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WO2019151807A1 - Composition de résine photosensible colorée, et dispositif de couleur et appareil d'affichage qui sont fabriqués à l'aide de celle-ci - Google Patents

Composition de résine photosensible colorée, et dispositif de couleur et appareil d'affichage qui sont fabriqués à l'aide de celle-ci Download PDF

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Publication number
WO2019151807A1
WO2019151807A1 PCT/KR2019/001385 KR2019001385W WO2019151807A1 WO 2019151807 A1 WO2019151807 A1 WO 2019151807A1 KR 2019001385 W KR2019001385 W KR 2019001385W WO 2019151807 A1 WO2019151807 A1 WO 2019151807A1
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WO
WIPO (PCT)
Prior art keywords
resin composition
photosensitive resin
contact angle
coloring
colored photosensitive
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/KR2019/001385
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English (en)
Korean (ko)
Inventor
김훈식
박슬기
이재을
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
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Filing date
Publication date
Application filed by Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Priority to JP2020534451A priority Critical patent/JP2021508087A/ja
Priority to CN201980011830.5A priority patent/CN111684357B/zh
Publication of WO2019151807A1 publication Critical patent/WO2019151807A1/fr
Anticipated expiration legal-status Critical
Priority to JP2022076613A priority patent/JP7541545B2/ja
Ceased legal-status Critical Current

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Classifications

    • 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
    • G03F7/0005—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
    • 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
    • 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
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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 a colored photosensitive resin composition, a color device manufactured using the same, and a display device.
  • Color devices are widely used in various display devices such as imaging devices and liquid crystal display devices (LCDs), and their application ranges are expanding.
  • Color elements are manufactured by dyeing, printing, pigment dispersion, electrodeposition, and the like, and in recent years, a cost reduction process using an inkjet method has been proposed in accordance with the enlargement of the display material substrate.
  • the partitions constituting the black matrix are previously formed by photolithography, and red, green, and blue inks are sprayed and applied to the openings surrounded by the partitions by an inkjet method to form pixels. Formed. This is the same also in the case of the quantum dot display device that is being studied recently.
  • the hole transport material and the light emitting material solution are sprayed and apply
  • the display can be classified into two types.
  • a light source exists at the rear side like a liquid crystal display (LCD) and a color is displayed through a filter or a light conversion layer, and light is generated by applying electricity such as an organic light emitting diode (OLED).
  • OLED organic light emitting diode
  • the light conversion layer may also serve as a light conversion layer and may generate light by applying electrical energy.
  • the inkjet method is the most typical method. Since the inkjet method uses the material only for desired pixels, it is possible to suppress unnecessary waste of material.
  • a partition requires the property which repels water, an organic solvent, etc. which are discharge liquids of an inkjet, what is called liquid repellency.
  • the side surface portion or the base portion of the partition wall is required to have wetness property, so-called lyophilic property, with respect to the discharge liquid.
  • Korean Patent Laid-Open Publication No. 10-2013-0132655 discloses a photosensitive resin composition, a photosensitive element using the same, a method of forming a partition of an image display apparatus, and a method of manufacturing an image display apparatus, but requirements still required for pixel implementation are not satisfied. I can't do it.
  • Republic of Korea Patent No. 10-1420470 is limited to the contact angle of propylene glycol methyl ether acetate (PGMEA) of more than 20 ° contact angle of water with a compound of a specific chemical structure in the manufacture of partitions having excellent light shielding and liquid repellency Doing.
  • PMEA propylene glycol methyl ether acetate
  • the partition wall manufactured according to the above invention falls within the range of Comparative Examples 3 to 7 of the present invention and shows a result of inferior inkjet characteristics.
  • An object of this invention is to provide the coloring photosensitive resin composition which is excellent in liquid repellency and can implement the partition which is excellent in the light-shielding property to light other than blue.
  • an object of this invention is to provide the coloring photosensitive resin composition which can form the pixel which a surface defect does not produce.
  • an object of this invention is to provide the color element and display apparatus which were manufactured using the coloring photosensitive resin composition mentioned above.
