KR20170009099A - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents
Compound, colorant composition comprising the same and resin composition comprising the same Download PDFInfo
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- KR20170009099A KR20170009099A KR1020150100555A KR20150100555A KR20170009099A KR 20170009099 A KR20170009099 A KR 20170009099A KR 1020150100555 A KR1020150100555 A KR 1020150100555A KR 20150100555 A KR20150100555 A KR 20150100555A KR 20170009099 A KR20170009099 A KR 20170009099A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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Abstract
The present invention relates to a novel compound, a colorant composition containing the same, and a resin composition containing the same.
Description
The present invention relates to a novel compound, a colorant composition containing the same, and a resin composition containing the same.
As a light source of a muscle liquid crystal display (LCD), an LED or an OLED element which does not drive liquid crystal but performs self-luminescence instead of a conventional CCFL is widely used. When an LED or an OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required.
However, it is generally not easy to adjust or adjust the required color coordinates using light emitted from an LED or OLED light source. In addition, the method of improving the color purity, luminance and contrast ratio in the production of a color filter using a pigment dispersion method using already developed color materials, in particular, a pigment has reached a limit.
Development of a new color material is required to overcome such a problem and satisfy the requirement.
The present invention provides a novel compound, a colorant composition containing the same, and a resin composition containing the same.
According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
Y1 is N or CR15, Y2 is N or CR16, Y3 is N or CR17, Y4 is N or CR18, Y5 is N or CR19, Y6 is N or CR20,
At least one of Y1 to Y6 is N,
R 1 to R 20 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted isoindolidinyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,
Q - is an anionic group.
According to another embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.
According to another embodiment of the present invention, there is provided a resin composition comprising the color material composition.
According to one embodiment of the present invention, there is provided a photosensitive material produced using the above resin composition.
According to one embodiment of the present disclosure, there is provided a color filter including the aforementioned photosensitive material.
Further, according to an embodiment of the present invention, there is provided a display device including the color filter described above.
According to one embodiment of the present invention, the colorant composition containing the compound represented by Formula 1 has excellent heat resistance and light resistance, and can be used not only as a small amount but also as a main colorant, A higher color reproduction ratio, a higher luminance, a higher contrast ratio, and the like can be achieved.
Hereinafter, the present specification will be described in more detail.
According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).
Examples of substituents in the present specification are described below, but are not limited thereto.
The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted isoindolidinyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
In the present specification,
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain 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 of 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 is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
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 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
In this specification, the amine group is -NH 2 ; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group and triphenylamine group, but are not limited thereto.
In the present specification, the N-alkylarylamine amine group means an amine group in which N in the amine group is substituted with an alkyl group and an aryl group.
In the present specification, the N-arylheteroarylamine group means an amine group in which N in the 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 N in the amine group is substituted with an alkyl group and a heteroarylamine group.
In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.
In the present specification, the boron group may be -BR 100 R 101 R 102 , wherein R 100 , R 101 and R 102 are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted,
As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "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 the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- 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 and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention 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 having at least two aryl groups may contain 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 this specification, the heteroaryl group in the present specification includes one or more non-carbon atoms and hetero atoms, and specifically, the hetero atom may be an atom selected from the group consisting of O, N, Se and S, . The number of carbon atoms is not particularly limited, but is preferably 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 pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.
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 having 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 at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the above heteroaryl groups.
In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
In this specification, the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.
According to one embodiment of the present invention, R 1 to R 4 in the general formula (1) are the same or different and each independently represents a substituted or unsubstituted isoindolinyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
According to one embodiment of the present invention, R 1 to R 4 in the general formula (1) are the same or different and each independently represents a substituted or unsubstituted isoindolinyl group; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present invention, in the general formula (1), R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
According to one embodiment of the present invention, R 1 to R 4 in the general formula (1) are the same or different and each independently represents a substituted or unsubstituted isoindolinyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted n-butyl group; Or a substituted or unsubstituted phenyl group.
