KR102291761B1 - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by Formula 1, a color material composition comprising the same, and a resin composition comprising the same.

Description

Compound, color material composition comprising the same, and resin composition comprising the 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 comprising the same, and a resin composition comprising the same.

Currently, as the light source of liquid crystal display (LCD), instead of CCFL, LED, OLED, as well as QD, etc. are being actively applied and developed. In general, it is not easy to match or adjust the required color coordinates using light emitted from an LED or OLED light source. Nevertheless, in order to improve the performance of the light source, in the case of LED, various light emitting materials are introduced into the LED, or organic or inorganic light emitting materials are introduced into the optical film through which the LED light source is transmitted to improve display quality.

In order to realize an image that is more similar to nature or identical to the display, a wider color gamut than before is possible, that is, wide color gamut_WCG is possible. is being demanded In addition, it is necessary to develop a display with a thinner thickness for space utilization.

A photosensitive resin composition (Photoresist) for manufacturing a color filter applied to such a display requires various materials such as a colorant, a binder, and an initiator. In particular, the color material is the most important material that influences the color quality and luminance of the color filter.

In general, 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, in the case of the pigment dispersion method, the method of improving color purity, luminance, and contrast ratio during the manufacture of the used color filter has reached its 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 color material composition comprising the same, and a resin composition comprising the same.

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

[Formula 1]

In 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; imid; amide group; carboxyl group (-COOH); -OC(=O)R; sulfonic acid group (-SO ₃ H); sulfonamide group; 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 alkylthio group; a substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a 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 above

has at least one halogen group.

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

According to another exemplary embodiment, a compound according to an exemplary embodiment of the present application; binder resin; polyfunctional monomers; photoinitiators; And it provides a resin composition comprising a solvent.

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

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

Finally, a display device 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 excellent in color characteristics, heat resistance, and solvent resistance, and has excellent absorption in the short wavelength region of visible light (380 nm to 430 nm), so that the coloring power of the red color filter is particularly strong. great.

In addition, the color material composition including the compound represented by Formula 1 has excellent color characteristics, heat resistance, light resistance and solvent resistance, and can achieve higher color reproducibility, high brightness, high contrast, and the like.

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

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.

Embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those of ordinary skill in the art to which the present invention pertains can easily carry out the present invention. However, the present invention may be embodied in many different forms and is not limited to the embodiments described herein.

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

In the case of the compound represented by Formula 1 according to the present invention, it is a compound having excellent color characteristics, solvent resistance, and particularly, excellent heat resistance. has

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

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; imid; amide group; carbonyl group; ester group; hydroxyl group; carboxyl group (-COOH); sulfonic acid group (-SO ₃ H); sulfonamide group; 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 alkylthio group; a substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

refers to a site bonded to another substituent or a bonding group.

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

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but preferably from 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 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 C1-C30 linear or branched alkyl group; a 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, and the number of carbon atoms 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.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and 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, etc., but are limited thereto it is not

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. 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, etc. may be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; monoalkylamine group; dialkylamine group; N-alkylarylamine group; monoarylamine group; diarylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine 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 is not limited thereto.

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

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroarylamine group are substituted with 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 alkylsulfoxy group, and the N-alkylheteroarylamine group is the same as the above-described alkyl group. Specifically, the alkyl thiooxy group includes a methyl thioxy group, ethyl thiooxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thiooxy group, etc., and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms 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 is not limited thereto.

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

In the present specification, the boron group may be -BR100R101, wherein R100 and R101 are the same or different, 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 C1-C30 linear or branched alkyl group; a 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 phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthyl phosphine 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, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl 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 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

etc. can be However, the present invention is not limited thereto.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. 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.

In the present specification, the aryl group in the monoarylamine group, diarylamine group, aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group and arylphosphine group is described above. It is the same as an example of an aryl group. Specifically, the aryloxy group includes 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, etc., and the arylthioxy group includes phenylthioxy group, 2- There is a methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, and the arylsulfoxy group includes a benzenesulfoxy group, a p-toluenesulfoxy group, and the like, but is not limited thereto.

