JP6897906B2 - Compounds, color material compositions containing them, and resin compositions containing them - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0023013 filed with the Korean Intellectual Property Office on February 26, 2018, the entire contents of which are incorporated herein by reference.

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

Currently, as a light source of a liquid crystal display (LCD), not only LEDs and OLEDs but also QDs and the like are actively applied and developed instead of CCFLs. In general, it is not easy to match or adjust the required color coordinates using the 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 emitters are introduced in the LED, or an organic or inorganic light emitter is introduced in the optical film through which the LED light source is transmitted to display the quality of the display. Is being developed to improve.

In order to realize a more natural-like or identical image on the display, it is possible to realize a wider color region than the existing one, that is, high color reproduction (Wide Color Gamut_WCG) is possible, and the amount of light transmitted by the display is increased. Therefore, an increase in color volume is required. And, in order to utilize the space, it is necessary to develop a display with a thinner thickness.

A photosensitive resin composition (Photoresist) for producing a color filter applied to such a display requires various materials such as a coloring material, a binder, and an initiator. In particular, in the case of a color material, it is the most important material that affects the color quality and brightness of the color filter.

Generally, pigments known to have excellent properties such as heat resistance and light resistance are used, and such pigments are dispersed (pigment dispersion method) and applied to a photosensitive resin composition. .. However, in the case of the pigment dispersion method, the method for improving the color purity, the brightness, and the contrast ratio has reached the limit point at the time of manufacturing the color filter used. In order to carry out the pigment dispersion method, the content of the pigment in the photosensitive resin composition is lowered by a pigment derivative, a dispersant, etc. added for dispersion together with the pigment, and in order to realize a desired color, The thickness of the color material in the color filter may increase, making it difficult to manufacture a thin film color filter.

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

The present specification provides a novel compound, a color material composition containing the same, and a resin composition containing the same.

前記化学式１において、
Ａは、Ｘ_１−Ｘ_２；またはＸ_３＝Ｘ_４であり、
Ｂは、直接結合；またはＣＱ_１Ｑ_２であり、
Ｘ_１およびＸ_２は、ＣＲ_ａＲ_ｂであり、
Ｘ_３およびＸ_４は、ＣＲ_ｃであり、
Ａｒ_１は、水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のヘテロアリール基であり、
Ｒ_ａ〜Ｒ_ｃ、Ｒ_ｘ、Ｑ_１およびＱ_２は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；カルボニル基；エステル基；イミド基；アミド基；カルボキシ基（−ＣＯＯＨ）；−ＯＣ（＝Ｏ）Ｒ"；スルホン酸基（−ＳＯ_３Ｈ）；スルホンアミド基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアリールオキシ基；置換もしくは非置換のアルキルチオキシ基；置換もしくは非置換のアリールチオキシ基；置換もしくは非置換のアルキルスルホキシ基；置換もしくは非置換のアリールスルホキシ基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシリル基；置換もしくは非置換のホウ素基；置換もしくは非置換のアミン基；置換もしくは非置換のアリールホスフィン基；置換もしくは非置換のホスフィンオキシド基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であるか、隣接した基は、互いに結合して置換もしくは非置換の環を形成し、
Ｒ"は、置換もしくは非置換のアルキル基であり、
ｐは、１〜６の整数であり、
ｎは、６−ｐの整数である。 One embodiment of the present application provides a compound represented by the following Chemical Formula 1.
[Chemical formula 1]

In the chemical formula 1,
A is X _1- X ₂ ; or X ₃ = X ₄ .
B is a direct bond; or CQ ₁ Q ₂ and
X ₁ and X ₂ are CR _a R _b and
X ₃ and X ₄ are CR _c and
Ar ₁ is a hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted heteroaryl group.
R _{a to} R _c , R _x , Q ₁ and Q ₂ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group. ; amide group; a carboxyl group (-COOH); - OC (= O) R "; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group Substituent or unsubstituted alkoxy group; Substituent or unsubstituted aryloxy group; Substituent or unsubstituted alkylthioxy group; Substituent or unsubstituted arylthioxy group; Substituent or unsubstituted alkylsulfoxy group; Substituent or unsubstituted Substituted 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 arylphosphine group; substituted or unsubstituted An unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
R "is a substituted or unsubstituted alkyl group.
p is an integer of 1 to 6 and
n is an integer of 6-p.

According to another embodiment, a color material composition containing a compound according to one embodiment of the present application is provided.

According to still another embodiment, there is provided a resin composition comprising a compound according to one embodiment of the present application; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

According to still another embodiment, there is provided a photosensitive material produced by using the resin composition according to one embodiment of the present application.

According to still another embodiment, there is provided a color filter containing a photosensitive material according to one embodiment of the present application.

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

In the case of the compound according to one embodiment of the present application, it is excellent in heat resistance and solubility in an organic solvent.

Further, the color material composition containing the compound represented by the chemical formula 1 is excellent in color characteristics, heat resistance, light resistance and solvent resistance, and prevents reaggregation of atomized pigments and dyes or generates foreign substances. It can be prevented and higher color recall and higher brightness, higher brightness / dark ratio, etc. can be achieved.

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

In the present specification, when a component is referred to as "contains" a component, this means that the other component can be further included rather than excluding the other component unless otherwise specified. To do.

Examples of the present invention will be described in detail with reference to the accompanying drawings so that a person having ordinary knowledge in the technical field to which the present invention belongs can easily carry out the present invention. However, the present invention is feasible in a variety of different forms and is not limited to the examples described herein.

According to one embodiment of the present specification, the compound represented by the chemical formula 1 is provided.

For the compound represented by Formula 1 according to the present invention, by introducing a -SO ₃ -Ar ₁ substituent and is capable increasing solubility in an organic solvent, preventing aggregation of the coloring material by an increase in solubility in an organic solvent When it is used as a photosensitive material later, it has a feature that the light-dark ratio can be improved.