When R 1 to R 4 are substituted, they may be substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and a hydroxyl group, or an isoindoline group substituted or unsubstituted with a nitro group.
According to one embodiment of the present invention, in the general formula (1), R1 and R2 or R3 and R4 of R1 to R4 are bonded to each other to form a substituted or unsubstituted ring.
According to one embodiment of the present invention, in the general formula (1), R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R1 and R2 or R3 and R4 are bonded to each other to form a substituted or unsubstituted ring. According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; An ethyl group; A cyclohexyl group; Or a phenyl group.
According to one embodiment of the present disclosure, R13 is hydrogen.
According to one embodiment of the present disclosure, R13 is an ethyl group.
According to one embodiment of the present invention, R13 is a cyclohexyl group.
According to one embodiment of the present invention, R13 is a phenyl group.
According to one embodiment of the present disclosure, R14 is hydrogen.
According to one embodiment of the present disclosure, R14 is an ethyl group.
According to one embodiment of the present disclosure, R14 is a cyclohexyl group.
According to one embodiment of the present invention, R14 is a phenyl group.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are bonded to each other to form a substituted or unsubstituted ring.
According to one embodiment of the present invention, in the above formula (1), R13 and R14 are bonded to each other to form a substituted or unsubstituted heterocycle.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are bonded to each other to form a substituted or unsubstituted piperidine ring.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are bonded to each other to form a piperidine ring.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or R13 and R14 are bonded to each other to form a substituted or unsubstituted ring.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group, or R13 and R14 are bonded to each other to form a substituted or unsubstituted piperidine ring.
According to one embodiment of the present invention, in the general formula (1), R13 and R14 are the same or different and each independently hydrogen; An ethyl group; A cyclohexyl group; Or a phenyl group, or R13 and R14 are bonded to each other to form a piperidine ring.
According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).
(2)
(3)
In the general formulas (2) and (3)
The definitions of R 1 to R 20 and Q - are the same as in the above formula (1).
According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (4) to (7).
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above formulas 4 to 7,
The definitions of R 1 to R 20 and Q - are the same as in the above formula (1).
According to one embodiment of the present invention, Q - is an anionic group, and the anionic group is not particularly limited, and examples thereof include U.S. Patent Nos. 7,939,644, 2006-003080, 2006-001917, Japanese Unexamined Patent Publication No. 2005-159926, Japanese Unexamined Patent Application No. 2007-7028897, Japanese Unexamined Patent Application No. 2005-071680, Korean Unexamined Patent Application Publication No. 2007-7000693, Japanese Unexamined Patent Application No. 2005-111696, Japanese Unexamined Patent Publication No. 2008-249663 Negative ions can be applied. Specific examples of the anion include a trifluoromethanesulfonic acid anion, a bis (trifluoromethylsulfonyl) amide anion, a bistrifluoromethanesulfonimide anion, a bisperfluoroethylsulfonimide anion, a tetraphenylborate anion, a tetra (Pentafluorophenyl) borate anion, tris trifluoromethanesulfonylmethane anion, nitrate ion, carbonate ion, sulfite ion, halogen group such as fluorine group, iodine group , And chlorine groups.
Also, Q - represents boron; Anions including aluminum; Tungsten, molybdenum, silicon and phosphorus, and an oxygen-containing anion. In particular, the Q < - & gt ; may include an anion of tungstophosphoric acid, an anion of tungstosilicic acid, or an anion of tungsten-based isopoly acid.
According to one embodiment of the present invention, in the general formula (1), Q - is a sulfonimidic acid containing a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen.
According to one embodiment of the present invention, the formula (1) is represented by any one of the following compounds 1 to 112.
According to one embodiment of the present invention, in the compounds 21 to 52, 61, 62, 71, 72, 81, 82, 91, 92, 101, 102, 111 and 112, X and Y are the same or different , Each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms,
Z is hydrogen; A hydroxy group; A nitro group; Or halogen.
According to one embodiment of the present invention, X and Y are the same or different and are each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group or a substituted or unsubstituted n-butyl group.
