WO1999045082A1 - Film - Google Patents

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Publication number
WO1999045082A1
WO1999045082A1 PCT/US1999/004804 US9904804W WO9945082A1 WO 1999045082 A1 WO1999045082 A1 WO 1999045082A1 US 9904804 W US9904804 W US 9904804W WO 9945082 A1 WO9945082 A1 WO 9945082A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymerizable mesogenic
weight
formula
retardation film
composition
Prior art date
Application number
PCT/US1999/004804
Other languages
English (en)
Inventor
Nicholas Sharples
Gabrielle Egan
Young Chung
Zhiming Zhuang
Zili Li
Bruce K. Winker
Jane H. Hanamoto
David Coates
Original Assignee
Rockwell International Corporation
Merck Patent Gmbh
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 Rockwell International Corporation, Merck Patent Gmbh filed Critical Rockwell International Corporation
Publication of WO1999045082A1 publication Critical patent/WO1999045082A1/fr
Priority to US09/652,553 priority Critical patent/US6599443B1/en

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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
    • C09K19/38—Polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C09K19/38—Polymers
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • C09K19/3842—Polyvinyl derivatives
    • C09K19/3852—Poly(meth)acrylate derivatives
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements
    • 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
    • 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

Definitions

  • the Invention relates to an optical retardation film comprising a layer of an a ⁇ isotropic polymer material with an optical axis substantially parallel to the plane of the layer, said optical retardaton film being obtainable by a process comprising the following steps
  • W is H or CH 3l 20 n Is an integer from 3 to 6, and is alky or alkoxy with 1 to 8 C atoms, b) 15 to 60 % by weight of a polymerizable mesogenic compound of formula II
  • Z 1 and Z 2 are each independently -COO- or -OCO-, and
  • X 1 and X 2 are each independently H or CH 3l 35 and c) 0.1 to 8 % by weight of a photoinittator, - 2 -
  • said mixture optionally being dissolved in an organic solvent in a concentration of up to 50 % by weight on a substrate In form of -a layer,
  • a PET or TAC film is used as the substrate onto which said polymerizable mesogenic composition Is coated in step A) of said process, and HI) prior to step A) of said process the surface of said PET or TAC film adjacent to said polymerizable mesogenic composition is rubbed unidirectionally or is covered by a polyimide layer which is rubbed unidirectionally.
  • the invention furthermore relates to a process of preparing an optical retardation as described above, to the use of such an optical retardation film in liquid crystal displays, and to a liquid crystal display device comprising a liquid crystal cell and such an optical retardation film.
  • Optical retardation films are used for light modulation in various optical applications.
  • a quarter wave retardation film QWF
  • optical retardation films can be used as cor pe ⁇ sators to improve the optical properties of liquid crystal displays, such as the contrast ratio or gray scale at large viewing angles.
  • birefring ⁇ nt optical films with an extraordinary optical axis parallel to the plane of the film are needed, which are also known as A-plates.
  • the WO 97/03676 describes an optical retardation film comprising a layer of anlsotropic polymer material with an optical axis that has a low tilt angle relative to the plane of the layer, which is prepared by coating a polymerizable mesogenic mixture onto a substrate, aligning and curing the mixture.
  • an A-plate optical retardation film that can be used to improve the optical properties of a liquid crystal display, is easy to fabricate in large scale as a flexible film with a large area, and has an optical axis substantially parallel, with substantially zero tilt angle, to the plane of the film.
  • One of the aims of the present invention is to provide such an optical retardation film.
  • Another aim of the invention is to provide a process of preparing such an optical retardation film.
  • Other aims of the present invention are immediately evident to the person skilled in the art from the following detailed description. -4 -
  • One object of the present Invention is an optical retardation film comprising a layer of an anisotropic polymer material with an optical axis substantially parallel to the plane of the layer, said optical retardation film being obtainable by a process comprising the following steps A) to D) as described above.
  • an optical retardation film wherein the tilt angle between the optical axis and the plane of the layer of said anisotropic polymer material is from 0 to 1 degrees.
  • ⁇ an optical retardation film obtainable by a process as described above, wherein said mixture of non-ionic fluoroalkyl-alkoxylate surfactants is comprising 50 to 2500, preferably 100 to 1200 ppm of at least two compounds of formula III.
  • an optical retardation film obtainable by a process as described above, wherein said mixture of non-ionic fluoroalkyl-alkoxylate surfactants is comprising 50 to 2500, preferably 600 to 1800 ppm of at lea ⁇ t two compounds of formula IV.
  • step A) of said process a PET film is used as a substrate, the surface of which being adjacent to the polymerizable mesogenic composition Is rubbed unidirectionally prior to step A).
  • Another object of the present invention is a process of preparing an optical retardation film comprising a layer of an anisotropic polymer material with an optical axis substantially parallel to the plane of the - 5 -
  • Another object of the present invention is the use of an optical retardation film as described above and below in liquid crystal displays.
