WO2015050346A1 - Composition de cristaux liquides - Google Patents

Composition de cristaux liquides Download PDF

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WO2015050346A1
WO2015050346A1 PCT/KR2014/009125 KR2014009125W WO2015050346A1 WO 2015050346 A1 WO2015050346 A1 WO 2015050346A1 KR 2014009125 W KR2014009125 W KR 2014009125W WO 2015050346 A1 WO2015050346 A1 WO 2015050346A1
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Prior art keywords
liquid crystal
formula
group
crystal composition
film
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PCT/KR2014/009125
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English (en)
Korean (ko)
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유수영
허두영
김성진
정철인
이지연
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주식회사 엘지화학
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Priority to EP14850746.0A priority Critical patent/EP3053989A4/fr
Priority to JP2015559208A priority patent/JP6155520B2/ja
Priority claimed from KR1020140130473A external-priority patent/KR101640990B1/ko
Priority to US14/606,558 priority patent/US20150147490A1/en
Publication of WO2015050346A1 publication Critical patent/WO2015050346A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K2019/2035—Ph-COO-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K2019/2078—Ph-COO-Ph-COO-Ph

Definitions

  • the present application relates to a liquid crystal composition, a liquid crystal film and a display device.
  • LCDs liquid crystal displays
  • PDPs plasma display panels
  • OLEDs organic liquid crystal displays
  • An optical film including a brightness enhancing film, a retardation film, a viewing angle compensation film, and the like can be used for reducing the color change of a display device, securing a viewing angle, and improving brightness.
  • stretched the polymer film and provided optical anisotropy is known, and the system using the optical anisotropy of the liquid crystal film manufactured by hardening
  • Patent document 1 has proposed the technique of using the said reactive liquid crystal compound.
  • the liquid crystal film is usually prepared by applying a coating solution in which RM (Reactive Mesogen) is dissolved in a solvent.
  • RM Reactive Mesogen
  • solvents that exhibit proper solubility for the RM are extremely limited, which leads to manufacturing problems due to the inability to maintain liquid state for a suitable time during solvent drying after coating.
  • stains may be generated due to thickness variation, and thus, a high solubility solvent must be used, thereby causing a problem of substrate erosion.
  • Patent Document 1 Republic of Korea Patent Publication No. 2013-0092816
  • the present application provides a liquid crystal composition, a liquid crystal film and a display device.
  • the present application can provide a liquid crystal composition capable of exhibiting excellent solubility even in a variety of solvents, especially those known to exhibit low solubility in conventional RMs, and thus stains due to thickness batting even when produced by large area coatings. Preventing and preventing the problem of substrate erosion provides a good quality liquid crystal film.
  • Exemplary liquid crystal compositions may include reactive liquid crystal compounds.
  • the term "reactive liquid crystal compound” may mean a compound including a moiety capable of exhibiting liquid crystal, for example, a skeleton of mesogen, and at least one reactive functional group, For example, it may mean a liquid crystal compound in a form including a backbone of the mesogen core and a spacer connecting a reactive functional group to the mesogen core.
  • the term “mesogen core” may mean a polymerizable mesogen or a liquid crystal compound which is a monomeric compound.
  • the term “spacer” refers to a flexible organic group, and may mean a compound that connects the reactive functional group to the mesogenic core that can be polymerized.
  • the term “reactive functional group” may mean a general term for a polymerizable group.
  • the liquid crystal composition may include a first reactive liquid crystal compound and a second reactive liquid crystal compound.
  • the first reactive liquid crystal compound and the second reactive liquid crystal compound may have a structure belonging to the following formula (1).
  • M C is a mesogen core
  • L is an alkylene group
  • R is an alkenyl group, epoxy group, carboxyl group, cyano group, acryloyl group, methacryloyl group, acryloyloxy group or methacryloyloxy group
  • n is 2 or more.
  • X in the first reactive liquid crystal compound and X in the second reactive liquid crystal compound are different from each other, or carbon number of the alkylene group of L in the first reactive liquid crystal compound and alkyl of L in the second reactive liquid crystal compound The carbon number of the len group is different from each other.
  • alkylene group in the present specification unless otherwise specified, an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified.
  • the alkylene group may be linear, branched or cyclic.
  • the alkylene group may be optionally substituted by one or more substituents.
  • alkenyl group in the present specification unless otherwise specified, an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms may be exemplified.
  • the alkenyl group may be linear, branched or cyclic.