According to one embodiment of the present invention, X and Y are the same or different from each other and are each independently a methyl group; An ethyl group; Propyl group; Isopropyl or n-butyl group.
According to one embodiment of the present disclosure, Z is selected from the group consisting of hydrogen; A hydroxy group; A nitro group; Fluorine; Goat; bromine; Or iodine.
The compound represented by the formula (1) can be prepared by referring to the following Production Examples.
According to one embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.
The colorant composition may further include at least one of a dye and a pigment in addition to the compound represented by the formula (1). For example, the colorant composition may include only the compound represented by the formula (1), but may include the compound represented by the formula (1) and one or more dyes, or the compound represented by the formula (1) , A compound represented by the formula (1), at least one dye, and at least one pigment.
In one embodiment of the present invention, there is provided a resin composition comprising the color material composition.
In one embodiment of the present invention, the resin composition comprises a binder resin; Multifunctional monomers; Photoinitiators; 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 made of a resin composition.
The binder resin may be a copolymer resin of a monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility. The binder resin may further include a binder generally used in the art.
The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.
Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate It is, but is not limited thereto.
Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.
Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.
Specific examples of the unsaturated imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.
Examples of the acid anhydride include maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.
The alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.
According to one embodiment of the present invention, the acid value of the binder resin is 50 to 130 KOH mg / g and the weight average molecular weight is 1,000 to 50,000.
The multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate. Species or a mixture of two or more species.
The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator is selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound Or more.
The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.
Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 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 may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] Methyl) -6- p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like .
The oxime-based compound may be 1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (O-acetyloxime) (CJ-i-242), N-1919 (Adeca), and the like.
The solvent is selected from the group consisting of 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 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one selected from the group consisting of citrate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.
According to one embodiment of the present invention, the content of the colorant composition is 5% by weight to 60% by weight, the content of the binder resin is 1% by weight to 60% by weight based on the total weight of solid components in the resin composition , The content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.
The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The standard of weight percentage based on solid content and solid content of each component can be measured by general analytical means used in the art such as liquid chromatography or gas chromatography.
According to one embodiment of the present invention, the resin composition is one or more than one selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, Further comprising an additive.
According to one embodiment of the present invention, 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 photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide; Benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.
As the curing accelerator, curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.
Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.
Specifically, the silicone surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F- TF-1116SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1025SF, TF- , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.
The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.
Specific examples of the antioxidant include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).
As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone may be used. Anything that is commonly used can be used.
Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.
The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.
Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.
The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.
According to one embodiment of the present invention, there is provided a photosensitive material produced using the resin composition.
More specifically, the resin composition of the present invention is applied onto a substrate by a suitable method to form a photosensitive material in the form of a thin film or a pattern.
The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.
Examples of the light source for curing the resin composition according to the present invention include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emits light having a wavelength of 250 nm to 450 nm.
The resin composition according to the present invention can be used as a pigment dispersing type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of an organic light emitting diode or a thin film transistor liquid crystal display (TFT LCD) And can be used for a photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board and a photosensitive material for a plasma display panel (PDP) Is not specifically set.
According to an embodiment of the present invention, there is provided a color filter including the photosensitive material.
The color filter can be produced by using the resin composition containing the color material composition. The resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.
The resin composition according to one embodiment of the present invention can provide a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance, have.
The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the kind thereof is not particularly limited.
The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
According to another embodiment, the color filter may further include an overcoat layer.
Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. 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 reflectivity of chrome, and environmental pollution caused by a chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.
The black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.
A display device including the color filter according to the present invention is provided.
The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD) A liquid crystal display (LCD), and a cathode ray tube (CRT).
Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.
Production Example 1. Preparation of Compound 1
1) Preparation of compound C-1
4.212 g (12.982 mmol) of A-1 was added to 250 ml of CHCl 3 in a 2-neck round bottom flask and stirred. Then 9.048 g (59.01 mmol) of POCl 3 was slowly added dropwise. 2.671 g (11.802 mmol) of the compound B-1 dissolved in a small amount of CHCl 3 was slowly added dropwise and reacted at 65 ° C for 24 hours. Cooled to room temperature, and precipitated in water. After washing three or four times with water, the organic layer was separated, passed through MgSO 4 , and the solvent was removed under reduced pressure. The compound C-1 was separated by column chromatography to obtain 3 g (5.27 mmol), and the yield was 40.5%.