In the present specification, examples of substituents will be described below, but the present invention is not limited thereto.

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

As used herein, the term "substituted or unsubstituted" refers to a heavy hydrogen; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxy group; a carboxy group (-COOH); a sulfonic acid group (-SO 3 _H); sulfonamido 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, substituted or Unsubstituted alkyltioxy groups; substituted or unsubstituted aryltyoxy groups; substituted or unsubstituted alkylsulfoxy groups; substituted or unsubstituted arylsulfoxy groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted alkenyl groups Cyril group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylphosphine group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl group; and substituted or unsubstituted Is substituted with one or more substituents selected from the group consisting of heterocyclic groups, or two or more of the above exemplified substituents are substituted with linked substituents, or It means that it does not have any substituents. For example, the "substituent in 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 in which two phenyl groups are linked.

は、他の置換基または結合部に結合する部位を意味する。 In the present specification

Means a site that binds to another substituent or bond.

As used herein, 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 those having 1 to 30 carbon atoms are preferable. Specifically, it may be a compound having the following structure, but is not limited thereto.

As used herein, the amide group may have the nitrogen of the amide group substituted with hydrogen, a linear, branched or ring-chain alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. .. Specifically, it may be a compound having 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 those having 1 to 30 carbon atoms are preferable. 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 replaced with a linear, branched or ring-chain alkyl group having 1 to 25 carbon atoms; a monocyclic or polycyclic ester group having 3 to 30 carbon atoms. It may be a cycloalkyl ester group substituted with a cycloalkyl group of, or an aryl ester group substituted with an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

As used herein, the sulfonamide group _{may be -SO 2} NR120R121, and the R120 and R121 are the same or different from each other and are independent of each other, hydrogen; heavy hydrogen; halogen; nitrile group; substituted or unsubstituted. A 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; a substituted or unsubstituted single ring having 6 to 30 carbon atoms. It may be selected from the group consisting of ring or polycyclic aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 1 to 30 are preferable. 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-dimethylheptyl, 1-ethyl- There are, but are not limited to, 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 one having 3 to 30 carbon atoms is preferable, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are, but are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc. Absent.

As used herein, the alkoxy group may be a straight chain, a branched chain or a ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but those having 1 to 30 carbon atoms are preferable. 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 used, but are limited thereto. It's not something.

As used herein, the amine group is -NH ₂ ; monoalkylamine group; dialkylamine group; N-alkylarylamine group; monoarylamine group; diarylamine group; N-arylheteroarylamine group; N-alkylhetero. It may be selected from the group consisting of an arylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but 1 to 30 is preferable. 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, a 9-methyl-anthrasenylamine group, a diphenylamine group, and the like. Ditrilamine group, N-phenyltrilamine 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, etc. It is not limited to.

As used herein, the N-alkylarylamine group means an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.

As used herein, the N-aryl heteroarylamine group means an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group.

As used herein, the N-alkyl heteroarylamine group means an amine group in which the N of the amine group is substituted with an alkyl group and a heteroarylamine 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 an example of the above-mentioned alkyl group. It's a street. Specifically, the alkylthioxy group includes a methylthioxy group, an ethylthioxy group, a tert-butyltioxy group, a hexylthioxy group, an octylthioxy group and the like, and the alkylsulfoxy group includes a mesyl, an ethylsulfoxy group, There are, but are not limited to, a propyl sulfoxy group, a butyl sulfoxy group, and the like.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 2 to 30 are preferable. 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 Il, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stillbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, or a phenylsilyl group. However, it is not limited to these.

In the present specification, the boron group may be -BR100R101, and the R100 and R101 are the same or different, respectively, and independently, hydrogen; heavy hydrogen; halogen; nitrile group; substituted or unsubstituted carbon number 3 ~ 30 monocyclic or polycyclic cycloalkyl groups; substituted or unsubstituted linear or branched alkyl groups with 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic carbon atoms 6 to 30 Aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms may be selected from the group.

In the present specification, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide.

In the present specification, the aryl group is not particularly limited, but one having 6 to 30 carbon atoms is preferable, and the aryl group may be a monocyclic type or a polycyclic type.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but those having 6 to 30 carbon atoms are preferable. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or 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, but those having 10 to 30 carbon atoms are preferable. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a peryleneyl group, a chrysenyl group, a fluorenyl group or the like, but is limited thereto. It's not a thing.

In the present specification, the fluorenyl group may be substituted, or adjacent groups may be bonded to each other to form a ring.

などになってもよい。ただし、これらに限定されるものではない。 If the fluorenyl group is substituted

And so on. However, it is not limited to these.

As used herein, an "adjacent" group is a substituent substituted with an atom in which the substituent is directly linked to an atom substituted, a substituent located sterically closest to the substituent, or the said group. It can mean another substituent in which the substituent is substituted with the substituted atom. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring are interpreted as "adjacent" groups to each other.

As used herein, aryl in a monoarylamine group, adiarylamine group, an aryloxy group, an aryltioxy group, an arylsulfoxi group, an N-arylalkylamine group, an N-arylheteroarylamine group, and an arylphosphin group. The groups are as exemplified by the aryl groups described above. Specifically, the aryloxy group includes a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group and a 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 There are a group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group and the like, and the aryltioxy group includes There are a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like, and examples of the arylsulfoxi group include a benzenesulfoxi group and a p-toluenesulfoxi group. It is not limited to.

In the present specification, the heteroaryl group contains one or more non-carbon atoms and heteroatoms, and specifically, the heteroatoms are selected from the group consisting of O, N, Se, S, and the like. Can contain one or more atoms. The number of carbon atoms is not particularly limited, but those having 2 to 30 carbon atoms are preferable, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, triazolyl group, acrizyl group and pyridadinyl group. Pyrazineyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, Benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and dibenzofuranyl group. However, it is not limited to these.

