WO2013027936A2 - Composition de résine photosensible noire et dispositif d'affichage d'images présentant ladite composition - Google Patents

Composition de résine photosensible noire et dispositif d'affichage d'images présentant ladite composition Download PDF

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Publication number
WO2013027936A2
WO2013027936A2 PCT/KR2012/006083 KR2012006083W WO2013027936A2 WO 2013027936 A2 WO2013027936 A2 WO 2013027936A2 KR 2012006083 W KR2012006083 W KR 2012006083W WO 2013027936 A2 WO2013027936 A2 WO 2013027936A2
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Prior art keywords
black
resin composition
photosensitive resin
weight
parts
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PCT/KR2012/006083
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English (en)
Korean (ko)
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WO2013027936A3 (fr
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배진영
김주성
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성균관대학교 산학협력단
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Publication of WO2013027936A2 publication Critical patent/WO2013027936A2/fr
Publication of WO2013027936A3 publication Critical patent/WO2013027936A3/fr

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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
    • 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
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • 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 black photosensitive resin composition and an image display apparatus having the same, and more particularly, to a black photosensitive resin having excellent electrical insulation and chemical resistance and having a high optical density, and an image display apparatus using the same.
  • LCD is a major product in the flat display market, and is composed of a color filter, a thin film transistor, and a liquid crystal.
  • Color filters used in color liquid crystal displays, imaging devices, and the like are usually uniformly coated by spin coating a photosensitive resin composition containing pigments corresponding to red, green, and blue colors on a substrate on which a black matrix is patterned. It is manufactured by exposing and developing the coating film formed by heat-drying, and performing heat-hardening further as needed for each color, and forming the pixel of each color.
  • the black matrix patterned here is usually formed from a black photosensitive resin composition.
  • the black photosensitive resin composition is an essential material for flat display panel materials such as color filters, liquid crystal displays (LCDs), organic light emitting displays (OLEDs), and plasma display panels (PDPs).
  • a black column spacer which can also serve as a column spacer capable of supporting the TFT-array layer and the color filter layer through the black matrix, in which case the even optical density required for the normal black matrix (Optical density (OD) as well as good electrical insulation are required.
  • Optical density (OD) optical density
  • the black matrix materials using inorganic compounds did not satisfy the properties required for the black column spacer because of low insulation.
  • electrical insulation directly affects the liquid crystal, so high insulation or low dielectric properties are required.
  • Japanese Laid-Open Patent Publication No. 2002-047423 in order to realize a black matrix having high blackness and insulation, cobalt oxides are contained and applied as a black pigment.
  • Japanese Unexamined Patent Publication No. 2007-071994 a perylene-based compound has been used as a black matrix material.
  • Japanese Patent No. 2552391 intends to form a light shielding film using a black matrix material containing an insulating organic pigment composed of a mixed organic pigment and carbon black.
  • the present invention has been made in an effort to provide a black photosensitive resin composition having low dielectric properties and a uniform optical density, and an image display apparatus using the same.
  • a black coating film prepared by polymerizing a black photosensitive resin composition comprising a black perylene-based organic pigment, insulating metal oxide particles, alkali-soluble binder resin, photopolymerizable compound, photopolymerization initiator and a solvent.
  • a black photosensitive resin composition comprising a black perylene-based organic pigment, insulating metal oxide particles, alkali-soluble binder resin, a photopolymerizable compound, a photopolymerization initiator and a solvent is prepared by polymerizing the solvent in the total composition.
  • the black organic pigment is provided with a black photosensitive resin composition containing 1 to 60 parts by weight, and the insulating particles 1 to 70 parts by weight.
  • perylene-based organic pigments, silica, alkali-soluble binder resin, and polymer including per 100 parts by weight of the perylene-based organic pigment, 1 to 60 parts by weight, the silica is 1 To 70 parts by weight, the perylene-based organic pigment and the silica is provided with a black photosensitive composition having a weight ratio of 1:19 to 19: 1.
  • a black coating film formed on a substrate by applying and polymerizing the black photosensitive resin composition to a predetermined substrate.
