WO2010044604A2 - Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same - Google Patents

Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same Download PDF

Info

Publication number
WO2010044604A2
WO2010044604A2 PCT/KR2009/005908 KR2009005908W WO2010044604A2 WO 2010044604 A2 WO2010044604 A2 WO 2010044604A2 KR 2009005908 W KR2009005908 W KR 2009005908W WO 2010044604 A2 WO2010044604 A2 WO 2010044604A2
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
optical compensation
crystal compounds
compensation film
nematic liquid
Prior art date
Application number
PCT/KR2009/005908
Other languages
French (fr)
Other versions
WO2010044604A3 (en
WO2010044604A9 (en
Inventor
Yonggyun Cho
Sangyeup Lee
Kinam Chung
Kwangjin Chung
Cholho Lee
Myounglae Kim
Hyukjun Kim
Kiyup Kim
Sungho Son
Wonseok Jang
Original Assignee
Sk Energy Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sk Energy Co., Ltd. filed Critical Sk Energy Co., Ltd.
Publication of WO2010044604A2 publication Critical patent/WO2010044604A2/en
Publication of WO2010044604A3 publication Critical patent/WO2010044604A3/en
Publication of WO2010044604A9 publication Critical patent/WO2010044604A9/en

Links

Images

Classifications

    • 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
    • C09K19/36—Steroidal liquid crystal compounds
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3477—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
    • 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3488—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133632—Birefringent elements, e.g. for optical compensation with refractive index ellipsoid inclined relative to the LC-layer surface
    • 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
    • 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133633—Birefringent elements, e.g. for optical compensation using mesogenic materials
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133635—Multifunctional compensators

