KR20190101728A - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, a color material composition comprising the same, and a resin composition comprising the same. In the chemical formula 1, A is -X1-; -X2 = X3-; or -X4-X5-, and B is N or CR16. The compound according to one embodiment of the present invention is a novel compound excellent in color characteristics, heat resistance, and solvent resistance.

Description

Compound, color material composition comprising same and resin composition comprising same {COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}

The present specification relates to a novel compound, a color material composition including the same, and a resin composition including the same.

Currently, the light source of the liquid crystal display (LCD) is actively applied and developed not only LED, OLED but also QD in place of CCFL. In general, it is not easy to adjust or adjust the required color coordinates using light from an LED or OLED light source. Nevertheless, in order to improve the performance of the light source, LEDs have been developed to improve display quality by introducing various light emitters in LEDs or by introducing organic or inorganic light emitters into optical films through which the LED light sources pass.

To realize more similar or identical images to the display, wider color gamuts are possible than before, that is, high color reproduction (Wide Color Gamut_WCG) is possible, and the color volume is increased by increasing the amount of light transmitted through the display. It is required. In order to use space, a thinner display is needed.

Photoresist for preparing a color filter applied to such a display requires various materials such as colorants, binders, initiators, and the like. In particular, the color material is the most important material that determines the color quality, brightness, etc. of the color filter.

Generally, pigments known to have excellent properties such as heat resistance and light resistance are used, and these pigments are dispersed (pigment dispersion method) and applied to the photosensitive resin composition. However, the method of improving the color purity, brightness, contrast ratio in the manufacturing of the color filter used in the pigment dispersion method has reached the limit.

In order to overcome these problems and satisfy the requirements, the development of new color materials is required.

Republic of Korea Patent Publication No. 2001-0009058

The present specification provides a novel compound, a colorant composition including the same, and a resin composition including the same.

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

[Formula 1]

In Chemical Formula 1,

A is -X _1- ; -X ₂ = X _3- ; Or -X ₄ -X _5- ,

X ₁ , X ₄ and X ₅ are O; S; NR ₁₁ ; C = O or CR ₁₂ R ₁₃ ,

X ₂ and X ₃ are N; Or CR ₁₄ ,

Y is a direct bond; O; S; Or CR ₁₅ ,

B is N or CR ₁₆ ,

R ₁ to R ₈ and R ₁₁ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Carboxy group (-COOH); -OC (= 0) R; Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

는 적어도 하나의 할로겐기를 가진다.In Formula 1

Has at least one halogen group.

According to another exemplary embodiment, a color material composition including a compound according to an exemplary embodiment of the present application is provided.

According to another exemplary embodiment, the compound according to the exemplary embodiment of the present application; Binder resins; Polyfunctional monomers; Photoinitiators; And it provides a resin composition comprising a solvent.

According to another exemplary embodiment, a photosensitive material manufactured using the resin composition according to the exemplary embodiment of the present application is provided.

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

Finally, a display apparatus including a color filter according to an exemplary embodiment of the present application is provided.

The compound according to an exemplary embodiment of the present application is a novel compound having excellent color characteristics, heat resistance, and solvent resistance, and is excellent in absorption of short wavelengths of visible light (380 nm to 430 nm), so that the color power of the red color filter is particularly excellent. great.

In addition, the color material composition comprising the compound represented by the formula (1) is excellent in color characteristics, heat resistance, light resistance and solvent resistance, it is possible to achieve a higher color reproduction and high brightness, high contrast ratio and the like.

Hereinafter, this specification is demonstrated in detail.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

Embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art may easily implement the present invention. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention.

According to an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.

In the case of the compound represented by Chemical Formula 1 according to the present invention, the compound having excellent color characteristics and solvent resistance, and particularly, excellent heat resistance, has excellent absorption in the short wavelength range of visible light, thereby improving the coloring power of the red color filter. Has

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; Carboxy group (-COOH); Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more substituents in the substituents exemplified above are substituted, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

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

Means a site which is bonded to another substituent or binding moiety.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, 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.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In the present specification, the sulfonamide group may be —SO ₂ NR′R ″, wherein R ′ and R ″ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of N-alkylheteroarylamine group, monoheteroarylamine group and diheteroarylamine group, carbon number 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, and 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.

