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WO2019045364A2 - Composé colorant et composition colorante le comprenant - Google Patents

Composé colorant et composition colorante le comprenant Download PDF

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Publication number
WO2019045364A2
WO2019045364A2 PCT/KR2018/009748 KR2018009748W WO2019045364A2 WO 2019045364 A2 WO2019045364 A2 WO 2019045364A2 KR 2018009748 W KR2018009748 W KR 2018009748W WO 2019045364 A2 WO2019045364 A2 WO 2019045364A2
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WIPO (PCT)
Prior art keywords
group
compound
carbon atoms
pigment
colorant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2018/009748
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English (en)
Korean (ko)
Other versions
WO2019045364A3 (fr
Inventor
박종호
최상아
양승진
이다미
박상균
김재준
이재용
이수연
정지혜
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LG Chem Ltd
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LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180098142A external-priority patent/KR102131993B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201880021164.9A priority Critical patent/CN110494502B/zh
Priority to JP2019548924A priority patent/JP6903854B2/ja
Publication of WO2019045364A2 publication Critical patent/WO2019045364A2/fr
Publication of WO2019045364A3 publication Critical patent/WO2019045364A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/04—Isoindoline dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to colorant compounds and to coloring compositions comprising them. More particularly, the present invention relates to a colorant compound having a novel structure showing excellent color characteristics, heat resistance and solubility, and a coloring composition comprising the same. BACKGROUND ART [0002]
  • a color filter used for a liquid crystal display (LCD) and an organic light emitting diode (OLED) is used for realizing a color image in a display device.
  • the color filter is coated on a basic substrate using various methods, Can be manufactured through the process of making.
  • the color filter is formed by a red, green, and blue pixel portions on a transparent substrate such as a glass.
  • Color filters used in an image display apparatus and a solid-state image pickup device are typically red (R), green And a blue (B) coloring pattern, and serves to color the passing light or to divide the light into three primary colors.
  • the dyes displaying red, green and blue are composed of fine particles, that is, dyes or pigments. These dyes are used for obtaining color display characteristics of a desired area, To display red, green, and blue.
  • Materials commonly used as coloring matters are required to have desirable absorption characteristics on the color reproducibility, light resistance under the conditions used, heat resistance, resistance to oxidizing gases such as ozone, and the like.
  • Patent Document 0001 Korean Patent Publication No. 10-2014-01252183 [Description of the Invention]
  • the present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide a colorant compound having a novel structure which is excellent in color reproducibility, color characteristics, heat resistance and solubility and can be used as a colorant for a color filter and a colorant composition containing the same do.
  • an embodiment of the present invention provides a colorant compound represented by the following general formula (1).
  • Each of R x to 3 ⁇ 4 is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, an N-alkylene-piperidine having at least one aromatic ring having 6 to 20 carbon atoms bonded thereto A piperidinedione or a N-alkylene-pyrrolidinedione;
  • Each of R 7 to R 10 is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms group or an alkoxy group having 1 to 30 carbon atoms;
  • Rn to O each represent hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, Or an alkoxy group having 1 to 30 carbon atoms,
  • At least one of R 7 to O is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 30 carbon atoms to be.
  • a coloring composition comprising the colorant compound.
  • a color filter comprising the coloring composition.
  • a display device including the color filter is provided.
  • the colorant compound of the present invention is a compound of a novel structure which is not known in the prior art and contains a specific group and can exhibit stable color reproducibility and excellent heat resistance and solubility.
  • the solubility of the pigment derivative and the dispersant in the solvent is excellent compared to the conventional art, the amount of the pigment derivative and the dispersant can be reduced when the pigment dispersion method is used.
  • the color filter according to the present invention can provide a high-resolution color filter having high color reproduction rate and high brightness and contrast ratio due to excellent color reproducibility and heat resistance.
  • colorant compound of the present invention and the coloring composition containing the colorant compound will be described in more detail.
  • the colorant compound according to one embodiment of the present invention is represented by the following formula (1). [Chemical Formula 1]
  • R 1 to R 5 are independently selected from the group consisting of hydrogen halide, an aliphatic group having 1 to 10 carbon atoms, an N-alkylene-piperidine dione having at least one aromatic ring having 6 to 20 carbon atoms bonded thereto, Pyrrolidinedione; < / RTI >
  • Each of R 7 to R 10 is independently selected from the group consisting of hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms group) or an alkoxy group having 1 to 30 carbon atoms;
  • Rn to O each represent hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, Or an alkoxy group having 1 to 30 carbon atoms,
  • At least one of R 7 to O is a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 30 carbon atoms.