In the present specification, the examples of the heteroaryl groups in the monoheteroarylamine group, the diheteroarylamine group, the N-arylheteroarylamine group, and the N-alkylheteroarylamine group are the above-mentioned examples of the heteroaryl group. It's a street.

As used herein, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

As used herein, a ring means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, an aliphatic, or a fused ring of an aromatic and an aliphatic, and is an example of the cycloalkyl group or the aryl group except for the non-monovalent one. It may be selected from.

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

In the present specification, the heterocycle contains one or more non-carbon atoms and heteroatoms, and specifically, the heterocycle is selected from the group consisting of O, N, Se, S, and the like. It can contain one or more atoms. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and the heteroaryl except for non-monovalent ones. It may be selected from the examples of the group.

［化学式１−ｂ］

前記化学式１−ａおよび１−ｂにおいて、Ａ、ＢおよびＡｒ_１の定義は、前記化学式１における定義と同じである。 In one embodiment of the present application, the chemical formula 1 provides a compound represented by any one of the following chemical formulas 1-a and 1-b.
[Chemical formula 1-a]

[Chemical formula 1-b]

In the chemical formulas 1-a and 1-b, _{the definitions of A, B and Ar 1} are the same as the definitions in the chemical formula 1.

In one embodiment of the present application, the A _is, X 1 -X _2; may be or _X 3 = _{X 4}

In one embodiment of the application, said X ₁ and X ₂ may be CR _a R _b and X ₃ and X ₄ may be CR _c.

In one embodiment of the application, said B may be a direct bond; or CQ ₁ Q ₂ .

In another embodiment, the B may be a direct bond.

In yet another embodiment, the B may be _{CQ 1} Q _2.

In one embodiment of the application, the Ar ₁ may be a hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted heteroaryl group.

In other embodiments, the Ar ₁ is hydrogen; _{an alkyl group of substituted or unsubstituted C 1 to} C ₆₀ ; a cycloalkyl group of substituted or unsubstituted C _{3 to} C ₆₀ ; or a substituted or unsubstituted C ₁ it may be a heteroaryl group -C _60.

In yet another embodiment, the Ar ₁ is hydrogen; a substituted or unsubstituted C _{1 to} C ₃₀ alkyl group; a substituted or unsubstituted C _{3 to} C ₄₀ cycloalkyl group; or a substituted or unsubstituted C. It may be a heteroaryl group of _{1 to} C _40.

In yet another embodiment, the Ar ₁ may be a substituted or unsubstituted C _{3 to} C ₆₀ cycloalkyl group.

In yet another embodiment, the Ar ₁ may be a substituted or unsubstituted C _{3 to} C ₄₀ cycloalkyl group.

In yet another embodiment, the Ar ₁ may be a cycloalkyl group of C _{3 to} C _40.

In yet another embodiment, the Ar ₁ may be a cyclohexyl group.

In one embodiment of the present application, _Ra- R _c , R _x , Q ₁ and Q ₂ are the same or different from each other and are independent of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; an ester group; an imide group; amide group; a carboxyl group (-COOH); - OC (= O) R "; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; Substituent or unsubstituted cycloalkyl group; Substituent or unsubstituted alkoxy group; Substituent or unsubstituted aryloxy group; Substituent or unsubstituted alkylthioxy group; Substituent or unsubstituted arylthioxy group; Substituent 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 Substituted arylphosphin groups; substituted or unsubstituted phosphine oxide groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, or adjacent groups are bonded to each other and substituted or unsubstituted. A ring may be formed.

In one embodiment of the present application, the R _x may be hydrogen.

In one embodiment of the present application, the Ra _{a to} R _c are the same or different from each other, and each independently is hydrogen, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring. Good.

は、下記化学式２−ａ〜２−ｆのうちのいずれか１つで表されるものである化合物を提供する。
［化学式２−ａ］

［化学式２−ｂ］

［化学式２−ｃ］

［化学式２−ｄ］

［化学式２−ｅ］

［化学式２−ｆ］

前記化学式２−ａ〜２−ｆにおいて、Ｑ_１およびＱ_２の定義は、前記化学式１における定義と同じであり、
Ｒ_１〜Ｒ_８は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；カルボニル基；エステル基；イミド基；アミド基；カルボキシ基（−ＣＯＯＨ）；−ＯＣ（＝Ｏ）Ｒ"；スルホン酸基（−ＳＯ_３Ｈ）；スルホンアミド基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアリールオキシ基；置換もしくは非置換のアルキルチオキシ基；置換もしくは非置換のアリールチオキシ基；置換もしくは非置換のアルキルスルホキシ基；置換もしくは非置換のアリールスルホキシ基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシリル基；置換もしくは非置換のホウ素基；置換もしくは非置換のアミン基；置換もしくは非置換のアリールホスフィン基；置換もしくは非置換のホスフィンオキシド基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であるか、隣接した基は、互いに結合して置換もしくは非置換の環を形成し、
Ｒ"は、置換もしくは非置換のアルキル基であり、
Ｒ_ａ１、Ｒ_ｂ１およびＲ_ｃ１は、互いに同一または異なり、それぞれ独立に、水素；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基である。 In one embodiment of the present application, the formula 1

Provides a compound represented by any one of the following chemical formulas 2-a to 2-f.
[Chemical formula 2-a]

[Chemical formula 2-b]

[Chemical formula 2-c]

[Chemical formula 2-d]

[Chemical formula 2-e]

[Chemical formula 2-f]

In Formula 2-A through 2-f, the definition of _{Q 1} and _{Q 2} are as defined in Formula 1,
R _{1 to} R ₈ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; carboxy group (-COOH). ); - OC (= O) R "; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; Substituent or unsubstituted aryloxy group; Substituent or unsubstituted alkylthioxy group; Substituent or unsubstituted arylthioxy group; Substituent or unsubstituted alkylsulfoxy group; Substituent or unsubstituted arylsulfoxy group; Substituent or unsubstituted Unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylphosphine group; substituted or unsubstituted phosphine oxide group; substituted or An unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
R "is a substituted or unsubstituted alkyl group.
R _a1 , R _b1 and R _c1 are the same or different from each other and are independently hydrogen; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

In one embodiment of the present application, the Q ₁ and Q _2, equal to or different from each other, each independently, is hydrogen, the adjacent groups, substituted or unsubstituted combine with each other to an aromatic hydrocarbon ring It may be formed.

