GB2240778A - Fluorinated terphenyls - Google Patents

Fluorinated terphenyls Download PDF

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GB2240778A
GB2240778A GB9002743A GB9002743A GB2240778A GB 2240778 A GB2240778 A GB 2240778A GB 9002743 A GB9002743 A GB 9002743A GB 9002743 A GB9002743 A GB 9002743A GB 2240778 A GB2240778 A GB 2240778A
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compounds
formula
liquid crystal
cyc
phe
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GB2240778B (en
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David Coates
John Anthony Jenner
Volker Reiffenrath
Ulrich Finkenzeller
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Merck Patent GmbH
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Merck Patent GmbH
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/124—Ph-Ph-Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3025—Cy-Ph-Ph-Ph

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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)

Abstract

Fluorinated terphenyls of the formula I <IMAGE> wherein R<1> and R<2> independently from each other are alkyl groups with up to 9 carbon atoms or such residues wherein one CH2 group is replaced by oxygen, Q is either trans-1,4-cyclohexylene, 1,4-phenylene or <IMAGE> and one or two of L<1> to L<5> represents fluorine and other substituents L are hydrogen, are suitable as components of liquid crystal media.

Description

Fluorinated Terphenyls The invention relates to fluorinated terphenyls of the formula I
wherein R1 and R2 independently from each other are alkyl groups with up to 9 carbon atoms or such residues wherein one CH group is replaced by oxygen, Q is either trans 1, 4-cyclohexylene, 1,4-phenylen or
and one or two of L1 to L5 represent fluorine and the other substituents L are hydrogen.
The compounds of the formula I can be used as components of liquid crystal media, in particular for displays which are based on the principle of the twisted nematic cell, including TN cells with a higher twist angle like STN, SBE, OMI etc., on the guest-host effect on the effect of deformation of orientated phases or on the effect of dynamic scattering (ECB displays).
A further field of use is nematic or smectic A PDLC (polymer dispersed liquid crystals).
Compounds similar to those of formula I are known from USP 4,695,131. These compounds correspond to the above formuLa -wherein Q denotes
The invention was based on the object of discovering new stable liquid crystalline or mesogenic compounds which are especially suitable for STN and ECB displays without exhibiting the shortcomings of the prior art compounds.
They exhibit very high values for the optical anisotropy and/or favorable elastic properties.
Surprisingly, it has been found that the compounds according to formula I meet these criteria to an outstanding degree and allow the realization of a very high resistivity and simultaneously favorable electro-optic characteristics. These compounds also show a surprisingly good solubility at -20 OC in many LC base materials from other compound classes.
Compounds of formula I can provide very attractive components of liquid crystal materials for electro-optical display applications. The following highly advantageous points can be noticed: (a) high clearing points and an extraordinarily wide nematic range which are advantageous in the formula tion of liquid crystalline media with wide nematic range; (b) as far as R and R are relatively short chain alkyl groups or residues derived thereof the compounds of the formula I show little tendency to form smectic phases in combination with nematic materials of posi tive dielectric anisotropy; the long alkyl chain versions are highly suitable for smectic A mixtures; (c) a high solubility in nematic materials of negative r or positive dielectric anisotropy; (d) the property of elevating the clearing point when added to mixtures with nematic materials already containing a high clearing point component; (e) a higher birefringence in comparison with other known materials with similar thermal and viscous properties; (f) a very low temperature dependence of threshold voltage; (g) good chemical and photochemical stability.
