WO2018182127A1 - Composition de résine photosensible et filtre coloré et dispositif d'affichage d'image fabriqués au moyen de celle-ci - Google Patents

Composition de résine photosensible et filtre coloré et dispositif d'affichage d'image fabriqués au moyen de celle-ci Download PDF

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Publication number
WO2018182127A1
WO2018182127A1 PCT/KR2017/013588 KR2017013588W WO2018182127A1 WO 2018182127 A1 WO2018182127 A1 WO 2018182127A1 KR 2017013588 W KR2017013588 W KR 2017013588W WO 2018182127 A1 WO2018182127 A1 WO 2018182127A1
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WIPO (PCT)
Prior art keywords
resin composition
photosensitive resin
group
formula
cardo
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PCT/KR2017/013588
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English (en)
Korean (ko)
Inventor
김형주
강덕기
왕현정
Original Assignee
동우화인켐 주식회사
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Priority claimed from KR1020170040619A external-priority patent/KR101958414B1/ko
Priority claimed from KR1020170109527A external-priority patent/KR101840348B1/ko
Application filed by 동우화인켐 주식회사 filed Critical 동우화인켐 주식회사
Priority to JP2019551963A priority Critical patent/JP6934062B2/ja
Priority to CN201780088307.3A priority patent/CN110419002B/zh
Publication of WO2018182127A1 publication Critical patent/WO2018182127A1/fr

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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
    • G03F7/004—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
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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 photosensitive resin composition comprising specific scattering particles and an alkali-soluble resin, a color filter and an image display device manufactured using the same.
  • the color filter is a thin film type optical component that extracts three colors of red, green, and blue from white light and makes them possible in fine pixel units.
  • the size of one pixel is about tens to hundreds of micrometers.
  • Such a color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundary between each pixel, and a plurality of colors (typically red (R), green (G) and The pixel units in which the three primary colors of blue (B) are arranged in a predetermined order are stacked in this order.
  • color filters are used in various fields, including various image display devices, not only excellent pattern characteristics but also high color reproducibility and excellent performance such as high brightness and high contrast ratio are required.
  • a color filter manufacturing method using a self-luminous photosensitive resin composition is proposed.
  • Republic of Korea Patent Publication No. 2013-0000506 relates to a display device, a plurality of wavelength conversion particles for converting the wavelength of light; And a color converter including a plurality of color filter particles that absorb light having a predetermined wavelength in the light.
  • the efficiency of the color filter may be somewhat degraded as the efficiency of the quantum dot, in particular, the blue quantum dot is reduced, and in the case of the blue quantum dot, there is a problem that the overall manufacturing cost increases. .
  • Patent Document 1 Republic of Korea Patent Publication No. 2013-0000506 (2013.01.03.)
  • An object of this invention is to provide the photosensitive resin composition which can prevent the fall of the efficiency of a blue pixel, and can lower manufacturing cost.
  • the present invention is to provide a color filter and an image display device including a blue pixel layer manufactured using the photosensitive resin composition described above. Specifically, the present invention is to provide a color filter and an image display device excellent in image quality, viewing angle, durability, reliability.
  • the photosensitive resin composition according to the present invention for achieving the above object is an alkali-soluble resin; And scattering particles comprising a metal oxide having an average particle diameter of 30 to 500 nm; wherein the alkali-soluble resin comprises a first cardo-based binder resin and a compound represented by the following Chemical Formula 2, including the compound represented by the following Chemical Formula 1. It characterized in that it comprises at least one selected from the group consisting of a second cardo-based binder resin to be polymerized.
  • R1 and R2 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms
  • R4 and R5 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms.
  • the present invention provides a color filter made of the photosensitive resin composition described above and an image display device including the same.
  • the photosensitive resin composition of this invention has the advantage that provision of the outstanding color reproduction characteristic and light efficiency is possible.
  • the color filter made of the photosensitive resin composition of the present invention and an image display device including the same can ensure high quality image quality, excellent viewing angle, high durability, and reliability, and can reduce manufacturing cost.
  • a member when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.
  • alkali-soluble resin comprising a first cardo-based binder resin and a compound represented by the following Chemical Formula 2, including the compound represented by the following Chemical Formula 1.
  • the alkali-soluble resin comprises a first cardo-based binder resin and a compound represented by the following Chemical Formula 2, including the compound represented by the following Chemical Formula 1.
  • a photosensitive resin composition comprising at least one selected from the group consisting of a second cardo-based binder resin to be polymerized, including.
  • R1 and R2 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms
  • R4 and R5 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms.
  • the photosensitive resin composition of the present invention is selected from the group consisting of a first cardo-based binder resin that is polymerized including a compound represented by the following Formula 1 and a second cardo-based binder resin that is polymerized including a compound represented by the following Formula 2 It includes one or more.
  • R1 and R2 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms
  • R4 and R5 are each independently
  • X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms.
  • the alkali-soluble resin has reactivity and alkali solubility by the action of light or heat.
  • the alkali-soluble resin may act as a binder resin for scattering particles, and may be soluble in an alkaline developer used in a developing step for manufacturing a color filter.
  • the alkali-soluble resin according to the present invention includes the first cardo-based binder resin polymerized by including the compound represented by the following Chemical Formula 1, thereby improving adhesion to the substrate and excellent development adhesion, thereby realizing a fine pattern for high resolution. There is an advantage to that.
  • R1 and R2 are each independently
  • X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably X is a hydroxyl group
  • R 3 is a hydrogen atom or a methyl group.