  • the contact angle with respect to the water of the coating film prepared after the photocuring and development is 100 ° to 160 °
  • the contact angle with respect to propylene glycol methyl ether acetate (PGMEA) is 40 ° to 70 °
  • the present invention also provides a color device manufactured using the above-mentioned colored photosensitive resin composition.
  • the present invention provides a display device including the color element.
  • the contact angle with respect to water and the contact angle with respect to propylene glycol methyl ether acetate (PGMEA) on the surface of the coating film after development respectively exhibit a specific range, and the relationship between each contact angle
  • PMEA propylene glycol methyl ether acetate
  • the coloring photosensitive resin composition of this invention can form the pixel which a surface defect does not produce.
  • the above-mentioned colored photosensitive resin composition can be usefully used for the production of color elements and display devices.
  • 1 to 3 are photographs showing pixel formation measurement results.
  • the contact angle with respect to water on the surface of the coating film prepared after the photocuring and development is 100 ° to 160 °
  • the contact angle with respect to propylene glycol methyl ether acetate (PGMEA) is 40 ° to 70 °
  • Contact angle: Contact angle with respect to propylene glycol methyl ether acetate (PGMEA) 1: 0.4-0.6 It relates to the colored photosensitive resin composition, the color element manufactured by the said composition, and a display apparatus.
  • the coloring photosensitive resin composition which concerns on this invention apply
  • the contact angle is an angle formed between the solid surface and the tangent to the liquid surface at the point of contact between the solid and the liquid, and is defined as the angle of the side containing the liquid.
  • the contact angle with respect to water (DIW, Deionized Water) is less than 100 ⁇ under the above conditions, water may be adsorbed on the partition by the inkjet method, and thus, the inkjet process may not be performed. If it exceeds 160 ⁇ , the hydrophobicity may increase. This may cause a problem of ink rolling on the partition wall.
  • PMEA propylene glycol methyl ether acetate
  • the coloring photosensitive resin composition of this invention which has the above-mentioned characteristic can contain (A) binder resin, (B) photopolymerizable compound, (C) photoinitiator, (D) coloring agent, and (E) solvent.
  • the colored photosensitive resin composition according to the embodiments of the present invention may include a binder resin that provides adhesion to a substrate to form a coating film, and an alkali-soluble resin may be used as the binder resin.
  • the alkali-soluble resin usually makes the non-exposed portion of the colored photosensitive resin layer formed using the colored photosensitive resin composition alkali-soluble and also acts as a binder resin and a dispersion medium for the colorant described later.
  • the alkali-soluble resin may be used without particular limitation as long as it is a polymer soluble in the alkaline developer used in the developing step for manufacturing the color filter.
  • an alkali-soluble resin including an epoxy group it is preferable to use an alkali-soluble resin including an epoxy group.
  • the said alkali-soluble resin can mention the monomer containing an epoxy group, the copolymer with the other monomer copolymerizable with the said monomer, etc. are mentioned, for example.
  • Monomers containing the epoxy groups are specifically, for example, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decane-9-ylacrylate, 3,4-epoxytricyclo [5.2.1.0 2,6 ] Decane-8-ylacrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, etc. are mentioned.
  • an monomer copolymerizable with the monomer containing the said epoxy group For example, unsaturated carboxylic acid aminoalkyl ester, unsaturated carboxylic acid glycidyl ester, carboxylic acid vinyl ester, unsaturated ether, a vinyl cyanide compound , Unsaturated amides, unsaturated imides, aliphatic conjugated dienes, and macromonomers having a monoacryloyl group or a monomethacryloyl group at the terminal of the polymer molecular chain of polysiloxane.
  • unsaturated carboxylic acid aminoalkyl ester unsaturated carboxylic acid glycidyl ester, carboxylic acid vinyl ester, unsaturated ether, a vinyl cyanide compound
  • Unsaturated amides unsaturated imides, aliphatic conjugated dienes, and macromonomers having a monoacryloyl group or a monomethacryloyl group at the terminal of the polymer molecular chain
  • the weight average molecular weight of the alkali-soluble resin is 3,000 to 20,000 g / mol, preferably 5,000 to 15,000 g / mol.