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. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazinyl group Jolyl group, acridyl 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 Nonthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are 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 formed by combining adjacent groups with each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

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

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

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms 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, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except for non-monovalent ones.

In an exemplary 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 Formulas 2 to 4,

Definitions of R ₁ to R ₈ , X ₁ to X ₅ , B and Y are the same as those in Formula 1 above.

In an exemplary embodiment of the present application, R _{1 To} R _{8 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; imid; amide group; carboxyl group (-COOH); -OC(=O)R; sulfonic acid group (-SO ₃ H); sulfonamide group; 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 alkylthio group; a substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a 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, the R _{1 To} R _{4 Are} the same as or different from each other, and each independently, hydrogen; halogen group; a 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, the R _{1 To} R _{4 Are} the same as or different from each other, and each independently, hydrogen; halogen group; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group, or adjacent groups may combine with each other to form a substituted or unsubstituted C ₆ to C ₆₀ aromatic hydrocarbon ring.

In another exemplary embodiment, the R _{1 To} R _{4 Are} the same as or different from each other, and each independently, hydrogen; halogen group; a substituted or unsubstituted C ₆ to C ₄₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group, or adjacent groups may combine with each other to form a substituted or unsubstituted C ₆ to C ₄₀ aromatic hydrocarbon ring.

In another exemplary embodiment, the R _{1 To} R _{4 Are} the same as or different from each other, and each independently, hydrogen; halogen group; C _{6 To} C ₄₀ Aryl group; Or a C ₂ to C ₄₀ heteroaryl group, or adjacent groups may combine with each other to form a C ₆ to C ₄₀ aromatic hydrocarbon ring.

In another exemplary embodiment, the 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 Formula 1

has at least one halogen group, and the halogen group may be one or more 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 above

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 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 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 Formulas 1-1 to 1-5,

The definitions of R ₁ to R ₄ are the same as those in Formula 1 above,

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; imid; amide group; carboxyl group (-COOH); -OC(=O)R; sulfonic acid group (-SO ₃ H); sulfonamide group; 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 alkylthio group; a substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a 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 R ₁ to R ₄ and R ₂₁ to R ₂₇ is a halogen group.

In an exemplary embodiment of the present application, R _{5 To} R _{8 Are} the same as or different from each other, and each independently, hydrogen; a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group. Adjacent groups may combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, the R _{5 To} R _{8 Are} the same as or different from each other, and each independently, hydrogen; a substituted or unsubstituted C ₆ to C ₄₀ 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 are the same as or different from each other, and each independently hydrogen, or adjacent groups may combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

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

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

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

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

In another exemplary embodiment, _{among R 5} to R ₈ , R ₅ -R ₆ or R ₇ -R ₈ may combine with each other to form a C ₂ to C ₄₀ aromatic hydrocarbon ring, and the remainder may be hydrogen.

In another exemplary embodiment, _{among R 5} to R ₈ , R ₅ -R ₆ or R ₇ -R ₈ may be combined with each other to form a benzene ring, and the remainder may be hydrogen.

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

In an exemplary 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; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group.

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

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

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

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

In another exemplary embodiment, the R ₁₁ to R ₁₄ are the same as or different from each other and each independently hydrogen; Or C ₁ to C _{60 It} may be a straight-chain alkyl group.

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

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

In an exemplary embodiment of the present application, Y may be _{CR 15 .}

In an exemplary embodiment of the present application, R ₁₅ may combine with 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 , R ₁₆ is hydrogen; Or it provides a compound that is a substituted or unsubstituted amine group.

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

In the exemplary embodiment of the present application, B may be _{CR 16 .}

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

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

According to an exemplary embodiment of the present specification, there is provided a color material composition comprising the compound represented by Formula 1 above.