  • the compound represented by Chemical Formula 1 may be synthesized using Chemical Formula 5 below, and the first cardo-based binder resin having alkali solubility may be obtained by further reacting an acid anhydride or an acid 2 anhydride compound.
  • the compound represented by Chemical Formula 5 is mixed with epichlorohydrin and t-butylammonium bromide, heated and reacted with a solvent, followed by dropwise addition of an aqueous alkali solution, precipitation and separation to synthesize an epoxy compound, and synthesis.
  • the resulting epoxy compound by reacting it with t-butylammonium bromide, acrylic acid, phenolic compound and solvent, and an acid anhydride, maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, anhydride.
  • hexahydrophthalic acid methyl endomethylenetetrahydrophthalic anhydride, chloric anhydride, methyltetrahydrophthalic anhydride or acid anhydride, pyromellitic anhydride, benzophenonetetracarboxylic acid anhydride, biphenyltetracarboxylic acid anhydride, biphenyl Aromatic polyhydric acids such as phenyl ether tetracarboxylic acid dianhydride It can be prepared by reacting at least one member selected from the group consisting of acids anhydride, but are not limited to this.
  • the alkali-soluble binder resin according to the present invention includes a second cardo-based binder resin polymerized by including the compound of the formula (2), thereby improving the adhesion to the substrate, excellent development adhesion and fine patterns for high resolution Enable to implement
  • R4 and R5 are each independently,
  • X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group
  • R6 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably X is a hydroxyl group
  • R6 is a hydrogen atom or a methyl group.
  • the compound represented by Chemical Formula 2 may be synthesized using the following Chemical Formula 6, and the second cardo-based binder resin having alkali solubility may be obtained by further reacting an acid anhydride or an acid 2 anhydride compound.
  • the compound represented by Chemical Formula 6 is mixed with epichlorohydrin, t-butylammonium bromide and a solvent, and then reacted by heating together, an aqueous alkali solution is added dropwise, precipitated and separated to synthesize an epoxy compound, and then synthesized.
  • the resulting epoxy compound by reacting it with t-butylammonium bromide, acrylic acid, phenolic compound and solvent, and an acid anhydride, maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, anhydride.
  • the position of the hydroxyl group (-OH) in the above formulas (5) and (6) is not particularly limited, and for example, may be 2-position, 3-position, and 4-position, and preferably 4-position (positioning is xanthene). And determine the carbon bonded to 1-top).
  • More specific examples of the compound represented by Formula 1 include 9,9-bis (3-cinnamic diester) fluorene, 9,9-bis ( 3-cinnamoyl, 4-hydroxyphenyl) fluorene (9,9-bis (3-cinnamoyl, 4-hydroxyphenyl) fluorene), 9,9-bis (glycidyl methacrylate ether) fluorene (9, 9-bis (glycidyl methacrylate ether) fluorene, 9,9-bis (3,4-dihydroxyphenyl) fluorene disinnamic ester, 3,4-dihydroxyphenyl) fluorene dicinnamic ester , 6-diglycidyl methacrylate ether spiro (fluorene-9,9-xanthene) (3,6-diglycidyl methacrylate ether spiro (fluorene-9,9-xanthene)), 9,9-bis (3- Allyl, 4-hydroxyphenylfluor
  • More specific examples of the compound represented by Formula 2 include 9,9-bis (3,4-methacrylic diester) xanthene, but are not limited thereto.
  • the acid value of the alkali-soluble binder resin may be 20 to 200 mgKOH / g, preferably 30 to 150 mgKOH / g.
  • the solubility in the developing solution is improved, so that the non-exposed part is easily dissolved and the sensitivity is increased, and as a result, the pattern of the exposed part remains at the time of development to improve the film remaining ratio. .
  • acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of an acrylic polymer, and can be obtained by titration using an aqueous potassium hydroxide solution.
  • the polystyrene reduced weight average molecular weight (hereinafter, simply referred to as 'weight average molecular weight') measured by gel permeation chromatography (GPC; tetrahydrofuran as an eluting solvent) is 2,000 to 200,000, preferably 3,000 to 100,000. Alkali-soluble resins are preferred.
  • the molecular weight is in the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility of the non-exposed portion in the developer is excellent and the resolution tends to be improved, which is preferable.
  • the said alkali-soluble resin it is preferable that it is 1.0-6.0, and, as for the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the said alkali-soluble resin, it is more preferable that it is 1.5-6.0.
  • the cardo-based binder resin is included in 1 to 50 parts by weight, preferably 5 to 40 parts by weight, more preferably 5 to 30 parts by weight based on 100 parts by weight of the total photosensitive resin composition. Can be.
  • the solubility in a developing solution is sufficient so that development residues are less likely to occur on the substrate of the non-pixel portion, and it is difficult to reduce the film portion of the pixel portion of the exposed portion during development. It is preferable because there is an advantage that the omission property tends to be good.
  • the alkali-soluble resin may further include a cardo-based binder resin comprising at least one repeating unit of the following formula (3) and (4).
  • R7 and R8 are each independently hydrogen, hydroxy group, thiol group, amino group, nitro group or halogen atom,
  • Ar1 is each independently a C6 to C15 aryl group
  • Y is an acid anhydride residue
  • Z is an acid 2 anhydride residue
  • A is O, S, N, Si or Se
  • a and b are each independently an integer of 1 to 6,
  • n are each independently an integer of 0 to 30,
  • the halogen atom F, Cl, Br or I The halogen atom F, Cl, Br or I.