  • Quot means a bond connected to another substituent.
  • a colorant compound according to another embodiment of the present invention is a colorant compound of the above formula (1), wherein R 2 > and R 5 are each hydrogen or halogen;
  • the above-mentioned group may be a functional group of the following formula (4) or a functional group of the following formula (5).
  • R 21 , R 22 and 3 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C1 to C20 hydroxyalkyl group, a substituted or unsubstituted C6 to C30 aryl group; The substituted or unsubstituted carbon number An arylalkyl group having 7 to 30 carbon atoms; A substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms; Wherein n, r, and n 2 may be an integer, 0 ⁇ ⁇ ⁇ 4, 0 ⁇ ⁇ 3, 0 ⁇ n 2 ⁇ 3.
  • n, n1 and n2 are to be interpreted to mean the number of functional groups substituted for the corresponding benzene rings.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O
  • the substituent group in which at least two of the substituents are bonded 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.
  • the alkyl group may be a straight chain or branched chain alkyl group having 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, n-butyl, n-butyl, 1-methylpentyl, N-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, Propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.
  • 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 thereof include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-octoxy, isobutoxy, tert- , Isopentyloxy, n-propyloxy, 3,3-dimethylbutyloxy, n-octyloxy, n-nonyloxy, n- Benzyloxy, p-methylbenzyloxy, and the like, but are not limited thereto.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group having 6 to 30 carbon atoms, or 6 to 20 carbon atoms, or 6 to 12 carbon atoms.
  • Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.
  • Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • the aryl group in the arylalkyl group and the alkylaryl group is the same as the aforementioned aryl group.
  • the alkyl group in the arylalkyl group and the alkylaryl group is the same as the alkyl group described above.
  • the colorant compound according to another embodiment of the present invention is a colorant compound of Formula 1 wherein at least one of R 7 to R 10 is a cyclic or straight chain alkyl thio group having 1 to 30 carbon atoms, An aryl thio group having 1 to 30 carbon atoms, and each of R u to R 20 is hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms.
  • the colorant compound according to another embodiment of the present invention is the colorant compound of Formula 1, wherein R 7 to R 10 are each hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, and at least one of Ru to R 14 , Or at least one of R 15 to O may be a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms or an aryl thio group having 1 to 30 carbon atoms.
  • At least one of R 7 to 3 ⁇ 4 0 represents a cyclic or straight-chain alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms Or an alkoxy group having 1 to 30 carbon atoms, and more specifically, a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms.
  • the valencies R 7 to R 20 may be a ring or a straight-chain alkyl thio group having 3 to 6 carbon atoms, Butylthio group.
  • the colorant compound of the formula (1) is a compound having at least one ring or straight-chain alkyl thio group having 1 to 30 carbon atoms in a specific position of a quinophthalone derivative compound, an alkyl thio group having 1 to 30 carbon atoms An aryl thio group or an alkoxy group having 1 to 30 carbon atoms, and more specifically a ring or straight-chain alkyl thio group having 1 to 30 carbon atoms, or And an aryl thio group having 1 to 30 carbon atoms may be substituted.
  • the colorant compound of formula (1) by introducing one or more alkylthio groups into the colorant compound of formula (1) as described above, it is possible to reduce the planarity of molecules and reduce the ⁇ - ⁇ interaction between molecules. As a result, the solubility of the colorant compound in the organic solvent may be increased as the molecules are easily solitated in the organic solvent.
  • the solubility of the colorant compound in an organic solvent for example, DMF
  • the amount of the pigment derivative and dispersant required when the coloring composition containing the colorant composition is prepared by the pigment dispersion method is remarkably reduced. Therefore, it is possible to increase the colorant compound or the pigment content in the coloring composition by the above ratio, thereby facilitating the production of the thin film color filter.
  • Specific examples of the above-described colorant compound include the compounds represented by the following formulas (6) to (47), but the present invention is not limited thereto.
  • the method of synthesizing the colorant compound of the above formula (1) can be widely used without any limitations.
  • the colorant compound of Formula 1 can be prepared by first introducing phthalimide (1) 111: 131 ⁇ 1 (16) or 1,8-naphthalimide into Pigment Yellow It is also possible to prepare an alkylthiol, for example 1-butanthiol, by reacting with it.
  • phthalimide (1) 111: 131 ⁇ 1 (16) or 1,8-naphthalimide into Pigment Yellow
  • an alkylthiol for example 1-butanthiol
  • a coloring composition comprising the colorant compound.
