JP2019501992A - Compound, coloring material composition containing the same, and resin composition containing the same - Google Patents

Abstract

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

Description

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0015691 filed with the Korean Patent Office on February 11, 2016, the entire contents of which are incorporated herein.

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

  Recently, as a light source of a liquid crystal display (LCD), an element such as an LED, an OLED, or a QD is often used instead of the existing CCFL. However, in order to fabricate thin film displays, flexible displays, and the like, display products have been developed and produced in which color filters are removed, that is, self-luminous light such as LEDs or OLEDs, QDs, etc. as unit pixels.

  However, in the case of a display using LEDs, OLEDs, QDs, etc. as unit pixels, it is difficult to increase the area, and even when using LEDs, OLEDs, QDs, etc., these are used as light sources, and display of a color filter is included. Much effort has been made in development.

  In order to realize a desired color, a light source and an appropriate color filter are required. Currently, a pigment dispersion method using a pigment as a colorant is generally applied.

  However, in the case of a pigment dispersion, not only does the pigment exist in the particle state and scatters light, but also the pigment surface area increases rapidly due to finer pigments, resulting in poor dispersion stability and uneven pigment particles. Is generated.

  Therefore, it is recognized that the limit point that has been difficult to satisfy recently required high quality requirements such as high luminance, high contrast ratio, and high definition is reached.

  In order to solve such problems and achieve high brightness, high contrast ratio and high resolution, it has recently been studied to use a dye instead of a pigment as a colorant. Of these, many attempts have been made using triarylmethane dyes as blue colorants. In general, triarylmethane dyes have an advantage of high transmittance at 420 to 450 nm, but when used in a coloring composition for a color filter, there is a disadvantage that heat resistance and light resistance are lowered.

  Korean Published Patent No. 2013-0130976 describes a color filter using a polymer containing a polymerizable triphenylmethane dye. However, although the color filter using the dye described in the above document has excellent spectral characteristics, it has a problem of insufficient light resistance.

  Therefore, development of a new color material is required in order to overcome such problems.

Korean open patent 2001-0009058 Korean open patent 2013-0130976

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

前記化学式１において、
Ｒ１〜Ｒ４、Ｒ１７およびＲ１８のうちの少なくとも１つは、下記化学式ａで表される構造であり、残りは、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、
Ｒ５〜Ｒ１６は、互いに同一または異なり、それぞれ独立に、水素；ハロゲン基；ヒドロキシ基；置換もしくは非置換のアルコキシ基；または置換もしくは非置換のアルキル基であり、
Ｚ⁻は、陰イオン性基であり、
［化学式ａ］

前記化学式ａにおいて、
Ｑは、−Ｒ１０１Ｃ（＝Ｏ）Ｒ１０２−；−Ｒ１０３ＯＣ（＝Ｏ）Ｒ１０４−；−Ｒ１０５Ｃ（＝Ｏ）ＯＲ１０６−；−Ｒ１０７ＯＣ（＝Ｏ）ＯＲ１０８−；

；
置換もしくは非置換のアルキレン基；または置換もしくは非置換のアルケニレン基であり、
Ｘは、ヒドロキシ基；アミン基；−ＯＣＯＯＲ１１５；−ＣＯＮＲ１１６Ｒ１１７；または−ＮＲ１１１８ＣＯＯＲ１１９であり、
Ｔは、置換もしくは非置換のアルキル基であり、
Ｒ１０１〜Ｒ１０９、Ｒ１１１、Ｒ１１２およびＲ１１４は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアルキレン基；置換もしくは非置換のシクロアルキレン基；または置換もしくは非置換のアルケニレン基であり、
Ｒ１１０、Ｒ１１３およびＲ１１５〜Ｒ１１９は、互いに同一または異なり、それぞれ独立に、水素；または置換もしくは非置換のアルキル基であり、
ｐおよびｑはそれぞれ、１〜４の整数であり、
２≦ｐ＋ｑ≦５であり、
ｐおよびｑがそれぞれ２以上の場合、２以上の括弧内の構造は、互いに同一または異なり、
＊は、化学式１に結合する部位である。 According to one embodiment of the present specification, a compound represented by the following Chemical Formula 1 is provided.
[Chemical Formula 1]

In Formula 1,
At least one of R1 to R4, R17, and R18 is a structure represented by the following chemical formula a, and the rest are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; An unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group, or adjacent groups joined together to form a substituted or unsubstituted ring;
R5 to R16 are the same or different from each other, and each independently represents hydrogen; a halogen group; a hydroxy group; a substituted or unsubstituted alkoxy group; or a substituted or unsubstituted alkyl group;
Z ⁻ is an anionic group,
[Chemical Formula a]

In the chemical formula a,
Q is -R101C (= O) R102-; -R103OC (= O) R104-; -R105C (= O) OR106-; -R107OC (= O) OR108-;

;
A substituted or unsubstituted alkylene group; or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; an amine group; -OCOOR115; -CONR116R117; or -NR1118COOR119;
T is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112 and R114 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted alkenylene group. ,
R110, R113 and R115 to R119 are the same or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group;
p and q are each an integer of 1 to 4,
2 ≦ p + q ≦ 5,
When p and q are each 2 or more, the structures in the 2 or more parentheses are the same or different from each other,
* Represents a site bonded to Chemical Formula 1.

