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WO1998011077A1 - Structures a fibres et son procede de production - Google Patents

Structures a fibres et son procede de production Download PDF

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Publication number
WO1998011077A1
WO1998011077A1 PCT/JP1996/002598 JP9602598W WO9811077A1 WO 1998011077 A1 WO1998011077 A1 WO 1998011077A1 JP 9602598 W JP9602598 W JP 9602598W WO 9811077 A1 WO9811077 A1 WO 9811077A1
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WO
WIPO (PCT)
Prior art keywords
chiral
chirooptical
several
liquid crystal
mol
Prior art date
Application number
PCT/JP1996/002598
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English (en)
Inventor
Dietrich Demus
Ryokichi Tarao
Hiroyuki Takeuchi
Kazutoshi Miyazawa
Original Assignee
Chisso Corporation
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 Chisso Corporation filed Critical Chisso Corporation
Priority to AU69443/96A priority Critical patent/AU6944396A/en
Priority to JP10513463A priority patent/JP2001501186A/ja
Priority to PCT/JP1996/002598 priority patent/WO1998011077A1/fr
Publication of WO1998011077A1 publication Critical patent/WO1998011077A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • 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
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/25—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing liquid crystals

Definitions

  • This invention relates to novel chemical compounds and their use in liquid crystal chirooptical devices. Such devices are useful for storage of information, which is inscribed by irradiation with light.
  • Optical storage can be applied in optical computers and storage systems for audio and video informations.
  • Optical storage can be applied in optical computers, storage systems for audio and video informations.
  • EDRAW systems erasable-direct-read- after-write systems
  • Devices of this kind typically consist of a layer of liquid crystal material, contained between two glass slides.
  • devices containing azo compounds change from the nematic to the isotropic state and reverse (for example, D. Demus, G. Pelzl, F. Kuschel DD WP 134 279).
  • thermo-optical liquid crystal devices have been proposed, based on thermally induced texture change of cholesteric phases (S. Kobayashi and A. Mochizuki, in: Liquid Crystals. Applications and Uses, ed. by B. Bahadur, World Scientific, Singapore 1992, vol. 3, p. 291-293) or smectic A phases (D. Coates, in: Liquid Crystals. Applications and Uses, ed. by B. Bahadur, World Scientific, Singapore 1990, vol 1, p. 275-303).
  • Thermo-electrooptic displays use the combined effect of heat and electric fields, in low-molecular glass forming liquid crystals (D. Demus and G. Pelzl, DD WP 242 624 Al ) resp. polymer glass forming liquid crystals (H. Finkel ann, W. Meier and H. Scheuermann, in: Liquid Crystals. Applications and Uses, ed. by B. Bahadur, World Scientific, Singapore 1992, Vol. 3, p. 345-370).
  • thermo-optical devices generally need a quite large energy for locally heating up the liquid crystal material.
  • the chiral materials induce a helical pitch in the nematic liquid crystal, and can be switched by irradiation with light of two different wavelengths to two different isomers or equilibrium mixtures of these isomers, inducing the said two different optical states.
  • these optical states must be stable for long periods without thermal isomerization.
  • the materials must allow reversible switching between the two different optical states, without deterioration processes in the materials.
  • the chiral materials must be sufficiently soluble in the nematic liquid crystals.
  • Ra, Rb, Re alkyl, alkoxy, hydrogen, hydroxy, nitro, dialkylamino
  • Xa, Xb oxygene, sulfur, ethylene.
