EP0946672A1 - Flüssigkristallmaterialien - Google Patents

Flüssigkristallmaterialien

Info

Publication number
EP0946672A1
EP0946672A1 EP97939250A EP97939250A EP0946672A1 EP 0946672 A1 EP0946672 A1 EP 0946672A1 EP 97939250 A EP97939250 A EP 97939250A EP 97939250 A EP97939250 A EP 97939250A EP 0946672 A1 EP0946672 A1 EP 0946672A1
Authority
EP
European Patent Office
Prior art keywords
independently
formula
formulas
group
chiral
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP97939250A
Other languages
English (en)
French (fr)
Inventor
Vladimir St. 575 Shin-Dong Bezborodov
Valery Iv. 575 Shin-Dong Lapanik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Samsung SDI Co Ltd
Original Assignee
Samsung Display Devices 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 Samsung Display Devices Co Ltd filed Critical Samsung Display Devices Co Ltd
Publication of EP0946672A1 publication Critical patent/EP0946672A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12Non-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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12Non-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
    • C09K19/126Compounds containing at least one asymmetric carbon atom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001Cyclohexane rings
    • C09K19/3003Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3098Unsaturated non-aromatic rings, e.g. cyclohexene rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to liquid crystal materials for use in ferroelectric liquid crystal display devices. More specifically, the invention relates to chiral, laterally substituted derivatives of cyclohexene, cyclohexane, benzene, biphenyl, terphenyl and quaterphenyl compounds, mixtures thereof, and liquid crystal displays utilizing the same.
  • Liquid crystal displays have been commonly employed in electronic devices for many years. In general, commercial displays operate by the twisted nematic (TN) or super twisted nematic (STN) technique. However, liquid crystal displays based on a ferroelectric technique are also known. Such displays have superior properties such as higher switching efficiencies in comparison to TN and STN displays. But ferroelectric liquid crystal displays have not been widely used in commercial or consumer applications, in spite of their advantages, due to their limited operable temperature range. Specifically, in order to utilize the ferroelectric effect, the liquid crystal material must exhibit a smectic C phase. Liquid crystal compounds that exhibit a smectic C phase do so over a narrow temperature range.
  • Liquid crystal compounds include derivatives of cyclohexane, cyclohexene, benzene, biphenyl, and terphenyl compounds. Such compounds are disclosed in Ferroelectrics 1991, vol. 114, p.
  • U.S. P. 4,784,793 addresses some of the problems encountered with ferroelectric liquid crystal materials and proposes the use of terpenoid derivatives, such as an ester of a terpenoid alcohol, as either a smectic host or a chiral dopant.
  • U.S. P. 5,382,380 and U.S. P. 5,494,605 both relate to p-terphenyl derivatives having lateral fluoro substitution. The compounds are described as exhibiting a smectic C phase over a wide temperature range.
  • the compounds of the prior art are not yet fully satisfactory and do not satisfy all of the requirements for some of the new applications for liquid crystal displays. Specifically, compounds are needed that will allow the formation of ferroelectric liquid crystal mixtures exhibiting a low crystalline to smectic C phase transition temperature as well as a wide smectic C phase and that has a stable orientation.
  • a further object of the invention is to provide a ferroelectric liquid crystal display device that is operable over a wide range of temperatures and at very low temperatures.
  • R 1 and $ are each independently selected from the group consisting of formulas S 1 , S 2 and S 3 : I I
  • Y 1 , Y 2 , Y 3 , and Y are each independently hydrogen, alkyl, F, CN, CF, or OCF 3 , n, p, and k are each independently an integer from 0 to 7. and m and 1 are each independently zero or 1, with the proviso that at least one of R 1 and R 2 is a chiral radical;
  • Z 1 and Z 2 are each independently a ring selected from the group consisting of formulas 2-11
  • a 1 , A 2 and A 3 are each independently a ring group selected from the group consisting of formulas 12-19:
  • the compounds of Formula (1) can have as few as one ring represented by Z 1 or a plurality of rings represented by Z 1 and any of A 1 -A 3 and/or Z 2 .
  • a is 0, then the substituent group R 1 is directly bonded to the group Z 1 .
  • b, c and d were each 0, the group R 2 would be directly bonded to the moiety Z 1 .
  • R 1 and R 2 are each independently represented by one of the formulas S 1 - S 3 with the proviso that at least one of R ! and R 2 is a chiral group.
  • R l and R 2 can both be chiral groups, although such is not required.
  • the compounds of Formula (1) are optically active.