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

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

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

In the present specification, the alkyl group in the monoalkylamine group, the dialkylamine group, the N-alkylarylamine group, the alkylthioxy group, the alkyl sulfoxy group and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

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

In the present specification, the boron group may be -BR100R101, and R100 and R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

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

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

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

,

,

및

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

,

,

And

And so on. However, the present invention is not limited thereto.

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

In the present specification, the aryl group in the monoarylamine group, the diarylamine group, the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is described above. It is similar to the example of an aryl group. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.

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

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are formed by bonding to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

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

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.

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

In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In one embodiment of the present application, Chemical Formula 1 provides a compound represented by the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

The definitions of R ₁ to R ₈ , X ₁ to X ₅ , B, and Y are the same as those defined in Chemical Formula 1.

In one embodiment of the present application, the R _{One To} R _{8 They} are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Carboxy group (-COOH); -OC (= 0) R; Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted C _{6 Through} C ₆₀ An aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted C ₆ to C ₆₀ aromatic hydrocarbon ring.

In another exemplary embodiment, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted C _{6 Through} C ₄₀ An aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted C ₆ to C ₄₀ aromatic hydrocarbon ring.

In another exemplary embodiment, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Halogen group; C _{6 Through} C ₄₀ An aryl group; Or a C ₂ to C ₄₀ heteroaryl group, or adjacent groups may be bonded to each other to form a C ₆ to C ₄₀ aromatic hydrocarbon ring.

In another exemplary embodiment, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Or a halogen group, or adjacent groups may combine with each other to form a benzene ring.

는 적어도 하나의 할로겐기를 가지며, 상기 할로겐기는 F, Cl, Br 및 I로 이루어진 군에서 선택되는 1 이상일 수 있다.In an exemplary embodiment of the present application, in Chemical Formula 1

Has at least one halogen group, the halogen group may be at least one selected from the group consisting of F, Cl, Br and I.

는 적어도 하나의 할로겐기를 가진다는 것은, R₁ 내지 R₄ 중 적어도 하나가 할로겐기이거나, R₁ 내지 R₄가 다른 치환기로 치환되고 그 치환기 중 적어도 하나가 다시 할로겐기로 치환되는 경우를 포함한다.In Formula 1

Has at least one halogen group includes a case in which at least one of R ₁ to R ₄ is a halogen group, or R ₁ to R ₄ is substituted with another substituent, and at least one of the substituents is again substituted with a halogen group.

는 하기 화학식 1-1 내지 1-5 중 어느 하나로 표시되는 것인 화합물을 제공한다.In an exemplary embodiment of the present application, in Chemical Formula 1

Provides a compound represented by any one of the following Chemical Formulas 1-1 to 1-5.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,

The definition of R ₁ to R ₄ is the same as the definition in Formula 1,

R ₂₁ to R ₂₇ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Carboxy group (-COOH); -OC (= 0) R; Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

At least one of the R ₁ to R ₄ and R ₂₁ to R ₂₇ is a halogen group.

In one embodiment of the present application, the R _{5 To} R _{8 They} are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted C _{6 Through} C ₆₀ An aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group. Adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, R ₅ to R ₈ are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted C _{6 Through} C ₄₀ An aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group. Adjacent groups may combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another exemplary embodiment, R ₅ to R ₈ may be the same as or different from each other, and each independently, hydrogen or an adjacent group may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another exemplary embodiment, R ₅ to R ₈ are the same as or different from each other, and each independently, hydrogen or adjacent groups combine with each other to form a substituted or unsubstituted C ₂ to C ₄₀ aromatic hydrocarbon ring. Can be.

In another exemplary embodiment, R ₅ to R ₈ may be the same as or different from each other, and each independently, hydrogen or an adjacent group may be bonded to each other to form an aromatic hydrocarbon ring of C ₂ to C ₄₀ .