  According to another embodiment of the present specification, a color material composition including the compound represented by Formula 1 is provided.

  According to another embodiment of the present specification, a resin composition including the color material composition is provided.

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

  According to one embodiment of the present specification, a color filter including the above-described photosensitive material is provided.

  In addition, according to an embodiment of the present specification, a display device including the above-described color filter is provided.

  According to one embodiment of the present specification, the color material composition containing the compound represented by Formula 1 is excellent in light resistance and can be used not only as a small amount but also as a main color material. Absorption and transmission spectra suitable for the light source can be obtained, and higher color reproduction, high luminance, high contrast ratio, and the like can be achieved.

  In addition, the color filter according to an embodiment of the present specification has excellent light resistance, can provide blue pixels of the color filter, and can satisfy the light resistance required for a display including the color filter. .

  Furthermore, the color filter according to an embodiment of the present specification can provide a blue pixel excellent in light resistance.

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

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

  In the present specification, examples of the substituent are described below, but are not limited thereto.

  The term “substituted” means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substituted position is the position where the hydrogen atom is substituted, that is, the substituent can be substituted. There is no limitation as long as it is a position, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

  In this specification, the term “substituted or unsubstituted” refers to a halogen group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxy group; a substituted or unsubstituted alkyl group; A cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group Means substituted with one or more of the above-mentioned substituents or no substituents.

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 this specification,

Means the site | part couple | bonded with another substituent or a coupling | bond part.

  In the present specification, the halogen group may be a fluoro group, a chloro group, a bromo group, or an iodine group.

In this specification, the carbon number 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.

In the present specification, in the amide group, the nitrogen of the amide group may be substituted 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 having the following structural formula, but is not limited thereto.

In the present specification, the carbon number 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, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 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 alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but those having 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- Propyl, 1,1-dimethyl-propyl, iso Hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl there are like, but is not limited thereto.

  In the present specification, the cycloalkyl group is not particularly limited, but those having 3 to 30 carbon atoms are preferable. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, Examples include 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl. Absent.

  In the present specification, the alkoxy group may be a straight chain, a branched chain or a ring chain. Although carbon number of an alkoxy group is not specifically limited, A C1-C30 thing is 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, and the like are limited thereto. It is not something.

In this specification, an amine group consists of —NH ₂ ; an alkylamine group; an N-arylalkylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group. The number of carbon atoms may be selected from the group, and the number of carbon atoms is not particularly limited. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, Examples include, but are not limited to, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, and triphenylamine group.

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

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

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

  In this specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group is as exemplified for the aforementioned alkyl group. 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 are not limited thereto.

  When the aryl group is a monocyclic aryl group, the carbon number 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.

In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group and a dinaphthylphosphine oxide, but the phosphine oxide group is not limited thereto.
When the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, but those having 10 to 30 carbon atoms are preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrycenyl group, fluorenyl group, or the like, but is not limited thereto.

  In the present specification, an “adjacent” group means a substituent substituted by an atom directly linked to an atom to which the substituent is substituted, a substituent that is three-dimensionally closest to the substituent, or It can mean other substituents in which the substituent is replaced by a substituted atom. For example, two substituents substituted in the ortho position on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring are interpreted as “adjacent” groups to each other.

  In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is an example of the aforementioned aryl group. It is as follows. Specifically, as the aryloxy group, 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. There are phenylthioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group, and arylsulfoxy The benzene sulfoxide group, p- there and toluene sulfoxide group, but is not limited thereto.

  In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

  In the present specification, a heteroaryl group includes one or more atoms that are not carbon and hetero atoms, and specifically, the hetero atoms are selected from the group consisting of O, N, Se, and S. One or more atoms may be included. 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 the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, triazolyl group, acridyl group, pyridazinyl group, Pyrazinyl 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, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolin, isoxazolyl, thiadiazolyl, phenothia Group, and the like dibenzofuranyl group, but is not limited thereto.

  In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group in which the heteroaryl group includes two or more may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the above-described examples of the heteroaryl group.

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

  In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. May be selected.

  In the present specification, an alkylene group means an alkyl group having two bonding positions, that is, a divalent group. The above explanation of the alkyl group is applicable except that these are each a divalent group.

  In the present specification, an alkenylene group means an alkenyl group having two bonding positions, that is, a divalent group. The above explanation of the alkenyl group is applicable except that each of these is a divalent group.

  In the present specification, 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.

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

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

  In the present specification, the heterocycle includes one or more atoms that are not carbon and heteroatoms, and specifically, the heteroatoms are selected from the group consisting of O, N, Se, S, and the like. One or more atoms can be included. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or an aromatic-aliphatic condensed ring, and the heteroaryl group or heterocycle except that which is not monovalent. You may select from the illustration of a cyclic group.