  • the acid value of the alkali-soluble resin is 50 to 200mgKOH / g on the basis of solid content, it is excellent in developability for alkali development within the above range, it is possible to suppress the occurrence of residue, and improve the adhesion of the pattern.
  • the alkali-soluble resin included as the binder resin is included in 30 to 60% by weight relative to the total weight of solids in the colored photosensitive resin composition, it is preferably included in 40 to 50% by weight.
  • the content of the alkali-soluble resin is within the above range, pattern formation is easy, and resolution and residual film ratio are improved, which is preferable.
  • Solid content in a coloring photosensitive resin composition in this invention means the sum total of the component which removed the solvent.
  • the photopolymerizable compound (B) is a compound capable of polymerization by the action of a photopolymerization initiator, and may include a fluorine compound. In the case of the fluorine-based compound, it has a photopolymerization characteristic together with the photopolymerizable compound.
  • 2,2,3,3,3-Pentafluoropropyl acrylate (CAS Number 2993-85-3) to Pentafluorophenyl acrylate (CAS Number 71195-85-2) to 2,2,3,3,3-Pentafluoropropyl acrylate (CAS Number 356-86-5) to 2,2,3,3-Tetrafluoropropyl Methacrylate (CAS Number 45102-52-1), such as a compound having a structure in which fluorine is introduced together with methacrylate to methacrylate It is preferable that it is a polyfunctional compound.
  • the photopolymerizable compound is contained in 10 to 40% by weight based on the total weight of solids in the colored photosensitive resin composition of the present invention, it is preferably included in 20 to 35% by weight.
  • the said photopolymerizable compound can make the intensity
  • the photopolymerization initiator (C) may be used without limitation as long as it can polymerize the photopolymerizable compound.
  • the acetophenone compound and the benzoin compound are considered in consideration of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price. It may be one or more compounds selected from the group consisting of benzophenone compounds, triazine compounds, biimidazole compounds, oxime compounds and thioxanthone compounds.
  • acetophenone-based compound for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] Propan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, etc. are mentioned.
  • benzoin type compound benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoisobutyl ether, etc. are mentioned, for example.
  • benzophenone compound examples include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4' -Tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned.
  • triazine compound examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloro) Rhomethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3, 5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-di Ethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,
  • biimidazole compound examples include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2 , 3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl ) Biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole, 2,2-bis (2,6-dichlorophenyl ), 4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, or an imidazole compound in which a phenyl group at the 4,4', 5,5 'position is substituted by a carboalk
  • 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) -4 , 4 ', 5,5'-tetraphenylbiimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4', 5,5'-tetraphenyl-1,2'-biimidazole Etc. can be mentioned.
  • oxime compound examples include o-ethoxycarbonyl- ⁇ -oxyimino-1-phenylpropan-1-one and the like, and commercially available products may include BASF's OXE01 and OXE02.
  • thioxanthone compound examples include 2-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, and 1-chloro-4-propoxythiok. Santon etc. can be mentioned.
  • the said photoinitiator can be used individually or in mixture of 2 or more types.
  • the photopolymerization initiator is contained in an amount of 2 to 20% by weight, preferably 5 to 15% by weight, based on the total weight of solids in the colored photosensitive resin composition.
  • the colored photosensitive resin composition may be highly sensitive to improve the strength of the pixel portion formed using the colored photosensitive resin composition and smoothness on the surface of the pixel portion.
  • a photoinitiator can be used in addition to a photoinitiator.
  • the photopolymerization initiation aid is a compound used to promote polymerization of the photopolymerizable compound in which polymerization is initiated by the photopolymerization initiator, and examples of the photopolymerization initiation aid include an amine compound or an alkoxy anthracene compound.
  • amine compound examples include triethanolamine, methyl diethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and benzoic acid 2.
  • alkoxy anthracene-based compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene and 2-ethyl-9,10- Diethoxy anthracene, and the like.
  • the said photoinitiator When using the said photoinitiator, it is preferable to use it normally with more than 0 and 10 mol or less and 0.01-5 mol with respect to 1 mol of photoinitiators.
  • the photopolymerization initiation aid is used in the range of more than 0 to 10 mol or less, the sensitivity of the colored photosensitive resin composition is higher, and the productivity of the color filter formed using the colored photosensitive resin composition can be improved.