In another exemplary embodiment, R ₅ to R ₈ may be the same as or different from each other, and each independently, hydrogen, or adjacent groups may be bonded to each other to form a benzene ring.

In one embodiment of the present application, R ₅ -R ₆ or R ₇ -R ₈ of the R ₅ to R ₈ are bonded to each other to form an aromatic hydrocarbon ring, the remainder may be hydrogen.

In another exemplary embodiment, R ₅ -R ₆ or R ₇ -R ₈ in R ₅ to R ₈ may be bonded to each other to form an aromatic hydrocarbon ring of C ₂ to C ₄₀ , and the other may be hydrogen.

In another exemplary embodiment, said R ₅ to R ₈ of R ₅ -R ₆ or R ₇ -R ₈ may form a benzene ring bonded to each other, and the other may be a hydrogen.

In one embodiment of the present application, A is -X _1- ; -X ₂ = X _3- ; Or -X ₄ -X _5- , X ₁ , X ₄ and X ₅ are O; S; NR ₁₁ ; C═O or CR ₁₂ R ₁₃ , X ₂ and X ₃ are N; Or CR ₁₄ .

In one embodiment of the present application, the R _{11 To} R _{14 Are} the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; Substituted or unsubstituted C _{6 Through} C ₆₀ An aryl group; Or a substituted or unsubstituted C _{2 Through} C _{60 It} may be a heteroaryl group.

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; Or a substituted or unsubstituted C ₁ to C ₆₀ alkyl group.

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; Or a C ₁ to C ₆₀ alkyl group.

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; Or a linear alkyl group of C ₁ to C ₆₀ .

In another exemplary embodiment, R ₁₁ to R ₁₄ are the same as or different from each other, and are each independently hydrogen; Or a methyl group.

In one embodiment of the present application, Y may be a direct bond.

In one embodiment of the present application, Y may be CR ₁₅ .

In one embodiment of the present application, R ₁₅ may be bonded to an adjacent group to form a benzene ring.

In another exemplary embodiment, R ₁₅ may be combined with an adjacent R ₁ to form a benzene ring.

In an exemplary embodiment of the present application, B is N or CR ₁₆ , and R ₁₆ is hydrogen; Or a substituted or unsubstituted amine group.

In one embodiment of the present application, B may be N.

In an exemplary embodiment of the present application, B may be CR ₁₆ .

In one embodiment of the present application, R ₁₆ may be a substituted or unsubstituted amine group.

In one embodiment of the present application, Chemical Formula 1 provides a compound represented by any one of the following compounds.

According to an exemplary embodiment of the present specification, it provides a color material composition comprising a compound represented by the formula (1).

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

In one embodiment of the present specification, a resin composition containing the color material composition is provided.

In one embodiment of the present specification, the resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.

In one embodiment of the present application, the content of the compound represented by Formula 1 is 0.1 wt% to 60 wt% based on the total weight of solids in the resin composition, and the content of the binder resin is 1 wt% to 60 Wt%, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the multifunctional monomer is 0.1% to 50% by weight.

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

The binder resin may use 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 to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (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 CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene 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 It is, but is not limited thereto.

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

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

The monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group. For example, (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 Although it is preferable to use 1 or more types, it 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, the weight average molecular weight is 1,000 to 50,000.

The polyfunctional monomer is a monomer that forms a photoresist image by light, 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, 1 type selected from the group consisting of trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Or a mixture of two or more kinds.

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

The acetophenone-based 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-hydroxycyclohexylphenylketone, 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.

As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.

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

The oxime compound is 1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGII242), N-1919 (Adecasa), 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, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.

Dimethylformamide (DMF) may be preferably used as the solvent.

According to one embodiment of the present specification, based on the total weight of solids in the resin composition, the content of the color material composition is 0.1 wt% to 60 wt%, and the content of the binder resin is 1 wt% to 60 wt% The content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the multifunctional monomer is 0.1 wt% to 50 wt%.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.