  • Yet another object of the present invention is a liquid crystal display device comprising a liquid crystal cell and an optical retardation film as described above and below.
  • the retardation of the inventive optical retardation film is preferably ranging from 20 to 600 nm. Particularly preferred are films with a retardation from 25 to 170 nm, furthermore films with a retardation from 300 to 600 nm.
  • the optical retardation film according to the present invention Is suitable for use as phase retarder or as compensator in electrooptical displays, in particular for displays based on the twisted nematic (TN) effect, such as TN, STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated birefringence), DAF (deformation of aligned phases), VAN/VAC (vertically aligned nematic/choleste ⁇ c), OM! (optical mode interference), or SBE (super birefringence effect), including displays of the active and passive matrix type, furthermore in displays of the guest-host-type, the IPS (in plane switching) type, the feiToelectric or antiferroelectric type.
  • TN twisted nematic
  • STN super twisted nematic
  • ECB electrically controlled birefringence
  • OCB optical compensated birefringence
  • DAF deformation of aligned phases
  • an inventive optical retardation film as a Q F together with a broadband reflective polarizer, wherein the retardation of the optical retardation film is substantially o.25 times the central wavelength of the wavelength band reflected by the reflective polarizer.
  • the inventive optical retardation film comprises a layer of a polymerized mesogenic material and is characterized by a significantly high birefringence. Furthermore, the optical properties of the optical retardation film, like e.g. the birefringence, can be - 6 -
  • the optical retardation film according to the resent invention -. comprises a layer of an anisotropic polymer having a major optical axis that is substantially parallel to the plane of the layer.
  • the tilt angle between the optical axis of said layer and the plane of said layer is preferably in the range from 0 to 1 degrees, in particular 0 to 0.5 degrees, very preferably from 0 to 0.3 degrees. Especially preferably the tilt angle is approximately 0 degrees.
  • the tilt angle of an inventive optical retardation film as referred to in the foregoing and the following is to be understood as the tilt angle through the entire film, which is an average of the tilt angles in different regions of the film.
  • the tilt angle as such defined is not necessarily identical with the tilt angle at the outer surface, i.e. the air surface, of the film and/or with the tilt angle at the inner surface of the film, i.e. the surface adjacent to the substrate on which the film Is prepared.
  • the inventive optical retardation film is obtainable by coating a polymerizable mesogenic composition on a substrate in form of a layer, aligning the material and polymerizing the aligned material.
  • PET polyathyleneterephthalate
  • TAC triacetylcellulose
  • PET films are commercially available e.g. from ICI Corp. under the trade name Melinex TAC films are commercially available e.g. from Lonza AG (Switzerland) or Fuji Film (Japan).
  • planar alignment in the coated layer of the polymerizable mesogenic composition i.e. an orientation wherein the mesogenic molecules in the composition are aligned substantially parallel to the plane of the layer, with a low tilt angle relative to the plane of the layer, is particularly achieved by
  • the surfactants used in the inventive process are a mixture of non- ionic fluoroalkylalkoxylate surfactants selected from formula 111 and IV
  • n is an integer from 4 to 12 and x is an integer from 5 to 15.
  • the surfactants of formula 111 are commercially available under the trade name Fluorad 171 (from 3M Co.), the surfactants of formula IV under the trade name Zonyl FSN (from DuPont).
  • the amount of surfactants is preferably from 500 to 2500 ppm, In particular from 1000 to 2500 ppm, very preferably from 1500 to 2500 ppm
  • the alignment quality is also depending on the rubbing angle, i.e. the angle between the major rubbing direction and the major optical axis of the substrate or the polyimide layer respectively.
  • rubbing is carried out unidirectionally in a direction substantially parallel to the major optical axis of the substrate.
  • rubbing can be achieved by means of a rubbing cloth or with a flat bar coated with a rubbing cloth, or by means of a rubbing roller, like e.g. a fast spinning roller that Is brushing over the substrate, or by putting the substrate between two rollers, wherein in each case one or both of the rollers are optionally covered with a rubbing cloth.
  • a rubbing roller like e.g. a fast spinning roller that Is brushing over the substrate, or by putting the substrate between two rollers, wherein in each case one or both of the rollers are optionally covered with a rubbing cloth.
  • rubbing cloth all materials can be used that are known to the skilled In the art for this purpose.
  • velvet of a commercially available standard type can be used as a rubbing cloth.
  • the ability of a substrate to induce alignment In the polymerizable mesogenic composition coated on this substrate after rubbing the substrate will further depend on the process parameters of the rubbing process, like the rubbing pressure and nibbing speed and, in case a rubbing roller is used, en the rotational velocity of the roller, the rubbing roller circumference and the tension on the substrate.
  • the rubbing length in the rubbing process according to the above described prefe ⁇ red embodiments is preferably from 0.2 to 5 metres, in particular from 0.5 to 3 metres, most preferably from 1.0 to 2.5 metres.
  • the polymerizable mesogenic composition is cured by photopolymerization, carried out by exposing the composition to UV light in the presence of a UV-absorbing photoinitiator, which decomposes under UV irradiation to produce free radicals that start the polymerization reaction.