  • the aryl group may be a C6 to C15 monocyclic aryl group, or a polycyclic aryl group.
  • the monocyclic aryl group may be a phenyl group, biphenyl group, terphenyl group, stilbenyl group and the like, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • Y in Formula 3 is a residue of an acid anhydride, and an acid anhydride capable of introducing residue Y is not particularly limited.
  • an acid anhydride capable of introducing residue Y is not particularly limited.
  • Hydrophthalic acid methylene anhydride, methylenetetrahydrophthalic acid, chlororenic acid anhydride, methyltetrahydrophthalic anhydride, and the like can be given.
  • Z in the formula (4) is a residue of the acid 2 anhydride
  • acid 2 anhydride compound that can introduce the residue Z is not particularly limited, for example, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, biphenyltetracarboxylic acid Dianhydride, bitenyl ether tetracarboxylic acid dianhydride, cyclohexyl dianhydride, cyclobutyl acid dianhydride, and the like.
  • the cardo-based binder resin according to the present invention is included in the photosensitive resin composition, there is an advantage that the light emission intensity, the diffusion rate and the external light reflectance may have more excellent effects.
  • the alkali-soluble resin further comprises a cardo-based binder resin including at least one repeating unit selected from the group consisting of Formula 3 and Formula 4
  • the cardo-based binder resin is 100 parts by weight of the total alkali-soluble resin. 1 to 50 parts by weight, preferably 5 to 40 parts by weight, and more preferably 5 to 30 parts by weight.
  • the cardo-based binder resin which may be further included, is included in the above range, the light emission intensity, the diffusion rate, and the external light reflectance may be more excellent.
  • the cardo-based binder resin including at least one repeating unit of Formulas 3 and 4 may be prepared by, for example, the following method.
  • a cardo-based binder resin including at least one repeating unit of Formulas 3 and 4 may be obtained by polymerizing a compound represented by Formulas 12 to 16 with carboxylic dianhydride.
  • A, R7, and R8 are as defined in Formulas 3 and 4.
  • A, Ar1, R7 and R8 are as defined in the formulas (3) and (4).
  • carboxylic dianhydride examples include pyromellitic dianhydride, 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride, and 2,3,3', 4'-biphenyltetracarboxylic dianhydride , 2,2 ', 3,3'-biphenyltetracarboxylic dianhydride, 3,3', 4,4'-benzophenonetetracarboxylic dianhydride, 2,2 ', 3,3'-benzo Phenonetetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1-bis ( 3,4-dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphen
  • the polymerization reaction may be performed at 100 to 130 ° C., or 110 to 120 ° C. for 2 hours to 24 hours, or 4 hours to 12 hours.
  • the carboxylic dianhydride may be added in an amount of 5 to 40 parts by weight, 10 to 30 parts by weight, or 10 to 20 parts by weight based on 100 parts by weight of the monomer represented by Formula 12 to 16, for example.
  • the method for preparing a cardo-based binder resin including at least one repeating unit of Chemical Formulas 3 and 4 may include, for example, reacting by adding an end-capping agent after initiation of the polymerization reaction. have.
  • the end capping reaction may be performed at 100 to 130 ° C., or 110 to 120 ° C. for 30 minutes to 4 hours, or 1 hour to 3 hours, for example.
  • the end capping agent may be added in an amount of 2 to 10 parts by weight, 2 to 5 parts by weight, or 3 to 5 parts by weight based on 100 parts by weight of the monomer represented by Formula 12 to 16, for example.
  • the end capping agent is preferably aromatic carboxylic anhydride, for example, phthalic anhydride, and the like, and in this case, excellent heat resistance, high permeability, and high refractive properties.
  • the weight average molecular weight of the cardo-based binder resin including at least one repeating unit of Formula 3 and Formula 4 is, for example, 1,000 to 100,000 g / mol, preferably 2,000 to 50,000 g / mol, more preferably 3,000 to It may be 10,000 g / mol, it is excellent in heat resistance within this range and the development speed of the photosensitive material and the development by the developing solution is suitable, there is an effect that the pattern formation is good.
  • the weight average molecular weight can be measured by gel permeation chromatography (GPC) method.
  • the degree of dispersion of the cardo-based binder resin resin including at least one repeating unit of Formulas 3 and 4 may be in the range of 1.0 to 5.0, preferably 1.5 to 4.0, and has excellent heat resistance within this range. And the development speed of the photosensitive material and the development by the developer is suitable, there is an effect that the pattern formation is good.
  • the dispersion degree of this description can be measured by GPC measuring method.
  • the alkali-soluble resin may further include an acrylic binder resin.
  • the alkali-soluble resin further includes the acrylic binder resin, it is preferable because the size of the minimum pattern that can be formed without loss of the pattern is small, which has advantages of high-resolution pattern implementation and pattern straightness.
  • acrylic binder resin examples include a carboxyl group-containing monomer and a copolymer with another monomer copolymerizable with the monomer.
  • unsaturated carboxylic acids such as unsaturated monocarboxylic acid, unsaturated polyhydric carboxylic acid, such as unsaturated polycarboxylic acid which has 1 or more carboxyl groups in molecules, such as unsaturated dicarboxylic acid and unsaturated tricarboxylic acid, are mentioned, for example.
  • unsaturated monocarboxylic acid acrylic acid, methacrylic acid, crotonic acid, (alpha)-chloroacrylic acid, cinnamic acid etc. are mentioned, for example.