  • an image display device including the black coating film.
  • a black coating film using a black photosensitive resin composition having low dielectric properties and having a uniform optical density can be prepared.
  • the black coating film has a low dielectric constant, chemical resistance, high film hardness, and can continuously maintain electrical properties and physical properties with respect to a post process.
  • the black photosensitive resin composition which concerns on this invention contains a black organic pigment (A1), insulating particle (A2), alkali-soluble binder resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E). .
  • the black photosensitive resin composition may optionally further include an additive (F).
  • a perylene-based black pigment (hereinafter simply referred to as a perylene-based pigment) is used as the black organic pigment used in the black photosensitive resin composition.
  • the perylene pigment represented by the following general formula (I) and the perylene pigment represented by the following general formula (II) are mentioned.
  • product names K0084, K0086 (made by BASF Corporation), etc. can be used preferably.
  • R ⁇ 1> , R ⁇ 2> represents a C1-C3 alkylene group each independently, and R ⁇ 3> , R ⁇ 4> represents a hydrogen atom, a hydroxyl group, a methoxy group, or an acetyl group each independently.
  • R ⁇ 5> represents a C1-C7 alkylene group each independently.
  • the method of Unexamined-Japanese-Patent No. 62-1753 and Unexamined-Japanese-Patent No. 63-26784 is used, for example.
  • the target object can be obtained by reprecipitating the obtained preparation in sulfuric acid or recrystallizing in water, an organic solvent, or these mixed solvent.
  • a perylene pigment may be used individually by 1 type and may use 2 or more types together.
  • the average particle diameter of a perylene pigment is 10-100000 nm.
  • content of the perylene pigment in the photosensitive resin composition for light-shielding layer formation of this invention 50-300 mass parts is preferable with respect to 100 mass parts of (B) alkali-soluble binder resin. More preferable range is 100-250 mass parts.
  • the black organic pigment resin composition may further include an additive such as a dispersant.
  • the dispersant serves to control agglomeration between the black organic particles.
  • the dispersant may be one containing a hydrophilic group and a hydrophobic group that can control the aggregation between the black organic particles.
  • grain resin composition can also be used beforehand treating with the dispersing agent.
  • the dispersant may be a urethane-based dispersant, an acrylic dispersant or an epoxy dispersant, but is not limited thereto.
  • Examples of the urethane-based dispersant include those selected from the group consisting of disperbyk 2150 (manufactured by BYK chemie), disperbyk 164 (manufactured by BYK chemie), disperbyk 163 (manufactured by BYK chemie) and combinations thereof.
  • Examples of the acrylic dispersant include disperbyk 2070 (manufactured by BYK chemie).
  • the insulating particles A2 inorganic metal oxide particles such as silica, alumina, titania, and zirconia may be used.
  • the said insulating particle (A2) can be used individually or in combination of 2 or more types, It is preferable to use what can provide the outstanding electrical insulation, mixing uniformly with a black organic pigment (A1).
  • Preferred examples of the insulating particles (A2) include silica or alumina particles.
  • the silica (SiO 2 ) or alumina (Al 2 O 3 ) used may be substantially spherical, sub-micron sized particles dispersed in an aqueous or other solvent medium.
  • the silica or alumina particles used in the present invention may have a size of less than 1 micrometer with an average particle diameter of 10 to 100 nm, preferably 10 to 50 nm. Average particle size can be determined using transmission electron microscopy.
  • silica or alumina particles generally have a surface area of greater than about 100 m 2 / gram.
  • the particles preferably have a narrow particle size distribution, ie the polydispersity may be 2.0 or less, preferably 1.5 or less. If desired, smaller amounts of larger silica or alumina particles may be added, but such addition may not contribute to an increase in shear value.
  • silica examples include, but are not limited to, nano silica (AEROSIL 200, TT 600; manufactured by Degussa) and hydrophobic nano silica (AEROSIL R972; manufactured by Degussa).
  • AEROSIL 200, TT 600 manufactured by Degussa
  • AEROSIL R972 hydrophobic nano silica
  • the shape of the particles is not limited.
