WO2020022081A1 - 表示素子および表示素子の製造方法 - Google Patents

表示素子および表示素子の製造方法 Download PDF

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Publication number
WO2020022081A1
WO2020022081A1 PCT/JP2019/027469 JP2019027469W WO2020022081A1 WO 2020022081 A1 WO2020022081 A1 WO 2020022081A1 JP 2019027469 W JP2019027469 W JP 2019027469W WO 2020022081 A1 WO2020022081 A1 WO 2020022081A1
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WIPO (PCT)
Prior art keywords
group
pattern
display element
coloring
parts
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PCT/JP2019/027469
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English (en)
French (fr)
Japanese (ja)
Inventor
怜史 倉
拓之 鈴木
大吾 一戸
聡司 福間
茂 井川
英一郎 漆原
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Jsr株式会社
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Priority to CN201980047510.5A priority Critical patent/CN112424652A/zh
Publication of WO2020022081A1 publication Critical patent/WO2020022081A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • 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
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • 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
    • G02F1/1339—Gaskets; Spacers; Sealing of 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
    • 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
    • G03F7/095—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer

Definitions

  • the present invention relates to a display element and a method of manufacturing the display element.
  • the display element has a liquid crystal panel formed by sandwiching liquid crystal between a pair of substrates such as a glass substrate.
  • An alignment film for aligning the liquid crystal can be provided on the surface of the substrate holding the liquid crystal.
  • the display element functions as a fine shutter for light emitted from a light source such as a backlight or external light.
  • the display element performs display by partially transmitting or blocking light.
  • the display element has excellent features such as thinness and light weight.
  • the red coloring pattern formed using the red coloring composition containing a dye because the dye has poor heat resistance, compared to the coloring pattern using a coloring composition containing a pigment, reliability, particularly, There is a problem that heat resistance is inferior. For example, when the red colored pattern is exposed to a high temperature during the production of the display element, the reliability of the display element may be reduced.
  • a second object of the present invention is to provide a method for manufacturing a display element having excellent reliability.
  • the present invention is, for example, as follows.
  • a display element having a red coloring pattern, a blue coloring pattern, and a green coloring pattern, and having a coloring agent represented by the following formula (1) and a coloring agent having a structural portion represented by the following formula (2)
  • Red-colored pattern (A) containing an agent and at least one colorant selected from the group of colorants having a structural site represented by the formula (3) described below, and 100 to 10,000 (wt) ppm of heavy metal.
  • the colorant in the red coloring pattern (A) is a colorant represented by the formula (4) described later, a colorant having a structural portion represented by the formula (5) described later, and a colorant having a structure represented by the formula (5) described later.
  • the red coloring pattern (A) further comprises a diketopyrrolopyrrole, anthraquinone, azo, isoindoline, polymethine (provided that the coloring agent represented by the formula (1), the structure represented by the formula (2)) Any of the above [1] to [6], including at least one colorant selected from the group consisting of a colorant having a moiety and a colorant having a structural moiety represented by the formula (3)), xanthene, and dioxazine.
  • the display element according to 1.
  • the first coloring pattern in step [1] is a red coloring pattern
  • the second coloring pattern in step [2] is a green coloring pattern
  • the third coloring pattern in step [3] is The method for manufacturing a display element according to the above [12], wherein the coloring pattern is a blue coloring pattern.
  • a coating film of a radiation-sensitive resin composition containing a resin having a crosslinkable group and a carboxyl group is formed on the first to third colored patterns or on the protective film (C). Irradiating at least part of the coated film with radiation, developing the coated film with radiation, and curing the developed coated film at 80 ° C. or more and 200 ° C. or less to form a spacer pattern (B).
  • a display element which is manufactured by low-temperature curing, has a highly reliable colored pattern, has excellent display characteristics and reliability, and a method for manufacturing the same.
  • FIG. 3 is a schematic cross-sectional view of the color filter substrate according to the present embodiment.