  • unsaturated dicarboxylic acid a maleic acid, a fumaric acid, itaconic acid, a citraconic acid, a mesaconic acid, etc. are mentioned, for example.
  • the unsaturated polyhydric carboxylic acid may be an acid anhydride, and specific examples thereof include maleic anhydride, itaconic anhydride and citraconic anhydride.
  • the unsaturated polyhydric carboxylic acid may be mono (2-methacryloyloxyalkyl) ester thereof, for example, succinic acid mono (2-acryloyloxyethyl), succinic acid mono (2-methacryloyloxyethyl ), Mono (2-acryloyloxyethyl) phthalate, mono (2-methacryloyloxyethyl) phthalate, etc. are mentioned.
  • the unsaturated polyhydric carboxylic acid may be mono (meth) acrylate of the sock end dicarboxy polymer, and examples thereof include? -Carboxypolycaprolactone monoacrylate and? -Carboxypolycaprolactone monomethacrylate. .
  • These carboxyl group-containing monomers can be used individually or in mixture of 2 or more types, respectively.
  • styrene (alpha) -methylstyrene, o-vinyl toluene, m-vinyl toluene, p-vinyl toluene, p-chloro styrene, o-methoxy styrene, m-meth Oxy styrene, p-methoxy styrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p- Aromatic vinyl compounds such as vinyl benzyl glycidyl ether and indene; Methyl acrylate, methyl methyl styrene, o-vinyl toluene, m-
  • Unsaturated carboxylic acid esters 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethyl Unsaturated carboxyl such as aminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate Acid aminoalkyl esters; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Un
  • Unsaturated imides such as N-cyclohexylmaleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; And monoacryloyl or monomethacryloyl groups at the terminal of the polymer molecular chain of polystyrene, polymethylacrylate, polymethylmethacrylate, poly-n-butylacrylate, poly-n-butylmethacrylate, polysiloxane. And macromonomers to have. These monomers can be used individually or in mixture of 2 or more types, respectively.
  • bulky monomers such as monomers having a norbornyl skeleton, monomers having an adamantane skeleton, and monomers having a rosin skeleton as the other monomers copolymerizable with the carboxyl group-containing monomer are preferable because they tend to lower the dielectric constant.
  • the acrylic binder resin may be included, for example, in an amount of 10 to 90 parts by weight, preferably 20 to 80 parts by weight, more preferably 30 to 70 parts by weight, based on 100 parts by weight of the alkali-soluble resin in total, in this case Fairness, such as implementation and pattern straightness, is advantageous.
  • the content of the alkali-soluble resin is usually in the range of 1 to 50 parts by weight, preferably 3 to 40 parts by weight, and still more preferably 5 to 30 parts by weight based on 100 parts by weight of the total photosensitive resin composition.
  • the solubility in a developing solution is sufficient so that development residues are less likely to occur on the substrate of the non-pixel portion, and the film portion of the pixel portion of the exposed portion is less likely to occur during development. Since the omission of a part tends to be good, it is preferable.
  • the photosensitive resin composition according to the present invention includes scattering particles containing a metal oxide having an average particle diameter of 30 to 500 nm.
  • the metal oxide is Li, Be, B, Na, Mg, Al, Si, K, Ca, Sc, V, Cr, Mn, Fe, Ni, Cu, Zn, Ga, Ge, Rb, Sr, Y, Mo, Cs, Ba, La, Hf, W, Tl, Pb, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, It may include one or more oxides selected from the group consisting of Ti, Sb, Sn, Zr, Nb, Ce, Ta, In and combinations thereof.
  • the metal oxide is Al 2 O 3 , SiO 2 , ZnO, ZrO 2 , BaTiO 3 , TiO 2 , Ta 2 O 5 , Ti 3 O 5 , ITO, IZO, ATO, ZnO It may include one or more selected from the group consisting of -Al, Nb 2 O 3 , SnO, MgO and combinations thereof, and a material surface-treated with a compound having an unsaturated bond such as acrylate may be used if necessary. .
  • the scattering particles limit the content in the average particle diameter and the total composition to maximize the light emission intensity of the color filter.
  • the "average particle diameter” may be a number average particle diameter, and can be obtained from an image observed by, for example, a field emission runner electron microscope (FE-SEM) or a transmission electron microscope (TEM). Specifically, several samples can be extracted from the observed images of FE-SEM or TEM, and the diameters of these samples can be measured to obtain arithmetic mean values.
  • FE-SEM field emission runner electron microscope
  • TEM transmission electron microscope
  • the metal oxide has an average particle diameter of 30 to 500 nm, preferably 30 to 300 nm.
  • the average particle diameter of the metal oxide satisfies the above range, the scattering effect is increased, and even though the photosensitive resin composition including the scattering particles does not include blue quantum dots, the blue oxide may serve as a blue pixel. Since the phenomenon which sinks in a composition can be prevented and the surface of a blue pattern layer of uniform quality can be obtained, it can adjust and use it suitably within the said range.
  • the scattering particles may be included in an amount of 0.1 to 50 parts by weight, preferably 0.5 to 30 parts by weight, more preferably 0.5 to 100 parts by weight of the total photosensitive resin composition. To 20 parts by weight.
  • the scattering particles are included in the above range, there is an advantage in that a color filter having excellent emission intensity can be manufactured.
  • the scattering particles when the scattering particles are included in the above range, it may be easy to ensure the emission intensity to be obtained, there is an advantage that can suppress the degradation of the composition stability.