前記化学式１−１において、
Ｒ１〜Ｒ４、Ｒ６、Ｒ１２〜Ｒ１８およびＺ⁻の定義は、前記化学式１と同じである。 According to one embodiment of the present specification, the Chemical Formula 1 is represented by the following Chemical Formula 1-1.
[Chemical Formula 1-1]

In Formula 1-1,
The definitions of R 1 to R 4, R 6, R 12 to R 18, and Z ⁻ are the same as those in Chemical Formula 1.

  According to one embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R4, R17, and R18 is a structure represented by Chemical Formula a, and the rest are the same or different from each other. Each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

  According to one embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R4, R17, and R18 is a structure represented by Chemical Formula a, and the rest are the same or different from each other. Each independently hydrogen; a hydroxy group, or an alkyl group substituted or unsubstituted with an alkyl group substituted or unsubstituted aryl group; or a halogen group substituted or unsubstituted aryl group.

  According to one embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R4, R17, and R18 is a structure represented by Chemical Formula a, and the rest are the same or different from each other. Each independently hydrogen; substituted or unsubstituted methyl group substituted or unsubstituted with alkyl group; substituted or unsubstituted ethyl group substituted with hydroxy group; propyl group; or substituted or unsubstituted alkyl group or halogen group Of the phenyl group.

  According to one embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R4, R17, and R18 is a structure represented by Chemical Formula a, and the rest are the same or different from each other. Each independently hydrogen; a methyl group substituted or unsubstituted with a methyl group substituted or unsubstituted phenyl group; a hydroxy group substituted or unsubstituted ethyl group; a propyl group; or a methyl group, an ethyl group, or a fluoro group A substituted or unsubstituted phenyl group.

  According to one embodiment of the present specification, in Formula 1, R5 to R16 are the same or different from each other, and each independently represents hydrogen; a halogen group; or a substituted or unsubstituted alkyl group.

  According to one embodiment of the present specification, in Formula 1, R5 to R16 are the same or different from each other, and are each independently hydrogen, a halogen group, or an alkyl group.

  According to one embodiment of the present specification, in Formula 1, R5 to R16 are the same as or different from each other, and are independently hydrogen, a fluoro group, or a methyl group.

  According to one embodiment of the present specification, in the chemical formula a, X is bonded to the ortho position with respect to the position where T is bonded to the phenyl group of the chemical formula a.

According to one embodiment of the present specification, in Formula 1, Z ⁻ is an anionic group, and the anionic group is not particularly limited. For example, US Pat. No. 7,939,644, Japanese Application No. 2006-003080, Japanese Application No. 2006-001917, Japanese Application No. 2005-159926, Korean Application No. 2007-7028897, Japanese Application No. 2005-071680, Korean Application No. 2007-700653. No., Japanese Application No. 2005-111696 and Japanese Application No. 2008-249663 are applicable.

  Specific examples of the anion include trifluoromethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate Anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tristrifluoromethanesulfonylmethide, phosphate ion, nitrate ion, carbonate ion, sulfite ion, halogen group such as bromo group, fluorine group , Iodine group, chlorine group and the like.

Z ⁻ means boron, an anion containing aluminum; an anion containing one or more elements selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen. In particular, the Z ⁻ may include an anion of tungstophosphoric acid, an anion of tungstosilicic acid, or an anion of tungsten isopolyacid.

According to one embodiment of the present specification, in Formula 1, Z ⁻ represents a sulfonimide acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; boron; an anion containing aluminum; or tungsten And an anion containing oxygen and at least one element selected from the group consisting of molybdenum, silicon, and phosphorus.

  According to one embodiment of the present specification, in the chemical formula a, Q is an alkylene group; or —R103OC (═O) R104—.

  According to one embodiment of the present specification, in the chemical formula a, Q is an ethylene group; or —R103OC (═O) R104—.

  According to another embodiment of the present specification, R103 and R104 are the same or different from each other and are each independently a direct bond; or a substituted or unsubstituted alkylene group.

  According to another embodiment of the present specification, R103 and R104 are the same or different from each other, and are each independently a direct bond; or an alkylene group.

  According to another embodiment of the present specification, R103 and R104 are the same or different from each other, and are each independently a direct bond; or an ethylene group.

  According to one embodiment of the present specification, in the chemical formula a, X is a hydroxy group; or -OCOOR115.

  According to another embodiment of the present specification, R115 is a substituted or unsubstituted alkyl group.

  According to another embodiment of the present specification, R115 is an alkyl group.

  According to another embodiment of the present specification, R115 is a t-butyl group.

  According to one embodiment of the present specification, in the chemical formula a, T is a substituted or unsubstituted alkyl group.

  According to one embodiment of the present specification, in the chemical formula a, T is an alkyl group.

  According to one embodiment of the present specification, in the chemical formula a, T is a t-butyl group.

前記化合物において、Ｚ⁻は、前述の通りである。 According to one embodiment of the present specification, Formula 1 may be selected from the following compounds, but is not limited thereto.

In the compound, Z ⁻ is as described above.

  The compound represented by Chemical Formula 1 can be produced with reference to the production examples described later.

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

  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. For example, the colorant composition may include only the compound represented by the chemical formula 1, but may include the compound represented by the chemical formula 1 and one or more dyes, or the compound represented by the chemical formula 1. And one or more pigments, or a compound represented by Formula 1 above, one or more dyes and one or more pigments.