The color material composition may further include at least one of a dye and a pigment in addition to the compound represented by Formula 1 above. For example, the color material composition may include only the compound represented by Formula 1, but includes the compound represented by Formula 1 and one or more dyes, or includes the compound represented by Formula 1 and one or more pigments, or , may include a compound represented by Formula 1, at least one dye, and at least one pigment.

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

In one embodiment of the present specification, the resin composition comprises a binder resin; polyfunctional monomers; photoinitiators; and a solvent.

In an exemplary 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 the solid content in the resin composition, and the content of the binder resin is 1 wt% to 60 wt% and the content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt% It provides a resin composition.

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

The polyfunctional monomer imparting the mechanical strength of the membrane is an unsaturated carboxylic acid ester; aromatic vinyls; unsaturated ethers; unsaturated imides; and an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydropuffril (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 It is not limited.

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. may be, but is not limited thereto.

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

The monomer imparting alkali solubility is not particularly limited as long as it contains an acid group, and 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 It is preferable to use one or more types, but is not limited thereto.

According to an exemplary embodiment of the present specification, the binder resin has an acid value of 50 to 130 KOH mg/g, and a weight average molecular weight of 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, One selected from the group consisting of trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate Or it may be a mixture of two or more types.

The photoinitiator is not particularly limited as long as it is an initiator that triggers crosslinking by generating radicals by light, for example, selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. There may be more than one type.

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-hydroxycyclohexylphenyl ketone, benzoinmethyl ether, benzoinethyl 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, etc. , but not limited thereto.

The triazine-based 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-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-based compound is 1,2-octadione-1-(4-phenylthio)phenyl-2-(o-benzoyloxime) (Ciba Geigisa, CGI 124), ethanone-1-(9-ethyl) -6-(2-methylbenzoyl-3-yl)-1-(O-acetyloxime) (CGI242), N-1919 (Adecas), and the like, but is 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 acetate, ethyl 3-ethoxy It may be at least one selected from the group consisting of propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto.

Preferably, dimethylformamide (DMF) may be used as the solvent.

According to an exemplary embodiment of the present specification, based on the total weight of the solid content in the resin composition, the content of the color material composition is 0.1% to 60% by weight, and the content of the binder resin is 1% to 60% by weight, and , The content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional 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 solid content and the basis of weight % based on the solid content of each component may be measured by general analytical means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the resin composition is one or two or more selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersing agent, and a leveling agent. Additives are further included.

According to an exemplary embodiment of the present specification, the content of the additive is 0.1 wt% to 20 wt% 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, 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, diisopropyl thioxanthone compound; xanthone-based compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. acridine-based compounds; dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo coumarin-based 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-mercaptopropionate), pentaerythritol Erythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropio) nate) may be used at least one selected from the group consisting of.

The adhesion promoter used herein includes methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxysilane. It is possible to select and use at least one type of methacryloyl silane coupling agent such as, and at least one type of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc. as the alkyl trimethoxysilane. You can choose to use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 manufactured by BYK-Chemie. , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.

The antioxidant may be at least one 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-based thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite 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 ester), such as a hindered phenol-based primary antioxidant; 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 dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, 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' -Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester) may be mentioned as a phosphite-based secondary antioxidant.

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, N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and may include one or more selected from the group consisting of phenothiazine (phenothiazine), but is not limited thereto. may include those generally known in the art.

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

Specifically, the dispersant is polyalkylene glycol and its esters, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylate esters, carboxylates, There is at least one selected from the group consisting of an alkylamide alkylene oxide adduct and an alkylamine, but is not limited thereto.

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

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

More specifically, the resin composition of the present specification is applied on a substrate by an appropriate method to form a thin film or patterned photosensitive material.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, etc. may be used, and in general, a spin coating method is widely used. In addition, after forming the coating film, in some cases, the residual solvent may be partially removed under reduced pressure.