  • FIG. 2 is a schematic cross-sectional view of a color liquid crystal display device including the color filter substrate according to the present embodiment.
  • radiation irradiated at the time of exposure is a concept including visible light, ultraviolet light, far ultraviolet light, X-ray, charged particle beam, and the like.
  • the first display element in this embodiment is a display element having a red coloring pattern, a blue coloring pattern, and a green coloring pattern, and includes a specific coloring agent described later and 100 to 10,000 (wt) ppm.
  • A and a spacer pattern (B) formed from a radiation-sensitive resin composition containing a resin having a crosslinkable group and a carboxyl group.
  • the second display element of this embodiment is a display element having a red coloring pattern, a blue coloring pattern, and a green coloring pattern, and includes a specific coloring agent described later and 100 to 10,000 (wt) ppm. And a protective film (C) formed from a resin composition containing a resin having a crosslinkable group (excluding a carboxyl group).
  • the display element is excellent in luminance, contrast, voltage holding ratio, and the like, and enables, for example, high image quality and high luminance in a liquid crystal display element.
  • the display element of the present embodiment has a red coloring pattern (A) (hereinafter, “red” may be omitted).
  • the coloring pattern (A) functions as a color filter.
  • the coloring pattern (A) includes a coloring agent represented by the formula (1), a coloring agent having a structural portion represented by the formula (2), and a coloring agent having a structural portion represented by the formula (3). At least one coloring agent selected from the group of (hereinafter also referred to as "specific coloring agent").
  • Such a colored pattern (A) is, for example, a colored composition containing an alkali-soluble resin [1], a polymerizable compound [2], a polymerization initiator [3], and a colorant [4] containing a specific colorant. (Hereinafter also referred to as “colored composition (A)”).
  • the coloring composition (A) may contain other optional components as long as the effects of the present invention are not impaired.
  • a blue coloring pattern and a green coloring pattern can be respectively produced by using a coloring composition containing the corresponding coloring agent as the coloring agent [4].
  • the alkali-soluble resin [1] includes, for example, a structural unit formed of at least one kind (hereinafter, also referred to as “compound (1-1)”) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. And a structural unit formed from another unsaturated compound (hereinafter, also referred to as “compound (1-2)”).
  • the alkali-soluble resin [1] can be produced, for example, by copolymerizing the compound (1-1) giving a carboxyl group-containing structural unit and the compound (1-2) in a solvent in the presence of a polymerization initiator. .
  • Examples of the compound (1-1) include unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, anhydrides of unsaturated dicarboxylic acids, and mono [(meth) acryloyloxyalkyl] esters of polycarboxylic acids.
  • the anhydrides of unsaturated monocarboxylic acids and unsaturated dicarboxylic acids are preferred, and acrylic acid, methacrylic acid and maleic anhydride are copolymerizable, soluble in aqueous alkali solutions and easily available. It is more preferable from the viewpoint of properties.
  • the compound (1-1) may be used alone or in combination of two or more.
  • the upper limit of the usage ratio of the compound (1-1) is preferably 30% by mass based on the total of all polymerizable monomers which are the raw materials of the alkali-soluble resin [1]. , More preferably 25% by mass, and the lower limit of the usage ratio of the compound (1-1) is preferably 5% by mass, more preferably 10% by mass.
  • ⁇ Compound (1-2) As the compound (1-2), an epoxy group-containing unsaturated compound, an alcoholic hydroxyl group-containing unsaturated compound, a phenolic hydroxyl group-containing unsaturated compound, a (meth) acrylic acid chain alkyl ester, a (meth) acrylic acid cyclic alkyl ester , Aryl (meth) acrylate, arylalkyl (meth) acrylate, alkoxyalkyl (meth) acrylate, unsaturated dicarboxylic acid diester, bicyclo unsaturated compound, maleimide compound, unsaturated aromatic compound, conjugated diene, Examples include unsaturated compounds having a tetrahydrofuran skeleton and the like, and other unsaturated compounds.