Such an attractive combination of properties offers the possibility of forming liquid crystal mixtures having properties superior to known mixtures.
By providing the compounds of the formula I, the range of liquid crystal substances which are suitable, under various technological aspects for the preparation of nematic mixtures is also quite generally widened considerably.
The compounds of the formula I have a wide field of application and they are preferably added to liquid crystal base materials from other classes of compounds, for example in order to increase the clearing point while having little effect on other physical properties.
The compounds of the formula I are colourless in the pure state and form liquid crystal mesophases in a temperature range which is favorably placed for electrooptical use. They are very stable towards chemicals, heat and light.
The invention thus relates to the compounds of the formula I and the use of these compounds as components of liquid crystal media. The invention furthermore relates to liquid crystal media containing at least one compound of the formula I and to liquid crystal display elements, in particular electrooptical display devices, which contain media of this type.
Above and below R1, Q, L1, L2 L3, L4, L5 and R2 have the mentioned meaning, unless expressly stated otherwise.
The compounds of the formula I accordingly include compounds of the part formulae Ia to Id:
In the compounds of these formulae R1 and R2 are preferably alkyl, furthermore also groups in which one CR2 group is replaced by oxygen.
If Rl and/or R2 are alkyl and/or alkoxy groups, these can be straight-chain or branched. Preferably, they are straight-chain and have 2, 3, 4, 5, 6, 7, 8, 9 or 10 C atoms and are accordingly preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy or decoxy, also methyl or methoxy.
Oxaalkyl is preferably straight-chain 2-oxapropyl (= methoxymethyl), 2-(= ethoxymethyl) or 3-oxybutyl (= 2methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl or 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl.
Compounds of the formula I with branched terminal groups R1 and/or R2 can be of importance because of a better solubility in the customary liquid crystal base materials, but in particular as chiral doping substances if they are optically active.
Branched groups oft this type as a rule contain not more than one chain branching. Preferred branched groups are isopropyl, 2-butyl (= l-methylpropyl), isobutyl (= 2methylpropyl), 2-methylbutyl, isopentyl, (= 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3methylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, l-methylheptoxy (= 2-octyloxy), 2-oxa-3-methylbutyl, 3-oxa-4methylpentyl, 4-methylhexyl and 6-methyloctoxy.
In the case of compounds with branched terminal groups, formula I includes both the optical antipodes and racemates as well as mixtures thereof.
Q is preferably trans-1,4-cyclohexylene or
is preferably one of the following ring system 1 to 4
Systems 1, 2 and 3 and in particular 2 being preferred.
5.
L is preferably hydrogen.
Of the compounds of the formula I and subformulae thereof, those in which at least one of the radicals contained therein has one of the preferred meanings given are preferred.
The compounds of the formula I and their precursors are prepared by methods which are known per se, e.g. by transition metal catalyzed coupling reaction, such as are described in the literature (for example E. Poetsch, Kontakte/Darmstadt 1988 (2), 15-28 and in the standard works, such as Houben-Weyl, Methoden der Organischen Chemie methods of Organic Chemistry, Georg-Thieme Verlag, Stuttgart), and in particular under reaction con ditions which are known and suitable for the reactions mentioned. Variants which are known per se and are not mentioned in more detail here can also be used in this connection.
