JP6631861B2 - Compound, coloring material composition containing the same and resin composition containing the same - Google Patents

Description

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

  The present specification relates to a novel compound, a coloring material 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 manufacture a thin-film display, a flexible display, and the like, a display product from which a color filter is removed, that is, a display product using self-emission such as an LED, an OLED, or a QD as a unit pixel has been developed and manufactured.

  However, in the case of a display using LEDs, OLEDs, QDs, and the like as unit pixels, it is difficult to increase the area. Even when LEDs, OLEDs, QDs, and the like are used, a display including a color filter including these as a light source A lot of effort has been put into development.

  In order to realize a desired color, a light source and an appropriate color filter are required. At present, 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 a particle state and scatters light, but also the pigment surface area increases sharply due to the refinement of the pigment, resulting in poor dispersion stability and uneven pigment particles. Is generated.

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

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

  Korean Patent Publication No. 2013-0130976 describes a color filter using a polymer containing a polymerizable triphenylmethane dye. However, the color filters using the dyes described in the above-mentioned documents have a problem that, although they have excellent spectral characteristics, they have insufficient light resistance.

  Therefore, development of a new coloring material is required to overcome such problems.

Korean Patent Application No. 2001-0009058 Korean Published Patent No. 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, there is provided a compound represented by Formula 1 below.
[Chemical formula 1]

In the above chemical formula 1,
At least one of R1 to R4, R17 and R18 has a structure represented by the following chemical formula a, and the others 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 are bonded to each other to form a substituted or unsubstituted ring;
R5 to R16 are the same or different and are each independently 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 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 two or more parentheses are the same or different from each other;
* Is a site that binds to Chemical Formula 1.

  According to another embodiment of the present specification, there is provided a colorant composition comprising the compound represented by Formula 1.

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

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

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

  According to one embodiment of the present specification, there is provided a display device including the above-described color filter.

  According to one embodiment of the present specification, the coloring material composition containing the compound represented by the above Chemical Formula 1 is excellent in light resistance and can be used as a main coloring material as well as being added in a small amount. An absorption and transmission spectrum suitable for a light source can be obtained, and a higher color reproducibility, a higher luminance, a higher contrast, and the like can be achieved.

  Further, the color filter according to an embodiment of the present specification has excellent light fastness, can provide blue pixels of the color filter, and can satisfy the light fastness required for a display including the above-described color filter. .

  Further, the color filter according to one embodiment of the present specification can provide a blue pixel with excellent light resistance.

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

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

  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 substitution position is the position where the hydrogen atom is substituted, that is, the substituent is substitutable. If it is a position, there is no limitation, and when two or more substituents are present, 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 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, and a substituted or unsubstituted group. Selected from the group consisting of 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. Is substituted with one or more substituents described above, or does not have any 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,

Represents a site bonded to another substituent or a bonding site.

  As used herein, a halogen group may be a fluoro, chloro, bromo, or iodine group.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably one having 1 to 30 carbon atoms. 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, the compound may have the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but preferably has 1 to 30 carbon atoms. 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, the compound may have 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 preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-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 preferably has 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, Examples include, but are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like. Absent.

  In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably one having 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n- It may be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, but is not limited thereto. Not something.

In this specification, the amine group, -NH _2; consisting of N- alkylheteroaryl amine groups and heteroaryl amine groups; alkylamine group; N- arylalkyl amine; arylamine group; N- aryl heteroaryl amine It may be selected from a group, and the number of carbon atoms is not particularly limited. 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-anthracenylamine group, a diphenylamine group, Examples include, but are not limited to, N-phenylnaphthylamine groups, ditolylamine groups, N-phenyltolylamine groups, triphenylamine groups, and the like.

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

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

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

  In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group is as exemplified above for the 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

  When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably has 6 to 30 carbon atoms. 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, the phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably one having 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, or the like, but is not limited thereto.

  As used herein, an `` adjacent '' group refers to a substituent substituted with an atom directly connected to the atom to which the substituent is substituted, the substituent sterically closest to the substituent, or the substituent Substituents can refer to other substituents substituted on the substituted atom. For example, two substituents substituted at the ortho position on a benzene ring and two substituents substituted on the same carbon on an aliphatic ring are taken to be "adjacent" groups to each other.