  • the compound (1-2) may be used alone or as a mixture of two or more.
  • the upper limit of the usage ratio of the compound (1-2) is preferably 95% by mass based on the total of all polymerizable monomers which are the raw materials of the alkali-soluble resin [1]. And more preferably 90% by mass, and the lower limit of the usage ratio of the compound (1-2) is preferably 70% by mass, more preferably 75% by mass.
  • the weight average molecular weight (Mw) of the alkali-soluble resin [1] is preferably 1,000 to 30,000, more preferably 5,000 to 20,000. By setting the Mw of the alkali-soluble resin [1] in the above range, the sensitivity and developability of the coloring composition can be increased.
  • the Mw and the number average molecular weight (Mn) of the polymer in the present specification can be measured by gel permeation chromatography (GPC) under the conditions described below.
  • the polymerizable compound [2] has an ethylenically unsaturated bond.
  • examples of the polymerizable compound [2] include dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri (2- (meth) acryloyloxyethyl) phosphate, and ethylene oxide-modified dipentaerythritol hexa ( In addition to (meth) acrylate, urethane (meth) acrylate, etc., compounds described in JP-A-2003-183551, JP-A-2008-40278, JP-A-2009-209275, JP-A-2014-71202, and the like are listed. Can be
  • the polymerization initiator [3] is a radiation-sensitive polymerization initiator, particularly a photopolymerization initiator, and is a component that generates an active species capable of initiating polymerization of the polymerizable compound [2] in response to radiation.
  • Examples of the polymerization initiator [3] include an O-acyl oxime compound, an acetophenone compound, and a biimidazole compound.
  • the polymerization initiator [3] may be used alone or in combination of two or more.
  • O-acyl oxime compound examples include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), and ethanone-1- [9-ethyl-6- (2- Methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime) and the like, as well as JP-A-2013-037349, JP-A-2013-15635, and JP-A-2016-151744. And the like.
  • Examples of the acetophenone compound include ⁇ -aminoketone compounds and ⁇ -hydroxyketone compounds.
  • Examples of the ⁇ -aminoketone compounds include 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one and 2-dimethylamino-2- (4-methylbenzyl) -1- (4 -Morpholin-4-yl-phenyl) -butan-1-one; 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one;
  • Examples of the ⁇ -hydroxyketone compound include 1-phenyl-2-hydroxy-2-methylpropan-1-one and 1- (4-i-propylphenyl) -2-hydroxy-2-methylpropan-1-one And 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, and the like.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole and 2,2′-bis (2,4- Dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5 ′ -Tetraphenyl-1,2'-biimidazole and the like, and 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole Is preferred.
  • the optionally substituted heterocycle in ring X 1 and ring X 2 contains one or more heteroatoms.
  • the heterocyclic ring may be monocyclic or polycyclic.
  • the hetero atom may be any atom selected from the elements of Group 15 or 16 in the periodic table, and examples include a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom.
  • heterocycle examples include an indole ring, a benzoindole ring, an indolenine ring, a benzoindolenine ring, an oxazole ring, a benzoxazole ring, a thiazole ring, a benzothiazole ring, a benzimidazole ring, and a quinoline ring.
  • Aliphatic carbonization such as alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group and tert-pentyl group A hydrogen group;
  • Aromatic hydrocarbon groups such as phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, mesityl, o-cumenyl, m-cumenyl and p-cumenyl;
  • Alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy and pentyloxy;
  • Aryloxy groups such as phenoxy groups;
  • An aralkyloxy group such as a aralkyloxy group
  • examples of the hydrogen atom include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group.
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
  • an indole ring, a benzoindole ring, an indolenine ring and a benzoindolenine ring are preferable, an indole ring and a benzoindolenine ring are more preferable, and an indole ring is further preferable.
  • the heterocyclic ring preferably has 1 to 4 alkyl groups or halogen atoms as substituents, more preferably 1 or 2 alkyl groups or halogen atoms.