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

  In one embodiment of the present specification, the resin composition may further include a binder resin; a multifunctional monomer; a photoinitiator; an antioxidant; and a solvent.

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

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

  The polyfunctional monomer imparting the mechanical strength of the film may be 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- Droxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri Propylene 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-hexafluo Isopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl It may be selected from the group consisting of acrylate and butyl α-hydroxymethyl acrylate, 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 ) -Chlorostyrene may be selected from the group consisting of, but not limited to.

  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. However, it is 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) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate Although it is preferable to use 1 or more types, it is not limited only to these.

  According to an 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 plays a role of forming a photoresist image by light. 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, Pentaerythritol tetramethacrylate and dipentaerythritol May be one or a mixture of two or more selected from the group consisting of Le hexa methacrylate.

  The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light and causes crosslinking. For example, the photoinitiator is selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. 1 or more types may be sufficient.

  The acetophenone compounds include 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-hydroxycyclohexyl phenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- ( 4-Bromo-benzyl-2-dimethylamino-1 (4-morpholinophenyl) - butan-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-one include, but are not limited to.

  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' Examples include, but are not limited to, tetraphenylbiimidazole, 2,2′-bis (o-chlorophenyl) -4,4,5,5′-tetraphenyl-1,2′-biimidazole.

  The triazine compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-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-triazin-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-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 However, it is not limited to these.

  The oxime compounds include 1,2-octadion-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Ciba Geigy, CG 124), ethanone-1- (9-ethyl) -6- ( Examples include 2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CSI 242) and N-1919 (Adeka), but are not limited thereto.

  The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether. , Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol Propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3- It may be one or more selected from the group consisting of ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is limited to this. It is not a thing.

  According to one embodiment of the present specification, the content of the color material composition is 0.1 wt% to 30 wt% based on the total weight of the solid content in the resin composition, and the binder resin The content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the antioxidant is 0.001% by weight to 20% by weight. The content of the polyfunctional monomer is 0.1% by weight to 50% by weight.

  The total weight of the solid content means the total of the total weight of the components excluding the solvent in the resin composition. The solid content and the percentage by weight based on 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 comprises a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and 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 photocrosslinking sensitizer includes 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 and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 A fluorenone compound such as fluorenone; a thioxanthone compound such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; Xanthone compounds such as nthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine Acridine compounds such as 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; Dicarbonyl compounds such as 7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione and 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6- Dimethoxybenzoyl) -2,4,4-trimethylpentyl Phosphine oxide compounds such as sphin oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2 , 5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone, etc. 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7 -Methoxy-coumarin, 10,10-ca Such as rubonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolizin-11-one One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthothiazoline can be used. .

  The curing accelerator is used to increase curing and mechanical strength. Specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-thiadiazole, 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) It is possible to use one or more selected.

  As an adhesion promoter used in the present specification, a methacryloylsilane coupling agent such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane, etc. One or more of them can be selected and used, and one or more of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like can be selected and used as the alkyltrimethoxysilane.

  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 manufactured by 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, and as the fluorine-based surfactant, IC (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. can be used. However, the present invention is not limited to this.

  The antioxidant is at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant. However, it is not limited to this.

  Specific examples of the antioxidant include phosphoric acid-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-tert-butyl-4-hydroxybenzyl) benzene, 3,5-di-tert-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) Nol), 4,4′-thiobis (3-methyl-6-tert-butylphenol), or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester ( Hindered phenol-based primary antioxidants such as Bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl- Amine-based secondary antioxidants such as β-naphthylamine, N, N′-diphenyl-p-phenylenediamine, or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, di Lauryl thiopropionate, distearyl thiopropionate, Thio secondary antioxidants such as lucaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenyl phosphite, tris (nonylphenyl) phosphite, tri Isodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Pentaerythritol Diphosphite, or (1,1′-biphenyl) -4,4′-diylbisphosphonic acid) Tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1′-Biphenyl) -4,4′-Diylbisphosphonoacid acid tetrakis [2, -bis (1,1-dimethylethyl) phenyl] ester phosphite secondary antioxidant such as) and the like.

  As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but are 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) -Butylphenol), 2-mercaptoimidazole, and phenothiazine, but is not limited thereto and is generally known in the art. It can include those are.

The dispersant can be used by a method of internally adding the pigment to the pigment in a form in which the pigment is surface-treated in advance or a method of adding the pigment to the pigment externally. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, non-ionic, or amphoteric interface. An active agent etc. are mentioned. These can be used either 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 at least one selected from the group consisting of a salt, 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 polymeric leveling agents include polyethyleneimine, polyamidoamine, reaction products of amines and epoxides, and non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric leveling agents. -Including but not limited to polymeric nitrogen-containing compounds, all commonly used in the art can be used.

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

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

  Although it does not restrict | limit especially as said application | coating method, Spray method, roll coating method, spin coating method etc. can be used, and spin coating method is generally used widely. Moreover, after forming a coating film, a part of residual solvent can be removed under reduced pressure depending on the case.