  • the insulating particles may preferably have a shape with an average particle diameter of 0.1 ⁇ m or less, which can be observed by an electron microscope.
  • the surface of the insulating particles may be treated with a silane coupling agent or the like. In this case, compatibility with the binder resin and adhesive properties can be improved.
  • the ratio of the two materials (A1) and (A2) may be contained in an amount of 5 to 95 parts by weight based on 100 parts by weight of the solid content
  • the insulating particles (A2) may be contained in an amount of 5 to 95 parts by weight based on 100 parts by weight of the solid content.
  • the black organic pigment (A1) may contain 10 to 70 parts by weight based on 100 parts by weight of solids in the black photosensitive resin composition. If the content of the black organic pigment (A1) is less than 10 parts by weight, the optical density is not sufficient, if more than 70 parts by weight, the optical density is sufficient, but pattern formation may be difficult.
  • the insulating particles (A2) may contain 1 to 70 parts by weight based on 100 parts by weight of solids in the black photosensitive resin composition. If the content of the insulating particles (A2) is less than 1 part by weight, the insulation is not sufficient, if more than 70 parts by weight, the insulation is sufficient, but pattern formation may be difficult.
  • the alkali-soluble binder resin (B) is applicable to those commonly used in the art, in particular, it is preferable that the alkali-soluble binder resin (B) is a copolymer of a compound having an unsaturated carboxyl group and other monomers copolymerizable therewith.
  • the compound having an unsaturated carboxyl group is not limited as long as it is a carboxylic acid compound having an unsaturated double bond that can be polymerized, and each compound can be used alone or in combination of two or more thereof.
  • the compound having an unsaturated carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid; And anhydrides of the dicarboxylic acids; Mono (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as ⁇ -carboxypolycaprolactone mono (meth) acrylate, monomethyl maleic acid, isoprene sulfonic acid, styrene sulfonic acid, 5-norbornene-2- Carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, or a mixture thereof.
  • acrylic acid and methacrylate monomethyl maleic acid
  • isoprene sulfonic acid
  • Other monomers copolymerizable with the monomer having a carboxyl group are monomers having a carbon-carbon unsaturated bond, and specific examples thereof include aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, and vinyltoluene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl methacrylate Unsaturated carboxylate compounds such as acrylates; Unsaturated aminoalkyl carboxylate compounds such as aminoethyl acrylate; Unsaturated glycidyl carboxylate compounds such as glycidyl methacrylate; Vinyl carboxylate compounds such as vinyl acetate and vinyl propionate; Vinyl cyanide compounds such as acrylonitrile, methacrylonit
  • alkali-soluble binder resin may be used a cardo resin generally used in the art.
  • the cardo-based resin is 3,3-bis (4-hydroxyphenyl) -2-benzofuran-1 (3H) -one, 3,3-bis (4-hydroxy-3-methylphenyl) -2-benzofuran -1 (3H) -one, 3,3-bis (4-hydroxy-2,5-dimethylphenyl) -2-benzofuran-1 (3H) -one, 3,3-bis (4-hydroxy- 1-naphthyl) -2-benzofuran-1 (3H) -one, 3,3-bis (4-hydroxy-5-isopropyl-2-methylphenyl) -2-benzofuran-1 (3H) -one , 3,3-bis (3,5-dibromo-4-hydroxyphenyl) -2-benzofuran-1 (3H) -one, 3,3-bis (4-hydroxy-3,5-di Iodinephenyl) -2-benzofuran-1 (3H) -one, 9,9-bis (4-hydroxyphenyl) -10-anthrone
  • the alkali-soluble binder resin (B) may be included in 5 to 60 parts by weight, preferably 10 to 40 parts by weight based on 100 parts by weight of solids in the black photosensitive resin composition.
  • the alkali-soluble binder resin (B) is within the content range on the basis of the above standard, the formation of a pattern is possible, and the resolution and the residual film ratio are improved.
  • the said photopolymerizable compound (C) is a compound which can superpose
  • monofunctional monomers include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N-vinylpyrroly Money, etc.
  • bifunctional monomers include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, Bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate, etc. are mentioned.
