WO2022092556A1 - Composition durcissable pour appareil électrophorétique, film durci l'utilisant et dispositif d'affichage - Google Patents

Composition durcissable pour appareil électrophorétique, film durci l'utilisant et dispositif d'affichage Download PDF

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WO2022092556A1
WO2022092556A1 PCT/KR2021/012468 KR2021012468W WO2022092556A1 WO 2022092556 A1 WO2022092556 A1 WO 2022092556A1 KR 2021012468 W KR2021012468 W KR 2021012468W WO 2022092556 A1 WO2022092556 A1 WO 2022092556A1
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curable composition
monomer
electrophoretic device
group
formula
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Korean (ko)
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윤진섭
김미선
김영민
김장혁
류동완
박영우
박철진
유은선
정지영
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삼성에스디아이 주식회사
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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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/28—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • 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 
    • G02F1/165—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 translational movement of particles in a fluid under the influence of an applied field
    • G02F1/166—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 translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
    • G02F1/167—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 translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis

Definitions

  • the present disclosure relates to a curable composition for an electrophoretic device, a cured film using the same, and a display device.
  • the LED is a semiconductor having a structure in which an n-type semiconductor crystal in which a plurality of carriers are electrons and a p-type semiconductor crystal in which a plurality of carriers are holes using the characteristics of a compound semiconductor are bonded to each other. It is a semiconductor device that is converted into light and expressed.
  • LED semiconductors have high light conversion efficiency, so they consume very little energy, have a semi-permanent lifespan and are environmentally friendly, so they are called the revolution of light as a green material.
  • compound semiconductor technology high-brightness red, orange, green, blue and white LEDs have been developed, and by using them, many fields such as traffic lights, mobile phones, automobile headlights, outdoor electric signs, LCD BLU (back light unit), and indoor/outdoor lighting It is being applied in and active research continues at home and abroad.
  • GaN-based compound semiconductors with a wide bandgap are materials used for manufacturing LED semiconductors that emit light in green, blue, and ultraviolet regions, and since it is possible to manufacture white LED devices using blue LED devices, a lot of research on this is being done
  • One embodiment is to provide a curable composition containing semiconductor nanorods capable of simultaneously performing patterning using inkjetting, dielectrophoresis, and wet etching.
  • Another embodiment is to provide a cured film prepared by using the curable composition for an electrophoretic device.
  • Another embodiment is to provide a display device including the cured film.
  • One embodiment is (A) a semiconductor nanorod; (B) a polymerizable monomer comprising a first monomer and a second monomer; (C) a polymerization initiator; and (D) a solvent, wherein the first monomer includes a thiol group, and the second monomer includes a carbon-carbon double bond at a terminal thereof.
  • the first monomer may further include an ester linking group.
  • the first monomer may include a functional group represented by Formula 1 below.
  • L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C1 to C20 alkylene group
  • n is an integer of 0 or 1.
  • the first monomer may include at least one compound selected from the group consisting of the following Chemical Formulas 1-1 to 1-3.
  • L 3 to L 5 are each independently a substituted or unsubstituted C1 to C20 alkylene group
  • R 1 is a substituted or unsubstituted C1 to C20 alkyl group
  • n1 is an integer from 0 to 3
  • n2 is an integer from 1 to 4
  • n1 + n2 4.
  • the first monomer is 1,2-ethanedithiol, 1,3-propanedithiol, 1,6-hexanedithiol, glycol dimercaptoacetate, glycol di-3-mercaptopropionate, thimethylolpropane tris(3-mercaptopropionate), pentaerythrithol tetrakis (3-mercaptopropionate), pentaerythrithol tetrakis (2-mercaptoacetate) or a combination thereof.
  • the second monomer may include a (meth)acrylic compound having a carbon-carbon double bond at the terminal thereof.
  • the first monomer and the second monomer may be included in a weight ratio of 9:1 to 1:9.
  • the solvent may include a compound represented by the following formula (4).
  • R 9 to R 11 are each independently a hydrogen atom or a C1 to C10 alkyl group
  • L 16 and L 17 are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
  • L 18 is *-O-*, *-S-* or *-NH-*.
  • the semiconductor nanorods may have a diameter of 300 nm to 900 nm.
