KR101953174B1 - 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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- KR101953174B1 KR101953174B1 KR1020150100555A KR20150100555A KR101953174B1 KR 101953174 B1 KR101953174 B1 KR 101953174B1 KR 1020150100555 A KR1020150100555 A KR 1020150100555A KR 20150100555 A KR20150100555 A KR 20150100555A KR 101953174 B1 KR101953174 B1 KR 101953174B1
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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 specification relates to a novel compound, a color material composition including the same, and a resin composition including the same.
Description
The present specification relates to a novel compound, a color material composition including the same, and a resin composition including the same.
As a light source of a near liquid crystal display (LCD), instead of the conventional CCFL, LEDs or OLED devices that emit light by themselves, not driving or liquid crystal, are used. If LED or OLED is used as a light source, it emits red, green, and blue light by itself, and thus does not require a separate color filter.
However, in general, using the light from the LED or OLED light source, it is not easy to adjust or adjust the required color coordinates. In addition, a method for improving color purity, brightness, and contrast ratio in manufacturing a color filter using a pigment material dispersion method using a color material, especially a pigment, which has already been developed, has reached a limit point.
In order to overcome these problems and satisfy the requirements, the development of new color materials is required.
The present specification provides a novel compound, a colorant composition including the same, and a resin composition including the same.
According to an exemplary embodiment of the present specification, a compound represented by the following formula (1) is provided.
[Formula 1]
In Chemical 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,
R1 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydrogen; heavy hydrogen; halogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted isoindolin ion group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring,
Q − is an anionic group.
According to yet an embodiment of the present disclosure, it provides a color material composition comprising a compound represented by the formula (1).
According to yet an embodiment of the present disclosure, it provides a resin composition comprising the color material composition.
According to one embodiment of the present specification, a photosensitive material manufactured using the above-described resin composition is provided.
According to an exemplary embodiment of the present specification, a color filter including the photosensitive material described above is provided.
In addition, according to one embodiment of the present specification, a display device including the color filter described above is provided.
According to the exemplary embodiment of the present specification, the color material composition including the compound represented by Chemical Formula 1 is excellent in heat resistance and light resistance, and may be used as a coloring material as well as a small amount, and an absorption and transmission spectrum suitable for a desired light source It is possible to obtain higher color reproducibility, higher luminance, higher contrast ratio, and the like.
Hereinafter, the present specification will be described in more detail.
According to an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.
Examples of substituents in the present specification are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; Substituted or unsubstituted isoindolin ion group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
In the present specification,
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
In the present specification, the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
In the present specification, the ester group may be substituted with oxygen of the ester group having a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, 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, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
In the present specification, the amine group is -NH 2 ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
In the present specification, the N-alkylarylamineamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
In the present specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.
In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.
In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. 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 as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.
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 a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.
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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
In the present specification, in the present specification, the heteroaryl group includes one or more atoms other than carbon and hetero atoms, and specifically, the hetero atoms include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. It may include. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.
In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
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 heteroaryl group described above.
In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.
In the present specification, in a substituted or unsubstituted ring in which adjacent groups are formed by bonding to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.
According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently substituted or unsubstituted isoindoleinda ion group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently substituted or unsubstituted isoindoleinda ion group; A substituted or unsubstituted linear or branched 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 an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, each independently represent 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 an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently substituted or unsubstituted isoindoleinda ion group; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted n-propyl group; Substituted or unsubstituted n-butyl group; Or a substituted or unsubstituted phenyl group.
When R1 to R4 are substituted, they may be substituted with a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and hydroxy group, nitro group-substituted or unsubstituted isoindolinate ion group.
According to an exemplary embodiment of the present specification, 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 an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R1 and R2 or R3 and R4 combine with each other to form a substituted or unsubstituted ring. According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted linear or branched 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 an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted linear or branched 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 an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted linear or branched 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 an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, 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 an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; Ethyl group; Cyclohexyl group; Or a phenyl group.
According to an exemplary embodiment of the present specification, R13 is hydrogen.
According to an exemplary embodiment of the present specification, R13 is an ethyl group.
According to an exemplary embodiment of the present specification, R13 is a cyclohexyl group.
According to an exemplary embodiment of the present specification, R13 is a phenyl group.
According to an exemplary embodiment of the present specification, R14 is hydrogen.
According to an exemplary embodiment of the present specification, the R14 is an ethyl group.
According to an exemplary embodiment of the present specification, R14 is a cyclohexyl group.