  • polyfunctional monomers include trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaeryte Lithol hexa (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc. are mentioned.
  • bifunctional or higher polyfunctional monomers are preferably used.
  • the photopolymerizable compound (C) may be used in the range of 5 to 80 parts by weight, preferably 10 to 70 parts by weight, based on 100 parts by weight of the alkali-soluble binder resin (B) and the photopolymerizable compound (C) based on solid content. Can be. If the photopolymerizable compound (C) is in the range of 5 to 80 parts by weight based on the above criteria, the pattern characteristic becomes good, and therefore it is preferable.
  • the said photoinitiator (D) is not restrict
  • triazine type compound it is 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1, 3, 5- triazine, 2, 4-bis (trichloromethyl)-, for example. 6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-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-tri Azine, 2,4-bis (trichloromethyl) -6- [2- (4-diethyla
  • acetophenone type compound diethoxy acetophenone, 2-hydroxy-2-methyl-1- phenyl propane- 1-one, benzyl dimethyl ketal, 2-hydroxy-1- [4- (2- Hydroxyethoxy) phenyl] -2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one , 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane- 1-one oligomer etc. are mentioned.
  • acetophenone-based compound may be a compound represented by the following formula (1).
  • R 1 to R 4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group which may be substituted by an alkyl group having 1 to 12 carbon atoms, or a benzyl which may be substituted by an alkyl group having 1 to 12 carbon atoms.
  • the naphthyl group which may be substituted by the group or the C1-C12 alkyl group is shown.
  • Specific examples of the compound represented by Formula 1 include 2-methyl-2-amino (4-morpholinophenyl) ethan-1-one, 2-ethyl-2-amino (4-morpholinophenyl) ethane-1 -One, 2-propyl-2-amino (4-morpholinophenyl) ethan-1-one, 2-butyl-2-amino (4-morpholinophenyl) ethan-1-one, 2-methyl-2 -Amino (4-morpholinophenyl) propane-1-one, 2-methyl-2-amino (4-morpholinophenyl) butan-1-one, 2-ethyl-2-amino (4-morpholino Phenyl) propane-1-one, 2-ethyl-2-amino (4-morpholinophenyl) butan-1-one, 2-methyl-2-methylamino (4-morpholinophenyl) propan-1-one , 2-methyl-2-dimethylamino (4-morpholinophenyl) propan-1-one,
  • biimidazole compound 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'- tetraphenyl biimidazole, 2,2'-bis (2,3-, for example) Dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimi Dazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole, and a phenyl group at the 4,4', 5,5 'position is carbo The imidazole compound substituted with the alkoxy group etc.
  • 2,2'bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole can be preferably used.
  • the other photoinitiator etc. which are normally used in this field can also be used together if it is a grade which does not impair the effect of this invention.
  • a benzoin compound, a benzophenone type compound, a thioxanthone type compound, an anthracene type compound, a polyfunctional thiol compound, etc. are mentioned, for example. These can be used individually or in combination of 2 types or more, respectively.
  • benzoin type compound benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc. are mentioned, for example.
  • benzophenone type compound benzophenone, methyl 0- benzoyl benzoate, 4-phenylbenzo phenone, 4-benzoyl-4'- methyl diphenyl sulfide, 3,3 ', 4, 4'- tetra ( tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned.
  • thioxanthone type compound 2-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro-4- propoxy thioxanthone, etc. are mentioned, for example. Can be mentioned.
  • anthracene-based compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and the like. Can be mentioned.
  • polyfunctional thiol compound examples include tris- (3-mercaptopropionyloxy) -ethyl-isocyanurate, trimethylolpropanetris-3-mercaptopropionate, and pentaerythritol tetrakis-3. Mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like.
  • a photoinitiator (D-1) together with a photoinitiator (D)
  • productivity at the time of forming a black matrix or a black column spacer using this is preferable.
  • photopolymerization initiation assistant (D-1) one or more compounds selected from the group consisting of amine compounds and carboxylic acid compounds can be preferably used.