  • the coloring photosensitive resin composition of this invention contains at least one of a blue coloring agent and a white coloring agent as a coloring agent.
  • the colorant may be used in combination of any one or two or more of a pigment, a dye, or a natural dye, and among these, an organic pigment is preferable in that it is excellent in heat resistance and color development.
  • organic pigments and inorganic pigments include compounds classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and pigments having the following color index (CI) numbers may be mentioned. It is not necessarily limited to these.
  • Pigments of color index (C.I.) numbers are for example C.I. Pigment blue 15 (15: 3, 15: 4, 15: 6, etc.), 16, 21, 28, 60, 64, and 76;
  • These pigments can be used individually or in combination of 2 or more types, respectively.
  • pigment pigments as the blue colorant, C.I. Pigment Blue 15: 6 to 60 is preferred, and the white colorant is C.I. Pigment White 6 is preferred.
  • the colorant included in the colored photosensitive resin composition of the present invention is included in 5 to 20% by weight, preferably 7 to 15% by weight based on the total weight of solids in the resin composition.
  • the colorant is included in the above-described range can be obtained an effect that the optical density is excellent.
  • the solvent used in the conventional colored photosensitive resin composition can be used without particular limitation, and in particular, ethers, acetates, aromatic hydrocarbons, ketones, Alcohols or esters are preferable.
  • Ethylene glycol monoalkyl ether such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether;
  • Diethylene glycol dialkyl ether such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether, etc. are mentioned.
  • acetates for example, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3 -Methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, methyl 3-methoxypropionate, propylene glycol methyl ether acetate, 3-methoxy-1- Butyl acetate, 1,2-propylene glycol diacetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, diethylene glycol monobutyl ether Acetate, ethylene glycol monomethyl
  • aromatic hydrocarbons benzene, toluene, xylene, mesitylene, etc. are mentioned, for example.
  • ketones methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, etc. are mentioned, for example.
  • alcohols examples include ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, 4-hydroxy-4-methyl-2-pentanone, and the like.
  • ester ethyl 3-ethoxy propionate, methyl 3-methoxy propionate, (gamma) -butyrolactone, etc. are mentioned, for example.
  • the said solvent can be used individually or in mixture of 2 or more types, respectively.
  • organic solvent whose boiling point is 100 degreeC-200 degreeC from the point of applicability
  • paintability and dryness For example, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 3- Ethyl ethoxy propionate, methyl 3-methoxypropionate, and the like.
  • the solvent is contained in 50 to 80% by weight, preferably 65 to 75% by weight relative to the total weight of the colored photosensitive resin composition. If the solvent is included in the range of 50 to 80% by weight, the coating property is good when applied with a coating device such as a roll coater, spin coater, slit and spin coater, slit coater (sometimes referred to as die coater) and inkjet Can be done.
  • a coating device such as a roll coater, spin coater, slit and spin coater, slit coater (sometimes referred to as die coater) and inkjet Can be done.
  • the coloring photosensitive resin composition of this invention contains other additive as needed by those skilled in the art in the range which does not impair the objective of this invention other than the above-mentioned components.
  • the additive may further comprise one or more additives selected from the group consisting of, for example, other polymeric compounds, curing agents, dispersants, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers and anti-agglomerating agents.
  • the other high molecular compound include curable resins such as epoxy resins and maleimide resins; And thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane.
  • curable resins such as epoxy resins and maleimide resins
  • thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane.
  • the curing agent is used to increase the core hardening and mechanical strength, and specific examples thereof include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound and an oxetane compound.
  • epoxy compound in the curing agent examples include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, noblock type epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin , Glycidyl ester resins, glycidylamine resins, or brominated derivatives of such epoxy resins, aliphatic, cycloaliphatic or aromatic epoxy compounds other than epoxy resins and their brominated derivatives, butadiene (co) polymer epoxides, isoprene ( Co) polymer epoxide, glycidyl (meth) acrylate (co) polymer, triglycidyl isocyanurate, and the like.
  • oxetane compound in the curing agent examples include carbonate bis oxetane, xylene bis oxetane, adipate bis oxetane, terephthalate bis oxetane, cyclohexane dicarboxylic acid bis oxetane and the like.