  • the semiconductor nanorods may have a length of 3.5 ⁇ m to 5 ⁇ m.
  • the semiconductor nanorods may include a GaN-based compound, an InGaN-based compound, or a combination thereof.
  • the semiconductor nanorods may have a surface coated with a metal oxide.
  • the metal oxide may include alumina, silica, or a combination thereof.
  • the semiconductor nanorods may be included in an amount of 0.01 wt% to 10 wt% based on the total amount of the curable composition for the electrophoretic device.
  • the ink composition for the electrophoresis device includes malonic acid; 3-amino-1,2-propanediol; silane-based coupling agent; leveling agent; fluorine-based surfactants; Or it may further include a combination thereof.
  • Another embodiment provides a cured film prepared using the ink composition for an electrophoretic device.
  • Another embodiment provides a display device including the cured film.
  • FIG. 1 is an example of a cross-sectional view of a semiconductor nanorod used in a curable composition for an electrophoretic device according to an embodiment.
  • FIG. 2 is a scanning electron microscope (SEM) photograph of a specimen patterned using the curable composition according to Example 1.
  • SEM scanning electron microscope
  • SEM scanning electron microscope
  • SEM scanning electron microscope
  • SEM scanning electron microscope
  • alkyl group means a C1 to C20 alkyl group
  • alkenyl group means a C2 to C20 alkenyl group
  • cycloalkenyl group means a C3 to C20 cycloalkenyl group
  • heterocycloalkenyl group means a C3 to C20 heterocycloalkenyl group
  • aryl group means a C6 to C20 aryl group
  • arylalkyl group means a C6 to C20 arylalkyl group
  • alkylene group means a C1 to C20 alkylene group
  • arylene group means a C6 to C20 arylene group
  • alkylarylene group means a C6 to C20 alkylarylene group
  • heteroarylene group means a C3 to C20 hetero It means an arylene group
  • alkoxyylene group means a C1 to C20 alkoxyylene group
  • substitution means that at least one hydrogen atom is a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, Azido group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, ether group, carboxyl group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C20 aryl group, C3 to C20 cycloalkyl group, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl group, C2 to C20 heterocycloal
  • F, Cl, Br, I
  • hetero means that at least one hetero atom among N, O, S and P is included in the formula.
  • (meth)acrylate means that both “acrylate” and “methacrylate” are possible
  • (meth)acrylic means “acrylic” and “methacrylic” “It means that both are possible.
  • semiconductor nanorod refers to a rod-shaped semiconductor having a nano-size diameter.
  • the curable composition for an electrophoretic device includes (A) a semiconductor nanorod; (B) a polymerizable monomer comprising a first monomer and a second monomer; (C) a polymerization initiator; and (D) a solvent, wherein the first monomer includes a thiol group, and the second monomer includes a carbon-carbon double bond.
  • the semiconductor nanorods may include a GaN-based compound, an InGaN-based compound, or a combination thereof, and the surface thereof may be coated with a metal oxide.
  • the semiconductor nanorod ink solution semiconductor nanorod + solvent
  • the present inventors after numerous trial and error studies, coated the surface of the semiconductor nanorods with a metal oxide containing alumina, silica, or a combination thereof to form an insulating film (Al 2 O 3 or SiO x ), thereby forming an insulating film (Al 2 O 3 or SiO x ). compatibility could be maximized.
  • the insulating layer coated with the metal oxide may have a thickness of 40 nm to 60 nm.
  • the semiconductor nanorod includes an n-type confinement layer and a p-type confinement layer, and a multi-quantum well active part ( MQW active region; multi quantum well active region) may be located.
  • MQW active region multi quantum well active region
  • the semiconductor nanorods may have a diameter of 300 nm to 900 nm, for example, 600 nm to 700 nm.
  • the semiconductor nanorods may have a length of 3.5 ⁇ m to 5 ⁇ m.
  • the semiconductor nanorod when it includes an alumina insulating layer, it may have a density of 5 g/cm 3 to 6 g/cm 3 .
  • the semiconductor nanorods may have a mass of 1 x 10 -13 g to 1 x 10 -11 g.
  • the surface coating of the metal oxide may be easy, and dispersion stability of the semiconductor nanorods may be maximized.
  • the semiconductor nanorods may be included in an amount of 0.01 wt% to 10 wt%, for example 0.02 wt% to 8 wt%, such as 0.03 wt% to 5 wt%, based on the total amount of the curable composition.
  • the semiconductor nanorods When the semiconductor nanorods are included within the above range, dispersion in ink is good, and the prepared pattern may have excellent luminance.
  • the patterning composition used in the existing display and electronic materials used an acryl-based or cardo-based binder resin, and after pattern exposure using the acidity of the carboxylic acid of the binder resin, an alkali developer (aq. KOH, TMAH solution) was used to the non-exposed part (uncured portion) was dissolved to make patterning.