Definitions

  • the present invention relates to nematic liquid crystal compounds, an optical compensation film thereof and a method of manufacturing the same, and more particularly, to nematic liquid crystal compounds capable of widening a viewing angle, an optical compensation film thereof for a Twisted Nematic (TN) Liquid Crystal Display (LCD), and a method of manufacturing the same.
  • TN Twisted Nematic
  • LCD Twisted Nematic
  • liquid crystal material is injected between two glass substrates, and voltage is applied from the outside so that electrical and optical properties of liquid crystal are used.
  • This LCD is distinguished from other existing displays in an aspect of using light incident from the outside. Also, the LCD has advantages of slim thickness, light weight and low power consumption and is used for various applications including televisions, monitors for personal computers, navigation systems for motor vehicles, digital cameras and cellular phones.
  • Modes of driving the liquid crystal include Twisted Nematic (TN) using nematic liquid crystal, Super Twisted Nematic (STN), In-Plane Switching (IPS), Vertical Alignment (VA) and Optically Compensated Bend (OCB).
  • TN Twisted Nematic
  • STN Super Twisted Nematic
  • IPS In-Plane Switching
  • VA Vertical Alignment
  • OCB Optically Compensated Bend
  • the liquid crystal in the driving modes is an isotropic material having two refractive indexes, i.e. ordinary refractive index and extraordinary refractive index, light path and birefringence are varied depending on incidence angles of the incident light. Therefore, Contrast Ratio (CR) variation and gray scale inversion occur depending on a viewing direction to a screen.
  • TN liquid crystal displays have disadvantages of narrow viewing angle and CR since they have large variation in phase difference ( ⁇ nd) depending on a traveling direction of the light.
  • a compensation film is used to compensate the phase difference and thus increase the viewing
  • Japanese Patent Publication No. 2004-240012 discloses a retardation plate, consisting of stacked three layers, in which the first optically anisotropic layer substantially has a phase difference of ⁇ at 550 nm wavelength, and the second optically anisotropic layer substantially has a phase difference of ⁇ /2 at 550 nm wavelength and the third optically anisotropic layer has negative optical anisotropy.
  • the ratios of the retardation/wavelength measured at 450 nm, 550 nm and 650 nm wavelengths are between 0.2 and 0.3, and at least one of the first and the second layer consist of liquid crystal molecules fixed in nematic alignment so as to be tilted by a tilt angle range of 5 to 35°.
  • the stacking of the three layers requires a lamination process using an adhesive.
  • the process becomes complex, and optical axis distortion may easily cause quality reduction and low yield resulting in the increase of production costs.
  • the characteristics of the anisotropy are affected by various conditions including molecular weight of polymer, temperature and extension speed, it is also difficult to control the anisotropy of the respective layer.
  • Japanese Patent Publication No. 2005-208414 discloses a reverse wavelength dispersion retardation film obtained by immobilizing a liquid crystal monomer having, in its molecule, discotic mesogen and nematic mesogen with a combined polymerizable moiety at the terminal group while maintaining such an orientation that the optical axes of the discotic mesogen and the nematic mesogen are oriented substantially in parallel to each other, and Japanese Patent Publication No.
  • 2006-78670 discloses an optical compensation sheet including an optically anisotropic layer having different refractive indexes in three directions and a transparent supporting body, wherein the optical anisotropic layer is formed by polymerizing discotic liquid crystal molecules having at least one polymerizable group with chemicals having a plurality of polymerizable groups.
  • the optical compensation sheet manufactured by the polymerization reaction still has a color shift problem originating from the discotic liquid crystal.
  • Japanese Patent Publication Nos. 2004-240012, 2006-78670, 2006-133652 and 2006-201579 disclose optical compensation sheet with improved viewing angle property by limiting the retardation ratio (Re/Rth).
  • Re/Rth retardation ratio
  • Embodiments of the present invention are directed to an optical compensation film with excellent viewing angle compensation ability and a method of manufacturing the same.
  • the present invention provides nematic liquid crystal compounds containing chemicals in which two or more mesogens have a predetermined bond angle.
  • the present invention provides nematic liquid crystal compounds containing chemicals according to the following Chemical Formula 1:
  • n and n are independently a natural number between 1 and 12;
  • a and A' are a discotic or rod-like mesogen and are the same or different from each other;
  • connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer;
  • B is a functional group maintaining geometrically a predetermined bond angle.
  • the present invention provides an optical compensation film including a transparent substrate layer; an alignment layer stacked on the transparent substrate layer; and a coated layer containing the nematic liquid crystal compounds, stacked on the alignment layer and containing the nematic liquid crystal compounds.
  • the present invention provides a method of manufacturing an optical compensation film by forming an alignment layer on a substrate layer; by coating a solution containing the nematic liquid crystal compounds on the formed alignment layer; and irradiating Ultra Violet ray (UV) to the formed layer at 50 to 150 °C.
  • UV Ultra Violet ray
  • Words of degree such as “About”, “Substantially”, and the like are used herein in the sense of “at, or nearly at, when given the manufacturing and material tolerances inherent in the stated circumstances” and are used to prevent the unscrupulous infringer from unfairly taking advantage of the invention disclosure where exact or absolute figures are stated as an aid to understanding the invention.
  • the present invention provides nematic liquid crystal compounds containing chemicals according to the following Chemical Formula 1:
  • n and n are independently a natural number between 1 and 12;
  • a and A' are a discotic or rod-like mesogen and are the same or different from each other;
  • B is a functional group maintaining a predetermined bond angle geometrically.
  • a and A' are independently discotic or rod-like, and may be all rod-like, all discotic or a mixture of discotic and rod-like. Preferably, A and A' are all discotic.
  • B is a functional group maintaining a predetermined bond angle geometrically.
  • B is a functional group having no variation in the bond angle without strain and functions to maintain a predetermined bond angle between the mesogens, thereby improving a viewing angle.
  • B can be selected from
  • connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer, and preferably two mesogens are linearly linked.
  • the linear linking of two mesogens is disclosed in Chem. Rev . 1999, Vol. 99, 1863, J. AM. CHEM. SOC. 2003, Vol. 125, 11062, J. Am. Chem. Soc. 1985, Vol. 107, 4192, J. Org. Chem. 2005,Vol. 70, 2745, Science, 2001, Vol. 293,79, J. Am. Chem. Soc. 2006, Vol. 128, 7670, Accounts of Chemical Research, 2004, Vol. 37, 735, Eur. J. Org. Chem. 2006, 3087.
  • R 1 -R 4 are independently (C1-C14)alkyl, (C1-C14)alkoxy, (C1-C14)alkylcarbonyl, (C6-C20)aryl, (C6-C20)arylcarbonyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl ;
  • the alkyl, the alkyl of alkylcarbonyl and the alkoxy of the alkoxy and alkoxycarbonyl in the R 1 -R 4 may be straight or branched chain and may contain saturated or unsaturated bond;
  • the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R 1 -R 4 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
  • R 1 -R 4 are independently (C1-C14)alkyl, (C6-C20)aryl, (C1-C14)alkanoyl, (C3-C20)alkenoyl, (C3-C20)alkynoyl, (C7-C20)aryloyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl; and
  • the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R 1 -R 4 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