2) Preparation of compound 1
1 g (1.757 mmol) of the compound C-1 was sufficiently dissolved in 20 g of methanol, and 0.756 g (2.635 mmol) of the compound D-1 was dissolved in a small amount of methanol and slowly added dropwise to 250 ml of a 1-neck round bottom flask. The reaction was carried out at room temperature for 4 hours, and the solvent was removed under reduced pressure. Extraction with methylene chloride and washing with water three times or four times. The water was then removed by passing through MgSO 4 and the solvent was removed under reduced pressure. Column chromatography was performed to obtain 1.287 g (1.581 mmol) of Compound 1, and the yield was 90%.
1 H NMR (500 MHz, DMSO, ppm): 8.73-8.72 (dd, ArH, 1H), 7.87-7.85 (d, NH, 1H), 7.58-7.56 (dd, ArH, 1H), 7.39-7.34 ArH, 2H), 7.25 (broad, ArH, 4H), 7.00-6.98 (d, ArH, 1H), 6.93 (broad, ArH, 4H), 3.72-3.63 (m, Cyclohexyl, q, - CH 2 -CH 3, 8H), 2.01-1.99 (m, Cyclohexyl, 2H), 1.76-1.73 (m, Cyclohexyl, 2H), 1.63-1.60 (m, Cyclohexyl, 1H), 1.51-1.15 (m , Cyclohexyl, 5H), 1.18-1.15 ( t, -CH 2 - CH 3, 12H)
Manufacturing example 2. Preparation of Compound 2
1) Preparation of Compound C-2
Under nitrogen injection, 3.51 g (10.76 mmol) of Compound A-1 were placed in 250 ml of 2-neck round bottom flask and stirred in 90 ml of CHCl 3 . POCl 3 (49.05 mmol) was slowly added dropwise. 2.22 g (9.81 mmol) of the compound B-2 was dissolved in a small amount of CHCl 3 and slowly added dropwise. The reaction was allowed to proceed at 65 占 폚 for 24 hours. The reaction was cooled to room temperature and precipitated in water. Additional water and methylene chloride were added to extract, and the organic layer was passed through MgSO 4 to remove water. The solvent was removed under reduced pressure. 1.8 g (3.162 mol) of the compound C-2 was obtained by column chromatography, and the yield was 32.2%.
1 H NMR (500 MHz, DMSO, ppm): 8.56 (s, ArH, 1H), 8.43-8.42 (d, ArH, 1H), 8.36-8.34 , 7.41-7.39 (d, ArH, 1H), 7.30 (b, ArH, 4H), 7.03-7.01 1H), 3.62-3.58 (q, - CH 2 -CH 3, 8H), 2.05-2.03 (d, Cyclohexyl, 2H), 1.83-1.81 (d, Cyclohexyl, 2H), 1.70-1.68 (d, Cycylohexyl, 1H ), 1.51-1.41 (m, Cyclohexyl, 5H), 1.21-1.18 (t, -CH 2 - CH 3, 12H)
2) Preparation of compound 2
0.5 g (0.878 mmol, LGC, 1 eq) of Compound C-2 was thoroughly dissolved in 100 g of methanol, and 0.302 g (1.054 mmol) of Compound D-1 was dissolved in a small amount of methanol and slowly added dropwise to 250 ml of a 1-neck round bottom flask. The reaction was carried out at room temperature for 4 hours, and the solvent was removed under reduced pressure. Extracted with methylene chloride and washed three times with water. The water was then removed by passing through MgSO 4 and the solvent was removed under reduced pressure. 0.7 g (0.86 mmol) of Compound 2 was obtained, and the yield was 97%.