  • a chiral moiety can be obtained by appropriately selecting the groups for the pair Y 1 and Y 2 or the pair Y 3 and Y 4 , as will be readily understood by workers skilled in the art.
  • the groups Y 1 -Y 4 are independently selected for R 1 and R 2 . That is, the Y 1 group of R 1 may be the same or different as the Y 1 group of R 2 .
  • the same is true of all other variables in the formulas S 1 - S 3 such that the values selected for R 1 are independent of the values selected for R 2 .
  • Y ] , Y 2 , Y 3 or Y 4 represents an alkyl, it may be straight or branched and typically has from 1 to 12 carbon atoms.
  • the alkyl group has from 1 to 8 carbon atoms.
  • examples of the alkyl group include methyl, ethyl, n-propyl, i-propyl, n-butyl, and t-butyl.
  • the subscripts n, p and k are each independently an integer from 0 to 7 while the subscripts m and 1 are each independently 0 or 1.
  • p and k, as well as 1, are 0.
  • Examples of chiral R 1 and R 2 groups include 2-methylbutyl, 2-methylpentyl, 2-methylhexyl, 4-methylhexyl, citronellyl, citronellyloxy, 2-methylhexyloxy, 2- methyloctyloxy, 2-cyanobutyloxy, and 2-fluorobutyloxy.
  • the non-chiral R 1 and R 2 groups include octyl, octyloxy, butyl, hexyl, hexyloxy, nonyl, nonyloxy, decyl, decyloxy, 2-octyloxyethyl, 2-octyloxyethyloxy, heptyloxymethyl, and heptyloxymethyloxy .
  • Z 1 and Z 2 each independently represent a six-membered ring selected from formulas 2-11 , each of which is substituted by a group X .
  • Each X independently represents O, F, Cl, OH, CN or a group represented by formulas L 1 - L 6 .
  • X can not be O on ring formulas 4, 5, and 8-11.
  • Z 2 is present (c is 1), each X group is independently selected.
  • L ' - L 6 examples include 2-methylbutyloxycarbonyl, 2-methylbutylcarbonyloxy, 2- methylhexyloxy, 2-methyloctyloxy, 2-methylbutyl, 2-methylbutyloxy, 2- chlorobutylcarbonyloxy, methyl, methyloxy, ethyl, and ethyloxy.
  • L 1 - L 6 can represent chiral or non- chiral groups.
  • a 1 - A 3 are each independently selected from the ring formulas 12 - 19.
  • 1 - X 4 are independently selected for each of A 1 - A 3 and are H, F, or Cl.
  • the chiral, laterally substituted compounds of formula (1) are liquid crystal compounds that exhibit a chiral smectic C phase.
  • the compounds exhibit a chiral smectic C phase over a broad temperature range, such as over a range of at least 20°C, more preferably at least 30°C, and most preferably over at least 40 °C range.
  • the compounds exhibit a chiral smectic C phase at low temperatures, including ambient temperatures. Accordingly, it is preferred that the lower end of the chiral smectic C phase is 20 °C or less, more preferably 10°C or less, and most preferably, 5°C or less.
  • the smectic C phase temperature values can be determined by conventional techniques known in the art; i.e., heating the compounds to the isotropic liquid phase, and then observing the phases and their transition temperatures during cooling and then heating again.
  • the transition temperatures were determined using a Mettler FP5 hotstage and control unit in conjunction with a polarizing microscope and these values were confirmed using differential scanning calorimetry (Perkin-Elmer DSC- 7).
  • the compound of formula (1) is represented by one of the formulas 1.1 - 1.39 set forth below.
  • R 3 and R 4 represent a group of formulas L 1 - L 6
  • R 1 , R 2 , and X 1 - X 4 have the same definition as in formula (1).
  • R 1 and R 2 are each independently selected from the group consisting of formulas S 1 , S 2 and S 3 :
  • Y 1 , Y 2 , Y 3 , and Y 4 are each independently hydrogen, alkyl, F, CN, CF 3 or OCF 3 , n, p, and k are each independently an integer from 0 to 7, and m and 1 are each independently zero or 1 , with the proviso that at least one of R 1 and R 2 is a chiral radical;
  • Z 1 and Z 2 are each independently a ring selected from the group consisting of formulas 2-11
  • the compounds of formula (1) can be prepared by workers skilled in this art without undue experimentation through conventional reactions that are per se known in the art and from conventional and/or commercially available starting materials. However, preferred reaction schemes are set forth hereinbelow. Liquid crystal compounds according to the present invention can be obtained by the transformation of 3,6-disubstituted cyclohex-2-enones. Synthesis of these starting compounds is shown in scheme 1. For convenience and clarity the compounds are shown without the subscripts a - d, but such should be assumed to be present.
  • Scheme 1 The process consists of heating acetoacetic esters with hydrochloride 4- substituted ⁇ -N-dimethylaminoprophio-phenones in the presence of an alkaline hydroxide. The 3,6-disubstituted cyclohex-2-enones can then be transformed into
  • the 3,6-disubstituted cyclohex-2-enones can be transformed into the corresponding 4,4-disubstituted 3-hydroxybiphenyls, te ⁇ henyls and quate ⁇ henyls (Formula 27) by aromatization in the presence of 10% palladium on carbon at 200°C or by the boiling of them in alcohols in the presence of iodine.