  • Ya, Yb independent upon another single bond, oxygene, sulfur, carbonyl, ester group, 1, 2-ethylene, 1, 2-ethenylene, 1, 2-ethynylene, 1, 4-butylene, methyleneoxy, oxymethylene, difluoro ethyleneoxy, ring system like substituted or unsubstituted benzene, cyclohexane, heterocyclic ring, biphenyl, bicyclohexyl;
  • azobenzene derivatives allow reversible optically induced switching between the trans and the cis isomers, corresponding to two states of different optical properties.
  • the cis isomer is less stable and has a strong tendency to thermal iso erization towards the stable trans isomer. This is, the optical state depending on the cis isomer cannot be stored for long periods, and therefore the devices containing simple azobenzene derivatives are not suited for long term storage of data and informations.
  • H. Rau and D. R ⁇ ttger Mol. Cryst. Liq. Cryst. 246, 143-146 (1994) described new azobenzenes (c) and (d) of the phane type with special optical properties.
  • R l r R 2 , R 3 , R 4 equal or unequal, H, F, Cl, R 5 , R 6 or
  • R 7 R 5 CN, NCS, CF 3 , 0CF 3 ,
  • R 4 , R 8 , R 9 is equal to R 6 , and not more than two of the groups R j , R 2 , R 3 , R 4 are equal to R 5 , can be switched between two stable optical states and are suited for use in chirooptical displays.
  • tt and cc isomers are thermally quite stable (half life time at least 1 year) in contrast to the cis-azo-isomer of ordinary azo compounds like azobenzene or 4, 4 '-bis substituted azobenzenes (half life time about 1 day down to some seconds), which under influence of thermal energy return to the trans state, which is more stable from the thermodynamic standpoint .
  • t,t azobenzophanes are characterized by a phane absorption band near 380 nm which is absent in cc and also in ordinary azobenzenes. Irradiation of tt with light of 366 n gives cc. Irradiation of cc with light of 436 ran gives tt again.
  • the isomer ct is quite unstable, appears after irradiation of tt or cc, and by irradiation switches to the stable forms cc resp. tt. ct also switches by thermal energy to tt. In the spectral region of 350-370 nm the absorption of tt and cc is very different up to a factor of 75. In addition to the change in absorption, the helical twisting power (HTP) of the chiral azophanes is changed. In nematic liquid crystals, by doping with the chiral azophanes the cholesteric phase is induced. Switching the materials from tt to cc isomeric state changes the pitch of the cholesteric mixtures, and by use in suited arrangements change of an optical contrast can be achieved.
  • HTP helical twisting power
  • the switching of the isomers occurs with light of high intensity. Probing with light of low intensity causes negligible loss of cc or tt. Storage of the isomers tt or cc is possible for long periods without thermal reaction. Storage of a cc sample at room temperature for several months does not give a change in absorption or HTP. These properties make the system suited for optically switched information storage systems.
  • nematic liquid crystal basic mixtures all known nematic compounds can be used, provided they do not have an optical absorption band in the respecive regions of irradiation. Ordinarily the following compounds (2-1) - (2-190) can be effectively used.
  • R 10 , R 11 alkyl, alkyloxy, alkenyl, alkynyl and other groups typical for liquid crystals).
  • liquid crystal basic mixtures should not have optical absorption bands in the region of the irradiation light switching between the two states. Because switching preferably is done with ultraviolet light, specially non-aromatic liquid crystal materials are useful, preferably compounds of the following general formulas (2-191) - (2-227).
  • nematic discotic liquid crystals can be used as basic mixtures for verifying the invention.