  • n is preferably 1 from the viewpoint of transmittance adjustment.
  • a compound having a methine chain having rings bonded to both ends is generally referred to as a cyanine dye.
  • the cyanine-based dye skeleton is positively charged.
  • the coloring agent represented by the above formula (1) is an ionic compound, and has an anion (Z ⁇ ) that ionically bonds to the cyanine dye skeleton.
  • L 0 represents a linking group formed by polymerization. That is, it refers to a portion forming a repeating unit corresponding to the main chain formed by the polymerization reaction.
  • L 0 is not particularly limited as long as it is a linking group formed from a known polymerizable monomer.
  • linking groups represented by the following (L-1) to (L-15) are preferable. -1), (M-2) acrylic connecting chains represented by (L-2), styrene connecting chains represented by (L-5) to (L-9), and (L-15) Most preferably, it is a vinyl connecting chain. In (L-1) ⁇ (L -15), indicating that it is linked to L 1 at a site indicated by *.
  • L 1 represents a single bond or a divalent linking group.
  • examples of the divalent linking group include a methylene group, a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms (such as an ethylene group, a trimethylene group, a propylene group, and a butylene group).
  • a substituted or unsubstituted arylene group having 6 to 30 carbon atoms such as a phenylene group or a naphthalene group
  • each R independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • the organometallic complex is preferably an azo metal complex whose central metal is cobalt, nickel or copper or a bisphenyldithiol metal complex, and an azo metal complex whose central metal is cobalt, nickel or copper is preferred. More preferred.
  • the Z - The organic sulfonate anion and R a1 -SO 2 -N - -SO 2 -R a1 is preferred.
  • the colorant represented by the formula (1), the colorant having the structural portion represented by the formula (2), and the colorant having the structural portion represented by the formula (3) are specifically represented by the formula (4).
  • each of ring X 3 and ring X 4 is independently a benzene ring which may have a substituent or a naphthalene ring which may have a substituent
  • substituent include the groups exemplified as the substituent of the above-described heterocyclic ring, preferably an alkyl group and a halogen atom, and the number of substituents is preferably one or two.
  • Z - and Z '- are each formula (1), (2), (3) in Z - and Z' - as synonymous.
  • Z ⁇ is preferably ionically bonded to the dye structure, and may be linked to a part of the resin having the dye structure (polymer chain or the like).
  • the colorant (resin) having the structural site (dye structure) represented by the formula (3) or (6) is a dye monomer having an ethylenically unsaturated bond from the viewpoint of suppressing residues on other color patterns and suppressing coating defects. It is preferably a radical polymer obtained by radical polymerization using (a monomer having a dye structure).
  • the colorant [4] preferably further contains an organic pigment in addition to the specific colorant.
  • C.I. I. Yellow pigments such as CI Pigment Yellow 11, 24, 31, 53, 83, 93, 99, 108, 109, 110, 138, 139, 147, 150, 151, 154, 155, 167, 180, 185, 199
  • I. Blue pigments such as CI Pigment Blue 15 (for example, CI Pigment Blue 15: 3, CI Pigment Blue 15: 4, CI Pigment Blue 15: 6, 60); I. Pigment Violet 1, C.I. I. Pigment Violet 19, C.I. I. Pigment Violet 23, C.I. I. Pigment Violet 29, C.I. I. Pigment Violet 32, C.I. I. Pigment Violet 36, C.I. I. Violet color pigments such as CI Pigment Violet 38;
  • organic pigments include C.I. I. Pigment Orange 36, 38, 43, 71; I. Pigment Red 81, 105, 122, 149, 150, 155, 171, 175, 176, 177, 209, 220, 224, 242, 254, 255, 264, 270; I. Pigment Violet 19, 23, 32, 39 and the like.
  • the blue coloring pattern preferably contains at least one colorant selected from phthalocyanine, dioxazine, triarylmethane, xanthene, and anthraquinone.
