.5 Solvent (PGMEA) 47.5 Total amount 100.0 Binder resin (alkali-soluble resin): a copolymer of benzyl methacrylate and methacrylic acid (molar ratio of 70:30, acid value is 113 KOH mg/g, weight average molecular weight measured by gel permeation chromatography (GPC) 20,000 g/mol , Molecular weight distribution (PDI) 2.0, solid content (SC) 25%, including solvent PGMEA
Polyfunctional monomer (photopolymerizable compound): Dipentaerythritol hexaacrylate (DPHA)
Photoinitiator: 2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio)phenyl)propan-1-one (2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio) phenyl)propan-1-one)

[Production of photosensitive resin composition Examples 2 to 4 and Comparative Examples 1 and 2]

In the preparation of the photosensitive resin composition Example 1, instead of the compound 1, the compounds shown in Table 2 were respectively applied, and other than that, the photosensitive resin composition Examples 2 to 4 were subjected to the same method and conditions as in the preparation of the photosensitive resin composition Example 1. , Comparative Examples 1 and 2 were prepared.

Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 compound One 2 3 4 Comparative Example Compound 1 Comparative Example Compound 2

<Experimental Example>

Fabrication of color filter substrate, evaluation of brightness and contrast ratio

A substrate was prepared using the photosensitive resin composition Examples 1 to 4 and Comparative Examples 1 and 2. Specifically, each photosensitive resin composition was spin-coated on glass (5 X 5 cm ² ), and a film was formed by performing a prebake at 100° C. for 100 seconds. The pre-heat treatment substrate (Prebake) prepared under the above conditions was subjected to post-heat treatment (post bake once) at 230° C. for 20 minutes, and then the substrate was subjected to an absorption spectrum in the 380-780 nm wavelength range using a spectrometer (MCPD, Otsuka Corporation). .

The prepared substrate was measured using a contrast meter (Tsubosaka), and the luminance when the upper and lower polarizing plates of the substrate were parallel and orthogonal was measured, and the contrast ratio was calculated by the following calculation formula 1. The luminance and contrast ratio (contrast, CR) are shown in Table 3 below.

[Calculation 1]

Contrast ratio (CR) = luminance when the upper and lower polarizing plates of the substrate are parallel / luminance when the upper and lower polarizing plates of the substrate are orthogonal

Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Luminance (Y) 57.20 59.08 60.86 57.36 49.21 56.20 Contrast ratio (contrast) 15,300 15,100 15,400 15,100 13,250 14,900

According to Table 3, it was confirmed that the luminance and contrast ratio of the example was higher than that of the comparative example. This was confirmed that the luminance and contrast ratio were excellent by using a compound having an amine group substituted with one or more aryl groups or heteroaryl groups at the position of the quinoline skeleton according to the present specification.

Color filter substrate heat resistance evaluation

The post-heat treatment substrate (one post bake) was additionally treated at 230°C for 20 minutes to obtain a transmittance spectrum in the same measuring range with the same equipment.

Using the values L*, a*, and b* obtained from the absorption spectrum obtained by using the C light source as a backlight, ΔEab was calculated by the following calculation formula 2 and shown in Table 4 below.

[Calculation 2]

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

In the above calculation formula 2, ΔEab is the difference between the ΔE(L*, a*, b*) value and ΔE(L*, a*, b*) after the post-heat treatment substrate is additionally treated at 230°C for 20 minutes Means, and L*, a*, and b* mean 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. And b* means the nearest degree between yellow and blue and has a positive/negative value.

The smaller the ΔEab value, the better the heat resistance, meaning less color change.

Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 △Eab 4.9 4.2 3.7 4.2 7.2 6.8

According to Table 4, it was confirmed that the ΔEab value of Examples 1 to 4 was smaller than the ΔEab value of the comparative example. Therefore, it was confirmed that it was possible to obtain a colored composition for a color filter and a color filter excellent in heat resistance by using the compound of Formula 1 of the present invention.

Claims (13)

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

In Formula 1,
Y is a direct bond; Or CQ1Q2,
R1 to R9, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)R; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring,
R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,
X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or X1 and X2 are bonded to each other to form a substituted or unsubstituted ring,
When any one of X1 and X2 is hydrogen, the rest other than hydrogen is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
When at least one of X1 and X2 is a substituted or unsubstituted heteroaryl group, the substituted or unsubstituted heteroaryl group is not a substituted or unsubstituted triazine group. The compound of claim 1, wherein the formula 1 is represented by the following formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of R1 to R9, Q1, Q2, X1, and X2 are the same as in Chemical Formula 1. The compound of claim 1, wherein X1 and X2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group. The method according to claim 1, X1 and X2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazolinyl group; Or a substituted or unsubstituted pyrimidinyl group, or X1 and X2 are bonded to each other to form a substituted or unsubstituted carbazole group, and when any one of X1 and X2 is hydrogen, the rest other than hydrogen is substituted or unsubstituted A cyclic phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazolinyl group; Or a substituted or unsubstituted pyrimidinyl group. The compound of claim 1, wherein X1 and X2 are bonded to each other to form a substituted or unsubstituted carbazole group. 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 6. The color material composition according to claim 7, further comprising a phthalocyanine-based compound. The color material composition according to claim 7; Binder resin; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition containing a solvent. The method according to claim 9, Based on the total weight of the solid content of 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 9. A color filter comprising the photosensitive material according to claim 11. A display device comprising the color filter according to claim 12.