As a light source for curing the resin composition according to the present specification, for example, a mercury vapor arc emitting light having a wavelength of 250 nm to 450 nm, a carbon arc, an Xe arc, etc., but is not necessarily limited thereto.

The resin composition according to the present specification is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode, Photosensitive material for forming overcoat layer, 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. does not specifically put

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

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

The resin composition according to an exemplary embodiment of the present specification has excellent heat resistance, and there is little change in color due to heat treatment. have.

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 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. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching may be used. However, in consideration of the high cost in the process, the high reflectivity of chromium, and environmental pollution caused by the chromium waste solution, a resin black matrix by 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 alone or a mixture of carbon black and a colored pigment can be used. At this time, since a colored pigment lacking in light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material is relatively increased. There are advantages to not being.

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

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 device (Thin FIlm Transistor-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 intended to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims, and substitutions and modifications thereof, and is not limited to the scope of the examples.

< manufacturing example >

<Synthesis of compounds>

< manufacturing example 1> -Preparation of compound A

2-methylbenzothiazole (1.4 g, 9.4 mmol) 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, stirred for 12 hours, and filtered under reduced pressure. During filtration under reduced pressure, it is washed several times with MeOH and dried. 1.8 g of Compound A was obtained. (Yield 57%)

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

< manufacturing example 2> -Preparation of compound B

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

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

< manufacturing example 3>-Preparation of compound C

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

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

< manufacturing 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 (3g) and methyl benzoate (2ml) were added and prepared in the same manner as in Compound A of Preparation Example 1 to obtain 2.19g of Compound D (yield 82%).

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

< manufacturing example 5> -Preparation of compound E

2,3,3-trimethyl-3H-indole (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), methyl benzoate (2ml) was added, prepared in the same manner as in Compound A of Preparation Example 1, and compound E 1.5g (yield 74%) was obtained.

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

< manufacturing example 6> -Preparation of compound F

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

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

< manufacturing example 7> -Preparation of compound G

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

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

< manufacturing example 8> -Preparation of compound H

Methylbenzooxazole (0.8g, 6.0mmol) and 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 in Compound A of Preparation Example 1, compound H 1.9g (yield 80%) got

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

< manufacturing example 9> -Preparation of compound I

2-methylnaphthothiazole (1.0 g, 5.0 mmol) and 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 in Compound A of Preparation Example 1, 1.7g of Compound I (yield 73%) was obtained.

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

< manufacturing 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 in Compound A of Preparation Example 1, compound J 2.2g (yield 77%) was obtained.

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

< Example >

[Resin composition comparative example 1 manufacture]

Based on 100 parts by weight of the total weight of the resin composition, 1 part by weight of the compound A prepared above, 36 parts by weight of the binder A, 17 parts by weight of a polyfunctional monomer (Dipentaerythritol hexaacrylate), 0.6 parts by weight of a leveling agent F-554, and an adhesive aid KBM-503 0.08 It was prepared by mixing parts by weight, 1.0 parts by weight of the initiator (PBG-3057), and 44.32 parts by weight of the solvent propylene glycol monomethyl ether acetate (PGMEA, Propylene Glycol monomethyl ether acetate).

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

Resin composition Comparative Examples 2 and Examples 1 to 8 were prepared in the same manner as in the preparation of the resin composition Comparative Example 1 except for changing the compound shown in Table 1 instead of Compound A during the preparation of the 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

[Substrate manufacturing]

The resin compositions prepared in Comparative Examples 1 and 2 and Examples 1 to 8 were always spin-coated on glass (5 cm X 5 cm) and prebake was performed at 100° C. for 100 seconds to form a film. The substrate on which the film was formed was irradiated with an exposure dose of 40 mJ/cm 2 on the entire surface of the substrate using an exposure machine. After that, the exposed substrate was developed in a developer (KOH, 0.05%) for 60 seconds, and post-bake at 230° C. for 20 minutes to prepare a substrate.