  • an alkali developer aq. KOH, TMAH solution
  • the entire solution was disadvantageous in terms of viscoelasticity and high temperature stability, and aggregation through binding on the surface of the semiconductor nanorods occurred, which adversely affected ink jetting properties, dispersion stability, and dielectrophoretic properties.
  • the curable composition according to an embodiment is a pattern-curing composition with a completely new concept from the prior art, which overcomes all conventional problems by newly designing a polymerizable monomer advantageous in inkjetting properties and dielectrophoretic properties.
  • the first monomer may further include an ester linking group.
  • the pKa of carboxylic acid which is the development site of the developable acrylic binder resin, is 5. aq.
  • the pKa of thiol attached to the alpha- and beta- positions of the ester is about 8 to 9.5, and aq.
  • a thiol compound is insoluble in neutral water and phase separated, but aq. In a basic aqueous solution such as KOH or TMAH, a salt is formed and dissolved immediately.
  • the curable composition according to an embodiment is composed only of monomers without an organic polymer (binder resin), it may be advantageous in ink jetting properties and dielectrophoretic properties compared to a developer including a conventional binder resin.
  • the first monomer may include a functional group represented by Formula 1 below.
  • L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C1 to C20 alkylene group
  • n is an integer of 0 or 1.
  • the first monomer may include at least one compound selected from the group consisting of the following Chemical Formulas 1-1 to 1-3.
  • L 3 to L 5 are each independently a substituted or unsubstituted C1 to C20 alkylene group
  • R 1 is a substituted or unsubstituted C1 to C20 alkyl group
  • n1 is an integer from 0 to 3
  • n2 is an integer from 1 to 4
  • n1 + n2 4.
  • the first monomer is 1,2-ethanedithiol, 1,3-propanedithiol, 1,6-hexanedithiol, glycol dimercaptoacetate, glycol di-3-mercaptopropionate, thimethylolpropane tris(3-mercaptopropionate), pentaerythrithol tetrakis (3-mercaptopropionate), pentaerythrithol tetrakis (2-mercaptoacetate) or a combination thereof, but is not necessarily limited thereto.
  • the second monomer may be a compound including a carbon-carbon double bond at the terminal.
  • the second monomer may have a different structure from the first monomer.
  • the second monomer may include a (meth)acrylic compound including a carbon-carbon double bond at the terminal.
  • the second monomer is a polymerizable compound used in conventional thermosetting or photocuring compositions, and is divinyl benzene, triallyl trimellitate, triallyl phosphate, triallyl phosphite, triallyl triazine, diallyl phthalate.
  • Ethylene glycol diacrylate triethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, pentaerythritol diacrylate, pentaerythritol Triacrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol pentaacrylate, pentaerythritol hexaacrylate, bisphenol A diacrylate, trimethylolpropane triacrylate, novolac Epoxy acrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol Dimethacrylate, polyfunctional epoxy (meth) acryl
  • the first monomer and the second monomer may be included in a weight ratio of 9:1 to 1:9.
  • the first monomer may be included in an amount of 2 wt% to 80 wt% based on the total amount of solids constituting the curable composition according to an embodiment.
  • the second monomer may be included in an amount of 2 wt% to 80 wt% based on the total amount of solids constituting the curable composition according to an embodiment.
  • the curable composition for an electrophoretic device includes a polymerization initiator, for example, a photopolymerization initiator, a thermal polymerization initiator, or a combination thereof.
  • a polymerization initiator for example, a photopolymerization initiator, a thermal polymerization initiator, or a combination thereof.
  • the photopolymerization initiator is an initiator generally used in the curable curable composition, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, an aminoketone-based compound and the like may be used, but is not necessarily limited thereto.
  • acetophenone-based compound examples include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloroacetophenone, p-t-Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.
  • benzophenone-based compound examples include benzophenone, benzoylbenzoic acid, methylbenzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethyl amino)benzophenone, 4,4 and '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
  • thioxanthone-based compound examples include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.
  • benzoin-based compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethyl ketal.
  • triazine-based compound examples include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4' -dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine , 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine , 2-Biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)- 4,6-bis(trichlor