  • Polyme ⁇ zatio ⁇ can be carried out under air or in an inert gas atmosphere, e.g. In a nitrogen atmosphere.
  • an inert gas atmosphere e.g. In a nitrogen atmosphere.
  • Irgacure 906 can be used, whereas for curing under a nitrogen atmosphere e.g. the commercially available Irgacure 651 or 184 (all from Ciba Qeigy AG) would be suitable.
  • the amount of photoinitiator in the polymerizable mesogenic composition Is 0.1 to 8 %, preferably 0.5 to 6 %, very preferably 1 to 5 % by weight of the total mixture. - 9 -
  • the polymerizable mesogenic composition is preferably dissolved in an organic solvent before being coated onto the substrate.
  • Suitable solvents are organic solvents such as methyl ethyl ketone, toluene, cyciohexanone or cyciope ⁇ tane. which are used preferably with a
  • Oo-solvent aside as xylene or isopropyl alcohol, or mixtures of two or more of these solvents.
  • the polymerization has to be carried out in the liquid crystal phase of the polymerizable mesogenic composition.
  • the curing temperatures is at least 40 ⁇ C below the clearing temperature of the polymerizable mesogenic composition.
  • curing temperatures from 30 to 60 ⁇ C.
  • UV light of high or medium pressure is used, with the irradiation wavelength being from preferably from 250 nm to 420 nm, in particular from 320 nm to 390 n .
  • the irradlance produced by the lamp used in the invention is preferably from 0.01 to 100 mW/cm 2 , especially preferably from 10 to 50 mVWcm 2 ,
  • the curing time according to the invention is preferably not longer than 1 minute, especially preferably less than 30 seconds, very preferably less than 5 seconds.
  • the thickness of the inventive optical retardation film obtained by the method as described above is preferably 0.5 to 30 ⁇ m, In particular 0.5 to 20 ⁇ , most preferably 0.5 to 15 ⁇ m.
  • the polymerizable mesogenic composition used to prepare the inventive optical retardation film is comprising the following polymerizable mesogenic compounds f - 10 -
  • W Is H or CHa wherein W Is H or CHa, n is an integer from 3 to 6, and
  • R is alky I or alkoxy with 1 to 8 C atoms, b) 15 to 60 % by weight of a polymerizable mesogenic compound of formula II x 1 fi
  • W is H or CHa.
  • n is an integer from 3 to 6,
  • Z 2 are each independently -COO- or -OCO-, and X 1 and X 2 are each independently H or Chfe,
  • compositions comprising one compound of formula la, one compound of formula lb and one compound of formula II.
  • R in formula la is preferably straight-chain alkyl.
  • W in formula la, lb and II is preferably H.
  • X 1 is denoting H and X 2 is denoting CH 3 . - 11 -
  • the amount of compounds of formula la In the polymerizable mesogenic composition Is preferably from 20 to 45 %, In particular from 30 to 40 % by weight of the total mixture.
  • the amount of compounds of formula lb is preferably from 10 to 30 %, in particular from 15 to 25 % by weight of the total mixture,
  • the amount of compounds of formula II is preferably from 20 to 55 %, in particular from 35 to 50 % by weight of the total mixture.
  • the polymerizable mesogenic compounds of formula la, lb and II can be prepared by methods which are known per se and which are described in the documents cited above and, for example, in standard works of organic chemistry such as, for example, Houben- Weyl, Methoden der organischen Chemie, Thieme-Veriag. Stuttgart.
  • the compounds of formula II are described e.g. in D.J.Broer et al., Makromol.Chem. 190, 3201-3215 (1989).
  • the compounds of formula la are described in the WO 97/00843.
  • the compounds (1) to (3) can be prepared according to or in analogy to the methods described in D. J.Broer et al., Mat romol.Chem. 190, 3201-3215 (1989) and in the WO 97/00843.
  • radlcalic photoinitiator irgacure 906 available from Ciba Geigy
  • the polymerizable composition comprising the photoinitiator is then dissolved in a concentration of 20 % by weight in an organic solvent mixture of 2:1:1 toluene/xylene/lsopropyl alcohol.
  • the solution is filtered to remove Impurities and small particles
  • the solution is coated as a film with a thickness of approximately 12 ⁇ on each of the above mentioned first and second PET sheets and the solvent is allowed to evaporate at 55 ⁇ C.
  • the mixture is then cured In air at 30 to 40 "C by irradiating witffUV light with a wavelength of 360 and an i adiance of 20 mW/cm 2 for a few seconds. In this way, two polymer films 1A and 2A are obtained that can be used as optical retardation films.
  • Film A1 was obtained on the PET sheet with 1000 mm rubbing length and film A2 on the PET sheet with 2000 mm rubbing length.
  • Two polymer films B1 and B2 are prepared as described in example A, with the difference being that 1000 ppm of the non-ionic fluorocarbon surfactant Fluorad FC171 (from 3M Co.) are added to the polymerizable composition in each case before dissolving the Dolymerizabie composition in the organic solvent mixture.
  • Fluorad FC171 from 3M Co.
  • Film B1 was prepared on a PET sheet with 1000 mm rubbing length and film B2 on a PET sheet with 2000 mm rubbing length
  • the retardation R of an inventive optical retardation film depending on the angle of incidence of the light ⁇ and the tilt angle ⁇ between the optical axis of the film and the plane of the film, can be expressed as the product of birefringence ⁇ n and film thickness d according to equation (1)
  • ⁇ n( ⁇ , ) is the birefringence of the film, which is defined as
  • ⁇ , and no can be measured using an Abbe refractometer, whereas the retardation R( ⁇ , ⁇ ) can be measured as described above at various angles of incidence ⁇ .
  • the average tilt angle ⁇ can be calculated from the measured retardation R, the incidence angle ⁇ of light incident on the film and the measured values ⁇ f n e and ⁇ ⁇ according to equations (1) and (2). - 15 -