  • the alkenyl group may be optionally substituted by one or more substituents.
  • Substituents which may be substituted with any compound or substituent in the present specification include alkyl, alkoxy, alkenyl, epoxy, cyano, carboxyl, acryloyl, methacryloyl, acryloyloxy and methacrylo Iloxy group or aryl group may be exemplified, but is not limited thereto.
  • the skeleton of the mesogen core included in the first reactive liquid crystal compound and the second reactive liquid crystal compound may be the same.
  • the term "same skeleton of the mesogenic core” means that the rigid parts constituting the mesogenic core are the same, that is, for example, the same of the aromatic moiety and the linker connecting the aromatic moiety. Where the substituents are different in some of the residues it may be meant to include them.
  • the liquid crystal composition of the present application exhibits high solubility in various solvents including the first reactive liquid crystal compound and the second reactive liquid crystal compound while having the same skeleton of the mesogen core, thereby forming a liquid crystal layer by coating on a large area.
  • Liquid crystal composition of the present application may be a number within the range of 2 to 10, 2 to 8, 2 to 6 or 2 to 5 in the formula (1).
  • the mesogen core may be represented by the following formula (2).
  • R 11 to R 15 each independently represent a hydrogen, a halogen, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group or a nitro group, wherein p substituents in R 11 to R 15 form a radical connected with X of Formula 1 .
  • halogen in the present specification, chlorine, bromine or iodine and the like can be exemplified.
  • alkyl group in the present specification unless otherwise specified, a straight or branched chain alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, or 3 to 20 carbon atoms, Cycloalkyl groups having 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms or 3 to 6 carbon atoms may be exemplified.
  • the alkyl group may be optionally substituted by one or more substituents.
  • alkoxy group in the present specification, unless otherwise specified, an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms can be exemplified.
  • the alkoxy group may be linear, branched or cyclic.
  • the alkoxy group may be optionally substituted by one or more substituents.
  • single bond may mean that no separate atom or atom group exists at the corresponding site.
  • single bond means a case where no separate atom is present in a portion represented by A or B.
  • W is a single bond in Formula 2, benzene on both sides of W may be directly connected to form a biphenyl structure.
  • n is a number in the range of 1 to 4
  • p may be 1 or 2.
  • the blending ratio of the first and second reactive liquid crystal compounds may be selected in an appropriate range without particular limitation in consideration of the desired effect, for example, in comparison to 100 parts by weight of the first reactive liquid crystal compound.
  • the second reactive liquid crystal compound may be included in the liquid crystal composition in a ratio of 1 part by weight to 1,000, 10 parts by weight to 500, 25 parts by weight to 250 parts by weight, or 50 parts by weight to 150 parts by weight.
  • the unit "parts by weight” may mean a ratio of weights between components.
  • the liquid crystal composition of the present application may include an additional reactive liquid crystal compound, for example, a third or fourth reactive liquid crystal compound, in addition to the first and second reactive liquid crystal compounds described above in consideration of the desired effect, and the additional reactive liquid crystal
  • the compound may have the same skeleton of the aforementioned first and second reactive liquid crystal compounds and the mesogen core.
  • the liquid crystal composition of the present application includes only two or more liquid crystal compounds having the same skeleton of the mesogenic core, and may exhibit appropriate solubility even in a solvent having low solubility as described below. A layer can be formed.
  • the liquid crystal composition of the present application may further include a polymerization initiator, and is not particularly limited, but the polymerization initiator may be, for example, a photopolymerization initiator.
  • the said photoinitiator can start superposition
  • irradiation of light refers to, for example, electromagnetic waves such as microwaves, infrared rays (IR), ultraviolet rays (UV), X-rays, and gamma rays, alpha-particle beams, and proton beams. It may mean irradiation of a particle beam such as a proton beam, a neutron beam, or an electron beam.
  • photoinitiator is not specifically limited, A suitable kind can be selected and used according to the objective.
  • benzyl also called bibenzoyl
  • benzoin isobutyl ether benzoin isopropyl ether
  • benzophenone benzoyl benzoic acid
  • methyl benzoyl benzoate 4-benzoyl-4'-methyldiphenyl sulfide
  • benzyl methyl Ketal dimethylaminomethylbenzoate, 2-n-butoxyethyl-4-dimethylaminobenzoate, p-methylaminobenzoic acid isoamyl, 3-3'-dimethyl-4-methoxybenzophenone, methyllobenzoylfo Mate, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane
  • the specific ratio of the photopolymerization initiator is not particularly limited, and an appropriate ratio may be selected according to the purpose.
  • the photopolymerization initiator may be included in a ratio of 1 part by weight to 10 parts by weight with respect to 100 parts by weight of the liquid crystal compound, but is not limited thereto. If the ratio of the photopolymerization initiator is too low, proper polymerization may not be induced. On the contrary, if the ratio of the photopolymerization initiator is too high, physical properties may deteriorate due to the remaining initiator after formation of the liquid crystal layer, and an appropriate ratio may be selected in consideration of this.
  • the liquid crystal composition may further comprise a surfactant.
  • a surfactant for example, a fluorocarbon-based or silicone-based surfactant may be exemplified.
  • Fluorocarbon-based surfactants can be exemplified by Fluorad FC4430, Fluorad FC4432, Fluorad FC4434, or Zonyl, Dupont, USA, and the like. Chemie BYK and the like can be exemplified, but is not limited thereto.
  • the ratio of the surfactant is not particularly limited, and may be included, for example, about 0.05 to 5 parts by weight based on 100 parts by weight of the horizontally oriented liquid crystal compound. If the ratio of the surfactant is too low, the surface state of the liquid crystal layer may be poor, and if it is too high, staining due to the surfactant may occur, an appropriate ratio may be selected in consideration of this.
  • the liquid crystal composition of the present application may further include a solvent.
  • the solvent is not particularly limited, but may be, for example, a solvent having a solubility at room temperature of 10 or less with respect to the reactive liquid crystal compound of Formula 4 below.
  • the term "solubility” may mean a gram number (g) of the solute as a conventionally used meaning, for example, the maximum amount of solute that can be dissolved in 100 g of a solvent at a constant temperature.
  • g / (solvent) 100 g "or the said unit may be abbreviate
  • the solute may mean the liquid crystal compound described above.
  • room temperature in the present specification is a natural temperature without heating or cooling, for example, may mean a temperature of about 10 °C to about 30 °C, about 15 °C to about 30 °C or about 25 °C. have.
  • the lower limit is not particularly limited in the present application because it is possible to select a variety of solvents, for example, the solubility of the solvent is 9, 8, 7, 6 for the reactive liquid crystal compound of Formula 4 at room temperature Or five.
  • the solubility of the solvent may vary depending on the type of specific solvent, for example, may be 10 or less, 15 or less or 20 or less with respect to the reactive liquid crystal compound of Formula 4 at room temperature.
  • the liquid crystal composition of the present application can exhibit appropriate solubility even in a solvent having a low solubility, and can form a liquid crystal layer on a base layer exhibiting erosion to a solvent.
  • the solvent include ketone solvents such as methyl ethyl ketone or methyl isobutyl ketone; Ether solvents such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol methyl ether, propylene glycol dimethyl ether or propylene glycol diethyl ether; Halogenated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane or 1,1,2-trichloroethene; Aromatic hydrocarbon solvents such as hexane, heptane, octane, cyclohexane, benzene, toluene or xylene; Alcohol solvents such as methanol, ethanol, isopropanol, propanol, butanol or t-butanol; Acetate solvents such as propylene glycol
  • liquid crystal composition may further include a known additive, for example, a stabilizer or a nonpolymerizable non-liquid crystal compound, if necessary.
  • the present application also relates to a liquid crystal film.
  • An exemplary liquid crystal film may include a liquid crystal layer formed by the liquid crystal composition.
  • the liquid crystal film includes, for example, a base layer 20;
  • the alignment layer 30 present on the substrate layer 20 and the liquid crystal layer 40 present on the alignment layer 30 may be included.
  • a base material layer contained in the said liquid crystal film For example, As a plastic base material layer, Cellulose base layers, such as TAC (triacetyl cellulose) or DAC (diacetyl cellulose); Cyclo olefin polymer (COP) substrate layers such as norbornene derivatives; An acrylic base layer such as poly (methyl methacrylate), a polycarbonate base layer, a polyolefin base layer such as polyethylene (PE) or polypropylene (PP), a polyvinyl alcohol (PVA) base layer; Polyether sulfone (PES) base layer; polyetheretherketon (PEEK) base layer; polyetherimide (PEI) base layer; polyethylene naphthalate (PEN, polyethylenenaphthatlate) base layer; polyethylene terephtalate A polyester base layer such as), a polyimide (PI) base layer, a polysulfone (PSF, polysulfone) base layer, or a fluoropolylene
  • an alignment film existing between the base layer and the liquid crystal layer may be a known alignment film, for example, an optical alignment film, without being limited in kind, and may be formed by other known methods such as rubbing polymerization.