  • a phthalocyanine pigment alone or a mixture of the phthalocyanine pigment and a dioxazine purple pigment can be used.
  • C.I. I. Pigment Blue 15: 6 alone, C.I. I. Pigment Blue 15: 6 and C.I. I. Pigment violet 23 is preferred.
  • the pigment dispersant may be a cationic, anionic, nonionic or amphoteric surfactant, such as a polyester surfactant, a polyamine surfactant, or an acrylic surfactant. Is mentioned.
  • a polyester surfactant such as a polyester surfactant, a polyamine surfactant, or an acrylic surfactant. Is mentioned.
  • One of these pigment dispersants may be used alone, or two or more thereof may be used in combination.
  • the upper limit of the heavy metal content is preferably 10,000 (wt) ppm, more preferably 8,000 (wt) ppm, and more preferably 6,000 (wt) ppm. Is preferably 100 (wt) ppm, more preferably 300 (wt) ppm, and still more preferably 500 (wt) ppm.
  • the heavy metal is preferably derived from a heavy metal complex such as a heavy metal organic complex.
  • the heavy metals of the heavy metal complex include iron (Fe), lead (Pb), gold (Au), platinum (Pt), silver (Ag), copper (Cu), chromium (Cr), cadmium (Cd), and mercury (Hg ), Zinc (Zn), arsenic (As), manganese (Mn), cobalt (Co), nickel (Ni), molybdenum (Mo), tungsten (W), tin (Sn), bismuth (Bi), uranium (U ), Plutonium (Pu) and the like.
  • the resin composition (B) has high curing reactivity even under low-temperature curing conditions.
  • the spacer pattern (B) in the display element can be formed.
  • the polymer [a] preferably has a structural unit having a (meth) acryloyloxy group.
  • the structural unit having a (meth) acryloyloxy group is, for example, a method of reacting a (meth) acrylic acid with an epoxy group in a polymer, a method of reacting a (meth) acrylate having an epoxy group with a carboxyl group in a polymer It can be formed by a method of reacting a (meth) acrylic acid ester having an isocyanate group with a hydroxyl group in a polymer, a method of reacting (meth) acrylic acid with an acid anhydride site in a polymer, or the like.
  • the polymer [a] is obtained by, for example, copolymerizing a compound (a1) giving a carboxyl group-containing structural unit and a compound giving another structural unit in a solvent in the presence of a polymerization initiator, It can be produced by reacting a compound (a2) which gives a (meth) acryloyl group-containing structural unit with a group-containing structural unit.
  • the anhydrides of unsaturated monocarboxylic acids and unsaturated dicarboxylic acids are preferred, and acrylic acid, methacrylic acid, and maleic anhydride are preferred because of their copolymerization reactivity, solubility in aqueous alkali solutions, and availability. More preferred.
  • the compound (a1) may be used alone or as a mixture of two or more.
  • Examples of the compound providing another structural unit include the other unsaturated compound (compound (1-2)) in the alkali-soluble resin [1] described above.
  • the structural unit having a (meth) acryloyloxy group of the polymer [a] is obtained by reacting a (meth) acrylic ester having an epoxy group with a carboxyl group in the copolymer, and the (meth) acryloyl after the reaction is obtained.
  • the structural unit having an oxy group is represented, for example, by the following formula (7a).
  • acid-modified cresol novolak type epoxy (meth) acrylate resin phenol novolak type epoxy (meth) acrylate resin, bisphenol A type epoxy (meth) acrylate resin, bisphenol F type epoxy (meth) acrylate resin, biphenyl Type epoxy (meth) acrylate resin and trisphenolmethane type epoxy (meth) acrylate resin.
  • an acid-modified cresol novolak type epoxy (meth) acrylate resin is preferable.