  • the photosensitive resin composition of this invention may further contain a blue coloring agent. Since the photosensitive resin composition according to the present invention further includes a blue colorant, the light of the light source reflected by the scattering particles, which will be described later, may be prevented from being reflected back by external light such as sunlight, thereby realizing high quality images. There is this.
  • the blue colorant may specifically include a blue pigment, and the blue pigment may specifically include a compound classified as a pigment in the color index (published by The society of Dyers and Colourists). Although the pigment of the same color index (CI) number is mentioned, It is not necessarily limited to these.
  • the blue colorant is C.I. Pigment Blue 15: 3, 15: 4, 15: 6, 16, 21, 28, 60, 64, 76 and at least one blue pigment selected from the group consisting of a combination thereof; may include.
  • C.I. Pigment Blue 15: 3 C.I. Pigment Blue 15: 4, Pigment Blue 15: 6, C.I. It is preferable to include at least one member selected from the group consisting of Pigment Blue 16 in view of the effect of suppressing external light reflection and high color reproducibility.
  • the blue colorant may further include one or more selected from the group consisting of dyes and purple pigments.
  • the purple pigment is not limited thereto, for example, C.I. Pigment violet 1, 14, 19, 23, 29, 32, 33, 36, 37, 38, and combinations thereof, and at least one selected from the group consisting of C.I. It is preferable to use pigment violet 23 in view of realizing high color reproducibility even through a small colorant content.
  • the dye may include a compound classified as a dye in the color index (Published by The Society of Dyers and Colourists) or a known blue or purple dye described in a dye note (color dyed yarn).
  • C.I. Solvent blue 35, 36, 44, 45 and 70; And C.I. It is preferred to include at least one member selected from the group consisting of solvent violet 13.
  • the said dye can be used individually or in combination of 2 or more types, respectively.
  • the blue colorant may be included in 0.1 to 50 parts by weight, preferably 0.5 to 30 parts by weight, more preferably 1 to 20 parts by weight based on 100 parts by weight of the total photosensitive resin composition. have.
  • the content of the blue colorant is less than the above range, it may be difficult to secure the external light reflection suppression effect to be obtained, on the contrary, when the content exceeds the above range, the increase in luminescence intensity may be slightly lowered, and the problem of lowering the viscosity stability of the composition may occur. Since it arises, it uses suitably within the said range.
  • the photosensitive resin composition is a photopolymerizable compound; Photopolymerization initiator; solvent; And it may further include one or more selected from the group consisting of additives.
  • the photopolymerizable compound contained in the photosensitive resin composition of this invention is a compound which can superpose
  • monofunctional monomers include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinyl py. A ralidone etc. are mentioned.
  • polyfunctional monomers include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, Dipentaerythritol hexa (meth) acrylate and the like.
  • bifunctional or higher polyfunctional monomers are preferably used.
  • the photopolymerizable compound is used in the range of 1 to 30 parts by weight, preferably 5 to 20 parts by weight based on 100 parts by weight of the total photosensitive resin composition.
  • the photopolymerizable compound satisfies the above range, the intensity and smoothness of the pixel portion tend to be good, which is preferable.
  • the said photoinitiator used by this invention contains an acetophenone type compound.
  • 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-morpholinopropane-1 -One, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl [4- (1-methylvinyl) phenyl] propane-1 Oligomer of -one, etc. are mentioned, Preferably 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one etc. are mentioned.
  • Photoinitiators other than the said acetophenone series can be used in combination.
  • Photopolymerization initiators other than the acetophenone series include active radical generators, sensitizers, and acid generators that generate active radicals by irradiation with light.
  • a benzoin type compound As said active radical generating agent, a benzoin type compound, a benzophenone type compound, a thioxanthone type compound, a triazine type compound, etc. are mentioned, for example.
  • benzoin type compound benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoisobutyl ether, etc. are mentioned, for example.
  • benzophenone type compound for example, benzophenone, methyl o-benzoyl benzoate, 4-phenylzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 2,4, 6-trimethyl benzophenone, etc. are mentioned.
  • thioxanthone type compound 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro, for example 4-propoxy city oxanthone etc. are mentioned.
  • Examples of the active radical generator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2, -bis (o-chlorophenyl) -4,4 ', 5,5'-tetra Phenyl-1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene Compounds and the like can be used.
  • Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate and 4-acetoxyphenyldimethylsulfonium p-toluenesulfo.
  • a triazine photopolymerization initiator is also used as an acid generator.
  • Content of the said photoinitiator used for the photosensitive resin composition which concerns on this invention is 0.1-40 weight part normally with respect to the total amount of the said alkali-soluble resin and the said photopolymerizable compound based on 100 weight part of solid content whole, Preferably it is 1-30. Parts by weight.
  • photoinitiator start adjuvant can be used.
  • the said photoinitiator adjuvant may be used in combination with the said photoinitiator, and is a compound used in order to accelerate superposition
  • An amine compound, an alkoxy anthracene type compound, a thioxanthone type compound etc. are mentioned as said photoinitiator starting adjuvant.
  • Examples of the amine compound include triethanolamine, methyl diethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylamino benzoic acid.
  • Ethyl, 2-ethylhexyl 4-dimethylaminobenzoic acid, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzphenone (commonly known as Michler's ketone), 4,4'-bis (diethyl Amino) benzophenone, 4, 4'-bis (ethylmethylamino) benzophenone, etc. are mentioned, Among these, 4,4'-bis (diethylamino) benzophenone is preferable.