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)
  • Liquid Crystal Substances (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un film à retard optique comprenant une couche de matériau polymère anisotrope présentant un axe optique sensiblement parallèle au plan de la couche. L'invention concerne également le procédé d'élaboration de ce film à retard optique ainsi que l'utilisation d'un tel film à retard optique dans des afficheurs à cristaux liquides. L'invention concerne enfin un afficheur à cristaux liquides comprenant une cellule à cristaux liquides et un tel film à retard optique.
PCT/US1999/004804 1998-03-05 1999-03-05 Film WO1999045082A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US09/652,553 US6599443B1 (en) 1998-03-05 2000-08-31 Film

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98103864.9 1998-03-05
EP98103864 1998-03-05

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/652,553 Continuation US6599443B1 (en) 1998-03-05 2000-08-31 Film

Publications (1)

Publication Number Publication Date
WO1999045082A1 true WO1999045082A1 (fr) 1999-09-10

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ID=8231534

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/004804 WO1999045082A1 (fr) 1998-03-05 1999-03-05 Film

Country Status (5)

Country Link
JP (1) JP4879378B2 (fr)
KR (1) KR100581655B1 (fr)
DE (1) DE69932272T2 (fr)
TW (1) TWI273113B (fr)
WO (1) WO1999045082A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1256617A1 (fr) * 2001-05-08 2002-11-13 MERCK PATENT GmbH Matériau liquide cristalline polymérisable
US7029728B2 (en) * 2001-05-08 2006-04-18 Merck Patent Gesellschaft Mit Beschraenkter Haftung Polymerizable liquid crystal material
US7160586B2 (en) 2003-08-29 2007-01-09 3M Innovative Properties Company Cholesteric liquid crystal copolymers and additives
EP1795575A1 (fr) * 2005-12-10 2007-06-13 Merck Patent GmbH Film polymère à cristaux liquides à stabilité améliorée
US7524436B2 (en) 2005-12-10 2009-04-28 Merck Patent Gmbh Liquid crystal polymer film with improved stability
US7597945B2 (en) 2004-11-09 2009-10-06 Chisso Corporation Polymerizable liquid crystal composition containing fluorine-substituted (meth) acrylate derivatives
TWI405840B (zh) * 2006-02-17 2013-08-21 Dainippon Ink & Chemicals 聚合性液晶組成物
US9481830B2 (en) 2011-09-12 2016-11-01 Fujifilm Corporation Cholesteric liquid crystal mixture, film, selective reflective plate, laminate, laminated glass