Manufacturing example 3. Preparation of Compound 3
Compound 3 was prepared in the same manner as in Production Example 1, except that Compound A-2 was used instead of Compound A-1 in Production Example 1.
Manufacturing example 4. Preparation of Compound 4
Compound 4 was prepared in the same manner as in Production Example 2, except that Compound A-2 was used instead of Compound A-1 in Production Example 2.
Manufacturing example 5. Preparation of Compound 5
Compound 5 was prepared in the same manner as in Production Example 1, except that Compound A-3 was used instead of Compound A-1 in Production Example 1.
Manufacturing example 6. Preparation of Compound 6
Compound 6 was prepared in the same manner as in Production Example 2, except that Compound A-3 was used instead of Compound A-1 in Production Example 2.
Manufacturing example 7. Preparation of Compound 7
Compound 7 was prepared in the same manner as in Production Example 1, except that Compound A-4 was used instead of Compound A-1 in Production Example 1.
Manufacturing example 8. Preparation of Compound 8
Compound 8 was prepared in the same manner as in Production Example 2, except that Compound A-4 was used instead of Compound A-1 in Production Example 2.
Manufacturing example 9. Preparation of Compound 9
Compound 9 was produced in the same manner as in Production Example 1, except that Compound A-5 was used instead of Compound A-1 in Production Example 1.
Manufacturing example 10. Preparation of Compound 10
Compound 10 was prepared in the same manner as in Production Example 2, except that Compound A-5 was used instead of Compound A-1 in Production Example 2.
Manufacturing example 11. Preparation of compound 11
Compound 11 was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 1.
Manufacturing example 12. Preparation of Compound 12
Compound 12 was prepared in the same manner as in Production Example 1 except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 2.
Manufacturing example 13. Preparation of Compound 13
Compound 13 was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 1.
Manufacturing example 14. Preparation of compound 14
Compound 14 was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 2.
Manufacturing example 15. Preparation of compound 15
Compound (15) was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 1.
Manufacturing example 16. Preparation of Compound 16
Compound (16) was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 2.
Manufacturing example 17. Preparation of Compound 17
Compound 17 was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 1.
Manufacturing example 18. Preparation of Compound 18
Compound 18 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 2.
Manufacturing example 19. Preparation of Compound 19
Compound 19 was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 1.
Manufacturing example 20. Preparation of Compound 20
Compound (20) was prepared in the same manner as in Production Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of bis (trifluoromethylsulfonyl) amide anion in Production Example 2.
Example . Preparation of Photosensitive Resin Composition
A photosensitive resin composition was prepared according to the composition shown in Table 1 below.
Example 1
Example 2
Example 3
Example 4
Example 5
Photoinitiator: I-369 (BASF)
Photopolymerizable compound: DPHA (Japanese explosive)
Additive: DIC F-475
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Comparative Example 1: Comparative Example Compound 
Evaluation example
Substrate fabrication conditions
The photosensitive resin composition was spin-coated on glass (5 x 5 cm) and pre-baked at 100 ° C for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 200 mu m and the entire substrate was irradiated with an exposure dose of 40 mJ / cm < 2 >
The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post baked at 230 캜 for 20 minutes to prepare a substrate.
Light resistance Evaluation condition
Substrates fabricated under the above conditions were placed in a light resistance measuring instrument, Suntest CPS +, and left at 400 mW / m 2 for 6 hours. The transmittance spectrum of the substrate in a visible light range of 380 nm to 780 nm was obtained through a spectroscope (MCPD-Otsuka). The obtained transmittance spectrum and the C light source backlight are used and ΔE is calculated by using the obtained value E (L * , a * , b * ) and shown in Table 1 below.
ΔE (L *, a *, b *) = {(ΔL *) 2 + (Δa *) 2 + (Δb *) 2} 1/2
The smaller value of? E means that the color change is small and the light resistance is excellent.