  • the acid-modified cresol novolak-type epoxy (meth) acrylate resin is, for example, an epoxy (meth) acrylate resin obtained by reacting (meth) acrylic acid with a cresol novolak-type epoxy resin, and an anhydride for alkali solubility. It is obtained by reacting an acid anhydride such as phthalic acid and 1,2,3,6-tetrahydrophthalic anhydride.
  • the acid-modified cresol novolak epoxy (meth) acrylate resin has a rigid main chain skeleton of cresol novolak epoxy resin, an ethylenically unsaturated group, and a carboxy group, so that it can be cured and fired at low temperatures. Regardless, it is possible to form a cured film having excellent film hardness, excellent solvent resistance and excellent heat resistance.
  • the acid value of the polymer [a] is such that the upper limit of the acid value of the polymer [a] is preferably 270 mgKOH / g, more preferably 250 mgKOH / g, and still more preferably 200 mgKOH / g.
  • the lower limit of the acid value is preferably 10 mgKOH / g, more preferably 30 mgKOH / g, and still more preferably 50 mgKOH / g.
  • the acid value represents the number of mg of KOH required to neutralize 1 g of the solid content of the polymer [a].
  • the alkali developability in addition to further improving the luminance, the alkali developability, the storage stability of the composition, the pattern shape, and the chromaticity characteristics can be improved.
  • the solid content is all components other than the solvent.
  • Photopolymerization initiator [c] examples include the aforementioned polymerization initiator [3].
  • the photopolymerization initiator [c] may be used alone or in combination of two or more.
  • the alkali developability in addition to further improving the luminance, the alkali developability, the storage stability of the composition, the pattern shape, and the chromaticity characteristics can be improved.
  • the solid content is all components other than the solvent.
  • Polymerizable compound [b-1] examples include the aforementioned polymerizable compound [2].
  • the photo-alignment group is a functional group that imparts anisotropy to the film by light irradiation.
  • a photo-decomposition reaction, a photo-isomerization reaction, and / or a photo-dimerization reaction occur. Is a group that gives anisotropy to the film.
  • the polyamic acid contained in the liquid crystal aligning agent is converted into a polyimide by dehydration ring closure and imidization.
  • a polyamic acid can be obtained, for example, by reacting a tetracarboxylic dianhydride with a diamine, and can be obtained as described in JP-A-2010-97188.
  • the polyamic acid ester can be obtained, for example, by a method of reacting a tetracarboxylic diester dihalide with a diamine compound, and can be obtained, for example, as described in JP-A-2017-200991.
  • a light-shielding layer (black matrix) is formed on the surface of the substrate so as to partition a portion where a colored pattern (pixel) is to be formed, if necessary.
  • a black matrix can be formed by forming a metal thin film of chromium or the like formed by sputtering or vapor deposition into a desired pattern by using a photolithography method, but using a coloring composition containing a black coloring agent, The pixel can be formed in the same manner as in the following pixel formation.
  • Examples of a method for applying the coloring composition to the substrate include a spray method, a roll coating method, a spin coating method (spin coating method), and a bar coating method. Of these, spin coating and slit die coating are preferred.
  • the partition walls have not only a light-shielding function but also a function of preventing the color compositions of the respective colors discharged in the partitions from mixing colors, and thus have a greater film thickness than the black matrix.
  • the thickness of the colored pattern (pixel) is usually 0.5 ⁇ m to 5.0 ⁇ m, preferably 1.0 ⁇ m to 3.0 ⁇ m.
  • a protective film (C) is formed as necessary on the colored pattern of the substrate on which the colored pattern has been formed.
  • the solid concentration of the resin composition (C) solution used in the coating method is preferably 5% by mass to 50% by mass, more preferably 10% by mass to 40% by mass, and particularly preferably 15% by mass to 35% by mass.
  • Exposure dose as a value measured by a luminometer intensity at a wavelength 365nm of the radiation emitted (OAI model 356, Optical Associates Ltd. Inc.), 100J / m 2 ⁇ 5,000J / m 2 is preferably, 200J / m 2 ⁇ 3,000J / m 2 is more preferable.