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

  The resin composition according to the present specification includes 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 materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, photosensitive materials for printed wiring boards, plasma display panel (PDP) photosensitive materials, etc. And there is no particular limitation on its use.

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

  The color filter can be produced 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 is excellent in heat resistance, has little color change due to heat treatment, has a high color reproducibility even in the curing process during the production of a color filter, and has a luminance and light / dark ratio. A high color filter can be provided.

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

  The color filter may 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. Chrome can be used as the black matrix material. In this case, it is possible to use a method in which chromium is deposited on the entire glass substrate and a pattern is formed by an etching process. However, a resin black matrix by a pigment dispersion method capable of fine processing can be used in consideration of high process cost, high reflectivity of chromium, and environmental contamination due to chromium waste liquid.

  In the black matrix according to an 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 carbon black and a color pigment can be mixed and used. At this time, since the color pigment having insufficient light shielding properties is mixed, the amount of the color material is relatively small. Even if it increases, there exists an advantage that the intensity | strength of a film | membrane or the adhesiveness with respect to a board | substrate does not fall.

  A display apparatus 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 liquid crystal display (LCD). 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 their substitutions and modifications, and is not limited to the scope of the examples.

フェニルイミダゾール（３．８６ｇ、２０ｍｍｏｌ）にジメチルホルムアミド（ＤＭＦ）１００ｍｌを添加し、室温でゆっくり水素化ナトリウム（１ｇ、２１ｍｍｏｌ）を添加して、水素が発生しなくなるまで撹拌した。その後、ベンジルクロライド（２．５ｇ、２０ｍｍｏｌ）を添加して、室温で撹拌した。反応終了後、蒸留水を添加し、トルエンで抽出して、有機層を硫酸ナトリウムで乾燥させ、減圧乾燥した。得られた生成物をカラム（エチルアセテート：ヘキサン１：４０の比率）で精製して、化合物Ａ３．２ｇ、５６％の収率で得た。 Production Example 1 Production of Compound A

To phenylimidazole (3.86 g, 20 mmol) was added 100 ml of dimethylformamide (DMF), sodium hydride (1 g, 21 mmol) was slowly added at room temperature, and the mixture was stirred until no more hydrogen was generated. Benzyl chloride (2.5 g, 20 mmol) was then added and stirred at room temperature. After completion of the reaction, distilled water was added and extracted with toluene, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by a column (ratio of ethyl acetate: hexane 1:40) to obtain 3.2 g of compound A in a yield of 56%.

フェニルイミダゾール（１．９３ｇ、１０ｍｍｏｌ）にジメチルホルムアミド（ＤＭＦ）５０ｍｌを添加し、室温でゆっくり水素化ナトリウム（０．５ｇ、１０．５ｍｍｏｌ）を添加して、水素が発生しなくなるまで撹拌した。その後、ヨウ化プロピル（２．０ｇ、１２ｍｍｏｌ）を添加して、室温で撹拌した。反応終了後、蒸留水を添加し、トルエンで抽出して、有機層を硫酸ナトリウムで乾燥させ、減圧乾燥した。得られた生成物をカラム（エチルアセテート：ヘキサン１：３０の比率）で精製して、化合物Ｂ１．６ｇ、６４％の収率で得た。 Production Example 2 Production of compound B

To phenylimidazole (1.93 g, 10 mmol) was added 50 ml of dimethylformamide (DMF), sodium hydride (0.5 g, 10.5 mmol) was slowly added at room temperature, and the mixture was stirred until no more hydrogen was generated. Then propyl iodide (2.0 g, 12 mmol) was added and stirred at room temperature. After completion of the reaction, distilled water was added and extracted with toluene, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by a column (ratio of ethyl acetate: hexane 1:30) to obtain 1.6 g of compound B in a yield of 64%.

窒素雰囲気下、フラスコに、４，４−ジフルオロベンゾフェノン（１５ｇ、６９ｍｍｏｌ）と２−エチルアミノエタノール（５０ｇ、５５２ｍｍｏｌ）を入れて、１５０℃で４８時間加熱還流を実施した。反応終了後、蒸留水を添加し、メチレンクロライドで抽出して、有機層を硫酸ナトリウムで乾燥させ、減圧乾燥を実施した。得られた生成物にエチルアセテートを入れて、室温で２時間撹拌後、フィルタして、米色のパウダー化合物Ｃを１９ｇ、７７％の収率で得た。 Production Example 3 Production of Compound C

Under a nitrogen atmosphere, 4,4-difluorobenzophenone (15 g, 69 mmol) and 2-ethylaminoethanol (50 g, 552 mmol) were added to the flask, and refluxed with heating at 150 ° C. for 48 hours. After completion of the reaction, distilled water was added and extracted with methylene chloride. The organic layer was dried over sodium sulfate and dried under reduced pressure. Ethyl acetate was added to the obtained product, stirred at room temperature for 2 hours, and then filtered to obtain 19 g of rice powder compound C in a yield of 77%.