  • amine compound in the photopolymerization initiation assistant (D-1) include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-dimethylamino Isoamyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoic acid, 2-dimethylaminoethyl benzoic acid, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), Aromatic amine compounds, such as 4,4'-bis (diethylamino) benzophenone, are mentioned.
  • aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine
  • methyl 4-dimethylaminobenzoate ethy
  • an aromatic amine compound is preferably used as the amine compound.
  • the carboxylic acid compound in the photopolymerization initiation assistant (D-1) include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, and dimethoxyphenyl
  • aromatic heteroacetic acids such as thioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.
  • the content of the photopolymerization initiator (D) is 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight based on 100 parts by weight of the total amount of the alkali-soluble binder resin (B) and the photopolymerizable compound (C) based on the solid content.
  • the content of the photopolymerization initiation assistant (D-1) is 0.1 to 50 parts by weight, preferably 1 to 1, based on 100 parts by weight of the total amount of the alkali-soluble binder resin (B) and the photopolymerizable compound (C) based on the solid content. 40 parts by weight.
  • the black photosensitive resin composition is highly sensitive, and thus the strength of the pixel portion formed using the composition and the smoothness on the surface of the pixel portion become good. desirable. Moreover, since the sensitivity of a black photosensitive resin composition becomes higher and the productivity of the color filter formed using this composition improves, when the usage-amount of a photoinitiator auxiliary (D-1) exists in said range on the said reference
  • the solvent (E) is not particularly limited, and various organic solvents commonly used in the art may be used.
  • the solvent (E) include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, and diethylene.
  • ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, and diethylene.
  • Diethylene glycol dialkyl ethers such as glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, and propylene glycol Alkoxy alkyl acetates, such as alkylene glycol alkyl ether acetates, such as a monomethyl ether acetate, a propylene glycol monoethyl ether acetate, and a propylene glycol monopropyl ether acetate, a methoxy butyl acetate, and a methoxy pentyl acetate,
  • Aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene Alcohols such as glycol and glycerin, esters such as 3-ethoxy propionate and methyl 3-methoxypropionate, and cyclic esters such as ⁇ -butyrolactone.
  • ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene Alcohols such as glycol and glycerin, esters such
  • organic solvents having a boiling point of 100 to 200 ° C in the solvents are preferable in terms of coating properties and drying properties, and more preferably alkylene glycol alkyl ether acetates, ketones and 3-ethoxypropionic acid.
  • Ester such as ethyl and 3-methoxy propionate, is mentioned, More preferably, propylene glycol monomethyl ether acetate, a propylene glycol monoethyl ether acetate, cyclohexanone, 3-ethoxy propionate, 3-methoxy Methyl propionate etc. are mentioned.
  • solvents (E) can be used individually or in mixture of 2 or more types, respectively.
  • Content of the said solvent (E) is 20-90 weight part with respect to 100 weight part of all black photosensitive resin compositions containing it, Preferably it is 60-85 weight part.
  • content of the said solvent (E) is the range of 20-90 weight part on the said reference
  • the black photosensitive resin composition of this invention can also use together the additive (F), such as another high molecular compound, a hardening
  • the additive (F) such as another high molecular compound, a hardening
  • thermosetting resins such as epoxy resins and maleimide resins
  • thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, polyurethanes, and the like. Can be mentioned.
  • curing agent is used in order to raise a deep part hardening and mechanical strength
  • curing agent an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, etc. are mentioned.
  • the epoxy compound in the curing agent examples include a bisphenol A epoxy resin, a hydrogenated bisphenol A epoxy resin, a bisphenol F epoxy resin, a hydrogenated bisphenol F epoxy resin, a noblock type epoxy resin, other aromatic epoxy resins, and an alicyclic epoxy resin.
  • 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
  • said hardening auxiliary compound polyhydric carboxylic acid, polyhydric carboxylic anhydride, an acid generator, etc. are mentioned, for example.
  • curing agent As said carboxylic anhydride, what is marketed can be used as an epoxy resin hardening
  • a brand name (Adekahadona EH-700) (made by Adeka Industrial Co., Ltd.), a brand name (Rikaditdo HH) (made by Nippon Ewha Co., Ltd.), a brand name (MH-700) are mentioned, for example. (Manufactured by Nippon Ewha Co., Ltd.).