In one embodiment of the present application, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, a substituted or unsubstituted bonded together with the adjacent group aromatic hydrocarbon ring It may be formed.

In another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, adjacent groups conjugated with an aromatic substituted or unsubstituted C ₆ -C ₆₀ with each other A hydrocarbon ring may be formed.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, C ₆ substituted or unsubstituted nitro group bonded together with adjacent group ~C ₆₀ aromatic hydrocarbon rings may be formed.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, C ₆ substituted or unsubstituted nitro group bonded together with adjacent group ~C _Forty aromatic hydrocarbon rings may be formed.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, form a benzene ring unsubstituted or substituted with a nitro group bonded to each other with adjacent groups You may.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, linked together with R ₁ to form a benzene ring unsubstituted or substituted with a nitro group You may.

In one embodiment of the present application, the R _{1 to} R ₈ are the same or different from each other and independently of each other, hydrogen; substituted or unsubstituted C _{1 to} C ₆₀ alkyl groups; substituted or unsubstituted alkoxy groups; carboxy. group (-COOH); a sulfonic acid group _(-SO 3 H); nitro group; -OC (= O) or a R "a halogen group, the adjacent groups, substituted or unsubstituted bound to each other _{C 6} Forming a ring of ~ C _60,
R "may be a substituted or unsubstituted C _{1 to} C ₆₀ alkyl group.

In other embodiments, the R _{1 to} R ₈ are the same or different from each other and are independent of each other: hydrogen; substituted or unsubstituted C _{1 to} C ₄₀ alkyl groups; substituted or unsubstituted alkoxy groups; carboxy groups ( -COOH); a sulfonic acid group _(-SO 3 H); nitro group; -OC (= O) R "or a halogen group, adjacent groups, _C 6 bond to a substituted or unsubstituted with one another ~C _{Form 40} rings,
R "may be a substituted or unsubstituted C _{1 to} C ₄₀ alkyl group.

In yet another embodiment, the R _{1 to} R ₈ are the same or different from each other and independently of each other _{, an alkyl group of hydrogen; C 1 to} C ₄₀ ; an alkoxy group; a carboxy group (-COOH); a sulfonic acid group (-). SO ₃ H); nitro group; -OC (= O) R "or a halogen group or adjacent groups bonded to each other _{consisting of a halogen group, a sulfonic acid group (-SO 3} H), and a nitro group. _{A substituted or unsubstituted C 6 to} C ₄₀ ring is formed with one or more substituents selected from the group.
R "may be an alkyl group of _{C 1 to} C _40.

In yet another embodiment, the _R 1 to R _8, equal to or different from each other, each independently, hydrogen, methyl; methoxy group; a carboxyl group (-COOH); a sulfonic acid group _(-SO 3 H); nitro group; -OC (= O) or a R "or halogen groups, adjacent groups, one selected from the group consisting of a halogen group, a sulfonic group (-SO 3 _H), and a nitro group bonded to each other A substituted or unsubstituted benzene ring is formed with the above substituents,
R "may be a methyl group.

In one embodiment of the present application, one of the R ₁ and R ₅ and one of the R ₄ and R ₈ may be coupled to each other to form a ring.

In one embodiment of the present application, one of the R ₁ and R ₅ and one of the R ₄ and R ₈ may be bonded to each other to form a ring or the remaining substituents. May be hydrogen.

In one embodiment of the present application, the Q ₁ and Q _2, equal to or different from each other, each independently, is hydrogen, the adjacent groups, substituted or unsubstituted combine with each other to an aromatic hydrocarbon ring It may be formed.

In one embodiment of the present application, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, a substituted or unsubstituted bonded together with the adjacent group aromatic hydrocarbon ring It may be formed.

In another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, adjacent groups conjugated with an aromatic substituted or unsubstituted C ₆ -C ₆₀ with each other A hydrocarbon ring may be formed.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one, the aromatic hydrocarbon ring C ₆ -C ₆₀ bonded to each other with adjacent groups It may be formed.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one may form a benzene ring bonded to each other with adjacent groups.

In yet another embodiment, the one of Q ₁ and Q ₂ are hydrogen, the remaining one may form a benzene ring bonded to each other with R _1.

In one embodiment of the application, Ra ₁ , R _b1 and R _c1 may be the same or different from each other and independently of hydrogen; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups. Good.

In other embodiments, Ra ₁ , R _{b 1} and R _{c 1} may be the same or different from each other and may be hydrogen independently of each other.

In one embodiment of the present application, the chemical formula 1 provides a compound represented by any one of the following chemical formulas.

According to one embodiment of the present specification, a color material composition containing the compound represented by the chemical formula 1 is provided.

The color material composition may further contain at least one of a dye and a pigment in addition to the compound represented by the chemical formula 1. For example, the coloring material composition may contain only the compound represented by the chemical formula 1, but contains the compound represented by the chemical formula 1 and one or more dyes, or is represented by the chemical formula 1. It may contain a compound and one or more pigments, or may contain a compound represented by the above chemical formula 1, one or more dyes, and one or more pigments.