  • curing agent can use together the hardening auxiliary compound which can make ring-opening-polymerize the epoxy group of an epoxy compound, and the oxetane skeleton of an oxetane compound with a hardening
  • the curing aid compound include polyhydric carboxylic acids, polyhydric carboxylic anhydrides, acid generators, and the like.
  • polyhydric carboxylic anhydride what is marketed can be used as an epoxy resin hardening
  • epoxy resin curing agent examples include commercially available products such as trade names (Adecahadona EH-700, manufactured by Adeka Industrial Co., Ltd.), trade names (manufactured by Rikashitdo HH, Nippon Ewha Co., Ltd.), trade names (MH-700, Shin-Japan Ewha Co., Ltd.) etc. are mentioned.
  • trade names Alcahadona EH-700, manufactured by Adeka Industrial Co., Ltd.
  • trade names manufactured by Rikashitdo HH, Nippon Ewha Co., Ltd.
  • trade names MH-700, Shin-Japan Ewha Co., Ltd.
  • the surfactant may be used to further improve the film formability of the photosensitive resin composition, and silicone-based surfactants or fluorine-based surfactants may be preferably used.
  • the silicone surfactant is, for example, commercially available products such as DC3PA, DC7PA, SH11PA, SH21PA and SH-8400 manufactured by Dow Corning Toray Silicone Co., Ltd., TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF- 4460, TSF-4452, etc. are mentioned.
  • the fluorine-based surfactants are, for example, Megapieces F-470, F-471, F-475, F-482, F-489, and F-554 (Daininib Kagaku Kogyo Co., Ltd.), BM-1000, BM as commercially available products.
  • the adhesion promoter is an additive used to improve the coating property and adhesion with the substrate, and includes a silane coupling agent including a reactive substituent selected from the group consisting of carboxyl group, methacryloyl group, isocyanate group, epoxy group and combinations thereof. It may include.
  • the silane coupling agent is specifically, for example, trimethoxysilyl benzoic acid, ⁇ -methacryl oxypropyl trimethoxy silane, vinyltriacetoxysilane, vinyl trimethoxysilane, ⁇ -isocyanate propyl triethoxysilane, r- Glycidoxy propyl trimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like.
  • antioxidants examples include 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.
  • ultraviolet absorber examples include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.
  • aggregation inhibitor examples include sodium polyacrylate and the like.
  • the additive may be included in an amount of 0.1 to 10% by weight based on 100% by weight of the colored photosensitive resin composition.
  • the additive is included in the above range with respect to the colored photosensitive resin composition, there is an advantage in that the desired performance of each additive can be imparted without degrading the performance of the color filter made of the colored photosensitive resin composition.
  • the present invention provides a color device or a color filter manufactured using the above-described colored photosensitive resin composition and a display device including the same.
  • the color element of this invention will not be specifically limited if it is manufactured using the well-known color element manufacturing method using said coloring photosensitive resin composition.
  • the color filter of the present invention comprises a substrate and a color layer formed on the substrate.
  • the substrate may be a glass plate, a silicon wafer and a plate of a plastic substrate such as polyethersulfone (PES), polyimide (PI), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • a plastic substrate such as polyethersulfone (PES), polyimide (PI), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • the color layer includes a binder resin, a photopolymerizable monomer, a photopolymerization initiator, a colorant, and a solvent, and a coloring photosensitive resin composition comprising an additive as necessary.
  • the colored photosensitive resin composition is coated on a substrate and formed in a predetermined pattern. After that, it may be a layer formed by exposure and development.
  • the pattern forming method of the color filter comprises the steps of applying a colored photosensitive resin composition to a substrate; A prebaking step of drying the solvent; Applying a photomask to the obtained film to irradiate active light to cure the exposed portion; Performing a developing process of dissolving the unexposed portion using an aqueous alkali solution; And performing drying and post-baking.
  • the substrate is a glass substrate or a polymer plate.
  • a glass substrate soda-lime glass, barium or strontium containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz, etc. can be used preferably.