  • an alkoxy anthracene type compound 9,10- dimethoxy anthracene, 2-ethyl-9,10- dimethoxy anthracene, 9,10- diethoxy anthracene, 2-ethyl-9, 10- diethoxy anthracene, for example.
  • Etc. can be mentioned.
  • a thioxanthone type compound 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro- 4-propoxy city oxanthone etc. are mentioned.
  • photoinitiators (D) may be used alone or in combination of a plurality thereof.
  • a commercially available thing can be used as a photoinitiator starter,
  • brand name "EAB-F” manufactured by Hodogaya Chemical Co., Ltd.
  • EAB-F manufactured by Hodogaya Chemical Co., Ltd.
  • the amount thereof is usually 10 mol or less, preferably 0.01 to 5 mol, per mol of the photopolymerization initiator. If it exists in the said range, since the sensitivity of the said photosensitive resin composition becomes higher and the productivity of the color filter formed using this composition tends to improve, it is preferable.
  • the solvent contained in the photosensitive resin composition of this invention is not specifically limited, Various organic solvents used in the field of the photosensitive resin composition can be used. Specific examples thereof 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, diethylene glycol diethyl 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, diethylene glycol diethyl ether, and diethylene.
  • Diethylene glycol dialkyl ethers such as glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, and propylene glycol Alkylene glycol alkyl ether acetates such as monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxy butyl acetate and methoxy pentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, methyl ethyl ketone, acetone , Ketones such as methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cycl
  • organic solvents having a boiling point of 100 ° C. to 200 ° C. in the coating properties and drying properties are preferable, and alkylene glycol alkyl ether acetates, ketones, and 3-ethoxy are more preferable.
  • Ester such as ethyl propionate and the methyl 3-methoxy propionate, is mentioned, More preferably, propylene glycol monomethyl ether acetate, a propylene glycol monoethyl ether acetate, cyclohexanone, 3-ethoxy propionate, 3- Methyl methoxy propionate etc. are mentioned.
  • the said solvent can be used individually or in mixture of 2 or more types, respectively.
  • Content of the said solvent in the photosensitive resin composition of this invention is 60-90 weight part normally with respect to 100 weight part of whole said photosensitive resin composition containing it, Preferably it is 70-85 weight part.
  • a coating device such as a roll coater, spin coater, slit and spin coater, slit coater (sometimes referred to as die coater), inkjet, or the like. It is preferable because there is.
  • the photosensitive resin composition of this invention is a filler, another high molecular compound, a pigment dispersant as needed. It is also possible to use additives, such as an adhesion promoter, an antioxidant, a ultraviolet absorber, and an aggregation inhibitor.
  • the filler include glass, silica, alumina and the like.
  • the other polymer compound include curable 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.
  • curable 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.
  • 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.
  • polyoxyethylene alkyl ether for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl peer ether, polyethyleneglycol diester, sorbitan fatty acid ester, fatty acid modified polyester, tertiary amine modified polyurethane , Polyethylenimine, etc.
  • trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products), MEGAFAC (manufactured by Dainippon Ink Chemical Industries, Ltd.), Florard (manufactured by Sumitomo 3M), Asahi guard, Surflon (above, manufactured by Asahi Glass), Sol SLSPERSE (made by Genka Corporation), EFKA (made by EFKA Chemicals), PB 821 (made by Ajinomoto Co., Ltd.), etc.
  • adhesion promoter for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminoprotriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2 -(3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyl Trimethoxysilane etc.
  • antioxidant examples include 2,2'-thiobis (4-methyl-6-t-butylphenol), 2,6-di-t-butyl-4-methylphenol, and the like.
  • ultraviolet absorber examples include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole, alkoxybenzophenone and the like.
  • aggregation inhibitor examples include sodium polyacrylate and the like.
  • the additive may be used by those skilled in the art in addition to an appropriate amount within the scope that does not impair the effects of the present invention.
  • the method of preparing the photosensitive resin composition is not limited thereto, and for example, the photosensitive resin composition may be prepared by the following method.
  • the scattering particles are mixed with the solvent in advance and dispersed using a bead mill or the like until the average particle diameter becomes 30 to 500 nm.
  • a dispersing agent can be further used as needed, and some or all of alkali-soluble resin may be mix
  • the remainder of alkali-soluble resin, a photopolymerizable compound, a photoinitiator, the other components used as needed, and the additional solvent as needed are further added to the obtained dispersion liquid (henceforth a mill base) so that it may become a predetermined concentration. To obtain the desired photosensitive resin composition.
  • Another aspect of the present invention relates to a self-luminous pixel-containing color filter comprising a blue pattern layer containing a cured product of the photosensitive resin composition described above.
  • the photosensitive resin composition may be a photosensitive resin composition for forming a blue pattern layer.
  • the said photosensitive resin composition does not contain a quantum dot.
  • the color filter according to the present invention is made of the photosensitive resin composition described above instead of blue quantum dots, the manufacturing cost can be lowered, and there is an advantage of having an excellent viewing angle.
  • the color filter includes a substrate and a blue pattern layer formed on the substrate.
  • the substrate may be the substrate of the color filter itself, or may be a portion where the color filter is positioned in a display device or the like, and is not particularly limited.
  • the substrate may be glass, silicon (Si), silicon oxide (SiOx), or a polymer substrate, and the polymer substrate may be polyethersulfone (PES) or polycarbonate (PC).
  • the blue pattern layer is a layer including the photosensitive resin composition of the present invention, and may be a layer formed by applying the photosensitive resin composition and exposing, developing, and thermosetting in a predetermined pattern, and the pattern layer is commonly known in the art. It can form by performing a method.