  • Examples of the oxime-based compound include an O-acyloxime-based compound, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, and 1-(O-acetyloxime) -1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl- ⁇ -oxyamino-1-phenylpropan-1-one, etc.
  • O-acyloxime-based compound examples include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione -2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime- O-acetate etc. are mentioned.
  • aminoketone-based compound examples include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 (2-Benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone -1) and the like.
  • a carbazole-based compound As the photopolymerization initiator, a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, or a biimidazole-based compound may be used in addition to the above compound.
  • the photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light to enter an excited state and then transferring the energy.
  • photosensitizer examples include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like. can be heard
  • thermal polymerization initiator examples include peroxide, specifically benzoyl peroxide, dibenzoyl peroxide, lauryl peroxide, dilauryl peroxide, di-tert-butyl peroxide, cyclohexane peroxide, methyl ethyl ketone peroxide Oxide, hydroperoxide (eg tert-butyl hydroperoxide, cumene hydroperoxide), dicyclohexyl peroxydicarbonate, 2,2-azo-bis(isobutyronitrile), t-butyl perbenzo ate, and the like, and 2,2'-azobis-2-methylpropionitrile, but is not necessarily limited thereto, and any one widely known in the art may be used.
  • peroxide specifically benzoyl peroxide, dibenzoyl peroxide, lauryl peroxide, dilauryl peroxide, di-tert-butyl peroxide, cyclohexane peroxide,
  • the polymerization initiator may be included in an amount of 1 wt% to 5 wt%, for example 2 wt% to 4 wt%, based on the total amount of solids constituting the curable composition for the electrophoretic device.
  • the polymerization initiator is included within the above range, curing occurs sufficiently during exposure or thermal curing to obtain excellent reliability.
  • the curable composition for an electrophoretic device includes a solvent.
  • Organic solvents such as propylene glycol monomethyl ether acetate (PEGMEA), ⁇ -butyrolactone (GBL), polyethylene glycol methyl ether (PGME), ethyl acetate, and isopropyl alcohol (IPA) used in conventional display and electronic materials have low viscosity.
  • PEGMEA propylene glycol monomethyl ether acetate
  • GBL ⁇ -butyrolactone
  • PGME polyethylene glycol methyl ether
  • IPA isopropyl alcohol
  • the solvent in the curable composition for an electrophoretic device may include a compound represented by the following Chemical Formula 4.
  • R 9 to R 11 are each independently a hydrogen atom or a C1 to C10 alkyl group
  • L 16 and L 17 are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
  • L 18 is *-O-*, *-S-* or *-NH-*.
  • the compound represented by Formula 4 may be citric acid.
  • the compound represented by Formula 4 may be represented by any one of Formulas 4-1 to 4-6, but is not limited thereto.
  • the solvent may be included in an amount of 15 wt% to 90 wt%, such as 15 wt% to 85 wt%, such as 20 wt% to 80 wt%, based on the total amount of the curable composition for the electrophoretic device.
  • the curable composition for an electrophoretic device may further include a polymerization inhibitor including a hydroquinone-based compound, a catechol-based compound, or a combination thereof.
  • a polymerization inhibitor including a hydroquinone-based compound, a catechol-based compound, or a combination thereof.
  • the curable composition according to an embodiment further includes the hydroquinone-based compound, the catechol-based compound, or a combination thereof, it is possible to prevent crosslinking at room temperature during exposure after printing (coating) the ink composition.
  • the hydroquinone-based compound, catechol-based compound, or a combination thereof is hydroquinone, methyl hydroquinone, methoxyhydroquinone, t-butyl hydroquinone, 2,5-di- t -butyl hydroquinone, 2,5- Bis(1,1-dimethylbutyl) hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl) hydroquinone, catechol, t-butyl catechol, 4-methoxyphenol, pyroga Rol, 2,6-di- t -butyl-4-methylphenol, 2-naphthol, tris(N-hydroxy-N-nitrosophenylaminato-O,O')aluminum (Tris(N-hydroxy-N) -nitrosophenylaminato-O,O')aluminium) or a combination thereof, but is not necessarily limited thereto.
  • the hydroquinone-based compound, the catechol-based compound, or a combination thereof may be used in the form of a dispersion, and the polymerization inhibitor in the dispersion form is 0.001 wt% to 1 wt%, such as 0.01 wt% to 0.1 wt%, based on the total amount of the curable composition can be included as
  • the stabilizer is included within the above range, it is possible to solve the problem of aging at room temperature and, at the same time, to prevent a decrease in sensitivity and a surface peeling phenomenon.