  • the present invention provides an optical compensation film containing the nematic liquid crystal compounds, and the optical compensation film of the present invention may be provided through the following processes.
  • the present invention provides a method of manufacturing an optical compensation film by forming an alignment layer on a substrate film; forming a layer by coating a solution containing the nematic liquid crystal compounds on the formed alignment layer; and irradiating Ultra Violet ray (UV) to the formed layer at 50 to 150 °C.
  • UV Ultra Violet ray
  • the optical compensation film of the present invention manufactured by the above method includes a transparent substrate layer; an alignment layer stacked on the transparent substrate layer; and a coated layer stacked on the alignment layer and containing the nematic liquid crystal compounds containing the chemicals according to the Chemical Formula 1.
  • a process of forming the alignment layer by coating an alignment solution on the substrate and then drying the alignment solution may be implemented.
  • the substrate layer is transparent and to be transparent means that a light transmittance is 80 % or over.
  • the substrate layer of the present invention may be selected from the group consisting of glass, olefin based resin, cycloolefin based resin, ester based resin, polycarbonate, polyacrylate and polysulfone, and mixture and copolymer thereof, and an example for the substrate layer includes cellulose ester, polycarbonate, polysulfone, polyether sulfone, polyacrylate, polymethacrylate and norbornene resin. More specifically, cellulose triacetate or polyethylene terephthalate in the form of a film may be used.
  • a thickness of the substrate layer is preferably 20 to 500 ⁇ m and more preferably 40 to 200 ⁇ m.
  • the substrate layer may be optically anisotropic film made by extension, and when the substrate layer is a cellulose ester film, retardation increasing agent may be added.
  • the substrate layer may be subject to glow discharge, corona discharge, UV treatment, flame treatment, alkali treatment, acid treatment or be given an adhesive layer.
  • a process of forming the alignment layer on the substrate layer may be implemented, and the alignment layer of the present invention is made of a resin selected from the group consisting of polyimide, polystyrene based polymer, gelatin and polyvinyl alcohol based polymer, and mixture and copolymer thereof, and more preferably contains polyvinyl alcohol based polymer.
  • the alignment layer is made by coating the polymer solutions on the substrate layer, dried and then by exposing it to magnetic field or light or rubbing its surface.
  • concentration of resins in the solutions is between 0.1 to 10 by weight% and the solutions may contain an additive helping alignment of the surface functional group in the layer.
  • the solutions can be coated on the substrate by various coating methods such as bar coating, gravure coating, die coating, roll coating and meniscus roll coating, dried at 40 to 200 °C, preferably at 50 to 100 °C, and then rubbed, thereby providing the alignment layer of the present invention.
  • a process of forming the layer by coating a solution containing the nematic liquid crystal compounds containing the chemical of the Chemical formula 1, in which two or more mesogens have a predetermined bond angle, on the alignment layer may be implemented.
  • n are a natural number between 1 and 12;
  • a and A' are a discotic or rod-like mesogen and are the same or different from each other;
  • B is a functional group maintaining geometrically a predetermined bond angle.
  • Connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer, and preferably two mesogens are linearly linked.
  • the mesogen are all discotic, all rod-like or mixture of discotic and rod-like, preferably are of the form including discotic, more preferably are all discotic.
  • nematic liquid crystal compounds containing the chemicals in which two or more mesogens have a predetermined bond angle includes chemicals according to the following Chemical Formula 3, but not limited thereto.
  • R 1 -R 8 are independently (C1-C14)alkyl, (C1-C14)alkoxy, (C1-C14)alkylcarbonyl, (C6-C20)aryl, (C6-C20)arylcarbonyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl;
  • the alkyl of the alkyl and alkylcarbonyl and the alkoxy of the alkoxy and alkoxycarbonyl of the R 1 -R 8 may be straight or branched chain and contain saturated or unsaturated bond; and the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R 1 -R 8 may be further substituted with one or more substituent
  • R 1 -R 8 are (C1-C14)alkyl, (C6-C20)aryl, (C1-C14)alkanoyl, (C3-C20)alkenoyl, (C3-C20)alkynoyl, (C7-C20)aryloyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl, and the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R 1 -R 8 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
  • the liquid crystal compounds may be 1 to 30 weight% in the entire solution.
  • the content of the liquid crystal compounds is less than 1 weight%, improvement in the optical compensation or color shift of the film is not expected.
  • the content of the liquid crystal compounds is over 30 weight%, waste of material is caused since effect corresponding to the exceeding content is not remarkable.
  • a thickness of the coating is preferably 0.5 to 10 ⁇ m.
  • An example for a method of coating the liquid crystal compounds of the present invention on the alignment layer includes bar coating, gravure coating, die coating, roll coating and meniscus roll coating, but not limited thereto.
  • optical compensation film of the present invention it is possible to obtain excellent viewing angle compensation effect and reduce color shift by using liquid crystal compounds containing two or more mesogens.
  • Fig. 1 is a graph showing the result of phase difference in an optical compensation film in accordance with a preferred embodiment of the present invention.
  • liquid crystal compound was obtained from heptoxy carbonylmethyl substituted porphyrin using 1.3 phenylene spacer through Ag(I)-promoted coupling method (refer to J. Am. Chem. Soc., 1985, Vol. 107, 4192).
  • alkyl substituted polyvinyl alcohol (PVA; R 1130, Kuraray Co., Ltd) was coated to 500 nm thickness.
  • PVA alkyl substituted polyvinyl alcohol
  • 1.5 g of R1130, 75 g of deionized water, 24 g of methanol, 0.15 g of 50% aqueous solution of glutaraldehyde and 1.1 g of 0.5M sulfuric acid were mixed to manufacture a PVA aqueous solution.
  • the PVA aqueous solution was coated using #16 Mayer bar, dried at 60 °C for 90 seconds, cooled for 2 minutes and then dried again at 80 °C for 150 seconds, thereby manufacturing an alignment layer on the cellulose triacetate film.
  • a surface of the manufactured alignment layer (PVA) was rubbed using a rubbing machine (Meere Company Inc.).
  • a coating solution containing 10% of the liquid crystal compound of Manufacturing Example 1 was coated to 2 ⁇ m thickness using #10 Mayer bar.
  • the liquid crystal solution was obtained by dissolving 2 g of the liquid crystal compound of Manufacturing Example 1, 0.01 g of a photoinitiator (IRGACURE 184, Ciba Inc.) and 18 g of methylethylketone, and was cured at 130 °C for 150 seconds using a UV curing machine (APO Co., Ltd.).
  • a photoinitiator IRGACURE 184, Ciba Inc.
  • a Phase difference of the manufactured film was measured with a birefringence analyzer (KOBRA-WPR manufactured by Oji Scientific Instrument) with varying an incident angle of light having 589 nm wavelength. The results were shown in Fig. 1.
  • Fig. 1 is a graph showing the result of the phase difference in the optical compensation film in accordance with a preferred embodiment of the present invention. Referring to Fig. 1, it can be appreciated that the optical compensation film of the present invention has viewing angle compensation effect from phase difference variation pattern and phase difference value according to an incident angle.
  • an optical compensation sheet capable of obtaining excellent viewing angle compensation effect and reducing color shift.
  • optical compensation film of the present invention it is possible to obtain excellent viewing angle compensation effect and reduce color shift by using liquid crystal compounds containing two or more mesogens.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)