  • curing agent and hardening auxiliary compound which were illustrated above can be used individually or in mixture of 2 or more types, respectively.
  • surfactants can be used as the pigment dispersant, and examples thereof include surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic and amphoteric. These can be used individually or in combination of 2 types or more, respectively.
  • surfactant for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyethylene glycol diester, sorbitan fatty acid ester, fatty acid modified polyester, tertiary amine modified polyurethane, polyethylene Imine, etc .; KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products), Mega Pack (MEGAFAC) (manufactured by Dainippon Ink Chemical Co., Ltd.), Florard (manufactured by Sumitomo 3M Inc.), Asahi guard, Suflon (manufactured by Asahi Glass Co., Ltd.), Solsperth (SOLSPERSE) (made by Lubrisol), EFKA (made by EFKA Chemicals), PB 821 (made by Ajinomoto Co., Ltd.
  • adhesion promoter examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyl tris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, and N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- ( 3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercapto propyltrimeth And oxysilane, 3-isocyanatepropyltrimethoxy
  • Each of the adhesion promoters may be used alone or in combination of two or more, and 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on 100 parts by weight of the solid content of the black photosensitive resin composition.
  • antioxidants include hindered phenols such as 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.
  • UV absorber 2- (3-tert- butyl- 2-hydroxy-5- methylphenyl) -5-chlorobenzothiazole, an alkoxy benzophenone, etc. are mentioned.
  • sodium polyacrylate is mentioned.
  • the black photosensitive resin composition of this invention can be manufactured by the following method, for example.
  • the black organic pigment (A1) is previously mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the black organic pigment becomes about 0.15 ⁇ m or less. At this time, a pigment dispersant is used as needed, and some or all of alkali-soluble binder resin (B) may be mix
  • the dispersion liquid of the obtained black organic pigment (A1) is mixed with the remainder of the solvent (E) in a fixed ratio using a stirrer or the like.
  • the insulating particle (A2) After adding the insulating particle (A2), the remainder of alkali-soluble binder resin (B), a photopolymerizable compound (C), a photoinitiator (D), and the additive (F) as needed to this liquid mixture, it is further added as needed. A solvent is further added so that it may become a predetermined concentration, and a desired black photosensitive resin composition is obtained.
  • a black coating film may be formed on the substrate.
  • a known coating method such as spin coating
  • a polymer is formed in the black photosensitive resin composition by heat or light, and the solvent is removed to cure to a solid phase.
  • the black coating film thus formed contains inorganic oxide particles, thereby providing excellent chemical resistance, low electrical insulation, and high surface hardness.
  • the image display device to which the black photosensitive resin composition is applied may have improved reflectivity and contrast ratio, thereby improving visibility of the screen, and since inorganic oxide particles are included in the film, chemical resistance, insulation, and durability are high.
  • a black organic pigment (A1) 60 parts by weight of a black organic pigment (A1), a dispersant (F1, F2), and a solvent (E1) were previously mixed into a container, followed by stirring for 3 minutes using a homogenizer. Dispersion was performed by repeating the process of performing ultrasonication for 3 minutes three times, and after dispersing was completed, 20 parts by weight of the remaining amount of the solvent (E1) were added to prepare black organic pigment dispersions BK 1 to 4.
  • Dispersant (F1) Disperbyk-2150 (manufactured by BYK chemi)
  • a 2 square inch glass substrate (# 1737, manufactured by Corning) was washed sequentially with a neutral detergent, water, and alcohol, and then dried.
  • the black photosensitive resin composition which concerns on the said Example and a comparative example was exposed by 100 mJ / cm ⁇ 2> exposure amount (365 nm), and spin-coating so that the film thickness after baking may be 3.0 micrometer when the image development process is skipped. Then, it was pre-dried at 100 degreeC for 3 minutes in the clean oven.