If desired, the starting substances can also be formed in situ, such that they are not isolated from the reaction mixture but are immediately reacted further to give the compounds of the formula I.
All steps are fully conventional and the reaction conditions are known to the skilled worker. The starting materials are known (e.g. E. Poetsch, Kontakte/Darmstadt 1988 (2), S.15-28) or easily prepared in analogy to known materials.
Other methods of making compounds of formula I are apparent to those skilled in the art.
In addition to one or more compounds of formula I the liquid crystal media according to the invention preferably contain 2-40 components and in particular 4-30 components. Liquid crystal media being composed of one or more compounds of formula I and 7-25 other components are especially preferred.
These additional components are preferably chosen from the nematic or nematogenic (monotropic or isotropic) substances; in particular from the classes of azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl cyclohexanecarboxylates, phenyl or cyclohexyl cyclohexylbenzoates, phenyl or cyclohexyl cyclohexylcyclohexanecarboxylates, cyclohexylphenylbenzoates, cyclohexylphenyl cyclohexanecarboxylates, cyclohexylphenyl cyclohexylcyclohexanecarboxylates, phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexenes, cyclohexylcyclohexylcyclohexene, 1,4-bis-cyclohexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, phenyl- or cyclohexylpyrimidines, phenyl- or cyclohexylpyridines, phenyl- or cyclohexyldioxanes, phenyl- or cyclohexyl-1,3-dithianes, 1,2-diphenylethanes, 1,2-dicyclohexylethanes, l-phenyl2-cyclohexylethanes, 1-cyclohexyl-2- (4-phenyl-cyclohexyl ) - ethanes, l-cyclohexyl-2-biphenylethanes, 1-phenyl-2cyclohexyl-phenylethanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted cinnamic acids.
The 1,4-phenylene groups of these compounds may be fluorinated.
The most important compounds which are possible constituents of liquid crystal media according to the invention can be characterized by the formalae 1, 2, 3, 4 and 5: R' -L-E-R" 1 R1 -L-COO-E-R" 2 R' -L-OOC-E-R" 3 R '-L-CH2CE2-E-R" 4 R' -L-C-C-E-R" 5 In the formulae 1, 2, 3, 4 and 5 L and E may be equal or different from each other.L and E independently from each other denote a bivalent residue selected from the group consisting of -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -G-Phe-, -G-Cyc- and their mirror images; in this compilation of residues Phe denotes unsubstituted or fluorinated 1,4-phenylen, Cyc trans- 1,4 cyclohexylene or 1,4-cyclohexenylen, Pyr pyrimidine-2,5diyl or pyridine-2,5-diyl, Dio 1,3-dioxane-2,5-diyl and G 2-(trans-1,4-cyclohexyl)-ethyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,3-dioxane-2,5-diyl.
One of the residues L and E is preferably Cyc, Phe or Pyr. E preferably denotes Cyc, Phe or Phe-Cyc. The liquid crystal media according to the invention preferably contain one or more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with L and E meaning Cyc, Phe and Pyr, said liquid crystal media further containing at the same time one ore more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with one of the residues L and E denoting Cyc, Phe and Pyr and the other residue being selected from the group consisting of -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -G-Cyc-, said liquid crystal media containing in addition to this optionally one or more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with L and E being selected from the group consisting of -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc.