According to one embodiment of the present specification, the resin composition is one or more selected from the group consisting of a photocrosslinking agent, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and a leveling agent. Further 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 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, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones 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 Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 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-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.

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

As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, 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, and the like. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 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 esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, 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 ' 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 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, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.

The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.

The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.

According to one embodiment of the present specification, a photosensitive material manufactured using the resin composition is provided.

In more detail, the resin composition of this specification is apply | coated on a base material by a suitable method, and forms the photosensitive material of a thin film or a pattern form.

Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.

As a light source for curing the resin composition according to the present specification, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc., which emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.

The resin composition according to the present disclosure may be a pigment dispersion photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, It can be used for photosensitive material for forming overcoat layer, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed circuit board, photosensitive material for plasma display panel (PDP), and the like. There is no special place.

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

The color filter may be manufactured using a resin composition including the color material composition. The resin composition may be applied onto a substrate to form a coating film, and the color filter may be formed by exposing, developing, and curing the coating film.

The resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having a high color reproducibility and a high luminance and contrast ratio by the curing process during the manufacture of the color filter. have.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the 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 black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present specification may use black pigment or black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.

Provided is a display device including a color filter according to the present specification.

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

Hereinafter, the present specification will be described in detail with reference to Examples. The following examples are provided to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims, their substitutions and changes, and is not limited to the examples.

< Production Example >

Synthesis of Compound

< Production Example  1> Preparation of Compound A

2-methylbenzothiazole (1.4g, 9.4mmol) and naphtho [2,3-c] furan-1,3-dione (Naphtho [2,3-c] furan-1.3-dione) ) (1.88g, 9.5mmol), benzoic acid (10g) and methyl benzoate (6ml) are added and reacted at 180 ~ 200 ℃ for 4 hours. After cooling, 100 ml of MeOH was added, followed by stirring under reduced pressure for 12 hours. After filtration under reduced pressure, the mixture is washed several times with MeOH and dried. 1.8 g of compound A was obtained. (Yield 57%)

It confirmed that m / z = 328 by the mass spectrometer MALDI-TOF.

< Production Example  2> Preparation of Compound B

2-methylbezothiazole (1.4g, 9.4mmol) and 5-methoxyisobenzofuran-1,3-dione (1.7g, 9.5mmol) ), Benzoic acid (10 g) and methyl benzoate (6 ml) were added thereto, and prepared in the same manner as Compound A of Preparation Example 1, to obtain 2.0 g of compound B (yield 68%).

It confirmed that m / z = 308 by the mass spectrometer MALDI-TOF.

< Production Example  3>-Preparation of Compound C

2-Methylbenzimidazole (0.7 g, 5.3 mmol), Tetrachlorophthalic anhydride (1.51 g, 5.3 mmol), benzoic acid (4 g), methyl benzoate (methyl benzoate) (3 ml) was added thereto, and the compound C was prepared in the same manner as in the compound A of Preparation Example 1, to obtain 1.36 g of the compound C (yield 64%).

It confirmed that m / z = 399 by the mass spectrometer MALDI-TOF.

< Production Example  4> Preparation of Compound D

2-Methyl-4 (3H) -quinazolinone (1 g, 6.23 mmol) and tetrachlorophthalic anhydride (1.78 g, 6.23 mmol), Benzoic acid (3 g) and methyl benzoate (2 ml) were added thereto, and the compound D was prepared in the same manner as Compound A to obtain 2.19 g (yield 82%) of compound D.

It confirmed that m / z = 427 by the mass spectrometer MALDI-TOF.

< Production Example  5> Preparation of Compound E

2,3,3-trimethyl-3H-indole (1.0 g, 6.3 mmol) and 5-chloroisobenzofuran-1,3-dione (5-Chloroisobenzofuran- 1,3-dione) (1.1g, 6.3mmol) benzoic acid (3g) and methyl benzoate (2ml) was added and prepared in the same manner as Compound A of Preparation Example 1 Compound E 1.5g (Yield 74%) was obtained.