窒素雰囲気下、３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフェニル）プロピオン酸（９．４ｇ、３３．７４ｍｍｏｌ）をテトラヒドロフラン１００ｍＬに溶かした後、アイスバス（ｉｃｅ ｂａｔｈ）を設けて０℃に冷却した。その後、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド（５．３ｇ、８４．３７ｍｍｏｌ）を添加し、１５分後、化合物Ｃ（４．１ｇ、１１．２２ｍｍｏｌ）をテトラヒドロフラン３０ｍＬに溶かしてゆっくり添加した。昇温して室温で２４時間撹拌後、蒸留水を添加し、メチレンクロライドで抽出して、有機層を硫酸ナトリウムで乾燥させ、減圧乾燥した。乾燥した生成物をメチレンクロライド２００ｍＬに溶かした後、炭酸水素ナトリウム飽和溶液１００ｍＬを添加して撹拌後、有機層を硫酸ナトリウムで乾燥させ、減圧乾燥した。得られた生成物はカラム（エチルアセテート：ヘキサン＝１：３）で精製して、化合物Ｄを５．０ｇ、５０．８％の収率で得た。 Production Example 4 Production of compound D

In a nitrogen atmosphere, 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid (9.4 g, 33.74 mmol) was dissolved in 100 mL of tetrahydrofuran, and then an ice bath was provided. Cooled to 0 ° C. Then, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (5.3 g, 84.37 mmol) was added, and 15 minutes later, compound C (4.1 g, 11.22 mmol) was dissolved in 30 mL of tetrahydrofuran. Slowly added. After heating up and stirring at room temperature for 24 hours, distilled water was added and extracted with methylene chloride, and the organic layer was dried over sodium sulfate and dried under reduced pressure. After the dried product was dissolved in 200 mL of methylene chloride, 100 mL of a saturated sodium bicarbonate solution was added and stirred, and then the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by a column (ethyl acetate: hexane = 1: 3) to obtain Compound D in a yield of 5.0 g and 50.8%.

ピリジン４０ｍＬに化合物Ｄ（３．２７ｇ、３．７ｍｍｏｌ）を溶かした後、ジ−ｔ−ブチル−ジカーボネート（８．１３ｇ、１１．２ｍｍｏｌ）をゆっくり添加した。次に、４−ジメチルアミノピリジン（０．９ｇ、７．４ｍｍｏｌ）を添加し、６０℃で３時間撹拌した。反応終了後、蒸留水５０ｍＬを添加し、メチレンクロライドで抽出した。分離された有機層は硫酸ナトリウムで乾燥させた後、減圧乾燥した。得られた生成物をカラム（エチルアセテート：ヘキサン＝１：５の比率）で精製して、化合物Ｅを３．２ｇ、８０％の収率で得た。 Production Example 5 Production of Compound E

Compound D (3.27 g, 3.7 mmol) was dissolved in 40 mL of pyridine, and then di-t-butyl-dicarbonate (8.13 g, 11.2 mmol) was slowly added. Next, 4-dimethylaminopyridine (0.9 g, 7.4 mmol) was added and stirred at 60 ° C. for 3 hours. After completion of the reaction, 50 mL of distilled water was added and extracted with methylene chloride. The separated organic layer was dried over sodium sulfate and then dried under reduced pressure. The obtained product was purified by a column (ratio of ethyl acetate: hexane = 1: 5) to obtain 3.2 g of Compound E in a yield of 80%.

製造例４における３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフェニル）プロピオン酸の代わりに３，５−ジ−ｔ−ブチル−４−ヒドロキシ安息香酸（８．４ｇ、３３．５５ｍｍｏｌ）を用いたことを除けば、製造例４と同様の方法で化合物Ｆ５．９ｇ、６４％の収率で得た。 Production Example 6 Production of compound F

3,5-Di-t-butyl-4-hydroxybenzoic acid (8.4 g, 33.55 mmol) instead of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid in Production Example 4 ) Was used in the same manner as in Production Example 4 to obtain Compound F (5.9 g, 64% yield).

窒素雰囲気下、トルエン３０ｍＬに化合物Ｄ（１．０ｇ、１．１４ｍｍｏｌ）をきれいに溶かす。その後、オキシ塩化リン（０．４４ｇ、２．８５ｍｍｏｌ）を添加して、しばらく撹拌した。次に、化合物Ａ（０．５４ｇ、１．９１ｍｍｏｌ）を添加して、９０〜９５℃で５時間撹拌する。次に、反応混合物を室温に冷却した後、トルエン１５０ｍＬと飽和食塩水１００ｍＬを添加し、３０分撹拌した。有機層を飽和食塩水１００ｍＬで洗浄し、硫酸ナトリウムで乾燥させた後、減圧乾燥した。得られた生成物をカラム（メチレンクロライド：メタノール：エチルアセテート＝６：１：２）で精製して、化合物Ｇを０．３ｇ、２２．３％の収率で得た。 Production Example 7 Production of compound G

In a nitrogen atmosphere, dissolve compound D (1.0 g, 1.14 mmol) cleanly in 30 mL of toluene. Thereafter, phosphorus oxychloride (0.44 g, 2.85 mmol) was added and stirred for a while. Compound A (0.54 g, 1.91 mmol) is then added and stirred at 90-95 ° C. for 5 hours. Next, after cooling the reaction mixture to room temperature, 150 mL of toluene and 100 mL of saturated brine were added and stirred for 30 minutes. The organic layer was washed with 100 mL of saturated brine, dried over sodium sulfate, and then dried under reduced pressure. The obtained product was purified by a column (methylene chloride: methanol: ethyl acetate = 6: 1: 2) to obtain 0.3 g of Compound G in a yield of 22.3%.