  • Discotic materials that are listed in LIQCRYST, Database of Liquid Crystalline Compounds for personal Computers, by V. Vill, Hamburg 1995, can be used. Because nematic discotic compounds usually have relatively high melting temperatures, multicomponent mixtures are necessary.
  • Discotic nematic materials are specially compatible with the chiral azophanes.
  • the following compounds (3-1) - (3-11) are suitable discotic materials for this invention.
  • the invented chiral azophanes ( 1 ) can be synthesized by combinations of general organic synthesis procedures described in publications.
  • the compound ( 1 ) is synthesized by a cross coupling reaction of azophanes according to the literatures, H. Rau and E. Luddecke, J. Am. Chem. Soc. , 104, 1616 (1982), V. Boekelheide, R. A. Hollius, J. Am. Chem. Soc, 95, 3201 (1973) and R. H. Mitchell, V. Boekelheide, J. Am. Chem. Soc, 96, 1547 (1974).
  • the literatures H. Rau and E. Luddecke, J. Am. Chem. Soc. , 104, 1616 (1982), V. Boekelheide, R. A. Hollius, J. Am. Chem. Soc, 95, 3201 (1973) and R. H. Mitchell, V. Boekelheide, J. Am. Chem. Soc, 96, 1547 (1974).
  • the coupling reaction preferably is carried out in aqueous alcoholic solution, such as aqueous ethanol or aqueous methanol. To avoid a homo coupling reaction, the reaction preferably is a high dilution reaction. After the reaction by ordinary work up procedures i.e., a chromatographic separation or a recrystallization, purified (1) can be obtained.
  • the compound ( 1 ) can also be synthesized by a thioetherification of the benzyl bromides (4) and thiols (6) using bases such as, sodium hydroxide, potassium hydroxide, calcium hydride, potassium carbonate, sodium carbonate, in alcoholic solution.
  • the thiols (6) can be derived from the bromides (5) by a treatment with thiourea followed by a hydrolysis.
  • halogen- ( fluorine- or chlorine- ) substituted compounds ( 8 ) can be derived from the benzylhalides ( 7 ) by a bromination under UV irradiation, according to A. Haars, Chem. Ber., 121, 1329 ( 1988 )( Scheme 5).
  • X 3 represents F and Cl
  • MG mesogene
  • the compounds ( 10 ) substituted by R 5 can be derived from (9) also by a bromination under UV irradiation (Scheme 6), according to the said literature.
  • Chiral or achiral alkyl substituted compounds ( 13 ) can be derived from benzaldehyde (11) by a reaction with nucleophiles followed by a bromination (Scheme 7).
  • Alkyl magnesium bromides or alkyl lithium reagents, derived from corresponding alkylhalides, can be used as the said nucleophiles.
  • the bromination can be done by using normally used bro inating reagents such as PBr 3 , SOBr 2 , Br 2 , NBS (N-bromosuccinimide) etc
  • the chiral alkyl bromides (R 6 Br) can be derived from corresponding alcohols (R 6 OH) that can be derived from natural chiral sources or can be prepared by asymmetric reactions, kinetic resolutions or mechanical resolutions, using chiral catalysts, recrystallizations, biocatalytic reactions or a chiral chromatography . These methods are well-described in the literatures, for example, Asymmetric Synthesis edited by J. D. Morrison, Academic Press (1983).
  • X ⁇ or X 2 is a disubstituted carbon atom
  • the compound (1) can be synthesized by an etherification of disubstituted dibromo carbon and diols that can be prepared according to Scheme 7.
  • R 6 is preferably 1-m thylpropyl, 1-methylbutyl, 1-methylpentyl, 1-methylhexyl, 1-methylheptyl, 1-methyloctyl, 1-methylnonyl, 2-methylbutyl, 2-methylpentyl, 1-ethylheptyl, 2-ethylheptyl, 1-trifluoromethylheptyl, 2-trifluoromethylheptyl, 2-cyanopentyl, 2-fluorobutyl, 2-fluoropentyl, 2-fluorohexyl, 3-fluorohexyl, 2-chloropentyl, 2-difluromethylpentyl, 2-fluoromethylpentyl, 2-trichlorometylpentyl, 2-fluorodichlorometylhexyl, 2-trifluoromethoxypentyl , 3-trifluoro ethoxyhexyl , R 7 is preferably alkyl, alkyloxy, al
  • FIG. 1 is a cross-sectional view of the hybrid cell in which the liquid crystals of the invention are filled.