  In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group, and the arylphosphine group is exemplified by the aforementioned aryl group. It is as follows. Specifically, examples of the aryloxy group include 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 Group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. As the arylthioxy group, Phenylthioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group and the like; 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, and 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 containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the above-described examples of the aryl group.

  In the present specification, the heteroaryl group includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atoms are selected from the group consisting of O, N, Se, and S. One or more atoms. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a 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, phenanthroline, 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, and a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the above-mentioned examples of the heteroaryl group.

  In the present specification, examples of the N-arylheteroarylamine group and the heteroaryl group in the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

  In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed aromatic-aliphatic ring. 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 description 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. Except that each of these is a divalent group, the description of the alkenyl group described above is applicable.

  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 heterocyclic ring.

  In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or fused ring of an aromatic and an aliphatic group. May be selected.

  In the present specification, the aromatic ring may be a monocyclic or polycyclic ring, and may be selected from the above-mentioned examples of the aryl group except for those having a non-monovalent structure.

  In the present specification, the heterocyclic ring includes one or more non-carbon atoms and hetero atoms, and specifically, the hetero atoms are selected from the group consisting of O, N, Se, S, and the like. It can contain one or more atoms. The heterocyclic ring may be a monocyclic or polycyclic ring, may be an aromatic, aliphatic or condensed aromatic and aliphatic ring. It may be selected from the examples of the ring 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 the chemical formula 1-1,
The definitions of R 1 to R 4, R 6, R 12 to R 18 and Z ⁻ are the same as in Chemical Formula 1.

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

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

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

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

  According to an 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 an alkyl group.

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

  According to one embodiment of the present specification, in Formula a, X is bonded at an ortho position with respect to the position at which T is bonded to the phenyl group of Formula a.

According to one embodiment of the present specification, in Chemical Formula 1, Z ⁻ is an anionic group, and the anionic group is not particularly limited. For example, US Pat. No. 7,939,644; Japanese Patent Application No. 2006-003080, Japanese Patent Application No. 2006-001917, Japanese Patent Application No. 2005-159926, Korean Application No. 2007-7028897, Japanese Patent Application No. 2005-071680, Korean Application No. 2007-70000063 Anion described in Japanese Patent Application No. 2005-111696 and Japanese Patent Application No. 2008-249663 can be applied.

  Specific examples of the anion include trifluoromethanesulfonate 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, for example, bromo group, fluorine group , An iodine group and a chlorine group.

Z ⁻ represents an anion containing 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, Z ⁻ may include an anion of tungstophosphoric acid, an anion of tungstosilicic acid, or an anion of tungsten-based isopolyacid.

According to one embodiment of the present specification, in Formula 1, Z ⁻ is a sulfonimidic acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; a boron; an anion containing an aluminum; , Molybdenum, silicon, and phosphorus, and an anion containing one or more elements selected from the group consisting of phosphorus and oxygen.

  According to one embodiment of the present specification, in Formula a, Q is an alkylene group; or -R103OC (= O) R104-.

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

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

  According to one embodiment of the present specification, in 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 an 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 Formula 1 can be produced with reference to Production Examples described below.

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

  The coloring material composition may further include 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 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 the above formula 1, one or more dyes, and one or more pigments.

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

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

  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.

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

  The polyfunctional monomer that imparts mechanical strength to the film is at least one of unsaturated carboxylic 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-nonylphenoxy polyethylene glycol (meth) acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl ( (Meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluoro 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, but is not limited thereto.

  Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

  Specific examples of the unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. However, the present invention 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 imparting 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- Carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate It is preferable to use one or more kinds, but it is not limited thereto.

  According to one 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 in 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, 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 which generates a radical by light to cause crosslinking, and is, for example, selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. One or more of these may be used.

  The acetophenone-based compound includes 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 phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- ( 4-bromo-benzyl-2-dimethylamino-1 (4-morpholinophenyl) - butan-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-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' -Tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like, but is not limited thereto.