In a preferred subgroup of the compounds of formulae 1, 2, 3, 4 and 5 (subgroup 1) R' and R" are independently from each other alkyl, alkenyl, alkoxy, alkenoxy with up to 8 carbon atoms. R' and R" differ from one another in most of these compounds, one of the residues usually being alkyl or alkenyl. In another preferred subgroup of the compounds of formulae 1, 2, 3, 4 and 5 (subgroup 2) R" denotes -CN, -CF3, -F, -C1 or -NCS while R' has the meaning indicated in subgroup 1 and is preferably alkyl or alkenyl. Other variants of the envisaged substituents in the compounds of formulae 1, 2, 3, 4 and 5 are also customary. Many such substances are commercially available.
All these substances are obtainable by methods which are known from the literature or by analogous methods.
The liquid crystal media according to the invention preferably contain in addition to components selected from subgroup 1 also components of subgroup 2, the percentage of these components being as follows: subgroup 1: 20 to 90 %, in particular 30 to 90 % subgroup 2: 10 to 50 %, in particular 10 to 50 % In these liquid crystal media the percentages of the compounds according to the invention and the compounds of subgroup 1 and 2 may add up to give 100 %.
The media according to the invention preferably contain 1 to 40 %, in particular 5 to 30 % of the compounds according to the invention. Media containing more than 40 %, in particular 45 to 90 % of the compounds according to the invention are further preferred. The media contain preferably 3, 4 or 5 compounds according to the invention.
The media according to the invention are prepared in a manner which is customary per se. As a rule, the components are dissolved in one another, advantageously at elevated temperature. The liquid crystal media according to the invention can be modified by suitable additives so that they can be used in all the types of liquid crystal display devices. Such additives are known to the expert and are described in detail in the literature (H. Kelker/R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980). For example, it is possible to add pleochroic dyestuffs to prepare colored guest-host systems or substances for modifying the dielectric anisotropy, the viscosity and/or the orientation of the nematic, phases.
The following examples are to be construed as merely illustrative and not limitative. m.p. = melting point, c.p. = clearing point. In the foregoing and in the following all parts and percentages are by weight and the temperatures are set forth in degrees Celsius. "Custo- mary work-up" means that water is added, the mixture is extracted with methylene chloride, the organic phase is seperated off, dried and evaporated, and the product is purified by crystallization and/or chromatography.
Further are: C: crystalline-solid state, S: smectic phase (the index denoting the typ of smectic phase), N: nematic phase, Ch: cholesteric phase, I: isotropic phase. The number being embraced by 2 of these symbols denotes the temperature of phase change.
Example 1
4-(4-Propylphenyl)-3-fluorophenyl boronic acid (6 g 0.0232 m) (made by the reaction of trimethylborate on the Grignard reagent of 4'-propyl-2-fluoro-4-bromobi- phenyl] was mixed with 4-(trans-4-propylcyclohexyl)4'-bromobiphenyl (5.95 g 0.02115 m), tetrakis triphenyl phosphine palladium (0.24 g), 2M sodium carbonate soln (20 ml), methylated spirits (1 ml) and toluene (42 ml).
The mixture was stirred and heated under reflux for 16 hrs. After the usual work up procedure, 6.3 g of the required product was isolated.
K 110 S 134 Sa 212.9 N 306 I.
Examples 2 to 16 The following compounds are prepared analogously R1 R2 Q L1 L2 L3 L4 L5 (2) C3H7 C3H7 Cy H F H H H (3) C3H7 C2H5 Cy H F H H H (4) C5H11 C3H7 Cy H F H H H (5) C3H7 C2H5 Ph-C2H4 H F H H H (6) C3H7 C3H7 Ph-C2H4 H F H H H (7) C5H11 C3H7 Ph-C2H4 H F H H H (8) C3H7 C2H5 Ph-C2H4 H H H F H (9) C3H7 C3H7 Ph-C2H4 H H H F H (10) 5H11 C3H7 Ph-C2H4 H H H F H (11) C2H5 C2H5 Ph F H H F H (12) C3H7 C3H7 Ph F H H F H, C83 SA187 N293I (13) C4H9 C4H9 Ph F H H F H, C106 SC115 SA216 N263I (14) C3H7 C2H5 Cy H F H F H (15) C3H7 C3H7 Cy H F H F H (16) C5Hl1 C3H7 Cy H F H F H (17) 93H7 C3H7 Ph F H H H H, C150 S184 5196 SA290 N329I (18) C4H9 C4H9 Ph F H H H H (19) C5Hl1 C5H1l Ph F H H H H (20) C7H15 C7H15 Ph F H H H H