  • a polycarbonate, an acryl, polyethylene terephthalate, a polyether sulfide, a poly sulfone, etc. are mentioned as a polymer board.
  • the coating may be performed by a wet coating method using a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), and an inkjet to obtain a desired thickness.
  • a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), and an inkjet to obtain a desired thickness.
  • Prebaking is performed by heating with an oven, a hot plate, etc.
  • the heating temperature and heating time in a prebaking are suitably selected according to the solvent to be used, and it is performed for 1 to 30 minutes at the temperature of 80 to 150 degreeC, for example.
  • the light to be irradiated may be visible light, ultraviolet light, X-ray, electron beam, or the like.
  • the aqueous solution of the carbonate of an alkali metal or alkaline-earth metal, etc. can be used, for example.
  • a developer or an ultrasonic cleaner is used at a temperature of 10 ° C to 50 ° C, preferably 20 ° C to 40 ° C. To perform.
  • Post-baking is performed to increase the adhesion between the patterned film and the substrate, and is carried out by heat treatment at a temperature of 10 to 120 minutes at 80 °C to 230 °C. Post bake is carried out using an oven, hot plate and the like, like prebaking.
  • a pixel or partition wall corresponding to the color of the colorant in the colored photosensitive resin composition can be obtained, and the pattern forming step can be carried out to produce a pattern for performing the inkjet method.
  • the structure of the device may be completed by forming the color ink on the partition wall formed by the inkjet method or by forming the self-luminous ink through the inkjet method, and the construction and the manufacturing method are well known to those skilled in the art. similar.
  • the display device includes a configuration known to those skilled in the art except that the display device includes a partition wall manufactured using the colored photosensitive resin composition of the present invention.
  • the partition wall manufactured using the coloring photosensitive resin composition of this invention contains the partition wall which is excellent in liquid repellency and excellent in light-shielding property to light other than blue. As a result, it is possible to prevent color mixing of ink between neighboring pixels, and to improve the reliability of the display device by forming pixels in which surface defects do not occur.
  • Dongwoo Phosphorus which is the composition of this invention containing the coloring agent containing at least one of (A) binder resin, (B) photopolymerizable compound, (C) photoinitiator, (D) blue coloring agent, and white coloring agent, and (E) solvent.
  • Chem's SY-O1410 or SY-O1533 solution was coated using a coating machine (Opticoat MS-A150, manufactured by Mikasa) at a rpm that can exhibit a certain thickness for each colored photosensitive resin composition, followed by a 90 ° C. hot plate (hot pre-baking for 1 to 10 minutes on the plate) to form a coating film.
  • the exposure machine (HB-50110AA, manufactured by Ushio) is irradiated with ultraviolet (UV) exposure according to the amount (mJ / cm 2) shown in Tables 1 to 2
  • UV ultraviolet
  • the resultant was developed in an alkaline aqueous solution for 80 seconds to dissolve and remove unnecessary portions, and washed with ultrapure water (DIW).
  • DIW ultrapure water
  • the SY-O1410 solution used above was C.I. Pigment Blue 15: 6 contains 13% solids and the SY-O1533 solution is C.I. Pigment White 6 pigment is 10% based on solids and C.I. Pigment Blue 15: 6 pigment is included 5% by solids.
  • the contact angles of the coating films prepared in Examples 1 to 6 and Comparative Examples 1 to 7 were measured using KRUSS's DSA100 product, and the contact angles of the solvents were measured at 25 ° C. in a 40% humidity atmosphere. Each contact angle was measured every 60 seconds for the contact angle of the solvent and the average value of each contact angle is shown in Tables 1-2.
  • Example 1 Example 2
  • Example 3 Example 4
  • Example 5 Photosensitive resin composition SY-O1410 SY-O1410 SY-O1410 SY-O1410 SY-O1533 SY-O1533 Film thickness ( ⁇ m) 3.8 3.8 8.0 3.8 4.2 8.5 Exposure amount (mJ / cm2) 50 80 80 150 80 80 Coating Surface Roughness (Ra, nm) 16 26 52 48 26 37 DIW contact angle 115 128 132 148 102 108 PGMEA contact angle 48 55 62 68 44 49 Value of PGMEA Contact Angle / DIW Contact Angle 0.42 0.43 0.47 0.46 0.43 0.45
  • a pattern substrate was prepared using the colored photosensitive resin compositions of Examples 1 to 6 and Comparative Examples 1 to 7 by an inkjet method using quantum dot inks, red inks, and transparent inks prepared as follows. Pixel formation was measured and evaluated. The results are shown in Table 3 below.