  • the curable composition for an electrophoretic device includes malonic acid in addition to the polymerization inhibitor; 3-amino-1,2-propanediol; silane-based coupling agent; leveling agent; fluorine-based surfactants; Or it may further include a combination thereof.
  • the curable composition for an electrophoretic device may further include a silane-based coupling agent having a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, and an epoxy group in order to improve adhesion to the substrate.
  • a silane-based coupling agent having a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, and an epoxy group in order to improve adhesion to the substrate.
  • silane-based coupling agent examples include trimethoxysilyl benzoic acid, ⁇ -methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, ⁇ -isocyanate propyl triethoxysilane, ⁇ -glycan Cydoxy propyl trimethoxysilane, ⁇ -epoxycyclohexyl)ethyltrimethoxysilane, etc. are mentioned, and these may be used individually or in mixture of 2 or more types.
  • the silane-based coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the curable composition for an electrophoretic device. When the silane-based coupling agent is included within the above range, adhesion and storage properties are excellent.
  • the curable composition for an electrophoretic device may further include a surfactant, such as a fluorine-based surfactant, to improve coating properties and prevent defect formation, if necessary.
  • a surfactant such as a fluorine-based surfactant
  • fluorine-based surfactant examples include BM-1000 ® , BM-1100 ® and the like by BM Chemie; Mecha Pack F 142D ® , Mecha Pack F 172 ® , Mecha Pack F 173 ® , Mecha Pack F 183 ® and the like of Dai Nippon Inki Chemical High School Co., Ltd.; Sumitomo 3M Co., Ltd.'s Prorad FC-135 ® , Prorad FC-170C ® , Prorad FC-430 ® , Prorad FC-431 ® and the like; Asahi Grass Co., Ltd.
  • the fluorine-based surfactant may be used in an amount of 0.001 parts by weight to 5 parts by weight based on 100 parts by weight of the curable composition for an electrophoretic device.
  • the fluorine-based surfactant is included within the above range, coating uniformity is secured, stains do not occur, and wettability to a glass substrate is excellent.
  • a predetermined amount of other additives such as antioxidants and stabilizers may be further added to the curable composition for an electrophoretic device within a range that does not impair physical properties.
  • Another embodiment provides a cured film using a curable composition for an electrophoretic device.
  • Another embodiment provides a display device including the cured film or a display device manufactured using the curable composition for an electrophoretic device.
  • Citric acid 100 g, 0.5205 mol
  • p-toluenesulfonic acid (0.99 g, 0.00521 mol)
  • p-toluenesulfonic acid 0..99 g, 0.00521 mol
  • the solvent is removed with a rotary evaporator, and 500 ml of ethyl acetate is added.
  • aq 500 ml of ethyl acetate is added.
  • aq After washing twice with 300ml of 10% NaHCO 3 aqueous solution, additionally wash once with brine.
  • celite filter is performed. After filtering, the solvent was dried to obtain a compound represented by the following Chemical Formula 4-4 (trimethyl o-acetylcitrate).
  • the method for measuring the dielectrophoretic properties is as follows.
  • nanorod ink composition 500 ⁇ l of the nanorod ink composition is applied to thin-film Gold basic interdigitated linear electrodes (ED-cIDE4-Au, Micrux), an electric field (25KHz, ⁇ 30v) is applied, and then waits for 1 minute. After drying the solvent using a hot plate, the number (ea) and the number (ea) aligned in the center between the electrodes were checked using a microscope to evaluate the dielectrophoretic properties.
  • ED-cIDE4-Au thin-film Gold basic interdigitated linear electrodes
  • Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Settling rate (mm/hr) 0.11 0.10 0.08 0.12 0.16 0.18 Dielectrophoretic properties (%) 92% 94% 93% 90% 92% 93%
  • the curable composition for an electrophoretic device according to the present invention greatly improves the dispersion stability of semiconductor nanorods and at the same time has very excellent dielectrophoretic properties, so that it is suitable for large-area coating and panel production.
  • the pattern resolution was determined by coating the curable composition to a thickness of 3 ⁇ m on a glass substrate using a spin coater (Mikasa, Opticoat MS-A150), respectively, and then using a hot-plate at 80° C. for 120 seconds. After baking (soft-baking), exposure was performed at a power of 60 mJ using an exposure machine (Ushio, ghi broadband). Then, using a developer (SVS, SSP-200) was developed with a 0.2 wt% potassium hydroxide (KOH) aqueous solution. Thereafter, the minimum ⁇ m of the remaining pattern was confirmed through an optical microscope, and the results are shown in Table 3 and FIGS. 2 to 5 below.
  • Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2
  • Initial viscosity (cPs) 83 24.6 24.9 24.4 29.5 31.3 ink jetting property Good Good Good Good error error Pattern resolution ( ⁇ m) 5 4.5 10 15 pattern loss pattern loss