  • the coloring composition may further include at least one of a dye (Dye) and a pigment (Pigment), wherein the dye and the pigment may be any one selected from yellow, red and green May be one containing at least one compound which exhibits color.
  • a dye Dye
  • a pigment Pigment
  • the yellow-emitting compound may be a metal-complex compound, an azo compound, a quinophthalone compound, An isoindoline-based compound, a styryl-based compound, and the like.
  • the red-emitting compound may be a metal-complex compound, an azo compound, a xanthene compound, diketopyrrolopyrrole ) Type compound, anthraquinone (⟨ 1 ⁇ 301110101) type compound, and perylene type compound.
  • a compound of the present invention may include one or more compounds selected from the group including compounds.
  • the pigment includes a yellow pigment group including PY129, PY138, PY139, PY150, and PY185; PR 48, PR 48: 1, PR 48: 2, A red pigment group including PR 48: 3, PR 48: 4, PR 177, PR 179, PR 207, PR 254, PR 255, PR 264 and PR 269; And green pigment groups including PG 7, PG 36, PG 58, and PG 59; And the like.
  • the coloring composition according to one embodiment of the present invention may further contain, in addition to the colorant compound, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.
  • the colorant compound may be contained in the colorant composition in an amount of 20 parts by weight or more, specifically 25 parts by weight or more, based on 100 parts by weight of the colorant composition , 50 parts by weight or less, specifically, 40 parts by weight or less.
  • the content of the colorant compound is less than the above range, it is difficult to realize a deep color. If the content of the colorant compound exceeds the above range, the curing reaction of the resin composition may not be performed properly.
  • 100 parts by weight of the coloring composition may be 100 parts by weight of the total of the colorant compound, the binder resin, the polyfunctional monomer and the photoinitiator contained in the coloring composition.
  • Sol id contents may be 100 parts by weight of the total of the colorant compound, the binder resin, the polyfunctional monomer and the photoinitiator contained in the coloring composition.
  • the coloring composition according to one embodiment of the present invention may be used alone or in a mixture of two or more kinds thereof.
  • the coloring composition according to one embodiment of the present invention may optionally include other known coloring agents in addition to the coloring agent compound of the above-mentioned formula (1).
  • the binder resin is not particularly limited, and the binder resin Those generally used in the technical field can be used, and resins which are preferably alkali-soluble can be used.
  • a (meth) acrylic resin, an acrylamide resin, a novolac resin, or the like can be used as the alkali-soluble resin, and preferably has a weight average molecular weight (Mw) of 3,000 to 150,000 g / But the present invention is not limited thereto. On the other hand, the weight average molecular weight is measured by GPC X Geel Permeation Chromatography using polystyrene as a standard material.
  • the binder resin may be contained in the coloring composition in an amount of 3 parts by weight or more, specifically 5 parts by weight or more, more specifically 10 parts by weight or more, and 30 parts by weight or less with respect to 100 parts by weight of the coloring composition , Specifically 20 parts by weight or less, more specifically 15 parts by weight or less.
  • the multifunctional monomer is not particularly limited and those generally used in the technical field to which the present invention belongs can be used.
  • the multifunctional monomer is a monomer having a role of forming a photoresist image by light, and specifically includes propylene glycol Methacrylate, dipentaerythritol triacrylate, dipentaerythritol triacrylate, neopentyl glycol diacrylate, 6-nucleic acid diacrylate, 1,6-nucleic acid diol acrylate tetraethylene glycol methacrylate , Bisphenoxy ethyl alcohol diacrylate, trishydroxy ethyl isocyanurate trimethacrylate, trimethyl propane trimethacrylate, diphenyl pentaerythritol triacrylate, pentaerythritol trimethacrylate , Pentaerythritol tetramethacrylate and dipenta And erythrides may be one or more species selected from the group consisting of nuclear methacrylates.
  • the multifunctional monomer may be contained in the coloring composition in an amount of 30 parts by weight or more, specifically 40 parts by weight or more, more specifically 50 parts by weight or more, and 80 parts by weight or less, Specifically not more than 70 parts by weight, more specifically not more than 60 parts by weight.
  • the photoinitiator may be selected from the group consisting of 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-methoxystyryl) , 4-trichloromethyl- (phenylon) 6-triazine, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2- hydroxy) propyl ketone, benzophenone, 2,4,6-trimethylaminobenzophenone, and the like can be used, but the present invention is not limited thereto.
  • the photopolymerization initiator may be contained in the coloring composition in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the coloring composition.
  • the coloring composition according to one embodiment of the present invention may further include a solvent for improving the applicability and workability.