化合物Ｇ（０．３ｇ、０．２５ｍｍｏｌ）をメタノール２０ｍＬに溶解させ、次に、ビストリフルオルメタンスルホンイミド（０．０７ｇ、０．３３ｍｍｏｌ）を添加して、２時間撹拌した。蒸留水１００ｍＬを添加して、しばらく撹拌した。得られた懸濁液を濾過して、化合物Ｈを０．３２ｇ、９２％の収率で得た。 Production Example 8 Production of compound H

Compound G (0.3 g, 0.25 mmol) was dissolved in 20 mL of methanol, then bistrifluoromethanesulfonimide (0.07 g, 0.33 mmol) was added and stirred for 2 hours. 100 mL of distilled water was added and stirred for a while. The obtained suspension was filtered to obtain 0.32 g of Compound H in a yield of 92%.

窒素雰囲気下、トルエン３０ｍＬに化合物Ｅ（１．０ｇ、０．９３ｍｍｏｌ）をきれいに溶かす。その後、オキシ塩化リン（０．２３ｇ、１．３９ｍｍｏｌ）を添加して、しばらく撹拌した。次に、化合物Ｂ（０．２７ｇ、１．１４ｍｍｏｌ）を添加して、９０℃〜９５℃で５時間撹拌する。次に、反応混合物を室温に冷却した後、トルエン１５０ｍＬと飽和食塩水１００ｍＬを添加し、３０分撹拌した。有機層を飽和食塩水１００ｍＬで洗浄し、硫酸ナトリウムで乾燥させた後、減圧乾燥した。得られた生成物をカラム（メチレンクロライド：メタノール：エチルアセテート＝６：１：２）で精製して、化合物Ｉを０．７ｇ、５７％の収率で得た。 Production Example 9 Preparation of Compound I

Dissolve compound E (1.0 g, 0.93 mmol) cleanly in 30 mL of toluene under a nitrogen atmosphere. Thereafter, phosphorus oxychloride (0.23 g, 1.39 mmol) was added and stirred for a while. Compound B (0.27 g, 1.14 mmol) is then added and stirred at 90 ° C. to 95 ° C. for 5 hours. Next, after cooling the reaction mixture to room temperature, 150 mL of toluene and 100 mL of saturated brine were added and stirred for 30 minutes. The organic layer was washed with 100 mL of saturated brine, dried over sodium sulfate, and then dried under reduced pressure. The obtained product was purified by a column (methylene chloride: methanol: ethyl acetate = 6: 1: 2) to obtain 0.7 g of Compound I in a yield of 57%.

製造例８における化合物Ｇの代わりに化合物Ｉを用いたことを除けば、同様の方法で化合物Ｊ０．７８ｇ、９４％の収率で得た。 Production Example 10 Production of Compound J

Except that Compound I was used instead of Compound G in Production Example 8, Compound J 0.78 g was obtained in a yield of 94% by the same method.

窒素雰囲気下、トルエン３０ｍＬに化合物Ｆ（１．０ｇ、１．２ｍｍｏｌ）をきれいに溶かす。その後、オキシ塩化リン（０．４４ｇ、１．８３ｍｍｏｌ）を添加して、しばらく撹拌した。次に、化合物Ａ（０．４１ｇ、１．４６ｍｍｏｌ）を添加して、９０℃〜９５℃で５時間撹拌する。次に、反応混合物を室温に冷却した後、トルエン１５０ｍＬと飽和食塩水１００ｍＬを添加し、３０分撹拌した。有機層を飽和食塩水１００ｍＬで洗浄し、硫酸ナトリウムで乾燥させた後、減圧乾燥した。得られた生成物をカラム（メチレンクロライド：メタノール：エチルアセテート＝６：１：２）で精製して、化合物Ｋを０．４ｇ、２９．２％の収率で得た。 Production Example 11 Production of compound K

In a nitrogen atmosphere, compound F (1.0 g, 1.2 mmol) is dissolved neat in 30 mL of toluene. Thereafter, phosphorus oxychloride (0.44 g, 1.83 mmol) was added and stirred for a while. Next, Compound A (0.41 g, 1.46 mmol) is added and stirred at 90-95 ° C. for 5 hours. Next, after cooling the reaction mixture to room temperature, 150 mL of toluene and 100 mL of saturated brine were added and stirred for 30 minutes. The organic layer was washed with 100 mL of saturated brine, dried over sodium sulfate, and then dried under reduced pressure. The obtained product was purified by a column (methylene chloride: methanol: ethyl acetate = 6: 1: 2) to obtain 0.4 g of Compound K in a yield of 29.2%.