According to an exemplary embodiment of the present specification, R14 is a phenyl group.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are combined with each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are combined with each other to form a substituted or unsubstituted hetero ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are combined with each other to form a substituted or unsubstituted piperidine ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are combined with each other to form a piperidine ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or R13 and R14 combine with each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, 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 combine with each other to form a substituted or unsubstituted piperidine ring.
According to an exemplary embodiment of the present specification, in the general formula 1, R13 and R14 are the same as or different from each other, and each independently hydrogen; Ethyl group; Cyclohexyl group; Or a phenyl group, or R13 and R14 combine with each other to form a piperidine ring.
According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.
[Formula 2]
[Formula 3]
In Chemical Formulas 2 and 3,
The definitions of R 1 to R 20 and Q − are the same as in the general formula (1).
According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4 to 7.
[Formula 4]
[Formula 5]
[Formula 6]
[Formula 7]
In Chemical Formulas 4 to 7,
The definitions of R 1 to R 20 and Q − are the same as in the general formula (1).
According to an exemplary embodiment of the present specification, Q - is an anionic group, and the anionic group is not particularly limited, for example, US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080, Japanese Patent Laid-Open No. 2006-001917, It is described in Japanese Unexamined Patent Application Publication No. 2005-159926, Japanese Unexamined Patent Publication No. 2007-7028897, Japanese Unexamined Patent Publication No. 2005-071680, Korean Patent Application Publication No. 2007-7000693, Japanese Patent Application No. 2005-111696, and Japanese Patent Application No. 2008-249663. Negative ions can be applied. Specific examples of the anion include trifluoromethanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion and tetra Kis (4-fluorophenyl) borate anion, tetrakis (pentafluorophenyl) borate anion, tristrifluoromethanesulfonylmethion anion, nitrate ion, carbonate ion, sulfite ion, halogen group such as fluorine group, iodine group And chlorine groups.
In addition, Q - is boron; Anions including aluminum; An anion comprising oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus. In particular, Q − may include an anion of tungstophosphoric acid, an anion of tungstosilicate acid, or an anion of tungsten-based isopoly acid.
According to an exemplary embodiment of the present specification, in the general formula 1, Q − is a sulfonimide acid containing a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion comprising oxygen and one or more elements selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus.
According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following compounds 1 to 112.
According to an exemplary embodiment of the present specification, 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 as or different from each other Each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
Z is hydrogen; Hydroxyl group; Nitro group; Or halogen.
According to an exemplary embodiment of the present specification, X and Y are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted n-propyl group; Substituted or unsubstituted isopropyl group or substituted or unsubstituted n-butyl group.
According to an exemplary embodiment of the present specification, X and Y are the same as or different from each other, and each independently a methyl group; Ethyl group; Profile group; Isopropyl group or n-butyl group.
According to an exemplary embodiment of the present specification, Z is hydrogen; Hydroxyl group; Nitro group; Fluorine; Goat; bromine; Or iodine.
The compound represented by Chemical Formula 1 may be prepared by referring to the preparation examples described later.
According to an exemplary embodiment of the present specification, it provides a color material composition comprising a compound represented by the formula (1).
The colorant composition may further include at least one of dyes and pigments in addition to the compound represented by Chemical Formula 1. For example, the colorant composition may include only the compound represented by Chemical Formula 1, but may include the compound represented by Chemical Formula 1 and one or more dyes, or may include the compound represented by Chemical Formula 1 and one or more pigments It may also include a compound represented by the formula (1), at least one dye and at least one pigment.
In one embodiment of the present specification, a resin composition containing the color material composition is provided.
In one embodiment of the present specification, the resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.
The binder resin is not particularly limited as long as it can exhibit physical properties such as strength, developability, and the like of the film made of the resin composition.
The binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; 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, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate , p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1 , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.
Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro It may be selected from the group consisting of styrene, but is not limited thereto.
Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.
Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.
The monomer which imparts the 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, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.
According to an exemplary embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg / g, the weight average molecular weight is 1,000 to 50,000.
The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.
The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking. For example, the photoinitiator is selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. It may be one or more kinds.
The acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, 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-morpholinopropan-1-one, and the like.
As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.
The triazine compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloro Methyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto. .
The oxime compound is 1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGII242), N-1919 (Adecasa), and the like, but are not limited thereto.
The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.
According to an exemplary embodiment of the present specification, based on the total weight of solids in the resin composition, the content of the color material composition is 5% by weight to 60% by weight, the content of the binder resin is 1% by weight to 60% by weight and The content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the multifunctional 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 weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.
According to one embodiment of the present specification, the resin composition is one or more selected from the group consisting of a photocrosslinking agent, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and a leveling agent. Further additives.