  • the solvent may include methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene Diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxypropanol, 2-mexyl propanol, 3-methoxybutane, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate , Propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, or dipropylene glycol monomethyl ether
  • One or more compounds may be used, but are not limited thereto.
  • the content of the solvent is not particularly limited as it is adjustable in consideration of coating properties and workability.
  • the solvent may be contained in an amount of 50 to 500 parts by weight based on 100 parts by weight of the coloring composition.
  • the coloring composition may further comprise, in addition to the components described above, a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, an ultraviolet absorber, a leveling agent, a photosensitizer, a plasticizer, And an additive that can be included in the conventional coloring composition for a color filter such as a surfactant.
  • curing accelerator examples include 2-mercaptobenzoimidazole, 2- Mercapto benzothiazole, 2-mercaptobenzooxazole, 2,5-dimer, and 3-mercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, (Mercapto propionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate) Trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), and trimethylolethane tris And the like.
  • the present invention is not limited thereto, and may include those generally known in the art to which the present invention belongs.
  • the coloring composition according to one embodiment of the present invention can be used for producing a color filter by a method generally known in the technical field of the present invention, for example, a printing method or a photolithography method.
  • the colored composition is applied onto a transparent substrate by a method such as spray coating, spin coating, slit coating, roll coating, or dipping.
  • An exposure process is selectively performed on the coating film through a mask having a predetermined pattern. Meanwhile, the pre-exposure baking and / or post-baking may be further performed.
  • the coloring composition is developed to form the desired photoresist pattern.
  • the developed substrate is washed and dried to obtain a color filter in which a desired type of photoresist pattern is formed.
  • the obtained color filter can be utilized in a display device or the like.
  • the colorant compound of the present invention is a compound of a novel structure which is not known in the prior art and contains a specific group, and can exhibit stable color reproducibility and excellent heat resistance and solubility.
  • the solubility of the pigment derivative and the dispersant in the solvent is excellent compared to the conventional art, the amount of the pigment derivative and the dispersant can be reduced when the pigment dispersion method is used.
  • the color filter according to the present invention can provide a high-resolution color filter having high color reproduction rate and high brightness and contrast ratio due to excellent color reproducibility and heat resistance. Further, due to the excellent solubility of the novel colorant compound, It becomes possible to increase the pigment content in the composition, thereby making it possible to manufacture a thin film color filter.
  • Compound A was obtained by the method described in U.S. Patent No. 6,849,116 B2. Specifically, 25.5 g of phthalimide and 7.4 g of paraformaldehyde were stirred and added to 560 g of fuming sulfuric acid at 3.6% by weight at 25 ° C. The mixture was heated to 50 ° C and stirred for 30 minutes.
  • Compound (B) Compound 2
  • Compound B was obtained in the same manner as in Production Example 1 except that 1, 8-naphthalimide was used instead of phthalimide according to the method described in U.S. Patent No. 6,849,116 B2.
  • Compound (C) Compound (D) Compound 3
  • Compound C was obtained according to the synthesis method described in Korean Laid-Open Patent Publication No. 2013-0137028, and Compound D was obtained by the method described in US Pat. No. 6,849,116 B2.
  • Compound (C) Compound (E) Compound 4
  • Compound C was obtained according to the synthesis method described in Korean Laid-Open Patent Publication No. 2013-0137028, and the compound described in US Pat. No. 6,849,116 B2 was used instead of phthalimide. 8-naphthalimide was used to obtain the compound E. ⁇
  • Compound (F) Compound (G) Compound F was used instead of PY138 in Preparation Example 1, and Compound 5 was synthesized using Compound G instead of Compound A.
  • Compound H (N) Compound g (O) Compound 9
  • Compound 0 was synthesized by using Compound N instead of PY138 in Preparation Example 1 above. Then, the compound (0) 2.231 (3.68 glu01) and 0.814 g (1-thiophenol) (7.36 g K2C032.03 14.72 g01) were added to 500 ml 1-neck RBF and stirred at 60 ° C for 24 hours . The solution was cooled to room temperature,
  • Compound 10 was synthesized by using cyclopentyl thiol instead of thiophenol in Synthesis Example 9 to prepare Compound 10. As a result of APCI negat ive MS analysis, the molecular weight 722 of Compound 10 was confirmed.
  • Pigment Yellow 138 used as a coloring material in the photosensitive resin composition was prepared.
  • Example 2 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 2 synthesized according to Preparation Example 2 was used.
  • Example 3 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 2 synthesized according to Preparation Example 2 was used.