It confirmed that m / z = 322 by the mass spectrometer MALDI-TOF.

< Production Example  6> Preparation of Compound F

1,1,2-trimethyl-1H-benzoindole (1,1,2-trimethyl-1H-benzoindole) (1.5 g, 7.2 mmol) and 5,6-dichloroisobenzofuran-1,3-dione ( 5,6-dichloroisobenzofuran-1,3-dione) (1.6g, 7.2mmol) benzoic acid (5g) and methyl benzoate (3ml) were added and the same method as in Compound A of Preparation Example 1 Prepared to give compound F 2.3g (yield 78%).

It confirmed that m / z = 407 by mass spectrometer MALDI-TOF.

< Production Example  7> Preparation of Compound G

Methylbenzothiazole (1.0 g, 6.7 mmol) and 4,5,6,7,8,9-hexachloronaphtho [2,3] furan-1,3-dione (4,5,6 Preparation Example 7,8,9-hexachloronaphtho [2,3] furan-1,3-dione (2.7 g, 6.7 mmol) benzoic acid (5 g) methyl benzoate (3 ml) Compound G was obtained in the same manner as in compound A of 1 to obtain 2.3 g (yield 65%).

It confirmed that m / z = 535 by the mass spectrometer MALDI-TOF.

< Production Example  8> Preparation of Compound H

Methylbenzooxazole (0.8 g, 6.0 mmol) with 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (4,5,6,7-tetrachloroisobenzofuran-1,3- dione) (1.71g, 6.0mmol) benzoic acid (4g) Methyl benzoate (2ml) was added and prepared in the same manner as Compound A of Preparation Example 1 Compound H 1.9g (yield 80%) Got.

It confirmed that m / z = 400 by the mass spectrometer MALDI-TOF.

< Production Example  9> Preparation of Compound I

2-methylnaphthothiazole (1.0 g, 5.0 mmol) with 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (4,5,6,7-tetrachloroisobenzofuran -1,3-dione) (1.4g, 5.0mmol) benzoic acid (3g) methyl benzoate (2ml) was added and prepared in the same manner as Compound A of Preparation Example 1 Compound I 1.7g (Yield 73%) was obtained.

It confirmed that m / z = 466 by the mass spectrometer MALDI-TOF.

< Production Example  10> Preparation of Compound J

2-methylquinoxaline (1.0 g, 6.9 mmol) and 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (4,5,6,7-tetrachloroisobenzofuran-1 , 3-dione) (2.0g, 6.9mmol) benzoic acid (5g) Methyl benzoate (3ml) was added and prepared in the same manner as Compound A of Preparation Example 1 Compound J 2.2g (Yield 77%).

It confirmed that m / z = 411 by the mass spectrometer MALDI-TOF.

< Example >

[Resin composition Comparative example  1, manufacture]

1 part by weight of Compound A prepared above, 36 parts by weight of binder A, 17 parts by weight of polyfunctional monomer (Dipentaerythritol hexaacrylate), 0.6 parts by weight of leveling agent F-554, and adhesive aid KBM-503 0.08 Part by weight, 1.0 part by weight of initiator (PBG-3057), and 44.32 parts by weight of solvent propylene glycol monomethyl ether acetate (PGMEA) were prepared.

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

Resin composition Comparative Example 2 and Examples 1 to 8 were prepared by the same method as the preparation of Resin Composition Comparative Example 1, except that Compound A was changed to the compound shown in Table 1 below in the preparation of Resin Composition Comparative Example 1.

Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 compound B C D E F G H I J

Board production

The resin compositions prepared by Comparative Examples 1 and 2 and Examples 1 to 8 were spin coated onto glass (5 cm × 5 cm) and subjected to prebake at 100 ° C. for 100 seconds to form a film. The exposure amount of 40 mJ / cm <2> was irradiated to the board | substrate whole surface using the exposure machine to the board | substrate which formed the film. Subsequently, the exposed substrate was developed for 60 seconds in a developing solution (KOH, 0.05%) and post-baked at 230 ° C. for 20 minutes to prepare a substrate.