[Heat resistance evaluation]

An absorption spectrum in a wavelength range of 380 to 780 nm was obtained by using a spectrometer (MCPD, Otsuka Co.) for the post-bake substrate prepared under the above conditions. In addition, the transmittance spectrum was obtained in the same measurement range as the same equipment by additionally processing the post heat treatment substrate (post bake once) at 230° C. for 60 minutes.

ΔEab was calculated using the values L*, a*, and b* obtained from the absorption spectrum obtained using the C light source as a backlight, and is shown in Table 2 below.

ΔEab = ((ΔL*)2+(Δa*)2+(Δb*)2)1/2

A small ΔEab value means less color change, indicating excellent heat resistance.

[Permeability evaluation]

An absorption spectrum in a wavelength range of 380 to 780 nm was obtained using a spectrometer (MCPD, Otsuka Co., Ltd.) for the post-heat treatment substrate (post bake once). The transmittance at the maximum absorption wavelength is shown in [Table 2] below.

A small transmittance value means that a relatively small amount of colorant can be used when combining a colorant for a color filter.

Heat resistance (ΔEab) Transmittance (%) 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 containing the compound represented by Formula 1 of the present application exhibited superior heat resistance and low transmittance compared to compounds A and B that did not. In particular, it was confirmed that the compound represented by Chemical Formula 1 of the present application contains halogen, and thus has particularly excellent heat resistance and low transmittance.

Claims (13)

A compound represented by any one of the following formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
X ₁ is O; S; NR ₁₁ ; or CR ₁₂ R ₁₃ ,
X ₂ and X ₃ are each independently N; or CR ₁₄ ,
X ₄ and X ₅ are each independently O; S; NR ₁₁ '; C=O or CR ₁₂ 'R ₁₃ ',
Y is a direct bond; or CR ₁₅ R ₁₅ ',
B is N or CR ₁₆ ,
R ₁ to R ₄ , R ₁₅ and R ₁₅ ' are the same as or different from each other, and each independently hydrogen; or a halogen group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
R ₅ to R ₈ are the same as or different from each other, each independently hydrogen, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
R ₁₁ to R ₁₃ and R ₁₁ ' to R ₁₃ ' are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
R ₁₄ is hydrogen,
R ₁₆ is hydrogen; Or a substituted or unsubstituted amine group,
in Formulas 2 to 4

is represented by any one of the following formulas 1-1 to 1-4,
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
R ₂₁ to R ₂₇ and R ₃₁ to R ₃₄ are the same as or different from each other, and each independently hydrogen; or a halogen group,
Formulas 1-1 to 1-4 have at least one halogen group,
i) In Formula 2, when X ₁ is S, B is N, and R ₅ to R ₈ are hydrogen, or
ii) in Formula 4, _{when any one of X 4} and X ₅ is C=O, B is N, and R ₅ to R ₈ are hydrogen,

is represented by any one of Formulas 1-1, 1-3, and 1-4. delete delete delete The compound according to claim 1, wherein R ₅ to R ₈ are the same as or different from each other, each independently hydrogen, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring. The method according to claim 1, wherein the compound is the formula 1-1 to 1-10, 2-1 to 2-10, 3-7 to 3-10, 4-1 to 4-10, 5-1 to 5-10, A compound represented by any one of 6-1 to 6-10, 7-1 to 7-10, 8-7 to 8-10, 9-1 and 9-2:

A color material composition comprising the compound according to any one of claims 1, 5 and 6. The color material composition according to claim 7, further comprising at least one of a dye and a pigment. the compound of any one of claims 1, 5 and 6; binder resin; polyfunctional monomers; photoinitiators; And a resin composition comprising a solvent. 10. The method of claim 9,
Based on the total weight of solids in the resin composition
The content of the compound is 0.1% to 60% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1 wt% to 20 wt%,
The content of the polyfunctional monomer is 0.1% by weight to 50% by weight of the resin composition. A photosensitive material manufactured using the 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 .