  • the liquid crystal layer which may be formed on the alignment layer in the liquid crystal film may be prepared by, for example, coating, aligning and curing the liquid crystal composition described above or a coating solution prepared using the same on the alignment layer.
  • the liquid crystal layer can be formed by, for example, applying the liquid crystal composition onto the alignment film, and aligning and polymerizing the liquid crystal compound.
  • the liquid crystal composition can be prepared, for example, by dissolving the polymerizable liquid crystal compound in an appropriate solvent.
  • a liquid crystal composition can be manufactured by dissolving a polymeric liquid crystal compound and a photoinitiator in a solvent.
  • a chiral agent, a surfactant, a polymerizable monomer, a polymer, and the like may be further added to the liquid crystal composition in a range that does not prevent the alignment of the liquid crystal molecules.
  • halogenated hydrocarbons such as chloroform, tetrachloroethane, trichloroethylene, tetrachloroethylene and chlorobenzene
  • Aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, cymene, methoxy benzene and 1,2-dimethoxybenzene
  • Ketones such as acetone, methyl ethyl ketone, cyclohexanone or cyclopentanone
  • Alcohols such as isopropyl alcohol or n-butanol
  • Solvents such as cellosolves such as methyl cellosolve, ethyl cellosolve or butyl cellosolve can be used.
  • drying After apply
  • the coating layer is irradiated with light, for example ultraviolet rays, to polymerize the liquid crystal compound.
  • light for example ultraviolet rays
  • Such polymerization can be done in the presence of a photoinitiator that absorbs wavelengths in the ultraviolet region.
  • the crosslinking reaction in the above-described alignment film may also be induced by the light irradiation.
  • Ultraviolet irradiation can be carried out in the atmosphere or under a nitrogen atmosphere in which oxygen is blocked to increase the reaction efficiency.
  • the ultraviolet irradiator may be generally performed using a medium or high pressure mercury ultraviolet lamp or a metal halide lamp with an intensity of 80 w / cm or more. If necessary, a cold mirror or other cooling device may be provided between the base layer and the ultraviolet lamp so that the surface temperature of the liquid crystal layer at the time of ultraviolet irradiation becomes a temperature range having a liquid crystal state.
  • the liquid crystal film may be used, for example, as a retardation film or a viewing angle compensation film for a display device, a protective film of a polarizer, or the like.
  • the manufacturing method of the required liquid crystal film other than the above-mentioned content can employ
  • the present application also relates to a display device such as a liquid crystal display device or the like.
  • a display device such as a liquid crystal display device or the like.
  • An exemplary liquid crystal display device may include the liquid crystal film.
  • the liquid crystal film may be useful, for example, as an optical compensation substrate layer for a liquid crystal display device, and thus the liquid crystal film may be included in the device as an optical compensation substrate layer.
  • the film may be, for example, a phase difference film such as a super twist nematic (STN) LCD, a thin film transistor-twisted nematic (TFT-TN) LCD, a vertical alignment (VA) LCD, or an in-plane switching (IPS) LCD. ; ⁇ / 2 waveplate; ⁇ / 4 waveplate; Reverse wavelength dispersion film; Optical compensation films; Color filters; Laminated film with a polarizing plate or a polarizer; It can be used as a polarizing plate compensation film or the like.
  • STN super twist nematic
  • TFT-TN thin film transistor-twisted nematic
  • VA vertical alignment
  • IPS in-plane switching
  • Optical compensation films Color filters
  • Laminated film with a polarizing plate or a polarizer It can
  • the liquid crystal display device includes a liquid crystal panel and first and second polarizing plates disposed on both surfaces of the liquid crystal panel, respectively, and the liquid crystal film is between the liquid crystal panel and the first polarizing plate and / or the liquid crystal.
  • the panel may be disposed between the panel and the second polarizing plate.
  • the first and / or second polarizing plate may include a protective film on one or both surfaces.
  • a protective film a TAC film, a polynorbornene film made of a ring opening metathesis polymerization (ROMP), a ring opening metathesis polymerization followed by hydrogenation (HROMP) polymer prepared by hydrogenating a cycloolefin polymer (COPP) which is ring-opened polymerized again, It may be a polyester film or a polynorbornene-based film prepared by addition polymerization, and the like, but a film made of a transparent polymer material may be used as a protective film, but is not limited thereto.
  • the liquid crystal composition according to the present application can form a liquid crystal layer which does not generate stains due to thickness differences even when a liquid crystal layer is formed by coating on a large area, and can exhibit proper solubility even in a solvent having low solubility.
  • a liquid crystal composition capable of forming a liquid crystal layer on a base material layer exhibiting erosion to a solvent may be provided.