  • the obtained coating film (in the case of forming a pattern using a radiation-curable resin composition as a resin composition (C) and patterned) is cured (also called post-baked) by a suitable heating device such as a hot plate or an oven. Thereby, a protective film (C) is obtained as a cured film.
  • a coating film is formed by a coating method
  • a solution of the radiation-sensitive resin composition (B) is coated on a substrate on which a colored pattern or the like is formed, and then the coating surface is preferably heated (prebaked) to form a coating.
  • a film can be formed.
  • a part of the coating film of the resin composition (B) is irradiated with radiation.
  • a method of irradiating through a photomask having a predetermined pattern can be used.
  • the radiation used for irradiation includes visible light, ultraviolet light, far ultraviolet light and the like. Among them, radiation having a wavelength in the range of 250 nm to 550 nm is preferable, and radiation containing ultraviolet light of 365 nm is more preferable.
  • FIG. 1 is a schematic sectional view of a color filter substrate having a colored pattern according to the present embodiment.
  • the curing temperature at the time of forming the colored pattern 6 can be adjusted in consideration of the fact that the protective film 8 is formed on the colored pattern 6. That is, the coloring pattern 6 is formed on the substrate 5 at a curing temperature lower than the optimal curing temperature for forming the coloring pattern 6 alone. Thereafter, by heating and curing the protective film 8 formed on the colored pattern 6, the colored pattern 6 can be heated. Similarly, at the time of manufacturing the color filter substrate 10, it is possible to adjust the curing temperature at the time of forming the colored pattern 6 in consideration of the fact that the spacer 9 is formed after the colored pattern 6 is formed.
  • FIG. 2 is a schematic cross-sectional view of a color liquid crystal display device having the color filter substrate of the present embodiment.
  • a red, green, and blue colored pattern 6 provided at a position facing the pixel electrode 3, a black matrix 7, a protective film 8 provided on the colored pattern 6,
  • a color filter substrate including an ITO electrode 4 provided on the substrate 5, a spacer 9 provided on the ITO electrode 4, and an alignment film 12 on the substrate 5 is arranged.
  • the ITO electrode 4 forms a common electrode in the liquid crystal display element 100.
  • ⁇ Preparation of resin composition for forming protective film> For 100 parts of the polymer [BS-1], 100 parts of a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (M-402 manufactured by Toagosei Co., Ltd.) as a polymerizable compound, and 1 part as a photopolymerization initiator. , 2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime) (Irgacure OXE01, manufactured by BASF) and 5 parts of ⁇ -glycidoxypropyltriol as an adhesion aid. After mixing 5 parts of methoxysilane, adding PGMEA so that the solid content concentration was 30% by mass, and filtering through a Millipore filter having a pore size of 0.5 ⁇ m, a resin composition (OC-1) was prepared.
  • M-402 dipentaery
  • the spacer-formed radiation-sensitive resin compositions (S-1) to (S-4) prepared above were applied to a non-alkali glass substrate using a spin coater. Next, the film was prebaked on a hot plate at 90 ° C. for 2 minutes to form a coating film having a thickness of 3.0 ⁇ m. Next, the obtained coating film was irradiated with radiation through a photomask having a predetermined pattern using a high-pressure mercury lamp at an exposure amount of 300 J / m 2 . Thereafter, shower development is performed by discharging a developing solution (a 0.04 mass% aqueous solution of potassium hydroxide at 23 ° C.) to the substrate, and then a curing temperature of 150 ° C. and a curing time of 30 minutes in an oven. To form a spacer pattern on the substrate. Then, it was confirmed by a scanning electron microscope that a spacer pattern was formed on the substrate with a desired forward taper shape and resolution.