  • the color filter may further include one or more selected from the group consisting of a red pattern layer and a green pattern layer.
  • the color filter according to the present invention may include the above-described blue pattern layer, and may further include a self-luminous pixel further comprising at least one selected from the group consisting of a red pattern layer and a green pattern layer.
  • the red pattern layer or the green pattern layer may include quantum dots and scattering particles.
  • the color filter according to the present invention may include a red pattern layer including a red quantum dot or a green pattern layer including a green quantum dot, and the red pattern layer or the green pattern layer may include scattering particles.
  • the red pattern layer or the green pattern layer may emit red light or blue light, respectively, by a light source emitting blue light, which will be described later.
  • the scattering particles may include a metal oxide having an average particle diameter of 30 to 500 nm, and the content of the scattering particles and the metal oxide may be applied to the content of the scattering particles and the metal oxide included in the photosensitive resin composition according to the present invention. Can be.
  • the shape, configuration, and content of the quantum dots included in the red pattern layer or the green pattern layer are not limited, and quantum dots commonly used in the art may be applied.
  • the color filter including the substrate and the pattern layer may further include a partition formed between each pattern, and may further include a black matrix, but is not limited thereto.
  • the above-described color filter And a light source emitting blue light.
  • the image display apparatus includes a color filter including a blue pattern layer including a cured product of the photosensitive resin composition described above, and a light source emitting blue light.
  • the color filter of the present invention can be applied to various image display devices such as electroluminescent display devices, plasma display devices, field emission display devices, as well as ordinary liquid crystal display devices.
  • the image display device includes a color filter including a blue pattern layer and the light source according to the present invention
  • a color filter including a blue pattern layer and the light source according to the present invention there is an advantage of having excellent light emission intensity or viewing angle.
  • the blue pattern layer included in the color filter according to the present invention does not include blue quantum dots, there is an advantage in that an image display device having low manufacturing cost can be manufactured.
  • a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping lot, and a nitrogen introduction tube was prepared, and as a monomer dropping lot, 74.8 g (0.20 mole) of benzylmaleimide, 43.2 g (0.30 mole) of acrylic acid, and vinyltoluene 118.0 g (0.50 mol), 4 g of t-butylperoxy-2-ethylhexanoate and 40 g of propylene glycol monomethyl ether acetate (PGMEA) were added thereto, followed by stirring and mixing.
  • PGMEA propylene glycol monomethyl ether acetate
  • n-dodecanethiol 6g and PGMEA24g were added, and the thing mixed with stirring was prepared. Thereafter, 395 g of PGMEA was introduced into the flask, and the atmosphere in the flask was changed to nitrogen from air, followed by stirring, thereby raising the temperature of the flask to 90 ° C. Subsequently, dropping of the monomer and the chain transfer agent was started from the dropping lot. The dropwise addition was performed for 2 h while maintaining 90 ° C., and after 1 h, the temperature was raised to 110 ° C. and maintained for 3 h.
  • the temperature was melt
  • the temperature was heated to 120 ° C. to completely dissolve it.
  • the acid value was measured and stirred until the acid value was less than 1.0 mgKOH / g. It took 11 hours to reach the target (0.8).
  • the temperature of the reactor was lowered to room temperature to obtain a colorless transparent compound of formula (2).
  • HLC-8120GPC manufactured by Tosoh Corporation
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • Photopolymerizable Compound (C) dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
  • the color filter was manufactured using the photosensitive resin composition manufactured according to the said Example and the comparative example. That is, each of the photosensitive resin composition was applied on a glass substrate by spin coating, and then placed on a heating plate and maintained at a temperature of 100 ° C. for 3 minutes to form a thin film.
  • test photomask having a transmissive pattern of horizontal ⁇ vertical 20 mm ⁇ 20 mm squares and a line / space pattern of 1 to 100 ⁇ m was placed on the thin film, and ultraviolet rays were irradiated with a distance of 100 ⁇ m from the test photomask.
  • the ultraviolet light source was irradiated with an exposure amount (365 nm) of 200 mJ / cm 2 under an atmospheric atmosphere using an ultrahigh pressure mercury lamp (trade name USH-250D) manufactured by Ushio Denki Co., Ltd., and no special optical filter was used.
  • an ultrahigh pressure mercury lamp (trade name USH-250D) manufactured by Ushio Denki Co., Ltd., and no special optical filter was used.
  • the thin film irradiated with ultraviolet rays was developed by soaking for 80 seconds in a KOH aqueous solution developing solution of pH 10.5.
  • the thin film coated glass plate was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 150 ° C. for 10 minutes to prepare a color filter pattern.
  • the film thickness of the color pattern prepared above was 5.0 ⁇ m.
  • Sensitivity The degree of formation of a flawless thin film of the sensitivity mask fine pattern (1 to 60) (the lower the value, the better the sensitivity).
  • Pattern Stability Pattern error after exposure of pattern mask at low exposure amount (20-100mJ)
  • Solvent resistance evaluation The color filter prepared above is immersed in solvent NMP (1-methyl- 2-pyrrolidinone) for 30 minutes, and the color change before and after evaluation is calculated and compared.
  • the equation used at this time is calculated by the following equation (1) representing the color change in the three-dimensional colorimeter defined by L * , a * , b * .
  • Heat resistance evaluation The color filter manufactured by the above method was calculated by Equation (1) to measure the color change before and after heating after heating for 2 hours in a heating oven at 230 °C.