  • the 3,6-disubstituted cyclohexanones can be transformed into the corresponding cis and trans alcohols (Formula 34) by reduction with NaBH 4 or LIA1H 4 in an appropriate solvent.
  • Fluorosubstituted compounds are prepared by heating ketones (Formula 24) with diethylaminosulfur trifluoride in benzene or methylene chloride and the resulting difluoroderivatives (Formula 36) are then treated with a base, advantageously KOH or with alcohalate.
  • the cyanounsaturated compounds (Formula 42, 43) are obtained by treating the ketones (Formula 24) with acetone cyanohydrine in the presence of tertiary amines or alkaline metal carbonates in dioxane or tetrahydrofuran and then by treating of the corresponding cyanoalcohols with POCl 3 in the presence of a tertiary aliphatic amine or pyridine.
  • the isomeric compounds (Formula 42, 43) are separated by crystallization.
  • the chlorine substituted compounds (Formulae 26, 30, 31) are obtained by heating ketone (Formula 23, 24) with PC1 5 , PCI, in hexane or benzene.
  • the isomeric compounds (Formula 30, 31) are separated by crystallization or used in a form of the isomeric mixtures.
  • Compounds of Formula 25 and 32 are obtained from ketone (Formula 23,
  • Compounds of Formula 36 are obtained by treating ketone 24 with triethyl orthoformate in the presence of p-toluenesulfonic acid in ethanol.
  • the chlorocyclohexane derivatives (Formula 33) are obtained by treating the corresponding alcohols (Formula 34) with PC1 5 , SOCl 2 , POCl 3 .
  • the fluorocyclohexane derivatives (Formula 40) are synthesized by treating the alcohols 34 with diethylaminosulfur trifluoride (DAST) in methylene chloride at temperature below 20°C.
  • DAST diethylaminosulfur trifluoride
  • the compounds of formula (1) are useful in liquid crystal display devices including TN, STN, and ferroelectric LC displays.
  • the compounds of Formula (1) are especially useful in creating compositions having various values of optical anisotropy and dielectric anisotropy as well as a wide temperature interval of the smectic C phase.
  • Compositions according to the present invention require at least two compounds, with at least one of them being a compound of Formula (1).
  • the compounds contained in the composition can be exclusively of formula (1) or a combination with other liquid crystal compounds.
  • compositions containing compounds of Formula (1) that have 2 or 3 rings show low or intermediate clearing temperatures.
  • Compositions containing compounds of Formula (1) that have 4 or 5 rings have a broadening of the smectic C phase, including broader than 100°C.
  • the compositions are useful in ferroelectric liquid crystal displays, TN, STN, and active matrix displays. The high chemical stability and resistivity of these mixtures enable the stable performance of the display.
  • the composition is a ferroelectric composition and exhibits a chiral smectic C phase over a broad temperature range, preferably over at least a 40 °C interval. Moreover, preferably the composition simultaneously exhibits a lower end of the chiral smectic C phase at 10°C or less, more preferably at 10°C or less, and most preferably at -30°C or less.
  • one or more compounds of Formula (1) is combined with at least one liquid crystal pyrimidine derivative.
  • the pyrimidine derivative exhibits a smectic C phase and is capable of forming a ferroelectric liquid crystal composition.
  • Such compounds include phenyl -substituted pyrimidines such as 2-alkoxyphenyl-5-alkylpyrimidines where the alkoxy and alkyl groups each contain from 1 to 12 carbon atoms.
  • the composition of the present invention can be used in any conventional liquid crystal display device.
  • such devices generally comprise two parallel electrodes, at least one of which is transparent, and having a layer of the liquid crystal composition disposed therebetween.
  • die liquid crystal layer is typically disposed between two parallel plates, one of which is transparent, that are in turn supported by (or surrounded by) the parallel electrodes. Between the parallel plates there may also be one or more of an aligning layer, isolating layer, and colored filter layer.
  • the display device is operated by the ferroelectric effect.
  • the compounds of formula (1) are useful in liquid crystal display devices including TN, STN, and ferroelectric LC displays.
  • the compounds of Formula (1) are especially useful in creating compositions having various values of optical anisotropy and dielectric anisotropy as well as a wide temperamre interval of the smectic C phase.
  • the compound of the present invention can be used in any conventional liquid crystal display device.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Pyridine Compounds (AREA)
EP97939250A 1996-09-12 1997-09-11 Flüssigkristallmaterialien Withdrawn EP0946672A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US71539396A 1996-09-12 1996-09-12
US715393 1996-09-12
PCT/KR1997/000169 WO1998011173A1 (en) 1996-09-12 1997-09-11 Liquid crystal materials