  • Step 1 Synthesis of optically active ( 1-hydroxy-3-methyl )- pentylbenzene ( S-1 ) To a mixture of benzaldehyde (3.2 mol) in 500 ml of tetrahydrofuran (hereinafter called THF),
  • Step 2 Synthesis of optically active (1-t- butyldimethylsilyloxy-3-methyl) pentylbenzene (S-2)
  • S-l optically active (1-t- butyldimethylsilyloxy-3-methyl) pentylbenzene
  • TBDMSC1 t-butyldimethylsilyl chloride
  • imidazole 4.0 mol
  • 600 ml of dimethylformamide hereinafter called DMF
  • the reaction mixture was poured into 500 g of crashed ice and extracted with hexane ( 500 ml ) .
  • the organic layer was washed with water ( 300 ml x 4 ) , then dried over anhydrous magnesium sulfate. Evaporation of the organic layer followed by a purification with a silica gel column chromatography ( eluted by hexane ) gave colorless oil (S-2) (2.1 mol).
  • Step 3 Synthesis of optically active 4-( 1-t-butyldi- methylsilyloxy-3-methyl ) pentyl-nitrobenzene (S-3) To a solution of (S-2) (2.1 mol) in acetic acid (550 ml), a mixture of sulfuric acid (2.1 mol) and fuming nitric acid (2.1 mol) was added under - 10°C in 2 hours.
  • Step 4 Synthesis of optically active 4-(l-t- butyldimethylsilyloxy-3-methyl )pentyl-aminobenzene (S-4) A mixture of (S-3) (0.55 mol), 5% Pd/C and ethanol
  • Step 5 Synthesis of optically active 4-( l-hydroxy-3- methyl )pentylaminobenzene (S-5)
  • TBAF tetrabutylammonium fluoride
  • Step 7 Synthesis of optically active 4-( l-bromo-3-methyl )- pentyl-4 ' -bromomethylazobenzene ( S-7 )
  • the solid material that was collected by filtration was subjected to a silica gel column chromatography ( eluted by a mixture of hexane and ethylenedichloride ) to give a slightly yellow solid as a main product (0.015 mol), which was a mixture of diastereomers .
  • the two diastereomers were separated by a silica gel column chromatography (eluted by a mixture of benzene and petroleum ether) to give a more polar fraction (more polar optically active l-( S-2-methylbutyl )- 2, 19-dithia [3.3] (4,4' )-trans-diphenyldiazeno( 2 )phane ) (0.009 mol) and a less polar fraction (less polar optically active l-(S-2-methylbutyl )-2, 19-dithia [3.3] ( 4, 4 ' )-trans- diphenyldiazeno( 2 )phane) (0.005 mol).
  • Step 1 Synthesis of optically active 4-(R-l-bromo-5- fluoroheptyl ) -4 ' -bromomethylazobenzene ( S-8 )
  • 4-(R-l-bromo-5-fluoroheptyl)-aminobenzene (0.33 mol )
  • S-8 4-(R-l-bromo-5-fluoroheptyl)-aminobenzene
  • Step 2 Synthesis of optically active 1- (R-4-fluorohexyl )- 18-pentyl-2,19-dithia[3.3] (4,4' )-trans- diphenyldiazeno( 2 )phane
  • (S-8) (0.20 mol)
  • optically active 4-( 1-bromohexyl )-4' -bromomethylazobenzene (0.20 mol) that was synthesized by the same procedures as Example 1 and step 1 of Example 2 from pentylmagnesiu bromide, and 400 ml of benzene was added simultaneously with a solution of sodium sulfide nonahydrate (0.8 mol) in 300 ml of 90% aqueous ethanol, to 2.5 liter of absolute ethanol with vigorous stirring over 4 hours.
  • Ph, PhF, Phf, PhFF, PhFf, Phff mean 1, 4-phenylene, 2-fluoro-l, 4-phenylene, 3-fluoro-l, 4- phenylene, 2, 6-difluoro-l, 4-phenylene, 2, 3-difluoro-1, 4- phenylene, 2, 6-difluoro-1 , 4-phenylene, respectively.
  • the cholesteric mixture was filled in a hybrid cell (Fig.
  • a holographic arrangement according to Fig. 2 was prepared, and the liquid crystal cell consisting of two parallel quartz plates with a cell gap of 15 mm, filled with the mixture used in Example 4, was inserted.
  • a laser beam with wavelength 366 nm was split into two beams, one of which was modulated by the modulator, transferring the information to the liquid crystal layer by interference with the second beam in the liquid crystal cell.
  • By irradiation with light of wavelength 436 nm the information could be erased.
  • the prodecure could be repeated many times.
  • Example 6 Use of chiral compounds in discotic nematics
  • a nematic discotic mixture comprising of