[Heat resistance evaluation]

The post-heat treated (post bake once) substrate manufactured under the conditions described above was used to obtain an absorption spectrum in the wavelength range of 380 to 780 nm using a spectrometer (MCPD, Otsuka Co., Ltd.). In addition, the post-heat treatment substrate (one post bake) was further treated at 230 ° C. for 60 minutes to obtain a transmittance spectrum in the same measurement range as the same equipment.

ΔEab was calculated using the values L *, a *, and b * obtained as absorption spectra obtained using the C light source as a backlight, and is shown in the following [Table 2].

ΔEab = ((ΔL *) 2+ (Δa *) 2+ (Δb *) 2) 1/2

The smaller ΔEab value means less color change, indicating excellent heat resistance.

[Permeability Evaluation]

Post-heat treated substrate (once post bake) The substrate was absorbed in the wavelength range of 380 ~ 780nm using a spectrometer (MCPD, Otsuka Co., Ltd.). The transmittance at the maximum absorption wavelength is shown in the following [Table 2].

The small transmittance value means that a relatively small amount of colorant content can be used when combining colorants for color filters.

Heat resistance (△ Eab) Permeability (%) Comparative Example 1 6.23 32.5 Comparative Example 2 5.87 38.9 Example 1 2.96 9.0 Example 2 1.48 12.4 Example 3 1.72 10.5 Example 4 3.73 23.7 Example 5 1.23 18.6 Example 6 1.58 25.8 Example 7 3.75 17.9 Example 8 1.41 10.8

Compounds C to J including the compound represented by Chemical Formula 1 of the present application had better heat resistance than Compound A and B which did not, and exhibited low permeability. In particular, the compound represented by the general formula (1) of the present application contains a halogen, it was confirmed that the heat resistance was particularly excellent, and also has a low permeability.

Claims (13)

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

In Chemical Formula 1,
A is -X _1- ; -X ₂ = X _3- ; Or -X ₄ -X _5- ,
X ₁ , X ₄ and X ₅ are O; S; NR ₁₁ ; C = O or CR ₁₂ R ₁₃ ,
X ₂ and X ₃ are N; Or CR ₁₄ ,
Y is a direct bond; O; S; Or CR ₁₅ ,
B is N or CR ₁₆ ,
R ₁ to R ₈ and R ₁₁ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Carboxy group (-COOH); -OC (= 0) R; Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
In Formula 1

Has at least one halogen group. The compound according to claim 1, wherein Formula 1 is represented by the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,
The definitions of R ₁ to R ₈ , X ₁ to X ₅ , B, and Y are the same as those defined in Chemical Formula 1. The method according to claim 1, Formula 1

Is a compound represented by any one of the following Formulas 1-1 to 1-5:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,
The definition of R ₁ to R ₄ is the same as the definition in Formula 1,
R ₂₁ to R ₂₇ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Carboxy group (-COOH); -OC (= 0) R; Sulfonic acid group (-SO ₃ H); Sulfonamide groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
At least one of the R ₁ to R ₄ and R ₂₁ to R ₂₇ is a halogen group. The method according to claim 1, wherein B is N or CR ₁₆ ,
R ₁₆ is hydrogen; Or a substituted or unsubstituted amine group. The compound of claim 1, wherein R ₅ to R ₈ are the same as or different from each other, and each independently hydrogen, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring. The compound of claim 1, wherein Formula 1 is represented by any one of the following compounds:

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 at least one of dyes and pigments. A compound of any one of claims 1 to 6; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent. The method according to claim 9,
Based on the total weight of solids in the resin composition
The content of the compound represented by Formula 1 is 0.1% by weight to 60% by weight,
The binder resin content is 1% by weight to 60% by weight,
The content of the photoinitiator is 0.1% by weight to 20% by weight,
The content of the multifunctional monomer is a resin composition of 0.1% by weight to 50% by weight. The photosensitive material manufactured using the resin composition of Claim 9. A color filter comprising the photosensitive material according to claim 11. Display device including a color filter according to claim 12.