Abstract

Provided are nematic liquid crystal compounds, an optical compensation film thereof and a method of manufacturing the same, more specifically, provided are an optical compensation film containing nematic liquid crystal compounds containing chemicals in which two or more mesogens have a predetermined bond angle and which is capable of compensating a viewing angle as well as reducing color shift, and a method of manufacturing the same.

Description

NEMATIC LIQUID CRYSTAL COMPOUNDS, OPTICAL COMPENSATION FILM THEREOF AND A METHOD OF MANUFACTURING THE SAME
The present invention claims priority of Korean Patent Application No. 10-2008-0100671, filed on October 14, 2008, which is incorporated herein by reference.
The present invention relates to nematic liquid crystal compounds, an optical compensation film thereof and a method of manufacturing the same, and more particularly, to nematic liquid crystal compounds capable of widening a viewing angle, an optical compensation film thereof for a Twisted Nematic (TN) Liquid Crystal Display (LCD), and a method of manufacturing the same.
In A liquid Crystal Display (LCD), liquid crystal material is injected between two glass substrates, and voltage is applied from the outside so that electrical and optical properties of liquid crystal are used. This LCD is distinguished from other existing displays in an aspect of using light incident from the outside. Also, the LCD has advantages of slim thickness, light weight and low power consumption and is used for various applications including televisions, monitors for personal computers, navigation systems for motor vehicles, digital cameras and cellular phones.
Modes of driving the liquid crystal include Twisted Nematic (TN) using nematic liquid crystal, Super Twisted Nematic (STN), In-Plane Switching (IPS), Vertical Alignment (VA) and Optically Compensated Bend (OCB). Since the liquid crystal in the driving modes is an isotropic material having two refractive indexes, i.e. ordinary refractive index and extraordinary refractive index, light path and birefringence are varied depending on incidence angles of the incident light. Therefore, Contrast Ratio (CR) variation and gray scale inversion occur depending on a viewing direction to a screen. Particularly, TN liquid crystal displays have disadvantages of narrow viewing angle and CR since they have large variation in phase difference (△nd) depending on a traveling direction of the light. In order to improve the aforementioned disadvantages, a compensation film is used to compensate the phase difference and thus increase the viewing angle.
Japanese Patent Publication No. 2004-240012 discloses a retardation plate, consisting of stacked three layers, in which the first optically anisotropic layer substantially has a phase difference of π at 550 nm wavelength, and the second optically anisotropic layer substantially has a phase difference of π/2 at 550 nm wavelength and the third optically anisotropic layer has negative optical anisotropy. In the plate, the ratios of the retardation/wavelength measured at 450 nm, 550 nm and 650 nm wavelengths are between 0.2 and 0.3, and at least one of the first and the second layer consist of liquid crystal molecules fixed in nematic alignment so as to be tilted by a tilt angle range of 5 to 35°. However, the stacking of the three layers requires a lamination process using an adhesive. Thus the process becomes complex, and optical axis distortion may easily cause quality reduction and low yield resulting in the increase of production costs. Also, since the characteristics of the anisotropy are affected by various conditions including molecular weight of polymer, temperature and extension speed, it is also difficult to control the anisotropy of the respective layer.
To overcome the aforementioned disadvantages, Japanese Patent Publication No. 2005-208414 discloses a reverse wavelength dispersion retardation film obtained by immobilizing a liquid crystal monomer having, in its molecule, discotic mesogen and nematic mesogen with a combined polymerizable moiety at the terminal group while maintaining such an orientation that the optical axes of the discotic mesogen and the nematic mesogen are oriented substantially in parallel to each other, and Japanese Patent Publication No. 2006-78670 discloses an optical compensation sheet including an optically anisotropic layer having different refractive indexes in three directions and a transparent supporting body, wherein the optical anisotropic layer is formed by polymerizing discotic liquid crystal molecules having at least one polymerizable group with chemicals having a plurality of polymerizable groups. However, the optical compensation sheet manufactured by the polymerization reaction still has a color shift problem originating from the discotic liquid crystal.
Japanese Patent Publication Nos. 2004-240012, 2006-78670, 2006-133652 and 2006-201579 disclose optical compensation sheet with improved viewing angle property by limiting the retardation ratio (Re/Rth). However, there occurs an increase of viewing angle dependency since difference between a retardation value (Re) in a plane direction of the film and a retardation value (Rth) in a thickness direction of the film increases.
Embodiments of the present invention are directed to an optical compensation film with excellent viewing angle compensation ability and a method of manufacturing the same.
To achieve the object of the present invention, the present invention provides nematic liquid crystal compounds containing chemicals in which two or more mesogens have a predetermined bond angle.
Also, the present invention provides nematic liquid crystal compounds containing chemicals according to the following Chemical Formula 1:
[Chemical formula 1]
[A]m- B -[A']n
where, m and n are independently a natural number between 1 and 12;
A and A' are a discotic or rod-like mesogen and are the same or different from each other;
connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer; and
B is a functional group maintaining geometrically a predetermined bond angle.
Further, the present invention provides an optical compensation film including a transparent substrate layer; an alignment layer stacked on the transparent substrate layer; and a coated layer containing the nematic liquid crystal compounds, stacked on the alignment layer and containing the nematic liquid crystal compounds.
Furthermore, the present invention provides a method of manufacturing an optical compensation film by forming an alignment layer on a substrate layer; by coating a solution containing the nematic liquid crystal compounds on the formed alignment layer; and irradiating Ultra Violet ray (UV) to the formed layer at 50 to 150 ℃.