  • the size of the pattern which was obtained through a line / space pattern mask designed to 100 ⁇ m among color filters manufactured using the photosensitive resins according to the above examples and comparative examples, was measured by OM equipment (ECLIPSE LV100POL Nikon). . The measurement results are shown in Table 10.
  • a negative value means a threshold value that causes a process defect.
  • Example 1 Developing speed Sensitivity Pattern stability Fine pattern Heat resistance Solvent resistance
  • Example 2 29 9 ⁇ 12 ⁇ ⁇ Example 3 28 9 ⁇ 11 ⁇ ⁇ Example 4
  • 30 8 ⁇ 6 ⁇ ⁇ Example 5 30 12 ⁇ 2 ⁇ ⁇ Example 6 27 14 ⁇ 12 ⁇ ⁇ Example 7 23 12 ⁇ 10 ⁇ ⁇ Example 8 19 11 ⁇ 13 ⁇ ⁇ Example 9 25 9 ⁇ 8 ⁇ ⁇ Example 10 21 12 ⁇ 11 ⁇ ⁇ Example 11 28 11 ⁇ 9 ⁇ ⁇ Example 12 29 8 ⁇ 10 ⁇ ⁇ Example 13 25 12 ⁇ 8 ⁇ ⁇ Example 14 23 9 ⁇ 6 ⁇ ⁇ Example 15 21 13 ⁇ 10 ⁇ ⁇ Example 16 16 14 ⁇ 9 ⁇ ⁇ Example 17 28 9 ⁇ 8 ⁇ ⁇ Example 18 27 11 ⁇ 7 ⁇ ⁇ Example 19 30 10 ⁇ 6 ⁇ ⁇ Example 20 28 11 ⁇ 7 ⁇ ⁇ Example 21 27 13 ⁇ 10 ⁇ ⁇ Example 22 28 10 ⁇ 14 ⁇ 14 ⁇
  • the optical intensity according to the viewing angle under the transmissive conditions was formed on the portion formed in the pattern of 20 ⁇ 20 mm square among the color filters manufactured using the photosensitive resin compositions prepared according to the above Examples and Comparative Examples (GC-5000L, Nippon). Denshoku) was used, and the diffusion rate was calculated using the following equation (2).
  • the measurement results are shown in Table 11.
  • I means light intensity measured at the viewing angle.
  • Spectrophotometer CM- was used to measure the light reflectance under light-transmitting conditions on the portion formed in the pattern of 20 ⁇ 20 mm square in the color filter manufactured using the photosensitive resin composition prepared according to Examples 22 to 46 and Comparative Examples 5 to 10. It was measured using 3600A (Konica Minolta Co., Ltd.) and the measurement results are shown in Table 8.
  • Example 1 28500 20.5 - Example 2 34700 43.5 - Example 3 31800 78.3 - Example 4 29800 78.1 - Example 5 28200 84.3 - Example 6 31300 53.5 - Example 7 26500 78.9 - Example 8 23900 48.6 - Example 9 36500 48.6 - Example 10 28500 82.1 - Example 11 34800 33.6 - Example 12 30800 78.1 - Example 13 27800 82.1 - Example 14 34200 51.3 - Example 15 31300 72.6 - Example 16 26500 74.9 - Example 17 21900 43.5 - Example 18 36500 49.7 - Example 19 25900 80.7 - Example 20 38600 42.1 - Example 21 271960 44.8 - Example 22 28500 20.5 3.1 Example 23 34700 43.5 3.8 Example 24 31800 78.3 2.8 Example 25 29800 78.1 2.6 Example 26 28200 84.3 2.7 Example 27 31300 53.5 3.6 Example 28 26500 78.9 3.8 Example 29 23900 48.6
  • the scattering particles of the metal oxide was found that the viewing angle is improved compared to the comparative example in the case of using the scattering particles of the metal oxide 30 to 500 nm average particle diameter.

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Abstract

Une composition de résine photosensible selon la présente invention comprend : une résine soluble en milieu alcalin ; et des particules de diffusion ayant un diamètre de particule moyen de 30 à 500 nm et comprenant un oxyde métallique. La résine soluble en milieu alcalin comprend l'un ou plusieurs choisis dans un groupe constitué d'une première résine liante à base de cardo qui comprend un composé représenté par la formule chimique (1) et est polymérisée et une deuxième résine liante à base de cardo qui comprend un composé représenté par la formule chimique (2) et est polymérisée. La composition de résine photosensible selon la présente invention peut conférer d'excellentes propriétés de reproduction de couleur et une efficacité lumineuse élevée et peut produire une image de haute qualité.
PCT/KR2017/013588 2017-03-30 2017-11-27 Composition de résine photosensible et filtre coloré et dispositif d'affichage d'image fabriqués au moyen de celle-ci WO2018182127A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2019551963A JP6934062B2 (ja) 2017-03-30 2017-11-27 感光性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置
CN201780088307.3A CN110419002B (zh) 2017-03-30 2017-11-27 感光性树脂组合物、利用其制备的滤色器和图像显示装置

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KR10-2017-0040619 2017-03-30
KR1020170040619A KR101958414B1 (ko) 2017-03-30 2017-03-30 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상 표시 장치
KR10-2017-0040620 2017-03-30
KR20170040620 2017-03-30
KR10-2017-0109527 2017-08-29
KR1020170109527A KR101840348B1 (ko) 2017-03-30 2017-08-29 청색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상 표시 장치

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