  • coated was irradiated with the exposure amount (365 nm) of 100 mJ / cm ⁇ 2> in air
  • optical density in 550 nm wavelength was measured for the black board
  • Optical density (OD) -Log 10 T (T is 550nm transmittance)
  • ⁇ : optical density is 3 or more
  • ⁇ optical density is 2 or more but less than 3
  • An aluminum electrode was formed on the black substrate made by the above method using an aluminum vacuum deposition apparatus and a mask. At this time, the aluminum electrode was deposited in a thickness of 0.075 ⁇ 0.025 ⁇ m on a black layer and an uncoated layer (ITO electrode) in a 5 mm diameter circular shape.
  • ITO electrode uncoated layer
  • ⁇ relative dielectric constant
  • ⁇ relative dielectric constant is 5 or more and 8 or less
  • the black photosensitive resin composition of the embodiment comprising a perylene-based pigment, which is a black organic pigment, and silica, which is an insulating particle, and which is included within a preferred range of the present invention, has excellent optical insulation while having a uniform optical density. It can be seen that a black matrix or black column spacer is obtained. However, in the case of Comparative Examples 1 to 3 without combining the insulating particles, it can be seen that the relative dielectric constant is not good compared to Examples 1 to 6 used by combining both the black organic pigment and the insulating particles.
  • a black coating film using a black photosensitive resin composition having low dielectric properties and having a uniform optical density may be manufactured.
  • the black coating film has a low dielectric constant, chemical resistance, high film hardness, and can continuously maintain electrical properties and physical properties with respect to a post process.

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Abstract

L'invention concerne une composition de résine photosensible noire contenant un pigment organique noir, des particules d'oxyde métallique isolantes, une résine de liaison soluble dans les alcalis, un composé photopolymérisable, un initiateur de photopolymérisation, et un solvant. La matière organique noire est une composition de résine photosensible contenant un pigment noir pérylène pour former une couche formant barrière optique.
PCT/KR2012/006083 2011-08-22 2012-07-31 Composition de résine photosensible noire et dispositif d'affichage d'images présentant ladite composition WO2013027936A2 (fr)

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WO2018194262A1 (fr) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 Film optique d'amélioration du rapport de contraste, plaque polarisante le comprenant et appareil d'affichage à cristaux liquides le comprenant
KR20180116739A (ko) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR20190006820A (ko) * 2017-07-11 2019-01-21 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
CN113296358A (zh) * 2020-02-21 2021-08-24 东友精细化工有限公司 黑色感光性树脂组合物、黑矩阵及图像显示装置

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CN108137443B (zh) * 2015-07-31 2021-06-08 克美 芴衍生物、包含其的光聚合引发剂及光致抗蚀剂组合物
KR101832097B1 (ko) 2016-10-31 2018-02-23 롬엔드하스전자재료코리아유한회사 착색 감광성 수지 조성물 및 이로부터 제조된 차광성 스페이서
KR102383518B1 (ko) * 2018-02-06 2022-04-06 동우 화인켐 주식회사 흑색 감광성 수지 조성물, 이를 이용하여 제조된 화소정의막, 유기발광소자 및 화상 표시 장치
WO2021106221A1 (fr) * 2019-11-29 2021-06-03 昭和電工マテリアルズ株式会社 Composition durcissable aux ultraviolets pour protection contre la lumière, film de protection contre la lumière et procédé de fabrication d'un article comprenant un film de protection contre la lumière

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JP2001115043A (ja) * 1998-10-08 2001-04-24 Toppan Printing Co Ltd 着色組成物とその製法およびそれを用いたカラーフィルタ、電極基板および液晶表示装置
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WO2018194262A1 (fr) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 Film optique d'amélioration du rapport de contraste, plaque polarisante le comprenant et appareil d'affichage à cristaux liquides le comprenant
KR20180116739A (ko) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR102184231B1 (ko) * 2017-04-17 2020-11-27 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR20190006820A (ko) * 2017-07-11 2019-01-21 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR102063203B1 (ko) * 2017-07-11 2020-01-07 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
CN113296358A (zh) * 2020-02-21 2021-08-24 东友精细化工有限公司 黑色感光性树脂组合物、黑矩阵及图像显示装置

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