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CA2410074A1 (fr) * 2000-05-22 2002-11-20 Kenichiro Yoshioka Procede pour ameliorer le rapport de contraste d'un projecteur a cristaux liquides
CA2431264A1 (fr) 2000-12-18 2002-06-27 Nippon Kayaku Kabushiki Kaisha Film optique et film polarisant ainsi utilise, et methode permettant d'ameliorer l'angle de vue du film polarisant
JP4259867B2 (ja) * 2001-01-23 2009-04-30 サウスウェスト リサーチ インスティテュート 液晶のレオロジー及び転移温度を調節するための新規な方法及びブレンド
EP1666930A1 (fr) 2003-08-28 2006-06-07 Nippon Kayaku Kabushiki Kaisha Films a decalage de phase produits a l'aide de derives de cellulose
US7575696B2 (en) 2006-07-28 2009-08-18 Fujifilm Corporation Liquid crystal composition and anisotropic material
JP5441311B2 (ja) * 2007-02-09 2014-03-12 株式会社Ａｄｅｋａ 重合性組成物
JP5470749B2 (ja) * 2007-08-10 2014-04-16 Ｄｉｃ株式会社 重合性液晶組成物
JP5678676B2 (ja) * 2011-01-17 2015-03-04 Dic株式会社 重合性液晶組成物、それを用いた硬化物、及び、光学異方体
JP5816232B2 (ja) * 2012-09-25 2015-11-18 富士フイルム株式会社 液晶組成物およびその製造方法ならびにフィルム
KR20140052241A (ko) * 2012-10-23 2014-05-07 동우 화인켐 주식회사 액정층 형성용 조성물 및 이를 이용하여 제조된 리타더
TWI635165B (zh) * 2013-08-09 2018-09-11 住友化學股份有限公司 Optical anisotropic layer forming composition
EP4276231A1 (fr) 2022-05-13 2023-11-15 Arçelik Anonim Sirketi Système de lavage/séchage de linge

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998004651A1 (fr) * 1996-07-26 1998-02-05 Merck Patent Gmbh Combinaison d'elements optiques

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2952449B2 (ja) * 1992-06-03 1999-09-27 日石三菱株式会社 液晶表示素子用補償板の製造法
JP3783787B2 (ja) * 1995-02-27 2006-06-07 大日本インキ化学工業株式会社 重合性液晶組成物及び光学異方体の製造方法
JP3672677B2 (ja) * 1995-07-24 2005-07-20 富士写真フイルム株式会社 光学補償シートを製造する方法
TW373100B (en) * 1996-07-01 1999-11-01 Merck Patent Gmbh Compensation film and liquid crystal display device containing the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998004651A1 (fr) * 1996-07-26 1998-02-05 Merck Patent Gmbh Combinaison d'elements optiques

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1256617A1 (fr) * 2001-05-08 2002-11-13 MERCK PATENT GmbH Matériau liquide cristalline polymérisable
US7029728B2 (en) * 2001-05-08 2006-04-18 Merck Patent Gesellschaft Mit Beschraenkter Haftung Polymerizable liquid crystal material
US7160586B2 (en) 2003-08-29 2007-01-09 3M Innovative Properties Company Cholesteric liquid crystal copolymers and additives
US7597945B2 (en) 2004-11-09 2009-10-06 Chisso Corporation Polymerizable liquid crystal composition containing fluorine-substituted (meth) acrylate derivatives
EP1795575A1 (fr) * 2005-12-10 2007-06-13 Merck Patent GmbH Film polymère à cristaux liquides à stabilité améliorée
US7524436B2 (en) 2005-12-10 2009-04-28 Merck Patent Gmbh Liquid crystal polymer film with improved stability
TWI405840B (zh) * 2006-02-17 2013-08-21 Dainippon Ink & Chemicals 聚合性液晶組成物
US9481830B2 (en) 2011-09-12 2016-11-01 Fujifilm Corporation Cholesteric liquid crystal mixture, film, selective reflective plate, laminate, laminated glass

Also Published As

Publication number Publication date
DE69932272D1 (de) 2006-08-24
KR100581655B1 (ko) 2006-05-22
JP2000098133A (ja) 2000-04-07
JP4879378B2 (ja) 2012-02-22
TWI273113B (en) 2007-02-11
DE69932272T2 (de) 2007-07-12
KR20010024952A (ko) 2001-03-26

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