製造例８における化合物Ｇの代わりに化合物Ｋを用いたことを除けば、同様の方法で化合物Ｌ０．３８ｇ、７８％の収率で得た。 Production Example 12. Production of Compound L

Compound L 0.38 g was obtained in a yield of 78% by the same method except that Compound K was used instead of Compound G in Production Example 8.

韓国公開特許第２０１２−００１４１１１号の実施例７における陰イオンをビストリフルオルメタンスルホンイミドを用いたことを除けば、同様に製造して化合物Ｍを０．８ｇ得た。（収率８０％） Production Example 13 Production of compound M

Except for using the bistrifluoromethanesulfonimide as an anion in Example 7 of Korean Patent No. 2012-0014111, 0.8 g of Compound M was obtained. (Yield 80%)

  <Production and Evaluation of Resin Composition>

Comparative Example 1
A photosensitive blue resin composition was produced with the following composition.

  As a blue dye compound, 0.4% by weight of the compound M according to Production Example 13 and a binder resin (a mass ratio of benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: 11: 25) ) 80.92% by weight, propylene glycol monomethyl ether acetate 18.0% by weight, leveling agent (TF-1740) 0.6% by weight, and adhesion assistant (KRM-503) 0.08% by weight. The blue resin composition was manufactured by stirring as described above.

Example 1
As a blue dye compound, a blue resin composition was produced with the same composition as Comparative Example 1 except that 0.4% by weight of Compound H was used instead of 0.4% by weight of Compound M.

Example 2
As a blue dye compound, a blue resin composition was produced with the same composition as Comparative Example 1, except that 0.4% by weight of Compound J was used instead of 0.4% by weight of Compound M of Comparative Example.

Method for Producing Substrate The photosensitive resin composition was spin-coated on glass (5 × 5 cm) and pre-baked at 100 ° C. for 100 seconds to form a film.

Experimental example. Measurement of light resistance For measurement of light resistance, the blue resin compositions for color filters produced in Examples 1 and 2 and Comparative Example 1 were spin-coated on a glass substrate of 5 cm × 5 cm, respectively, and hot-hot at 100 ° C. The plate was pre-baked for 2 minutes and then cooled at room temperature for 2 minutes.

  Next, after performing a post-bake for 20 minutes at 230 ° C. convection oven, the color characteristics were confirmed using a spectrophotometer. Thereafter, the substrate was placed in a light resistance tester Sun test CPS + and left for 6 hours. After the substrate was taken out, the color difference in the C light source was measured, and the color difference change rate ΔEab was calculated and shown in Table 1.

  From the above, it is possible to obtain a color filter coloring composition and a color filter excellent in light resistance by using the amine dye having a specific substituent introduced therein.

Claims (11)

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

In Formula 1,
At least one of R1 to R4, R17, and R18 is a structure represented by the following chemical formula a, and the rest are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; An unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group, or adjacent groups joined together to form a substituted or unsubstituted ring;
R5 to R16 are the same or different from each other, and each independently represents hydrogen; a halogen group; a hydroxy group; a substituted or unsubstituted alkoxy group; or a substituted or unsubstituted alkyl group;
Z ⁻ is an anionic group,
[Chemical Formula a]

In the chemical formula a,
Q is -R101C (= O) R102-; -R103OC (= O) R104-; -R105C (= O) OR106-; -R107OC (= O) OR108-;

;
A substituted or unsubstituted alkylene group; or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; an amine group; -OCOOR115; -CONR116R117; or -NR1118COOR119;
T is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112 and R114 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted alkenylene group. ,
R110, R113 and R115 to R119 are the same or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group;
p and q are each an integer of 1 to 4,
2 ≦ p + q ≦ 5,
When p and q are each 2 or more, the structures in the 2 or more parentheses are the same or different from each other,
* Represents a site bonded to Chemical Formula 1.   2. The compound according to claim 1, wherein X is bonded to the ortho position with respect to the position where T is bonded to the phenyl group of Formula a. Z ⁻ represents one or more selected from the group consisting of a sulfonimidic acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; a boron; an anion containing aluminum; or tungsten, molybdenum, silicon, and phosphorus. The compound according to claim 1, which is an anion containing any of the above elements and oxygen. The compound according to claim 1, wherein the chemical formula 1 is selected from the following compounds:

In said compound, Z ^- the definition is the same as Formula 1.   The coloring material composition containing the compound of any one of Claims 1-4.   The colorant composition according to claim 5, further comprising at least one of a dye and a pigment.   A resin composition comprising: the compound represented by Chemical Formula 1 according to claim 1; a binder resin; a polyfunctional monomer; a photoinitiator; an antioxidant; Based on the total weight of the solid content in the resin composition,
The content of the compound represented by Formula 1 is 0.1 wt% to 30 wt%,
The content of the binder resin is 1% by weight to 90% by weight,
The content of the photoinitiator is 0.1 wt% to 20 wt%,
The content of the antioxidant is 0.001 wt% to 20 wt%,
The resin composition according to claim 7, wherein the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.   A photosensitive material produced using the resin composition according to claim 7.   A color filter comprising the photosensitive material according to claim 9.   A display device comprising the color filter according to claim 10.