  • a developing solution a 0.04 mass%
  • a liquid crystal aligning agent AL3046 (trade name, manufactured by JSR Corporation) is applied to the substrate on which the spacer pattern is formed using a printing machine for coating a liquid crystal alignment film, and then dried at 180 ° C. for 1 hour. A coating of an aligning agent having a thickness of 0.05 ⁇ m was formed. Thereafter, a rubbing treatment was carried out using a rubbing machine having a roll in which a polyamide cloth was wound around the coating film, at a roll rotation speed of 500 rpm and a stage moving speed of 1 cm / sec. At this time, the presence or absence of pattern scraping or peeling was evaluated.
  • a red composition (R-1) having a concentration of 15% by mass was prepared.
  • each of the dispersions shown in Table 6 and The red compositions (R-2) to (R-23) were prepared in the same manner as in the preparation of the red composition (R-1) except that the solution was used and PGMEA was mixed as a solvent to adjust the solid content concentration. Prepared.
  • the resin solution, the polymerizable compound, the photopolymerization initiator, and the fluorine-based surfactant are commonly blended.
  • the red composition (R-1) is dried on a hot plate at 90 ° C. Pre-baking was performed for 2 minutes to form a coating film having a thickness of 2.4 ⁇ m. After the substrate was cooled to room temperature, the coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm and 436 nm at a dose of 400 J / m 2 through a photomask using a high-pressure mercury lamp.
  • the first coloring composition was (G-1)
  • the second coloring composition was (B-1)
  • the third coloring composition was (R-1).
  • a color filter substrate was prepared in the same manner as in CF-OC-1, except that the color filter substrate described above was used.
  • R indicates a red composition
  • G indicates a green composition
  • B indicates a blue composition
  • OC indicates a resin composition for forming a protective film.
  • the color filter substrate is sandwiched between two polarizing plates, and the front polarizing plate is rotated while irradiating with a fluorescent lamp (wavelength range of 380 to 780 nm) from the back side, and the luminance meter LS-100 (manufactured by Minolta Co., Ltd.) is used.
  • the maximum and minimum values of the transmitted light intensity were measured.
  • a value obtained by dividing the maximum value by the minimum value was defined as a contrast ratio. “ ⁇ ” when the contrast ratio is 9,000 or more, “ ⁇ ” when it is 8,000 or more but less than 9,000, “ ⁇ ” when it is 7,000 or more and less than 8,000, and when it is less than 7,000.
  • Table 7 shows the evaluation results.

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PCT/JP2019/027469 2018-07-23 2019-07-11 表示素子および表示素子の製造方法 WO2020022081A1 (ja)

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JP2013041165A (ja) * 2011-08-17 2013-02-28 Jsr Corp カラーフィルタ、液晶表示素子およびカラーフィルタの製造方法
JP2014240953A (ja) * 2013-03-21 2014-12-25 Jsr株式会社 着色組成物、着色硬化膜及び表示素子
JP2015018208A (ja) * 2013-06-12 2015-01-29 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2015125396A (ja) * 2013-12-27 2015-07-06 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ

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CN102692661B (zh) * 2011-03-24 2016-01-06 Jsr株式会社 彩色滤光片、彩色滤光片的制造方法及液晶显示元件
JP5786451B2 (ja) * 2011-05-19 2015-09-30 Jsr株式会社 カラーフィルタ、液晶表示素子およびカラーフィルタの製造方法
JP5934664B2 (ja) * 2012-03-19 2016-06-15 富士フイルム株式会社 着色感放射線性組成物、着色硬化膜、カラーフィルタ、着色パターン形成方法、カラーフィルタの製造方法、固体撮像素子、及び画像表示装置

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013041165A (ja) * 2011-08-17 2013-02-28 Jsr Corp カラーフィルタ、液晶表示素子およびカラーフィルタの製造方法
JP2014240953A (ja) * 2013-03-21 2014-12-25 Jsr株式会社 着色組成物、着色硬化膜及び表示素子
JP2015018208A (ja) * 2013-06-12 2015-01-29 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2015125396A (ja) * 2013-12-27 2015-07-06 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ

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