According to an exemplary 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 solids in the resin composition.
The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone 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-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.
The curing accelerator is used to increase the curing and mechanical strength, 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), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.
As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.
The surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's 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-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.
The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
Specific examples of the antioxidant include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' Phosphite-based secondary antioxidants such as -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, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.
Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.
The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.
The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.
According to one embodiment of the present specification, a photosensitive material manufactured using the resin composition is provided.
In more detail, the resin composition of this specification is apply | coated on a base material by a suitable method, and forms the photosensitive material of a thin film or a pattern form.
Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.
As a light source for curing the resin composition according to the present specification, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc., which emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.
The resin composition according to the present disclosure may be a pigment dispersion photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, It can be used for photosensitive material for forming overcoat layer, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed circuit board, photosensitive material for plasma display panel (PDP), and the like. There is no special place.
According to an exemplary embodiment of the present specification, a color filter including the photosensitive material is provided.
The color filter may be manufactured using a resin composition including the color material composition. The resin composition may be applied onto a substrate to form a coating film, and the color filter may be formed by exposing, developing, and curing the coating film.
The resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having a high color reproducibility and a high luminance and contrast ratio by the curing process during the manufacture of the color filter. 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 type 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 exemplary embodiment, the color filter may further include an overcoat layer.
A black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by 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 specification may use black pigment or black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.
Provided is a display device including a color filter according to the present specification.
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 thin film transistor. The liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
Hereinafter, the present specification will be described in detail with reference to Examples. The following examples are provided to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims, their substitutions and changes, and is not limited to the examples.
Preparation Example 1 Preparation of Compound 1
1) Preparation of Compound C-1
To 250 ml of a 2-neck round bottom flask, 4.212 g (12.982 mmol) of A-1 was added to 60 ml of CHCl 3 and stirred. Then 9.048 g (59.01 mmol) of POCl 3 was slowly added dropwise. 2.671 g (11.802 mmol) of Compound B-1 dissolved in a small amount of CHCl 3 were slowly added dropwise and reacted at 65 ° C. for 24 hours. Cool to room temperature and precipitate in water. After washing with water three or four times, the organic layer was separated, passed through MgSO 4 , and the solvent was removed under reduced pressure. 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
In 250 ml of a 1-neck round bottom flask, 1 g (1.757 mmol) of Compound C-1 was sufficiently dissolved in 20 g of methanol, and 0.756 g (2.635 mmol) of Compound D-1 was dissolved in a small amount of methanol and slowly added dropwise thereto. The reaction was carried out at room temperature for 4 hours, and the solvent was removed under reduced pressure. The mixture was extracted with methylene chloride and washed with water three or four times. Thereafter, water was removed through MgSO 4 to remove the solvent under reduced pressure. 1.287 g (1.581 mmol) of Compound 1 were obtained by column chromatography, 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 (m , 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, 1H), 3.57-3.53 ( 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)
Production 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 was added to 90 ml of CHCl 3 , and stirred in 250 ml of a 2-neck round bottom flask. POCl 3 7.52 g (49.05 mmol) was slowly added dropwise. 2.22 g (9.81 mmol) of Compound B-2 were dissolved in a small amount of CHCl 3 and slowly added dropwise. It was made to react at 65 degreeC for 24 hours. The reaction was cooled to room temperature and precipitated in water. Water and methylene chloride were further added and extracted, and the organic layer was passed through MgSO 4 to remove moisture. The solvent was removed under reduced pressure. Compound C-2 1.8g (3.162mol) was obtained through 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 (d, ArH, 1H), 7.70-7.68 (d, NH , 1H), 7.41-7.39 (d, ArH, 1H), 7.30 (b, ArH, 4H), 7.03-7.01 (d, ArH, 1H), 6.99 (b, ArH, 4H), 3.70 (b, Cyclohexyl, 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 sufficiently dissolved in 100 g of methanol in 250 ml of a 1-neck round bottom flask, and 0.302 g (1.054 mmol) of a small amount of Compound D-1 was slowly added dropwise thereto. 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 or four times. Thereafter, water was removed through MgSO 4 to remove the solvent under reduced pressure. 0.7 g (0.86 mmol) of compound 2 were obtained and the yield was 97%.
Production Example 3. Preparation of Compound 3
Compound 3 was prepared in the same manner as in Preparation Example 1, except that Compound A-2 was used instead of Compound A-1 in Preparation Example 1.
Production Example 4. Preparation of Compound 4
Compound 4 was prepared in the same manner as in Preparation Example 2, except that Compound A-2 was used instead of Compound A-1 in Preparation Example 2.