Table 2 shows the results of measuring the light resistance of the Example and Comparative Example 1. As shown in Table 2, it was confirmed that the color change (DELTA E) in Comparative Example 1 was smaller than that in Example 1. [
Claims (13)
[Chemical Formula 1]
In Formula 1,
Y1 is N or CR15, Y2 is N or CR16, Y3 is N or CR17, Y4 is N or CR18, Y5 is N or CR19, Y6 is N or CR20,
At least one of Y1 to Y6 is N,
R 1 to R 20 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted isoindolidinyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,
Q - is an anionic group.
(2)
(3)
In the general formulas (2) and (3)
The definitions of R 1 to R 20 and Q - are the same as in the above formula (1).
In the compounds 21 to 52, 61, 62, 71, 72, 81, 82, 91, 92, 101, 102, 111 and 112,
X and Y are the same or different and each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms,
Z is hydrogen; A hydroxy group; A nitro group; Or halogen.
Based on the total weight of the solid content in the resin composition
The content of the compound represented by Formula 1 is 5 wt% to 60 wt%
The content of the binder resin is 1 wt% to 60 wt%
The content of the photoinitiator is 0.1 wt% to 20 wt%
And the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020150100555A KR101953174B1 (en) | 2015-07-15 | 2015-07-15 | Compound, colorant composition comprising the same and resin composition comprising the same |
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| KR1020150100555A KR101953174B1 (en) | 2015-07-15 | 2015-07-15 | Compound, colorant composition comprising the same and resin composition comprising the same |
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| Publication Number | Publication Date |
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| KR20170009099A true KR20170009099A (en) | 2017-01-25 |
| KR101953174B1 KR101953174B1 (en) | 2019-02-28 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017122221A (en) * | 2016-01-08 | 2017-07-13 | エルジー・ケム・リミテッド | Compound, color material composition containing the same, and resin composition containing the same |
| KR20200051728A (en) | 2018-08-23 | 2020-05-13 | 무쓰비시 고무 가부시키가이샤 | Balloon for obstructing vent piping of liquefied gas storage tanks and mechanism for obstructing vent piping |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010009058A (en) | 1999-07-07 | 2001-02-05 | 성재갑 | Photosensitive resin composition |
| JP5082284B2 (en) * | 2006-04-24 | 2012-11-28 | コニカミノルタホールディングス株式会社 | Copper chelate dye, coloring composition, colored fine particle dispersion, ink jet ink using them, ink jet recording method, color filter |
| KR20130130976A (en) * | 2012-05-23 | 2013-12-03 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
| KR20150040566A (en) * | 2013-10-07 | 2015-04-15 | 주식회사 엘지화학 | Dye and color filter manufactured by the same |
| KR20150062977A (en) * | 2013-11-29 | 2015-06-08 | 주식회사 엘지화학 | Resin composition, photosensitive material, color filter and display appratus |
-
2015
- 2015-07-15 KR KR1020150100555A patent/KR101953174B1/en active IP Right Grant
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010009058A (en) | 1999-07-07 | 2001-02-05 | 성재갑 | Photosensitive resin composition |
| JP5082284B2 (en) * | 2006-04-24 | 2012-11-28 | コニカミノルタホールディングス株式会社 | Copper chelate dye, coloring composition, colored fine particle dispersion, ink jet ink using them, ink jet recording method, color filter |
| KR20130130976A (en) * | 2012-05-23 | 2013-12-03 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
| KR20150040566A (en) * | 2013-10-07 | 2015-04-15 | 주식회사 엘지화학 | Dye and color filter manufactured by the same |
| KR20150062977A (en) * | 2013-11-29 | 2015-06-08 | 주식회사 엘지화학 | Resin composition, photosensitive material, color filter and display appratus |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017122221A (en) * | 2016-01-08 | 2017-07-13 | エルジー・ケム・リミテッド | Compound, color material composition containing the same, and resin composition containing the same |
| KR20200051728A (en) | 2018-08-23 | 2020-05-13 | 무쓰비시 고무 가부시키가이샤 | Balloon for obstructing vent piping of liquefied gas storage tanks and mechanism for obstructing vent piping |
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| Publication number | Publication date |
|---|---|
| KR101953174B1 (en) | 2019-02-28 |
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