Hereinafter, preferred embodiments of the present invention will be described in detail. In other instances, well known functions and structures have not been described in detail in order not to unnecessarily obscure the present invention.
Words of degree, such as "About", "Substantially", and the like are used herein in the sense of "at, or nearly at, when given the manufacturing and material tolerances inherent in the stated circumstances" and are used to prevent the unscrupulous infringer from unfairly taking advantage of the invention disclosure where exact or absolute figures are stated as an aid to understanding the invention.
That is to say, the present invention provides nematic liquid crystal compounds containing chemicals according to the following Chemical Formula 1:
[Chemical formula 1]
[A]m- B -[A']n
where, m and n are independently a natural number between 1 and 12;
A and A' are a discotic or rod-like mesogen and are the same or different from each other;
B is a functional group maintaining a predetermined bond angle geometrically.
In the formula, A and A' are independently discotic or rod-like, and may be all rod-like, all discotic or a mixture of discotic and rod-like. Preferably, A and A' are all discotic.
B is a functional group maintaining a predetermined bond angle geometrically.
B is a functional group having no variation in the bond angle without strain and functions to maintain a predetermined bond angle between the mesogens, thereby improving a viewing angle.
In a specific example, B can be selected from
Figure PCTKR2009005908-appb-I000001
Connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer, and preferably two mesogens are linearly linked. The linear linking of two mesogens is disclosed in Chem. Rev. 1999, Vol. 99, 1863, J. AM. CHEM. SOC. 2003, Vol. 125, 11062, J. Am. Chem. Soc. 1985, Vol. 107, 4192, J. Org. Chem. 2005,Vol. 70, 2745, Science, 2001, Vol. 293,79, J. Am. Chem. Soc. 2006, Vol. 128, 7670, Accounts of Chemical Research, 2004, Vol. 37, 735, Eur. J. Org. Chem. 2006, 3087.
Also, the liquid crystal compounds of the present invention include one in which m=1, n=1 and both A and A' are chemicals according to the following Chemical Formula 2, but not limited thereto.
[Chemical formula 2]
Figure PCTKR2009005908-appb-I000002
where, R1-R4 are independently (C1-C14)alkyl, (C1-C14)alkoxy, (C1-C14)alkylcarbonyl, (C6-C20)aryl, (C6-C20)arylcarbonyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl ;
the alkyl, the alkyl of alkylcarbonyl and the alkoxy of the alkoxy and alkoxycarbonyl in the R1-R4 may be straight or branched chain and may contain saturated or unsaturated bond; and
the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R1-R4 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
In the formula, R1-R4 are independently (C1-C14)alkyl, (C6-C20)aryl, (C1-C14)alkanoyl, (C3-C20)alkenoyl, (C3-C20)alkynoyl, (C7-C20)aryloyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl; and
the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R1-R4 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
The present invention provides an optical compensation film containing the nematic liquid crystal compounds, and the optical compensation film of the present invention may be provided through the following processes.
The present invention provides a method of manufacturing an optical compensation film by forming an alignment layer on a substrate film; forming a layer by coating a solution containing the nematic liquid crystal compounds on the formed alignment layer; and irradiating Ultra Violet ray (UV) to the formed layer at 50 to 150 ℃.
The optical compensation film of the present invention manufactured by the above method includes a transparent substrate layer; an alignment layer stacked on the transparent substrate layer; and a coated layer stacked on the alignment layer and containing the nematic liquid crystal compounds containing the chemicals according to the Chemical Formula 1.
In order to manufacture the optical compensation film of the present invention, a process of forming the alignment layer by coating an alignment solution on the substrate and then drying the alignment solution may be implemented.
The substrate layer is transparent and to be transparent means that a light transmittance is 80 % or over. The substrate layer of the present invention may be selected from the group consisting of glass, olefin based resin, cycloolefin based resin, ester based resin, polycarbonate, polyacrylate and polysulfone, and mixture and copolymer thereof, and an example for the substrate layer includes cellulose ester, polycarbonate, polysulfone, polyether sulfone, polyacrylate, polymethacrylate and norbornene resin. More specifically, cellulose triacetate or polyethylene terephthalate in the form of a film may be used.
A thickness of the substrate layer is preferably 20 to 500 ㎛ and more preferably 40 to 200 ㎛. Also, the substrate layer may be optically anisotropic film made by extension, and when the substrate layer is a cellulose ester film, retardation increasing agent may be added. Further, the substrate layer may be subject to glow discharge, corona discharge, UV treatment, flame treatment, alkali treatment, acid treatment or be given an adhesive layer.
A process of forming the alignment layer on the substrate layer may be implemented, and the alignment layer of the present invention is made of a resin selected from the group consisting of polyimide, polystyrene based polymer, gelatin and polyvinyl alcohol based polymer, and mixture and copolymer thereof, and more preferably contains polyvinyl alcohol based polymer.
The alignment layer is made by coating the polymer solutions on the substrate layer, dried and then by exposing it to magnetic field or light or rubbing its surface. The concentration of resins in the solutions is between 0.1 to 10 by weight% and the solutions may contain an additive helping alignment of the surface functional group in the layer.
The solutions can be coated on the substrate by various coating methods such as bar coating, gravure coating, die coating, roll coating and meniscus roll coating, dried at 40 to 200 ℃, preferably at 50 to 100 ℃, and then rubbed, thereby providing the alignment layer of the present invention.
After that, a process of forming the layer by coating a solution containing the nematic liquid crystal compounds containing the chemical of the Chemical formula 1, in which two or more mesogens have a predetermined bond angle, on the alignment layer may be implemented.
[Chemical formula 1]
[A]m- B -[A']n
where, m and n are a natural number between 1 and 12;