  • Example 3 A photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 2 synthesized according to Preparation Example 2 was used.
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 3 synthesized in accordance with Preparation Example 3 was used.
  • Example 4
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 4 synthesized in accordance with the preparation example 4 was used.
  • Example 5
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 5 synthesized in accordance with Preparation Example 5 was used.
  • Example 6
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 6 synthesized in accordance with Preparation Example 6 was used.
  • Example 7
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 7 synthesized in accordance with Preparation Example 7 was used.
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 8 synthesized in accordance with the preparation of Example 8 was used.
  • Example 9
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 9 synthesized in accordance with the ninth preparation was used.
  • Example 10 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 9 synthesized in accordance with the ninth preparation was used.
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 10 synthesized according to Preparation Example 10 was used.
  • Example 11
  • a photosensitive resin composition was prepared in the same manner as in Example 1 except that Compound 11 synthesized according to Preparation Example 11 was used. Comparative Example 1
  • a photosensitive resin composition was prepared in the same manner as in Example 1, except that the above-prepared compound was used. Board Fabrication
  • the photosensitive resin compositions according to Examples 1 to 11 and Comparative Example 1 were used for the substrate production, respectively. Specifically, the photosensitive resin compositions according to the Examples and Comparative Examples were spin-coated on glass (5 x 5 cm) and pre-baked at 100 ° C for 100 seconds to form a film.
  • the substrate prepared according to the above-described substrate-aiding method was used to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm using a spectroscope (MCPD-Otsuka). Also, the prebake substrate was further postbaked at 230 ° C for 20 minutes, and the transmittance spectrum was obtained in the same equipment and measurement range.
  • the color change (hereinafter referred to as A Eab) was calculated using the obtained transmittance spectrum and the C light source backlight using the obtained value E (L *, a *, b *) and shown in Table 2 below. Specifically, the equation for calculating the AEab is as follows.
  • the colorant compound of Comparative Example 1 is a commercial material whose color change (AEab) is as small as 0.29.
  • the respective coloring agent compounds applied to Examples 1 to 11 were also excellent in color heat resistance so that the color change (AEab) was smaller than 3 and could reach a similar level to that of the coloring agent compound of Comparative Example 1, It is confirmed that it can be used as a pigment.
  • Experiment 3 Contrast evaluation
  • the photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 were prepared by coinciding with the constituent components and composition ratios (unit: g) shown in Table 3 below. Using the photosensitive resin composition thus prepared, a substrate was prepared according to the above-described substrate manufacturing method.
  • Contrast ratio (CR) Brightness when the polarizer is parallel to the top and bottom of the substrate / Brightness when the top and bottom polarizers of the substrate are orthogonal Number
  • the results are shown in Table 1 below.
  • F-475 as a photopolymerizable compound
  • DPHA Japanese explosive
  • PGMEA polypropylene glycol monomethyl ether acetate
  • the contrast ratios of the substrates made of the photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 are shown in Table 4 below.
  • the substrate using the photosensitive resin composition according to Examples 12 to 22 of the present invention is a substrate using a photosensitive resin composition containing a pigment (PY 138) having a low solubility in an organic solvent 2) Contrast ratio was improved by reducing light scattering.

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Abstract

La présente invention concerne un colorant et une composition colorante le comprenant. Plus spécifiquement, la présente invention concerne une nouvelle structure de colorant qui présente d'excellentes caractéristiques de couleur, de résistance à la chaleur et de solubilité, et peut donc être utilisée pour fabriquer des filtres colorés, ainsi qu'une composition colorante la comprenant.
PCT/KR2018/009748 2017-09-04 2018-08-23 Composé colorant et composition colorante le comprenant Ceased WO2019045364A2 (fr)

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CN201880021164.9A CN110494502B (zh) 2017-09-04 2018-08-23 着色剂化合物和包含其的着色组合物
JP2019548924A JP6903854B2 (ja) 2017-09-04 2018-08-23 着色剤化合物およびこれを含む着色組成物

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KR101988047B1 (ko) * 2012-09-17 2019-06-11 엘지디스플레이 주식회사 Ｌｃｄ용 고투과 녹색 염료 및 그 제조 방법
KR101711922B1 (ko) * 2014-04-04 2017-03-03 제일모직 주식회사 신규한 화합물, 상기 화합물을 포함하는 감광성 수지 조성물, 및 컬러 필터
KR101711921B1 (ko) * 2014-09-30 2017-03-03 삼성에스디아이 주식회사 감광성 수지 조성물 및 이를 이용한 컬러필터

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