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Abstract

L'invention concerne une composition durcissable pour un appareil électrophorétique, un film durci préparé à l'aide de la composition durcissable pour un appareil électrophorétique et un dispositif d'affichage l'utilisant, la composition durcissable comprenant : (A) une nanotige de semi-conducteur ; (B) un monomère polymérisable contenant un premier monomère et un deuxième monomère ; (C) un initiateur de polymérisation ; et (D) un solvant, le premier monomère contenant un groupe thiol, le deuxième monomère contenant une double liaison carbone-carbone.
PCT/KR2021/012468 2020-10-27 2021-09-14 Composition durcissable pour appareil électrophorétique, film durci l'utilisant et dispositif d'affichage WO2022092556A1 (fr)

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KR10-2020-0140312 2020-10-27

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JP2017037761A (ja) * 2015-08-07 2017-02-16 新日鉄住金化学株式会社 金属ナノ粒子組成物、インクジェット用インク及びインクジェット装置、並びに金属ナノ粒子組成物用分散媒組成物
KR20170032315A (ko) * 2014-07-15 2017-03-22 이섬 리서치 디벨러프먼트 컴파니 오브 더 히브루 유니버시티 오브 예루살렘 엘티디. 발광 시드된 나노로드의 패턴
KR20180109929A (ko) * 2016-02-16 2018-10-08 헨켈 아게 운트 코. 카게아아 나노결정 에폭시 티올 복합체 물질 및 나노결정 에폭시 티올 복합체 필름
KR20200006941A (ko) * 2018-07-10 2020-01-21 삼성전자주식회사 조성물, 패턴화된 막, 및 이를 포함하는 전자 소자

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US9778510B2 (en) * 2013-10-08 2017-10-03 Samsung Electronics Co., Ltd. Nanocrystal polymer composites and production methods thereof

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Publication number Priority date Publication date Assignee Title
KR20150041581A (ko) * 2013-10-08 2015-04-16 삼성전자주식회사 나노 결정 폴리머 복합체 및 그 제조 방법
KR20170032315A (ko) * 2014-07-15 2017-03-22 이섬 리서치 디벨러프먼트 컴파니 오브 더 히브루 유니버시티 오브 예루살렘 엘티디. 발광 시드된 나노로드의 패턴
JP2017037761A (ja) * 2015-08-07 2017-02-16 新日鉄住金化学株式会社 金属ナノ粒子組成物、インクジェット用インク及びインクジェット装置、並びに金属ナノ粒子組成物用分散媒組成物
KR20180109929A (ko) * 2016-02-16 2018-10-08 헨켈 아게 운트 코. 카게아아 나노결정 에폭시 티올 복합체 물질 및 나노결정 에폭시 티올 복합체 필름
KR20200006941A (ko) * 2018-07-10 2020-01-21 삼성전자주식회사 조성물, 패턴화된 막, 및 이를 포함하는 전자 소자

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