A and A' are a discotic or rod-like mesogen and are the same or different from each other; and
B is a functional group maintaining geometrically a predetermined bond angle.
Connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer, and preferably two mesogens are linearly linked.
In the nematic liquid crystal compounds containing the chemicals in which two or more mesogens have a predetermined bond angle, the mesogen are all discotic, all rod-like or mixture of discotic and rod-like, preferably are of the form including discotic, more preferably are all discotic. By adding the nematic liquid crystal compounds in which two or more mesogens selected from the aforementioned forms are connected, it is possible to obtain an optical compensation film with improved viewing angle and color shift. The alignment of the liquid crystals with the two or more mesogens connected to maintain a predetermined angle is stably immobilized by a light irradiation, producing optical anisotropy in the film.
An example of the nematic liquid crystal compounds containing the chemicals in which two or more mesogens have a predetermined bond angle includes chemicals according to the following Chemical Formula 3, but not limited thereto.
[Chemical formula 3]
Figure PCTKR2009005908-appb-I000003
where, R1-R8 are independently (C1-C14)alkyl, (C1-C14)alkoxy, (C1-C14)alkylcarbonyl, (C6-C20)aryl, (C6-C20)arylcarbonyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl; the alkyl of the alkyl and alkylcarbonyl and the alkoxy of the alkoxy and alkoxycarbonyl of the R1-R8 may be straight or branched chain and contain saturated or unsaturated bond; and the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R1-R8 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
More specifically, in the formula, R1-R8 are (C1-C14)alkyl, (C6-C20)aryl, (C1-C14)alkanoyl, (C3-C20)alkenoyl, (C3-C20)alkynoyl, (C7-C20)aryloyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl, and the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl and sulfamoyl of the R1-R8 may be further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
Synthesis of the liquid crystals is disclosed in J. Am. Chem. Soc., 1985, Vol. 107, 4192, Tetrahedron Lett., Vol. 23, 1913, 1982, J. Org. Chem. 2000, Vol. 65, 1650 and J. Am. Chem. Soc., 2005, Vol. 127, 534.
In the solution containing the nematic liquid crystal compounds containing the chemicals in which two or more mesogens have a predetermined bond angle, the liquid crystal compounds may be 1 to 30 weight% in the entire solution. When the content of the liquid crystal compounds is less than 1 weight%, improvement in the optical compensation or color shift of the film is not expected. Whereas, when the content of the liquid crystal compounds is over 30 weight%, waste of material is caused since effect corresponding to the exceeding content is not remarkable.
A thickness of the coating is preferably 0.5 to 10 ㎛.
An example for a method of coating the liquid crystal compounds of the present invention on the alignment layer includes bar coating, gravure coating, die coating, roll coating and meniscus roll coating, but not limited thereto.
After that, a process of irradiating UV on the formed film containing the liquid crystal compounds at 50 to 150 ℃ is implemented, thereby capable of manufacturing an optical compensation film of the present invention.
In accordance with an optical compensation film of the present invention, it is possible to obtain excellent viewing angle compensation effect and reduce color shift by using liquid crystal compounds containing two or more mesogens.
Fig. 1 is a graph showing the result of phase difference in an optical compensation film in accordance with a preferred embodiment of the present invention.
The advantages, features and aspects of the invention will become apparent from the following description of the embodiments with reference to the accompanying drawings, which is set forth hereinafter.
Manufacturing Example 1
The following liquid crystal compound was obtained from heptoxy carbonylmethyl substituted porphyrin using 1.3 phenylene spacer through Ag(I)-promoted coupling method (refer to J. Am. Chem. Soc., 1985, Vol. 107, 4192).
Figure PCTKR2009005908-appb-I000004
Example 1
On a cellulose triacetate film with 60 ㎛ thickness, alkyl substituted polyvinyl alcohol (PVA; R 1130, Kuraray Co., Ltd) was coated to 500 nm thickness. In order to make a PVA coating solution, 1.5 g of R1130, 75 g of deionized water, 24 g of methanol, 0.15 g of 50% aqueous solution of glutaraldehyde and 1.1 g of 0.5M sulfuric acid were mixed to manufacture a PVA aqueous solution. The PVA aqueous solution was coated using #16 Mayer bar, dried at 60 ℃ for 90 seconds, cooled for 2 minutes and then dried again at 80 ℃ for 150 seconds, thereby manufacturing an alignment layer on the cellulose triacetate film. A surface of the manufactured alignment layer (PVA) was rubbed using a rubbing machine (Meere Company Inc.). On the rubbed alignment layer, a coating solution containing 10% of the liquid crystal compound of Manufacturing Example 1 was coated to 2 ㎛ thickness using #10 Mayer bar. The liquid crystal solution was obtained by dissolving 2 g of the liquid crystal compound of Manufacturing Example 1, 0.01 g of a photoinitiator (IRGACURE 184, Ciba Inc.) and 18 g of methylethylketone, and was cured at 130 ℃ for 150 seconds using a UV curing machine (APO Co., Ltd.).
A Phase difference of the manufactured film was measured with a birefringence analyzer (KOBRA-WPR manufactured by Oji Scientific Instrument) with varying an incident angle of light having 589 nm wavelength. The results were shown in Fig. 1.
Fig. 1 is a graph showing the result of the phase difference in the optical compensation film in accordance with a preferred embodiment of the present invention. Referring to Fig. 1, it can be appreciated that the optical compensation film of the present invention has viewing angle compensation effect from phase difference variation pattern and phase difference value according to an incident angle.
In accordance with the present invention, it is possible to industrially provide an optical compensation sheet capable of obtaining excellent viewing angle compensation effect and reducing color shift.
While the present invention has been described with respect to the specific embodiments, it will be apparent to those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the following claims.
In accordance with an optical compensation film of the present invention, it is possible to obtain excellent viewing angle compensation effect and reduce color shift by using liquid crystal compounds containing two or more mesogens.