Publications (1)

Publication Number Publication Date
EP0946672A1 true EP0946672A1 (de) 1999-10-06

Family

ID=24873849

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97939250A Withdrawn EP0946672A1 (de) 1996-09-12 1997-09-11 Flüssigkristallmaterialien

Country Status (5)

Country Link
EP (1) EP0946672A1 (de)
JP (1) JP2001500502A (de)
KR (1) KR20000036036A (de)
AU (1) AU4138097A (de)
WO (1) WO1998011173A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100325849B1 (ko) * 1999-03-03 2002-03-07 김순택 3-아릴-6-치환된 사이클로헥스-2-엔온, 이를 포함한 액정 조성물및 이 액정 조성물을 이용한 액정표시소자
KR20040078712A (ko) * 2003-03-04 2004-09-13 삼성전자주식회사 시클로헥산 유도체, 이를 포함한 액정 조성물 및 이 액정조성물을 이용한 액정표시소자
JP2014015595A (ja) * 2011-09-07 2014-01-30 Dainippon Printing Co Ltd 強誘電性液晶組成物および液晶表示素子
JP2013067775A (ja) * 2011-09-07 2013-04-18 Dainippon Printing Co Ltd 強誘電性液晶組成物および液晶表示素子
WO2013035811A1 (ja) * 2011-09-07 2013-03-14 大日本印刷株式会社 強誘電性液晶組成物および液晶表示素子
CN114106850B (zh) * 2021-12-17 2022-11-18 重庆汉朗精工科技有限公司 一种正性液晶组合物及其在液晶显示装置中的应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178647B1 (de) * 1984-10-18 1993-09-29 Chisso Corporation Ferroelektrische chirale smektische Flüssigkristallzusammensetzung
US5250222A (en) * 1987-08-25 1993-10-05 Hoffmann-La Roche Inc. Optically active compounds used for liquid crystalline mixtures
JP2655333B2 (ja) * 1988-09-01 1997-09-17 関東化学 株式会社 新規なp‐ターフエニル誘導体並びに液晶組成物
FR2673190B1 (fr) * 1991-02-26 1994-09-16 Thomson Csf Cristaux liquides fluores.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9811173A1 *

Also Published As

Publication number Publication date
KR20000036036A (ko) 2000-06-26
AU4138097A (en) 1998-04-02
WO1998011173A1 (en) 1998-03-19
JP2001500502A (ja) 2001-01-16

Similar Documents

Publication Publication Date Title
JP2693525B2 (ja) アルケニルビシクロヘキサン
CA2088771A1 (en) Vinyl compounds, and a liquid-crystalline medium
JPH04501576A (ja) ハロゲン化ベンゼン誘導体および液晶相
EP0789067A1 (de) Cyclopentyl-Derivate als Flüssigkristalle
JP4006030B2 (ja) ベンゼン誘導体
KR100235265B1 (ko) 아세틸렌
JP2000119207A (ja) ベンゼン誘導体および液晶相
JPH04501864A (ja) フェニルシクロヘキサン化合物および液晶相
US5185098A (en) Liquid crystalline mixtures containing 3,4-difluorophenyl-substituted bicyclohexyls
JP3828169B2 (ja) ベンゼン誘導体及び液晶媒質
US5399292A (en) Fluoro-substituted phenyl-cyclohexylacetylenes
US5102578A (en) Liquid crystalline mixtures and method of making same
JPH072832A (ja) ハロフェニルで置換されたジオキサン、その製造方法及び使用
JP4577537B2 (ja) ナフタレン誘導体である新規液晶性化合物とそれを含有する液晶組成物
EP0946672A1 (de) Flüssigkristallmaterialien
Dong et al. The synthesis and electro-optic properties of liquid crystalline 2-(2, 3-difluorobiphenyl-4′-yl)-1, 3-dioxanes
JPH1112271A (ja) アキシアルにフッ素置換基を有する1,3−ジオキサン誘導体
KR100251144B1 (ko) 4개의 고리를 갖는 화합물
EP0471287B1 (de) Alkyloxypropenyl Derivate
JPH07145099A (ja) ベンゼン誘導体および液晶性媒体
Skelton et al. Nematic tolanes and acetylenes
DE4336265A1 (de) 3-Trifluormethylbenzole und ihre Verwendung in Flüssigkristallmischungen
GB2270913A (en) Liquid crystalline compounds with a chlorodifluoromethoxyphenyl terminus
JPH0689331B2 (ja) 液晶混合物
DE4336391A1 (de) 3,5-Bis(trifluormethyl)benzole und ihre Verwendung in Flüssigkristallmischungen

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19990401

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB

17Q First examination report despatched

Effective date: 19991125

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20001228