  • FIG. 1 is a figure which shows typically the structure of the liquid crystal film which concerns on one example of this application.
  • liquid crystal compositions prepared in Examples and Comparative Examples were frozen for 24 hours at a temperature of ⁇ 8 ° C. and then visually observed whether the injected liquid crystal compositions were precipitated and evaluated according to the following evaluation criteria.
  • the liquid crystal film is positioned between the two polarizing plates having the absorption axis of the polarizing plate at an angle of 90 degrees on the backlight. After the optical axis of the liquid crystal film was matched with the absorption axis of one of the two polarizing plates, the number of brightly bright spots (bright spots) was measured based on 1 m 2 .
  • the liquid crystal composition was coated to have a thickness of about 1 ⁇ m after drying, and then heated in an oven at 60 ° C. for 2 minutes to remove the solvent inside the coating film. Subsequently, the dried coating film was irradiated with ultraviolet rays (light source: 300mJ / cm 2 high pressure mercury lamp) and cured to prepare a liquid crystal film.
  • ultraviolet rays light source: 300mJ / cm 2 high pressure mercury lamp
  • Example 1 a solvent (B) obtained by mixing methyl ethyl ketone, propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 4: 2: 4 instead of the solvent (A) was added at a concentration of 25% by weight. Except that, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Example 1.
  • Example 1 Except that in Example 1, instead of the solvent (A), a solvent (C) mixed with toluene, propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 4: 2: 4 was added so as to have a concentration of 25% by weight. Then, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Example 1.
  • Example 4 a solvent (B) obtained by mixing methyl ethyl ketone, propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 4: 2: 4 instead of the solvent (A) was added at a concentration of 25% by weight. Except that, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Example 4.
  • Example 4 Except that in Example 4, instead of the solvent (A), toluene, propylene glycol methyl ether acetate and 2-butoxyethanol were mixed in a weight ratio of 4: 2: 4 so that the solvent (C) was added at a concentration of 25% by weight. Then, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Example 4.
  • Example 4 Except that in Example 4, instead of the solvent (A), the solvent (D) mixed with propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 6: 4 was added so as to have a concentration of 25% by weight, A liquid crystal composition and a liquid crystal film were prepared in the same manner as in 4.
  • 2-Methyl-1,4-phenylene bis (4-(((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate) which is a liquid crystal compound of the formula (A) as a liquid crystal compound (2-methyl- Liquid crystal composition in the same manner as in Example 1, except that only 100% of 1,4-phenylene bis (4-(((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate, LC242, manufactured by BASF Corporation) was used. And a liquid crystal film.
  • Comparative Example 1 a solvent (B) obtained by mixing methyl ethyl ketone, propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 4: 2: 4 instead of the solvent (A) was added to a concentration of 25% by weight. Except that, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Comparative Example 1.
  • 2-methyl-1,4-phenylene bis (4-(((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate) which is a liquid crystal compound represented by the above formula (A) (2-methyl -1,4-phenylene bis (4-(((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate, LC242, manufactured by BASF Corporation) and 2-methyl-1,4- which are liquid crystal compounds of the formula (B) Phenylene bis (4- (3- (acryloyloxy) propoxy) benzoate) (2-methyl-1,4-phenylene bis (4- (3- (acryloyloxy) propoxy) benzoate, RM 257, MERCK company (C) and 4-cyanophenyl 4- (4- (acryloyloxy) butoxy) benzoate, which is a liquid crystal compound represented by the following formula (D), RM23 ) And a liquid crystal composition and a liquid crystal film were prepared in the same manner as
  • Comparative Example 5 a solvent (B) obtained by mixing methyl ethyl ketone, propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 4: 2: 4 instead of the solvent (A) was added so as to have a concentration of 25% by weight. Except that, a liquid crystal composition and a liquid crystal film were prepared in the same manner as in Comparative Example 5.
  • Comparative Example 5 except that the solvent (D) mixed with propylene glycol methyl ether acetate and 2-butoxyethanol in a weight ratio of 6: 4 instead of the solvent (A) was added to a concentration of 25% by weight, Comparative Example A liquid crystal composition and a liquid crystal film were produced in the same manner as in 5.
  • the liquid crystal composition according to the present application may exhibit appropriate solubility even in a solvent having low solubility, and may not only form a liquid crystal layer on a base layer exhibiting erosion to a solvent.
  • the liquid crystal layer is formed by coating on a large area, it was confirmed that a liquid crystal layer can be formed in which unevenness due to a thickness difference does not occur.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Polarising Elements (AREA)