Claims (13)

  1. Nematic liquid crystal compounds, comprising chemicals according to the following Chemical Formula 1:
    [Chemical formula 1]
    [A]m- B -[A']n
    where, m and n are independently a natural number between 1 and 12,
    A and A' are a discotic or rod-like mesogen and are the same or different from each other;
    connection of A' and A' or A and A can be made through direct linkage between two mesogens or by a spacer; and
    B is a functional group maintaining geometrically a predetermined bond angle.
  2. The nematic liquid crystal compounds of claim 1, wherein the connection of A and A or A' and A' are made by linear linking, and
    B is a functional group having no variation in the bond angle.
  3. The nematic liquid crystal compounds of claim 2, wherein B is selected from
    Figure PCTKR2009005908-appb-I000005
  4. The nematic liquid crystal compounds of claim 1, wherein A or A' is a chemical according to the following Chemical Formula 2:
    [Chemical formula 2]
    Figure PCTKR2009005908-appb-I000006
    where, R1-R4 are independently (C1-C14)alkyl, (C1-C14)alkoxy, (C1-C14)alkylcarbonyl, (C6-C20)aryl, (C6-C20)arylcarbonyl, (C1-C14)alkoxycarbonyl, (C6-C20)aryloxycarbonyl, carbamoyl or sulfamoyl;
    the alkyl of the alkyl and alkylcarbonyl and the alkoxy of the alkoxy and alkoxycarbonyl of the R1-R4 may be straight chain or branched chain and contain saturated or unsaturated bond; and
    the alkyl, aryl, alkanoyl, alkenoyl, alkynoyl, aryloyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl or sulfamoyl of the R1-R4 are further substituted with one or more substituent selected from the group consisting of halogen, cyano and hydroxyl.
  5. An optical compensation film, comprising:
    a transparent substrate layer;
    an alignment layer stacked on the transparent substrate layer; and
    a coating layer stacked on the alignment layer and containing nematic liquid crystal compounds of one of claims 1 to 4.
  6. The optical compensation film of claim 5, wherein the substrate layer is selected from the group consisting of glass, olefin based resin, cycloolefin based resin, polycarbonate, polyacrylate, polysulfone, polyether sulfone, polymethacrylate, norbornene resin, cellulose triacetate and polyethylene terephthalate, and mixture and copolymer thereof.
  7. The optical compensation film of claim 5, wherein the alignment layer is selected from the group consisting of polyimide, polystyrene based polymer, gelatin and polyvinyl alcohol based polymer, and mixture and copolymer thereof.
  8. The optical compensation film of claim 7, wherein the alignment layer is polyvinyl alcohol based polymer.
  9. A method of manufacturing an optical compensation film, comprising:
    forming an alignment layer on a transparent substrate layer;
    forming a layer by coating a solution containing the nematic liquid crystal compounds according to the following Chemical Formula 1 on the formed alignment layer; and
    irradiating Ultra Violet ray (UV) to the formed layer at 50 to 150 ℃;
    [Chemical formula 1]
    [A]m- B -[A']n
    where, m and n are independently a natural number between 1 and 12;
    A and A' are a discotic or rod-like mesogen and are the same or different from each other; and
    B is a functional group maintaining geometrically a predetermined bond angle.
  10. The method of claim 9, wherein the alignment layer is rubbed.
  11. The method of claim 10, in the liquid crystal solution, the liquid crystal compounds are contained by 1 to 30 weight%.
  12. A polarization plate, comprising an optical compensation film of claim 5.
  13. A liquid crystal display using an optical compensation film of claim 5.
PCT/KR2009/005908 2008-10-14 2009-10-14 Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same WO2010044604A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2008-0100671 2008-10-14
KR1020080100671A KR20100041469A (en) 2008-10-14 2008-10-14 Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same

Publications (3)

Publication Number Publication Date
WO2010044604A2 true WO2010044604A2 (en) 2010-04-22
WO2010044604A3 WO2010044604A3 (en) 2010-07-22
WO2010044604A9 WO2010044604A9 (en) 2010-09-10