Claims (8)

  1. Claims 1. Fluorinated terphenyls of the formula I
    wherein R1 and R2 independently from each other are alkyl groups with up to 9 carbon atoms or such residues wherein one CH2 group is replaced by oxygen, Q is either trans-1,4-cyclohexylene, 1,4-phenylen or
    and one or two of L1 to L5 represent fluorine and the other substituents L are hydrogen.
  2. 2. Terphenyl according to claim 1, characterized by formula Ia
  3. 3. Terphenyl according to claim 1, characterized by formula Ib
  4. 4. Terphenyl according to claim 1, characterized by formula Ic
  5. 5. Terphenyl according to claim 1, characterized by formula Id
  6. 6. Liquid crystalline medium being a mixture of at least two compounds, characterized in that at least one compound is a terphenyl according to formula I.
  7. 7. Liquid crystal display device, characterized in that it contains a liquid crystalline medium according to claim 6.
  8. 8. Electrooptical display device, characterized in that it contains a liquid crystalline medium according to claim 6.
GB9002743A 1990-02-07 1990-02-07 Fluorinated terphenyls Expired - Lifetime GB2240778B (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032942A1 (en) * 1996-03-07 1997-09-12 Chisso Corporation Liquid crystal composition and liquid crystal display device
WO1998008792A1 (en) * 1996-08-28 1998-03-05 Chisso Corporation Tetracyclic compound having lateral halogen substituent and liquid crystal composition comprising the same
EP0857774A2 (en) * 1997-02-10 1998-08-12 Chisso Corporation Liquid crystal composition and liquid crystal display device
EP0959061A1 (en) * 1996-11-25 1999-11-24 Chisso Corporation 3,3'-difluorobiphenyl derivatives, liquid crystal compositions, and liquid crystal display elements
DE10211597A1 (en) * 2002-03-15 2003-10-02 Merck Patent Gmbh Process for the production of ring connections
WO2004035710A1 (en) * 2002-10-15 2004-04-29 Merck Patent Gmbh Photostable liquid crystalline medium
US6936312B2 (en) * 2002-04-09 2005-08-30 Chisso Corporation Liquid crystal composition and liquid crystal display
US7074836B1 (en) 1996-07-31 2006-07-11 Shionogi & Co., Ltd. Para-terphenyl compounds
EP1724324A1 (en) * 2005-05-21 2006-11-22 Merck Patent GmbH Liquid crystalline medium
EP1911827A2 (en) 2006-10-12 2008-04-16 MERCK PATENT GmbH Liquid crystalline medium
EP2075601A1 (en) 2007-12-24 2009-07-01 Lofo High Tech Film GmbH Optical compensation film for liquid crystal displays and related inventions
JP2010111686A (en) * 2009-12-24 2010-05-20 Chisso Corp Tetracyclic compound having lateral halogen substituent group and liquid crystal composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989002425A1 (en) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Fluorinated oligophenyls and their use in liquid crystal materials
WO1990001526A1 (en) * 1988-08-15 1990-02-22 MERCK Patent Gesellschaft mit beschränkter Haftung Liquid crystal display devices and liquid crystal medium to be used therein

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989002425A1 (en) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Fluorinated oligophenyls and their use in liquid crystal materials
WO1990001526A1 (en) * 1988-08-15 1990-02-22 MERCK Patent Gesellschaft mit beschränkter Haftung Liquid crystal display devices and liquid crystal medium to be used therein

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032942A1 (en) * 1996-03-07 1997-09-12 Chisso Corporation Liquid crystal composition and liquid crystal display device
US7074836B1 (en) 1996-07-31 2006-07-11 Shionogi & Co., Ltd. Para-terphenyl compounds
US7220783B2 (en) 1996-07-31 2007-05-22 Shionogi & Co., Ltd. Para-terphenyl compounds
US7101915B1 (en) * 1996-07-31 2006-09-05 Shionogi & Co., Ltd. P-terphenyl compounds
US6174458B1 (en) 1996-08-28 2001-01-16 Chisso Corporation Tetracyclic compound having lateral halogen substituent and liquid crystal composition comprising the same
WO1998008792A1 (en) * 1996-08-28 1998-03-05 Chisso Corporation Tetracyclic compound having lateral halogen substituent and liquid crystal composition comprising the same
JPH1072384A (en) * 1996-08-28 1998-03-17 Chisso Corp Tetracyclic compound having lateralhalogen substituent group and liquid crystal composition
EP0959061A4 (en) * 1996-11-25 2000-08-23 Chisso Corp 3,3'-difluorobiphenyl derivatives, liquid crystal compositions, and liquid crystal display elements
US6197217B1 (en) 1996-11-25 2001-03-06 Chisso Corporation 3,3′-difluorobiphenyl derivatives, liquid crystal compositions, and liquid crystal display elements
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JP4451932B2 (en) * 1996-11-25 2010-04-14 チッソ株式会社 3,3'-Difluorobiphenyl derivative, liquid crystal composition, and liquid crystal display device
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