  • Quantum dots generally refer to nano-sized particles that emit light at a specific wavelength when injecting light or electrons.
  • the quantum dot particles used in this experiment were designed to see the blue light source, green and red light that were not completely absorbed when the blue light source was inputted with 1: 2 ratio of green and red particles manufactured by Nanoco. .
  • 230mg of green quantum dot particles and 460mg of red quantum dot particles were placed in a 3-neck flask, and BYK's DISPERBYK-111 dispersant was calculated as a solid and 30% of the particles were added.
  • Quantum dot ink was prepared by adding 8.3 g of SPCY-1L resin, Nippon Showa Polymer Co., Ltd., propylene glycol monomethyl ether acetate (PGMEA), and propylene glycol diacetate (PGDA) at a ratio of 8/2.
  • SPCY-1L resin Nippon Showa Polymer Co., Ltd.
  • PGMEA propylene glycol monomethyl ether acetate
  • PGDA propylene glycol diacetate
  • DPHA DIPENTAERYTHRITOL PENTA / HEXA ACRYLATE, Nippon Gunpowder Co., Ltd. 12 g was used in addition to 3 ratios to prepare a transparent ink.
  • the color layer was formed by inkjet method using quantum dot inks, red inks, and transparent inks prepared in Synthesis Examples 1) to 3). Were formed to produce color pixels, and pixel formation was measured and evaluated. Pixel evaluation criteria are as follows, and the results are shown in Table 3 below.
  • Examples 1 to 6 showed excellent pixel formation when manufacturing color pixels by inkjet method using different inks of quantum dot ink, red ink, and transparent ink. On the other hand, in Comparative Examples 1 to 7, it can be seen that the formation of the pixel is poor.
  • the contact angle with respect to water and the contact angle with respect to propylene glycol methyl ether acetate (PGMEA) on the surface of the coating film after development each exhibit a specific range, and the relationship between the contact angles has a value within a specific relation range.
  • the coloring photosensitive resin composition by this invention can prevent the ink mixing between the pixels which adjoin each other.
  • the coloring photosensitive resin composition of this invention can form the pixel which a surface defect does not produce.
  • the above-mentioned colored photosensitive resin composition can be usefully used for the production of color elements and display devices.

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Abstract

La présente invention concerne : une composition de résine photosensible colorée caractérisée en ce qu'une surface de film fabriquée après la réalisation d'un durcissement et d'un développement de rayonnement a un angle de contact avec de l'eau de 100-160° et un angle de contact avec l'acétate d'éther méthylique de propylène glycol (PGMEA) de 40 à 70°, et le rapport de l'angle de contact avec l'eau à l'angle de contact avec le PGMEA est de 1 à 0,4-0,6; et un dispositif de couleur et un appareil d'affichage qui utilisent celui-ci.
PCT/KR2019/001385 2018-02-05 2019-01-31 Composition de résine photosensible colorée, et dispositif de couleur et appareil d'affichage qui sont fabriqués à l'aide de celle-ci Ceased WO2019151807A1 (fr)

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JP2020534451A JP2021508087A (ja) 2018-02-05 2019-01-31 着色感光性樹脂組成物、およびそれを用いて製造されたカラー素子並びに表示装置
CN201980011830.5A CN111684357B (zh) 2018-02-05 2019-01-31 着色感光性树脂组合物及使用其制造的滤色器元件和显示装置
JP2022076613A JP7541545B2 (ja) 2018-02-05 2022-05-06 着色感光性樹脂組成物、およびそれを用いて製造されたカラー素子並びに表示装置

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CN111684357B (zh) 2023-10-13
KR20230023678A (ko) 2023-02-17
JP2022103263A (ja) 2022-07-07
JP2021508087A (ja) 2021-02-25
KR20190094731A (ko) 2019-08-14
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