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

In one embodiment of the specification, the resin composition may further comprise a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

In one embodiment of the present application, the content of the compound represented by the chemical formula 1 is 0.1% by weight to 60% by weight based on the total weight of the solid content in the resin composition, and the binder resin. The content of the photoinitiator is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight to 50% by weight. Provided is a resin composition which is by weight%.

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

As the binder resin, a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility can be used, and a binder generally used in the art may be further contained.

The polyfunctional monomer that imparts mechanical strength to the film is any one or more of unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. There may be.

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 (meth) acrylate. , T-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (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, ethoxydiethylene 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 may be selected from the group, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p). ) -Choose from the group consisting of chlorostyrene, but is not limited to these.

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 may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. , Not limited to these.

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

The monomer that imparts 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, monomethylmaleic acid, 5-norbornene-2- Selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethylphthalate, mono-2-((meth) acryloyloxy) ethylsuccinate, ω-carboxypolycaprolactone mono (meth) acrylate. It is preferable to use one or more, but the present invention is not limited to these.

According to one embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOHmg / g, and the weight average molecular weight is 1,000 to 50,000.

The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6 -Hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, It may be one or a mixture of two or more selected from the group consisting of pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce cross-linking, and is, for example, a group consisting of an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound. It may be one or more selected from the above.

The acetphenone compounds are 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-). Hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-Methyl- (4-methylthio) Phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, 2-( 4-Bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one And are not limited to these.

Examples of the biimidazole compound include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 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 and the like, but not limited to these.

The triazine compounds are 3-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, cyclohexyl-2-{4- [ 2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} Acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s -Triazine-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -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 not limited to these.

The oxime compounds include 1,2-octadion-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Ciba Geigy, CGI124) and ethanone-1- (9-ethyl) -6- (2). -Methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGI242), N-1919 (Adeca), and the like, and are not limited thereto.

The solvent used 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-trichloroethane, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl One or more selected from the group consisting of ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. There may be, but it is not limited to this.

As the solvent, preferably, dimethylformamide (DMF) can be used.

The compound according to one embodiment of the present application has a -SO _3- Ar ₁ substituent and can increase the solubility in an organic solvent, and the increase in the solubility in an organic solvent prevents aggregation of the coloring material, and later When used as a photosensitive material, it has the characteristic of improving the light-dark ratio.

According to one embodiment of the present specification, the content of the colorant composition is 0.1% by weight to 60% by weight based on the total weight of the solid content in the resin composition, and the binder resin. The content of the photoinitiator is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight to 50% by weight. By weight%.

The total weight of the solid content means the total weight of the components excluding the solvent from the resin composition. The weight% reference based on the solid content and the solid content 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 a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant. , And one or more additives selected from the group consisting of leveling agents.

According to one 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 the solid content in the resin composition.

The photocrosslinked sensitizers are benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 -Fluolenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; xanthone, 2-methylxanthone, etc. Xanthone compounds; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylaclydin, 1,7-bis ( Acrydin compounds such as 9-acrydinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7-trimethyl-bicyclo [2] , 2,1] Dicarbonyl compounds such as heptane-2,3-dione, 9,10-phenanthrenquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4 , 4-trimethylpentylphosphine oxide and other phosphine oxide compounds; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate and the like. Benzophenone compounds; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl -Amino synergists such as 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-carboni Rubis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidine-11-one, etc. One or more selected from the group consisting of chalcone compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthiazoline; can be used. ..

The curing accelerator is used to enhance curing and mechanical strength, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-Tiasazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2) -Mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) selected from the group 1 More than seeds can be used.

Adhesion promoters used herein include metaacryloylsilane coupling agents such as metaacryloyloxypropyltrimethoxysilane, metaacryloyloxypropyldimethoxysilane, metaacryloyloxypropyltriethoxysilane, and metaacryloyloxypropyldimethoxysilane. One or more of them can be selected and used, and as the alkyltrimethoxysilane, one or more can be selected and used from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like. ..

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK of BYK-Chemie. -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 can be used, and as the fluorine-based surfactant, F-114, F-177, F-410, F-411, F-450, F-493, F of DIC (Dai Nippon Inc & Chemicals) can be used. -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. can be used, but are limited thereto. is not it.

The antioxidant is one or more selected from the group consisting of a hidden phenolic antioxidant, an amine-based antioxidant, a thio-based antioxidant, and a phosphine-based antioxidant. It may be, but it is not limited to this.

Specific examples of the antioxidant are phosphate-based heat 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-hydroxybenzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphite 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'-tart-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-) Hindered phenol primary antioxidants such as 3'-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p- Amine-based secondary antioxidants such as phenylenediamine, or N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzo Thio-based secondary antioxidants such as thiazole, or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, Bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Phenaerythritol Diphosphite, or (1,1'-biphenyl) -4,4'-diylbisphosphonoate tetrakis [2, 4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous a Examples thereof include phosphite-based secondary antioxidants such as cid tetrakis [2,4-bis (1,1-dimethylyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone and the like can be used, but the ultraviolet absorber is not limited thereto. Anything commonly used in the industry can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine 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) It can include, but is not limited to, one or more selected from the group consisting of −butylphenol), 2-mercaptoimidazole, and phenothiazine, but is generally known in the art. Can include those that are.

The dispersant can be used by a method of internally adding the pigment to the pigment in a form of surface treatment in advance, or a method of externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic or amphoteric dispersant can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, amphoteric interface can be used. Activators and the like can be mentioned. These can be used individually or in combination of two or more.

Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, and carboxylic acid. There is, but is not limited to, one or more selected from the group consisting of salts, alkylamide alkylene oxide adducts, and alkylamines.

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

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

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

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

Examples of the light source for curing the resin composition according to the present specification include, but are not limited to, a mercury vapor arc (arc), a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm. Not done.

The resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode. Used for coating layer forming photosensitive material, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printing wiring board, photosensitive material for plasma display panel (PDP), etc. There are no particular restrictions on its use.

According to one embodiment of the present specification, a color filter containing the photosensitive material is provided.

The color filter is manufactured by using a resin composition containing the color material composition. A color filter can be formed by applying the resin composition onto a substrate to form a coating film, and exposing, developing, and curing the coating film.

The resin composition according to one embodiment of the present specification has excellent heat resistance, little color change due to heat treatment, high color reproduction rate even during the manufacturing process of a color filter and a curing process, and high brightness and light-dark ratio. Color filters can be provided.

The substrate may be a glass plate, a silicon wafer, and a plate of a plastic base material such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited. Absent.

The color filter can include a red pattern, a green pattern, a blue pattern, and a black matrix.

According to another embodiment, the color filter may further include an overcoat layer.

A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method capable of fine processing can be used.

In the black matrix according to one embodiment of the present specification, a black pigment or a black dye can be used as a coloring material. For example, carbon black can be used alone or a mixture of carbon black and a coloring pigment can be used. At this time, since the coloring pigment having insufficient light-shielding property is mixed, the amount of the coloring material is relatively large. There is an advantage that the strength of the film or the adhesion to the substrate does not decrease even if the amount is increased.

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

The display device includes a plasma display panel (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Device, LED), an organic light emitting element (Organic Light Emitting Device, OLED), a liquid crystal display device (Liquid Crystal Disk), and a liquid crystal display device (Liquid Crystal Display). It may be any one of a liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (Cathode Ray Tube, CRT).

Hereinafter, the present specification will be described in detail with reference to examples. The following examples are for the purposes of the present specification, and the scope of the present specification includes the scope described in the following claims and their substitutions and modifications, and is not limited to the scope of the examples.

<Example>

<Compound synthesis>

<Synthesis of compound 1>

２５０ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆ（Ｒｏｕｎｄ ｂｏｔｔｏｍｅｄ ｆｌａｓｋ）に、メチレンクロライド（Ｍｅｔｈｙｌｅｎｅ ｃｈｌｏｒｉｄｅ）１００ｇと２−メチルキノリン−８−オール（２−ｍｅｔｈｙｌｑｕｉｎｏｌｉｎ−８−ｏｌ）４．３１４ｇ（２７．０９８ｍｍｏｌ）、トリエチルアミン（Ｔｒｉｅｔｈｙｌａｍｉｎｅ）１３．８４ｇ（１３６．８５９ｍｍｏｌ）を入れて、常温で３０分間撹拌させた。 1. 1. Synthesis of A-1

250 ml 2-neck-R. B. F (Round bottomed flash), 100 g of methylene chloride, 4.314 g (27.098 mmol) of 2-methylquinolin-8-ol, 13.84 g of triethylamine (Triethylamine). 136.859 mmol) was added, and the mixture was stirred at room temperature for 30 minutes.

Then, 5 g (27.372 mmol) of cyclohexanesulfonyl chloride was slowly added dropwise, and the mixture was stirred at 45 ° C. for 3 hours. The reaction solution was cooled to room temperature, placed in 500 ml of DI-Water and stirred.

The organic layer was separated using a Separatory funnel. Extraction of 100 g of methylene chloride was added. The organic layer was _{passed through 4} and the solvent was removed under reduced pressure. 7.94 g (26.39 mmol) of A-1 is obtained, and the yield is 96%.

Ionization mode APCI +: m / z = 306 [M + H], Exact Mass: 305

１００ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆに、メチルベンゾエート（Ｍｅｔｈｙｌｂｅｎｚｏａｔｅ）３０ｇとＡ−１ ３ｇ（９．８２ｍｍｏｌ）とＢ−１ １．４６ｇ（９．８２ｍｍｏｌ）を入れて撹拌させた。 2. Synthesis of compound 1

100 ml of 2-neck-R. B. To F, 30 g of methylbenzoate, 3 g (9.82 mmol) of A-1, and 1.46 g (9.82 mmol) of B-1 were added and stirred.

After reacting at 180 ° C. for 8 hours, the solvent was removed under reduced pressure. A small amount of MeOH was added and stirred. The precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 1 1.17 g (3.93 mmol) is obtained, and the yield is 40%.

Ionization mode APCI +: m / z = 436 [M + H], Exact Mass: 435

１００ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆに、メチルベンゾエート（Ｍｅｔｈｙｌｂｅｎｚｏａｔｅ）３０ｇとＡ−１ ３ｇ（９．８２ｍｍｏｌ）とＢ−２ ２．８０ｇ（９．８２ｍｍｏｌ）を入れて撹拌させた。 <Synthesis of compound 2>

100 ml of 2-neck-R. B. To F, 30 g of methylbenzoate, 3 g (9.82 mmol) of A-1, and 2.80 g (9.82 mmol) of B-2 were added and stirred.

After reacting at 180 ° C. for 8 hours, the reaction solution was brought to room temperature and precipitated in 150 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 2 4.61 g (8.04 mmol) has been obtained, and the yield is 81.9%.

Ionization mode APCI +: m / z = 572 [M + H], Exact Mass: 571

１００ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆに、メチルベンゾエート（Ｍｅｔｈｙｌｂｅｎｚｏａｔｅ）３０ｇとＡ−１ ３ｇ（９．８２ｍｍｏｌ）とＢ−３ １．９５ｇ（９．８２ｍｍｏｌ）を入れて撹拌させた。 <Synthesis of compound 3>

100 ml of 2-neck-R. B. To F, 30 g of methylbenzoate, 3 g (9.82 mmol) of A-1, and 1.95 g (9.82 mmol) of B-3 were added and stirred.

After reacting at 180 ° C. for 8 hours, the reaction solution was brought to room temperature and precipitated in 150 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 3 3.34 g (6.87 mmol) was obtained, and the yield was 70.0%.