Production Example 5. Preparation of Compound 5
Compound 5 was prepared in the same manner as in Preparation Example 1, except that Compound A-3 was used instead of Compound A-1 in Preparation Example 1.
Production Example 6. Preparation of Compound 6
Compound 6 was prepared in the same manner as in Preparation Example 2, except that Compound A-3 was used instead of Compound A-1 in Preparation Example 2.
Production Example 7. Preparation of Compound 7
Compound 7 was prepared in the same manner as in Preparation Example 1, except that Compound A-4 was used instead of Compound A-1 in Preparation Example 1.
Production Example 8. Preparation of Compound 8
Compound 8 was prepared in the same manner as in Preparation Example 2, except that Compound A-4 was used instead of Compound A-1 in Preparation Example 2.
Production Example 9. Preparation of Compound 9
Compound 9 was prepared in the same manner as in Preparation Example 1, except that Compound A-5 was used instead of Compound A-1 in Preparation Example 1.
Production Example 10. Preparation of Compound 10
Compound 10 was prepared in the same manner as in Preparation Example 2, except that Compound A-5 was used instead of Compound A-1 in Preparation Example 2.
Production Example 11. Preparation of Compound 11
Compound 11 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 1.
Production Example 12. Preparation of Compound 12
Compound 12 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 2.
Production Example 13. Preparation of Compound 13
Compound 13 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 1.
Production Example 14. Preparation of Compound 14
Compound 14 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 2.
Production Example 15. Preparation of Compound 15
Compound 15 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 1.
Production Example 16. Preparation of Compound 16
Compound 16 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 2.
Production Example 17. Preparation of Compound 17
Compound 17 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 1.
Production 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 the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 2.
Production Example 19. Preparation of Compound 19
Compound 19 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 1.
Production Example 20. Preparation of Compound 20
Compound 20 was prepared in the same manner as in Preparation Example 1, except that tetrakis (pentafluorophenyl) borate anion was used instead of the bis (trifluoromethylsulfonyl) amide anion in Preparation Example 2.
Example . Preparation of Photosensitive Resin Composition
The photosensitive resin composition was prepared as shown in Table 1 below.
Example 1
Example 2
Example 3
Example 4
Example 5
Photoinitiator: I-369 (BASF)
Photopolymerizable Compound: DPHA
Additive: DIC F-475
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Comparative Example 1: Comparative Compound
Evaluation example
Board Fabrication Conditions
The photosensitive resin composition was spincoated on glass (5 × 5 cm) and subjected to prebake 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 µm, and the exposure amount of 40 mJ / cm 2 was irradiated on the entire surface of the substrate using an exposure machine.
The exposed substrate was developed for 60 seconds in a developing solution (KOH, 0.05%), and subjected to postbake at 230 ° C. for 20 minutes to prepare a substrate.
Light resistance Evaluation condition
The substrate manufactured under the above conditions was placed in the Suntest CPS +, a light resistance measuring instrument, and left at 400 mW / m 2 for 6 hours. The transmittance spectrum of the visible region in the range of 380 nm to 780 nm was obtained through the spectrometer (MCPD-Otsuka Co., Ltd.). Using the obtained transmittance spectrum and C light source backlight, ΔE was calculated using the obtained values E (L * , a * , b * ) and shown in Table 1 below.
ΔE (L * , a * , b * ) = {(ΔL * ) 2 + (Δa * ) 2 + (Δb * ) 2 } 1/2
The small value of ΔE means that the color change is small and the light resistance is excellent.
Table 2 shows the light resistance measurement results of Example and Comparative Example 1. As shown in Table 2, it was confirmed that the color change (ΔE) is smaller in Comparative Example 1 than in Example 1.
Claims (13)
[Formula 1]
In Chemical 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,
R1 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydrogen; heavy hydrogen; halogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted isoindolin ion group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring,
Q − is an anionic group.
[Formula 2]
[Formula 3]
In Chemical Formulas 2 and 3,
The definitions of R1 to R20 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 as or different from each other, each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
Z is hydrogen; Hydroxyl group; Nitro group; Or halogen.
Based on the total weight of solids in the resin composition
The content of the compound represented by Formula 1 is 5% by weight to 60% by weight,
The binder resin content is 1% by weight to 60% by weight,
The content of the photoinitiator is 0.1% by weight to 20% by weight,
The content of the multifunctional monomer is a resin composition of 0.1% by weight to 50% by weight.
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| KR101629066B1 (en) * | 2013-10-07 | 2016-06-09 | 주식회사 엘지화학 | Dye and color filter manufactured by the same |
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