  The triazine-based compound includes 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 and the like. However, the present invention is not limited to these.

  The oxime-based compound includes 1,2-octadion-1- (4-phenylthio) phenyl-2- (o-benzoyl oxime) (Ciba Geigy, CGI 124), and ethanone-1- (9-ethyl) -6- ( Examples include, but are not limited to, 2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGI 242), N-1919 (ADEKA).

  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 not limited thereto. Not something.

  According to one embodiment of the present specification, based on the total weight of solids in the resin composition, the content of the coloring material composition is 0.1 wt% to 30 wt%, and the binder resin Is from 1% by weight to 90% by weight, the content of the photoinitiator is from 0.1% by weight to 20% by weight, and the content of the antioxidant is from 0.001% by weight to 20% by weight. %, And the content of the polyfunctional monomer is 0.1% by weight to 50% by weight.

  The total weight of the solid content means the sum of the total weight of 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 includes 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, Benzophenone-based 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 Fluorenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; Xanthone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine , 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane and other acridine-based compounds; benzyl, 1,7, 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 sphine 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 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 rubonyl bis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidin-11-one; Coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; and at least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline can be used. .

  The curing accelerator is used for increasing curing and mechanical strength, and 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.

  Examples of the adhesion promoter used in the present specification include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, and methacryloylsilane coupling agents such as methacryloyloxypropyldimethoxysilane. One or more of these can be selected and used, and as the alkyltrimethoxysilane, one or more can be selected 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-300, 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 or the like can be used. 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-577, 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, the present invention is not limited to this.

  Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, and 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) Phenol), 4,4′-thiobis (3-methyl-6-t-butylphenol), or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester ( Primary antioxidants based on hindered phenols such as Bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester); phenyl-α-naphthylamine, phenyl- amine secondary antioxidants such as β-naphthylamine, N, N′-diphenyl-p-phenylenediamine, or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, diamine Lauryl thiopropionate, distearyl thiopropionate, Thio-based secondary antioxidants such as rucaptobenzothiazole 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′-Diylbisphosphonous acid tetrakis [2, -bis (1,1-dimethylethyl) phenyl] ester phosphite secondary antioxidant such as) and the like.

  Examples of the ultraviolet absorber include 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone, but are not limited thereto. Everything commonly used in the art 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 are not limited thereto and are generally known in the art. It can include those are.

The dispersant can be used in a method in which the pigment is internally added to the pigment in a form where the pigment is subjected to a surface treatment, or a method in which the dispersant is externally added to the pigment. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used, and a fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric interface can be used. Activators and the like. These can be used individually or in combination of two or more.
Specifically, the dispersant is a polyalkylene glycol and an ester thereof, a polyoxyalkylene polyhydric alcohol, an ester alkylene oxide adduct, an alcohol alkylene oxide adduct, a sulfonic acid ester, a sulfonic acid salt, a carboxylic acid ester, or a carboxylic acid. There is at least one member 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 the polymeric leveling agent include polyethyleneimine, polyamidoamine, and a reaction product of an amine and an epoxide. Specific examples of the non-polymeric leveling agent include non-polymeric sulfur-containing and non-polymeric leveling agents. -All but commonly used in the art, including but not limited to polymeric nitrogen containing compounds.

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

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

  The application method is not particularly limited, but a spray method, a roll coating method, a spin coating method and the like can be used, and the spin coating method is generally widely used. After the formation of the coating film, the residual solvent can be partially removed under reduced pressure, if necessary.

  As a light source for curing the resin composition according to the present specification, for example, a mercury vapor arc (arc) that emits light having a wavelength of 250 nm to 450 nm, a carbon arc, a Xe arc, and the like include, but are not necessarily limited to, these. Absent.

  The resin composition according to the present invention is a pigment-dispersed photosensitive material for producing a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode. Used for photosensitive material for coat layer formation, column spacer photosensitive material, photo-curable paint, photo-curable ink, photo-curable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. And there is no particular limitation on its use.