Ionization mode APCI +: m / z = 486 [M + H], Exact Mass: 485

１００ｍｌの２−ｎｅｃｋ Ｒ．Ｂ．Ｆに、メチルベンゾエート（Ｍｅｔｈｙｌｅｎｚｏａｔｅ）３０ｇとＡ−１ ３ｇ（９．８２ｍｍｏｌ）とＢ−４ １．８８ｇ（９．８２ｍｍｏｌ）を入れて撹拌させた。 <Synthesis of compound 4>

100 ml 2-neck R. B. To F, 30 g of methylbenzoate, 3 g (9.82 mmol) of A-1, and 1.88 g (9.82 mmol) of B-4 were added and stirred.

After reacting at 180 ° C. for 8 hours, the reaction solution was brought to room temperature and precipitated in 150 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 4 3.05 g (6.48 mmol) has been obtained, and the yield is 64.8%.

Ionization mode APCI +: m / z = 480 [M + H], Exact Mass: 479

<Synthesis of compound 5>

２５０ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆ（Ｒｏｕｎｄ ｂｏｔｔｏｍｅｄ ｆｌａｓｋ）に、メチレンクロライド（Ｍｅｔｈｙｌｅｎｅ ｃｈｌｏｒｉｄｅ）１００ｇと２−メチルキノリン−８−オール（２−ｍｅｔｈｙｌｑｕｉｎｏｌｉｎ−８−ｏｌ）４．３１ｇ（２７．０９８ｍｍｏｌ）、トリエチルアミン（Ｔｒｉｅｔｈｙｌａｍｉｎｅ）１３．８４ｇ（１３６．８５９ｍｍｏｌ）を入れて、常温で３０分間撹拌させた。 1. 1. Synthesis of A-2

250 ml 2-neck-R. B. In F (Round bottomed flash), 100 g of methylene chloride, 4.31 g (27.098 mmol) of 2-methylquinolin-8-ol, and 13.84 g of triethylamine (Triethylamine). 136.859 mmol) was added, and the mixture was stirred at room temperature for 30 minutes.

Then, 4.81 g (27.372 mmol) of benzenesulfonyl chloride was slowly added dropwise, and the mixture was stirred at 45 ° C. for 3 hours. The reaction solution was cooled to room temperature, placed in 500 ml of DI-Water and stirred.

The organic layer was separated using a Separatory funnel. Extraction of 100 g of methylene chloride was added. The organic layer was _{passed through 4} and the solvent was removed under reduced pressure. A-2 7.56 g (25.27 mmol) is obtained, and the yield is 93%.

Ionization mode APCI +: m / z = 300 [M + H], Exact Mass: 299

１００ｍｌの２−ｎｅｃｋ Ｒ．Ｂ．Ｆに、メチルベンゾエート（Ｍｅｔｈｙｌｅｎｚｏａｔｅ）３０ｇとＡ−２ ３ｇ（１０．０３ｍｍｏｌ）とＢ−１ １．４８ｇ（１０．０３ｍｍｏｌ）を入れて撹拌させた。 2. Synthesis of compound 5

100 ml 2-neck R. B. In F, 30 g of methylbenzoate, 3 g of A-23 (10.03 mmol) and 1.48 g of B-1 (10.03 mmol) were added and stirred.

After reacting at 180 ° C. for 8 hours, the reaction solution was brought to room temperature and precipitated in 150 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 5, 3.25 g (7.57 mmol) has been obtained, and the yield is 75.5%.

Ionization mode APCI +: m / z = 430 [M + H], Exact Mass: 429

１００ｍｌの２−ｎｅｃｋ−Ｒ．Ｂ．Ｆに、ベンゾイックアシッド（Ｂｅｎｚｏｉｃ ａｃｉｄ）３０ｇとＡ−３ ３ｇ（１２．７ｍｍｏｌ）とＢ−３ ２．５１ｇ（１２．７ｍｍｏｌ）を入れて撹拌させた。 <Synthesis of compound 6>

100 ml of 2-neck-R. B. To F, 30 g of benzoic acid, 3 g (12.7 mmol) of A-3 and 2.51 g (12.7 mmol) of B-3 were added and stirred.

After reacting at 200 ° C. for 7 hours, the reaction solution was brought to room temperature and precipitated in 150 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. Compound 6 3.37 g (8.12 mmol) has been obtained, and the yield is 63.9%.

Ionization mode APCI +: m / z = 416 [M + H], Exact Mass: 415

<Compound 7>

<Experimental example>

Solubility Evaluation Compounds 1 to 7 were prepared, and their solubility in 100 g of dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP) was measured, and the results are shown in Table 1 below. Specifically, when the solubility is 1% or more, it is indicated as O, and when it is less than 1%, it is indicated as X.

<Example 1>

Production of Photosensitive Resin Composition 5.554 g of Compound 1, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20 measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

<Example 2>

Production of Photosensitive Resin Composition 5.554 g of Compound 2, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20 measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

<Example 3>

Production of Photosensitive Resin Composition 5.554 g of Compound 3, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20 measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

<Example 4>

Production of Photosensitive Resin Composition 5.554 g of Compound 4, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20 measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

<Comparative example 1>

Production of photosensitive resin composition Compound 5, 5.554 g, copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20 measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

<Comparative example 2>

Production of photosensitive resin composition Compound 6, 5.554 g, copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20, measured by GPC, 000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable A photosensitive resin composition was prepared by mixing 12.443 g of DPHA (Nippon Kayaku) as a compound, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of F-475 of DIC as an additive. Manufactured.