Family

ID=42107051

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2009/005908 WO2010044604A2 (en) 2008-10-14 2009-10-14 Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same

Country Status (3)

Country Link
KR (1) KR20100041469A (en)
TW (1) TW201020315A (en)
WO (1) WO2010044604A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9817262B2 (en) 2010-09-17 2017-11-14 Mitsubishi Gas Chemical Company, Inc. Front plate of TN liquid crystal panel

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000111914A (en) * 1998-09-30 2000-04-21 Fuji Photo Film Co Ltd Retardation raising agent for low fatty acid cellulose ester film, optical compensation sheet and liquid crystal display device
JP2000284126A (en) * 1999-01-27 2000-10-13 Fuji Photo Film Co Ltd Phase difference plate, circular polarization plate and reflection type liquid crystal display device
JP2003262728A (en) * 2002-03-11 2003-09-19 Fuji Photo Film Co Ltd Optical retardation plate and circularly polarizing plate
KR20040074610A (en) * 2003-02-19 2004-08-25 코니카 미노루따 호르딩구스 가부시끼가이샤 Optical compensation film, integral polarizing plate with viewing angle compensation, and liquid crystal display device
JP2005062673A (en) * 2003-08-19 2005-03-10 Fuji Photo Film Co Ltd Optically anisotropic layer, method for manufacturing the same, retardation plate using the same, elliptically polarizing plate and liquid crystal display
JP2007031481A (en) * 2005-07-22 2007-02-08 Fujifilm Corp Cellulose-compound composition, cellulose-compound film, polarizing plate, and liquid crystal display device
KR20080066673A (en) * 2005-10-12 2008-07-16 코니카 미놀타 옵토 인코포레이티드 Retardation film, polarizing plate, and vertically aligned liquid crystal display

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000111914A (en) * 1998-09-30 2000-04-21 Fuji Photo Film Co Ltd Retardation raising agent for low fatty acid cellulose ester film, optical compensation sheet and liquid crystal display device
JP2000284126A (en) * 1999-01-27 2000-10-13 Fuji Photo Film Co Ltd Phase difference plate, circular polarization plate and reflection type liquid crystal display device
JP2003262728A (en) * 2002-03-11 2003-09-19 Fuji Photo Film Co Ltd Optical retardation plate and circularly polarizing plate
KR20040074610A (en) * 2003-02-19 2004-08-25 코니카 미노루따 호르딩구스 가부시끼가이샤 Optical compensation film, integral polarizing plate with viewing angle compensation, and liquid crystal display device
JP2005062673A (en) * 2003-08-19 2005-03-10 Fuji Photo Film Co Ltd Optically anisotropic layer, method for manufacturing the same, retardation plate using the same, elliptically polarizing plate and liquid crystal display
JP2007031481A (en) * 2005-07-22 2007-02-08 Fujifilm Corp Cellulose-compound composition, cellulose-compound film, polarizing plate, and liquid crystal display device
KR20080066673A (en) * 2005-10-12 2008-07-16 코니카 미놀타 옵토 인코포레이티드 Retardation film, polarizing plate, and vertically aligned liquid crystal display

Also Published As

Publication number Publication date
KR20100041469A (en) 2010-04-22
TW201020315A (en) 2010-06-01
WO2010044604A3 (en) 2010-07-22
WO2010044604A9 (en) 2010-09-10

Similar Documents

Publication Publication Date Title
JP3883134B2 (en) Liquid crystal display
WO2010098594A2 (en) Optical compensation film with hybrid arrangement of nematic liquid crystals consisting of connected mesogens with an angle and the method of manufacturing the same
JP5376473B2 (en) In-plane switching mode liquid crystal display device
US7643117B2 (en) Liquid crystal panel and liquid crystal display apparatus
JPWO2003032060A1 (en) Liquid crystal display element and use of retardation film used therefor
US7643118B2 (en) Liquid crystal panel and liquid crystal display device
WO2012070808A2 (en) Anti-reflective polarizing plate and image display apparatus including same
JP4347466B2 (en) Optical film and liquid crystal display element
JP5248235B2 (en) Liquid crystal panel and liquid crystal display device
JPWO2018207797A1 (en) Liquid crystal display
JP2009092847A (en) Liquid crystal panel and liquid crystal display device
JP3950468B2 (en) Liquid crystal display
JP4789139B2 (en) Liquid crystal panel and liquid crystal display device using the same
JP3967764B2 (en) Liquid crystal panel and liquid crystal display device
WO2010044604A2 (en) Nematic liquid crystal compounds, optical compensation film thereof and a method of manufacturing the same
JP5048279B2 (en) Liquid crystal panel and liquid crystal display device
US20230408860A1 (en) Optical display device module and optical display device including same
JP2010160238A (en) Liquid crystal panel and liquid crystal display apparatus
CN112513696B (en) Polarizing plate and liquid crystal display device
JP2007264588A (en) Liquid crystal panel and liquid crystal display using the same
JP4640929B2 (en) Liquid crystal display device
TWI708079B (en) Liquid crystal display device
KR101211602B1 (en) Phase difference compensation film for in plane switching mode liquid crystal display device and in plane switching mode liquid crystal display device having the same
JP2007286235A (en) Liquid crystal panel and liquid crystal display device
JP4911573B2 (en) LCD panel

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09820754

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09820754

Country of ref document: EP

Kind code of ref document: A2