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Liquid Crystal (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

L'invention concerne des composés chiraux de formule (1), dans laquelle R1, R2, R3, R4 = sont égaux ou pas à = H, F, Cl, R5, R6 or R7, R5 = CN, NCS, CF3, OCF3, R6 = alkyle, alcényle, alcynyle, ou fluoroalkyle chiral, présentant une longueur de chaîne pouvant atteindre 15 atomes de carbone, un ou plusieurs atomes C asymétriques étant substitués par -CH3, -C2H5, -CN, halogène, -CF3, -CHF2, CH2F, -CC13, -CF2Cl, -CFCl2, -OCF3, -OCHF2, -OCH2F où un ou plusieurs groupes CH2 peuvent être remplacés indépendamments les uns des autres par -S-, -O-, cyclobutane, [1.1.1]bicyclopentane, cyclopropane, oxirane, thiirane, -CO-, -COO-, -OCO-, -OCOO-, -OOCO-, R7 = alkyle, alcényle, alcynyle ou fluoroalkyle non chiral, présentant une longueur de chaîne pouvant atteindre 15 atomes de carbone, un ou plusieurs atomes C pouvant être substitués par -CH3, -C2H5, -CN, halogène, -CF3, -CHF2, CH2F, -CCl3, -CF2Cl, -CFCl2, -OCF3, -OCHF2, -OCH2F, et dans lesquels ou un plusieurs groupes CH2 peuvent être remplacés indépendamment les uns des autres par -S-, -O-, cyclobutane, [1.1.1]bicyclopentane, cyclopropane, oxirane, thiirane, -CO-, -COO-, -OCO-, -OCOO-, -OOCO-; les cycles A1, A2, A3, A4 = séparéments un cycle 1,4-phényl substitué ou non; X1, X2 = séparément S, C(R8 R9), R8, R9 = H, F, Cl, R5, R6, R7, à condition qu'au moins un des groupes R1, R2, R3, R4, R8, R9 soit égal à R6, et qu'au plus deux des groupes R1, R2, R3, R4 soient égaux à R5. Ces composés peuvent être mis en alternance dans deux états optiques stables et sont à utiliser dans des affichages chiro-optiques.
PCT/JP1996/002598 1996-09-12 1996-09-12 Structures a fibres et son procede de production WO1998011077A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU69443/96A AU6944396A (en) 1996-09-12 1996-09-12 Materials for chirooptical devices
JP10513463A JP2001501186A (ja) 1996-09-12 1996-09-12 キロ光学デバイス用材料
PCT/JP1996/002598 WO1998011077A1 (fr) 1996-09-12 1996-09-12 Structures a fibres et son procede de production

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104892431A (zh) * 2003-08-29 2015-09-09 三井化学株式会社 农园艺用杀虫剂的制备中间体
WO2018010540A1 (fr) * 2016-07-14 2018-01-18 京东方科技集团股份有限公司 Composé chiral, matériau à cristaux liquides, leur procédé de fabrication et dispositif d'affichage

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007238510A (ja) * 2006-03-09 2007-09-20 Institute Of Physical & Chemical Research 光学活性化合物、光記録用材料、光学フィルムおよび情報記録媒体

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD134279A1 (de) * 1977-12-02 1979-02-14 Dietrich Demus Verfahren zur speicherung optischer informationen
JPH0224190A (ja) * 1988-07-13 1990-01-26 Toyobo Co Ltd 光記録材
DE4324309C1 (de) * 1993-07-20 1994-12-01 Hermann Prof Dr Rau Phototropes Material für optische Datenspeicherung und für strahlungsinduzierte dauerhafte, aber durch Strahlung wieder rückgängig zu machende Veränderung von Stoffeigenschaften

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD134279A1 (de) * 1977-12-02 1979-02-14 Dietrich Demus Verfahren zur speicherung optischer informationen
JPH0224190A (ja) * 1988-07-13 1990-01-26 Toyobo Co Ltd 光記録材
DE4324309C1 (de) * 1993-07-20 1994-12-01 Hermann Prof Dr Rau Phototropes Material für optische Datenspeicherung und für strahlungsinduzierte dauerhafte, aber durch Strahlung wieder rückgängig zu machende Veränderung von Stoffeigenschaften

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CHEMICAL ABSTRACTS, vol. 113, no. 22, 26 November 1990, Columbus, Ohio, US; abstract no. 201443, TAMAOKI N: "Photochromic recording materials using cyclic compound having two photoisomerizable units" XP002030005 *
HERMANN RAU: "Photochromic Azobenzenes which are stable in the trans and cis forms", MOLECULAR CRYSTALS AND LIQUID CRYSTALS (INC NONLINEAR OPTICS )., vol. 246, 1994, READING GB, pages 143 - 146, XP000670836 *
WOLTER F. JAGER: "A highly stereoselective optical switching process based on donor-acceptor substituted dissymmetric alkenes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION., vol. 34, no. 3, 1995, WEINHEIM DE, pages 348 - 350, XP000670166 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104892431A (zh) * 2003-08-29 2015-09-09 三井化学株式会社 农园艺用杀虫剂的制备中间体
WO2018010540A1 (fr) * 2016-07-14 2018-01-18 京东方科技集团股份有限公司 Composé chiral, matériau à cristaux liquides, leur procédé de fabrication et dispositif d'affichage
US10619100B2 (en) 2016-07-14 2020-04-14 Boe Technology Group Co., Ltd. Chiral compound, liquid crystal material, preparation method thereof, and display device

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JP2001501186A (ja) 2001-01-30

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