Preparation of Substrate The photosensitive resin compositions according to Examples 1 to 4 and Comparative Examples 1 and 2 were used for preparing a substrate, respectively. Specifically, the photosensitive resin compositions according to the above-mentioned Examples and Comparative Examples ^{are spin-coated on glass (5 × 5 cm) 2} and preheat-treated (prebake) at 100 ° C. for 100 seconds to form a film. It was formed.

The distance between the substrate on which the film was formed and the photomask (photomask) was set to 250 μm, and the entire surface of the substrate was irradiated with an exposure amount ^{of 40 mJ / cm 2 using an exposure device.} Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and then heat-treated (postbake) at 230 ° C. for 20 minutes to prepare a substrate.

Heat resistance evaluation A transmittance spectrum in the visible light region in the range of 380 nm to 780 nm was obtained using a spectroscope (MCPD-Otsuka Co., Ltd.) on the substrate prepared by the method for producing the substrate. Further, the preheat treatment (prebake) substrate was additionally heat-treated (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.

Using the obtained transmittance spectrum and the backlight of the C light source, the color change (hereinafter, ΔEab) was calculated using the obtained values E (L *, a *, b *), and the results are shown in Table 2 below. Indicated.

Specifically, the formula for calculating ΔEab is as follows.
ΔE (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2

In the above formula, a small ΔEab value means that the color heat resistance is excellent, and generally, when the value of ΔEab <3, it means a color material having excellent heat resistance.

The color material composition containing the compound represented by the chemical formula 1 according to one embodiment of the present application is excellent in color characteristics, heat resistance, light resistance and solvent resistance, and prevents reaggregation of atomized pigments and dyes. Alternatively, it is possible to prevent the generation of foreign matter and achieve a higher color reproduction rate, higher brightness, higher light-dark ratio, and the like.

In particular, as can be seen from Table 1, it was confirmed that the compound according to one embodiment of the present application has excellent heat resistance and solubility in an organic solvent as compared with the compound which does not. ..

Further, as can be seen from Table 2, ΔEab is found in the case of the substrate formed of the composition containing the compounds of Examples 1 to 4 as compared with the case of the substrate formed of the composition containing the compounds of Comparative Examples 1 and 2. It was confirmed that the value was very low, which was particularly excellent in color heat resistance when the compound according to one embodiment of the present application was contained.

Claims (12)

Compound represented by the following chemical formula 1:
[Chemical formula 1]

In the chemical formula 1,
A is X _1- X ₂ ; or X ₃ = X ₄ .
B is a direct bond; or CQ ₁ Q ₂ and
X ₁ and X ₂ are CR _a R _b and
X ₃ and X ₄ are CR _c and
Ar ₁ is a substituted or unsubstituted C _{3 to} C ₆₀ cycloalkyl group .
R _{a to} R _c , R _x , Q ₁ and Q ₂ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group. ; amide group; a carboxyl group (-COOH); - OC (= O) R "; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group Substituent or unsubstituted alkoxy group; Substituent or unsubstituted aryloxy group; Substituent or unsubstituted alkylthioxy group; Substituent or unsubstituted arylthioxy group; Substituent or unsubstituted alkylsulfoxy group; Substituent or unsubstituted Substituted 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 arylphosphine group; substituted or unsubstituted An unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
R "is a substituted or unsubstituted alkyl group.
p is an integer of 1 to 6 and
n is an integer of 6-p. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-a and 1-b.
[Chemical formula 1-a]

[Chemical formula 1-b]

In the chemical formulas 1-a and 1-b, _{the definitions of A, B and Ar 1} are the same as the definitions in the chemical formula 1. The chemical formula 1

Is the compound according to claim 1 or 2, which is represented by any one of the following chemical formulas 2-a to 2-f:
[Chemical formula 2-a]

[Chemical formula 2-b]

[Chemical formula 2-c]

[Chemical formula 2-d]

[Chemical formula 2-e]

[Chemical formula 2-f]

In Formula 2-A through 2-f, the definition of _{Q 1} and _{Q 2} are as defined in Formula 1,
R _{1 to} R ₈ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; carboxy group (-COOH). ); - OC (= O) R "; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; Substituent or unsubstituted aryloxy group; Substituent or unsubstituted alkylthioxy group; Substituent or unsubstituted arylthioxy group; Substituent or unsubstituted alkylsulfoxy group; Substituent or unsubstituted arylsulfoxy group; Substituent or unsubstituted Unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylphosphine group; substituted or unsubstituted phosphine oxide group; substituted or An unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
R "is a substituted or unsubstituted alkyl group.
R _a1 , R _b1 and R _c1 are the same or different from each other and are independently hydrogen; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups. The R _{1 to} R ₈ are the same or different from each other, and independently of each other, hydrogen; _{an alkyl group of substituted or unsubstituted C 1 to} C ₆₀ ; a substituted or unsubstituted alkoxy group; a carboxy group (-COOH); a sulfonic acid. Groups (-SO ₃ H); nitro groups; -OC (= O) R "or halogen groups or adjacent groups combine with each other to form substituted or unsubstituted C _6- C ₆₀ rings. ,
The compound according to claim 3, wherein "R" is a substituted or unsubstituted _{alkyl group of C 1 to} C _60. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas:

.. A color material composition containing the compound according to any one of claims 1 to 5. The color material composition according to claim 6 , further comprising at least one of a dye and a pigment. A resin composition comprising the compound according to any one of claims 1 to 5 ; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. Based on the total weight of the solid content in the resin composition,
The content of the compound represented by the chemical formula 1 is 0.1% by weight to 60% by weight.
The content of the binder resin is 1% by weight to 60% by weight.
The content of the photoinitiator is 0.1% by weight to 20% by weight.
The resin composition according to claim 8 , wherein the content of the polyfunctional monomer is 0.1% by weight to 50% by weight. A photosensitive material produced by using the resin composition according to claim 8 or 9. A color filter containing the photosensitive material according to claim 10. A display device including the color filter according to claim 11.