Abstract

La présente invention concerne une composition de cristaux liquides, un film de cristaux liquides et un dispositif d'affichage. La présente invention concerne une composition de cristaux liquides qui peut former une couche de cristaux liquides qui empêche l'apparition d'une tache provoquée par une différence d'épaisseur ou analogue, même dans le cas de la formation d'une couche de cristaux liquides sur une grande zone au moyen d'un revêtement, et qui peut également être soluble de manière adéquate, même dans un solvant présentant une faible solubilité, et former la couche de cristaux liquides, même sur une couche de matériau de base présentant une corrosivité par rapport à une matière première.
PCT/KR2014/009125 2013-10-01 2014-09-29 Composition de cristaux liquides WO2015050346A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP14850746.0A EP3053989A4 (fr) 2013-10-01 2014-09-29 Composition de cristaux liquides
JP2015559208A JP6155520B2 (ja) 2013-10-01 2014-09-29 液晶組成物
US14/606,558 US20150147490A1 (en) 2013-10-01 2015-01-27 Liquid crystal composition

Applications Claiming Priority (4)

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KR20130117089 2013-10-01
KR10-2013-0117089 2013-10-01
KR10-2014-0130473 2014-09-29
KR1020140130473A KR101640990B1 (ko) 2013-10-01 2014-09-29 액정 조성물

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US14/606,558 Continuation US20150147490A1 (en) 2013-10-01 2015-01-27 Liquid crystal composition

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WO2015050346A1 true WO2015050346A1 (fr) 2015-04-09

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080103430A (ko) * 2007-05-23 2008-11-27 후지필름 가부시키가이샤 광학 필름, 광학 보상 필름, 편광판, 및 액정 표시 장치
US7862867B2 (en) * 2006-10-05 2011-01-04 Nissan Chemical Industries, Ltd. Bifunctional polymerizable compound, polymerizable liquid crystal composition, and oriented film
KR20110039267A (ko) * 2008-06-17 2011-04-15 바스프 에스이 단열 필름 및 라미네이트
US8313814B2 (en) * 2005-11-25 2012-11-20 Fujifilm Corporation Cellulose acylate film, method of producing the same, cellulose derivative film, optically compensatory film using the same, optically-compensatory film incorporating polarizing plate, polarizing plate and liquid crystal display device
KR20130092816A (ko) 2012-02-13 2013-08-21 (주)켐넥스 반응성 메소젠 화합물, 이를 포함하는 액정 조성물, 표시 패널의 제조 방법 및 표시 패널
US20130250229A1 (en) * 2010-11-19 2013-09-26 Fujifilm Corporation Birefringence pattern transfer foil

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8313814B2 (en) * 2005-11-25 2012-11-20 Fujifilm Corporation Cellulose acylate film, method of producing the same, cellulose derivative film, optically compensatory film using the same, optically-compensatory film incorporating polarizing plate, polarizing plate and liquid crystal display device
US7862867B2 (en) * 2006-10-05 2011-01-04 Nissan Chemical Industries, Ltd. Bifunctional polymerizable compound, polymerizable liquid crystal composition, and oriented film
KR20080103430A (ko) * 2007-05-23 2008-11-27 후지필름 가부시키가이샤 광학 필름, 광학 보상 필름, 편광판, 및 액정 표시 장치
KR20110039267A (ko) * 2008-06-17 2011-04-15 바스프 에스이 단열 필름 및 라미네이트
US20130250229A1 (en) * 2010-11-19 2013-09-26 Fujifilm Corporation Birefringence pattern transfer foil
KR20130092816A (ko) 2012-02-13 2013-08-21 (주)켐넥스 반응성 메소젠 화합물, 이를 포함하는 액정 조성물, 표시 패널의 제조 방법 및 표시 패널

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3053989A4 *

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