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

  The color filter can be manufactured using a resin composition containing the coloring material composition. A color filter can be formed by applying the resin composition on 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, has a small change in color due to heat treatment, has a high color reproducibility even by a curing process during the production of a color filter, and has a high luminance and contrast ratio. A high color filter can be provided.

  The substrate may be a glass plate, a silicon wafer, a plate of a plastic base material such as polyethersulfone (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 the contrast. Chromium can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution due to chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

  The black matrix according to an embodiment of the present specification can use a black pigment or a black dye 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. There is an advantage that the strength of the film or the adhesion to the substrate does not decrease even if it increases.

  A display device including the 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 Diode, LED), an organic light emitting device (Organic Light Emitting Diode, OLED), a liquid crystal display device (Liquid Crystal, LCD Disp. 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) may be used.

  Hereinafter, the present specification will be described in detail with reference to examples. The following examples are provided to illustrate the present specification, and the scope of the present specification includes the scope described in the following claims, and substitutions and modifications thereof, 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

100 ml of dimethylformamide (DMF) was added to phenylimidazole (3.86 g, 20 mmol), and sodium hydride (1 g, 21 mmol) was slowly added at room temperature, followed by stirring until no more hydrogen was generated. Thereafter, benzyl chloride (2.5 g, 20 mmol) was added, and the mixture was stirred at room temperature. After completion of the reaction, distilled water was added, the mixture was extracted with toluene, the organic layer was dried over sodium sulfate, and dried under reduced pressure. The obtained product was purified by 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. Preparation of Compound B

50 ml of dimethylformamide (DMF) was added to phenylimidazole (1.93 g, 10 mmol), 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. Thereafter, propyl iodide (2.0 g, 12 mmol) was added, and the mixture was stirred at room temperature. After completion of the reaction, distilled water was added, the mixture was extracted with toluene, 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: 30 ratio) 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. Preparation of Compound C

Under a nitrogen atmosphere, 4,4-difluorobenzophenone (15 g, 69 mmol) and 2-ethylaminoethanol (50 g, 552 mmol) were put in a flask, and the mixture was heated under reflux at 150 ° C. for 48 hours. After the completion of the reaction, distilled water was added, the mixture was 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 filtered to obtain 19 g of rice-colored 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. Preparation of Compound D

Under a nitrogen atmosphere, 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid (9.4 g, 33.74 mmol) was dissolved in tetrahydrofuran (100 mL), and an ice bath (ice bath) was provided. Cooled to 0 ° C. Thereafter, 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. Added slowly. After heating and stirring at room temperature for 24 hours, distilled water was added, extracted with methylene chloride, and the organic layer was dried over sodium sulfate and dried under reduced pressure. After dissolving the dried product in 200 mL of methylene chloride, 100 mL of a saturated solution of sodium hydrogen carbonate was added, and the mixture was stirred. 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 5.0 g of Compound D in a yield of 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 Preparation of Compound E

After dissolving Compound D (3.27 g, 3.7 mmol) in 40 mL of pyridine, 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 the mixture was stirred at 60 ° C for 3 hours. After the reaction was completed, 50 mL of distilled water was added, and the mixture was 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 (ethyl acetate: hexane = 1: 5 ratio) 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

Instead of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid in Production Example 4, 3,5-di-t-butyl-4-hydroxybenzoic acid (8.4 g, 33.55 mmol) 5.9 g of compound F was obtained in a yield of 64% in the same manner as in Preparation Example 4 except that) was used.

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 Preparation of Compound G

Dissolve Compound D (1.0 g, 1.14 mmol) neatly in 30 mL of toluene under a nitrogen atmosphere. Thereafter, phosphorus oxychloride (0.44 g, 2.85 mmol) was added, and the mixture was stirred for a while. Next, compound A (0.54 g, 1.91 mmol) is added, and the mixture is stirred at 90 to 95 ° C. for 5 hours. Next, after cooling the reaction mixture to room temperature, 150 mL of toluene and 100 mL of saturated saline were added, and the mixture was stirred for 30 minutes. The organic layer was washed with 100 mL of saturated saline, 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 Preparation of Compound H

Compound G (0.3 g, 0.25 mmol) was dissolved in 20 mL of methanol, and 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 resulting 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

Compound E (1.0 g, 0.93 mmol) is dissolved in 30 mL of toluene under a nitrogen atmosphere. Thereafter, phosphorus oxychloride (0.23 g, 1.39 mmol) was added, and the mixture was stirred for a while. Next, compound B (0.27 g, 1.14 mmol) is added, and the mixture is 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 saline were added, and the mixture was stirred for 30 minutes. The organic layer was washed with 100 mL of saturated saline, 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

Compound J 0.78 g was obtained in a similar manner except that compound I was used instead of compound G in Production Example 8 in a yield of 94%.

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

Compound F (1.0 g, 1.2 mmol) is dissolved neatly in 30 mL of toluene under a nitrogen atmosphere. Thereafter, phosphorus oxychloride (0.44 g, 1.83 mmol) was added, and the mixture was stirred for a while. Next, compound A (0.41 g, 1.46 mmol) is added, and the mixture is 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 saline were added, and the mixture was stirred for 30 minutes. The organic layer was washed with 100 mL of saturated saline, 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. Preparation of Compound L

Compound L 0.38 g was obtained in a similar manner except that Compound K was used instead of Compound G in Production Example 8 in a yield of 78%.

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 Preparation of Compound M

Compound M was obtained in the same manner as in Example 7 of Korean Patent Publication No. 2012-0014111 except that bistrifluoromethanesulfonimide was used as an anion in Example 7 to obtain 0.8 g of Compound M. (80% yield)

  <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 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, 18.0% by weight of propylene glycol monomethyl ether acetate, 0.6% by weight of a leveling agent (TF-1740), and 0.08% by weight of an adhesion aid (KRM-503) were uniformly mixed. To produce a blue resin composition.

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

Example 2
A blue resin composition was prepared in 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 as a blue dye compound.

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

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

  Next, after a post heat treatment (post-bake) at 230 ° C. in a reaction open for 20 minutes, 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 taking out the substrate, the color difference in the C light source was measured, and the color difference change rate ΔEab was calculated.

  As described above, the use of the amine-based dye of the present invention into which a specific substituent has been introduced makes it possible to obtain a color filter coloring composition and a color filter having excellent light fastness.

Claims (11)

A compound represented by the following chemical formula 1:
[Chemical formula 1]

In the above chemical formula 1,
At least one of R1 to R4 has a structure represented by the following chemical formula a, and R1 to R4, which are not the structure represented by the following chemical formula a, are the same or different from each other, and each independently represents hydrogen; A substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group ,
R17 and R18 are the same or different and are each independently a structure represented by the following chemical formula a, hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group Or adjacent groups are bonded to each other to form a substituted or unsubstituted ring ,
R5 to R16 are the same or different and are each independently 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 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 two or more parentheses are the same or different from each other;
* Is a site that binds to Chemical Formula 1.   2. The compound according to claim 1, wherein said X is such that T is bonded at the ortho position relative to the bonded position of the phenyl group of formula a. Z ⁻ is a sulfonimidic acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; a boron; an anion containing aluminum; or one or more selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus. The compound according to claim 1, which is an anion containing the element and oxygen. The compound of claim 1, wherein the compound of formula 1 is selected from the following compounds:

In the above compound, the definition of Z ⁻ is the same as in the above Chemical Formula 1.   A coloring material composition comprising the compound according to claim 1.   The coloring material composition according to claim 5, further comprising at least one of a dye and a pigment.   A resin composition comprising the compound represented by Formula 1 according to claim 1, a binder resin, a polyfunctional monomer, a photoinitiator, an antioxidant, and a solvent. Based on the total weight of solids in the resin composition,
The content of the compound represented by Formula 1 is 0.1% by weight to 30% by weight,
The content of the binder resin is 1% by weight to 90% by weight,
The content of the photoinitiator is from 0.1% by weight to 20% by weight,
The content of the antioxidant is 0.001% by weight to 20% by weight,
The resin composition according to claim 7, wherein the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight.   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.