WO1998020004A1 - 2-(4-alkylphenyl)-5-alkylthiadiazoles - Google Patents

2-(4-alkylphenyl)-5-alkylthiadiazoles Download PDF

Info

Publication number
WO1998020004A1
WO1998020004A1 PCT/JP1997/003896 JP9703896W WO9820004A1 WO 1998020004 A1 WO1998020004 A1 WO 1998020004A1 JP 9703896 W JP9703896 W JP 9703896W WO 9820004 A1 WO9820004 A1 WO 9820004A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
thiadiazole
iso
compound
ferroelectric liquid
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.)
Ceased
Application number
PCT/JP1997/003896
Other languages
English (en)
Japanese (ja)
Inventor
Shinichi Saito
Ryushi Shundo
Eiji Okabe
Hideo Saito
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.)
JNC Corp
Original Assignee
Chisso Corp
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 Corp filed Critical Chisso Corp
Priority to AU47245/97A priority Critical patent/AU4724597A/en
Publication of WO1998020004A1 publication Critical patent/WO1998020004A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms

Definitions

  • the present invention relates to a liquid crystal compound that can be suitably used for a ferroelectric liquid crystal display device.
  • liquid crystal display devices have been widely used.
  • a TN (twisted nematic) display element is most widely used as a low-quality display element.
  • This TN type display element has many advantages such as low driving voltage and low power consumption.
  • the power response speed is remarkably inferior to light emitting type display elements such as a cathode ray tube, an electronic luminescence and a plasma display.
  • a new type of TN display element with a twist angle of 180 ° to 270 °, the so-called STN display element, has been developed, and the display capacity has increased dramatically, but the response speed is still limited .
  • display devices in which each pixel of a TN display device has a switch device have appeared on the market.
  • TFT devices thin film transistor devices
  • the screen size is limited to more than twenty inches, and the time division capability is also said to be limited to about 1,000 lines. Production costs are also problematic.
  • the ferroelectric liquid crystal display device which is the subject of the present invention, has the potential of realizing both a large screen of more than twenty and a few inches and a reduction in production cost, which the TFT device cannot realize.
  • This display method uses a chiral smectic phase such as a chiral smectic C phase (hereinafter abbreviated as Sc * phase) that exhibits strong dielectric properties, and is called a surface stabilized ferroelectric liquid crystal display (SS FLC). It is being commercialized by home appliance manufacturers and material manufacturers, and its characteristics are being improved and commercialized.
  • ferroelectric liquid crystal element has the following features in principle. 1. High-speed response, 2. Memory—
  • a ferroelectric liquid crystal composition having a negative dielectric anisotropy ( ⁇ ⁇ 0, ⁇ represents dielectric anisotropy) is used. (Le Paris et al., Paris Liquid 'Crystal' Conference, p. 217 (1989)). This method is called the AC stabilizing effect.
  • Liquid crystal molecules with negative ⁇ in a cell subjected to homogenous alignment treatment tend to be oriented parallel to the glass substrate (the major axis of the molecule is perpendicular to the direction of the electric field) when an electric field is applied.
  • the spontaneous polarization responds to the electric field, and when the direction of the electric field is reversed, the liquid crystal molecules move accordingly to the other stable state, and the substrate remains as it is due to the effect of ⁇ .
  • the spontaneous polarization cannot follow the reversal of the electric field, and only ⁇ is effective. Even if the direction of the electric field is reversed, the liquid crystal molecules do not move and remain parallel to the substrate. Become. This is the mechanism of developing memory properties using the AC stabilization effect. Thereby, a high contrast is obtained.
  • This example has been reported by Jyuari et al. (S ID '85 Digest p. 128 (1989)).
  • a ferroelectric liquid crystal material having a negative dielectric anisotropy can be applied to a display element utilizing the AC stabilizing effect and r-Vmin.
  • the ferroelectric liquid crystal composition can be composed of a ferroelectric liquid crystal compound alone, a non-chiral smectic smectic phase such as C, F, G, H, and I (hereinafter referred to as Sc, etc.).
  • a compound or composition that exhibits the following formula is used as a basic substance, and one or more ferroelectric liquid crystal compounds or non-liquid crystal optically active compounds are mixed with the compound or composition to form a ferroelectric liquid crystal phase as a whole.
  • There is a method of making a composition By the way, many liquid crystal compounds containing a thiadiazole ring are already known. For example, J. Prakt. Chemie., Vol. 322, pp. 933 (1980)), DD2 4 7 2 2 1 A1, and DD2 7 6 9 4 A1 Is disclosed in
  • compositions using these compounds are disclosed, for example, in W088 / 809.
  • a liquid crystal compound having a thiadiazole ring there are disclosed in Japanese Patent Application Laid-Open Nos. 2-275688 and 2-28069. Further, the present inventors have already applied for a liquid crystal composition using thiadiabule (Japanese Patent Application Laid-Open No. 7-70564). These compounds are shown below.
  • liquid crystal compound having a thiadiabule ring can be suitably used for a ferroelectric liquid crystal.
  • compounds having three or more ring structures in the molecule, for example, the following compounds are expected to have high viscosity, and the temperature range in which the Sc phase is exhibited is also high. Disclosure of the invention
  • an object of the present invention is to provide a liquid crystal compound having a low viscosity and a low temperature range in which an Sc phase is exhibited, and which can be suitably used for a ferroelectric liquid crystal. Therefore, the present inventors have searched for a liquid crystal compound having a thiadiazole ring having a two-ring structure. As described in the Background Art section, it has already been reported that a compound having the above structure has an Sc phase appearing in a temperature region slightly higher than room temperature, and can be suitably used in a ferroelectric liquid crystal composition. . However, a compound in which the alkoxy group at the left end in the above structural formula is substituted with a corresponding alkyl group has been used as a liquid crystal.
  • Ra represents an alkyl group having 5 to 15 carbon atoms
  • Rb represents an alkyl group having 5 to 15 carbon atoms.
  • a compound represented by the general formula (1), and a compound having an alkoxy group at the left end corresponding thereto, response is synonymous with viscous is the main object of the present invention ⁇ : A comparison was made by the time .
  • the ferroelectric liquid crystal composition containing 50% of the compound of the present invention has a response speed shorter than that of the liquid crystal composition containing 50% of the comparative compound by about 30% or more. I have. This indicates the superiority of the compound of the present invention.
  • the 4-alkylbenzoic acid (a) is converted to a lower ester (eg, ethyl ester).
  • dihydrazide (d) reacts with hydrazine hydrate to form hydrazide (c). Then, in a basic solvent, react with alkanoic acid chloride to obtain dihydrazide (d).
  • a basic solvent reacts with alkanoic acid chloride to obtain dihydrazide (d).
  • pyridine, triethylamine and the like can be suitably used as the basic solvent.
  • the desired compound (1) can be obtained by reacting the dihydrazide (d) with a phosphorylation reagent.
  • a phosphorylation reagent as the oxidizing reagent, io alone, a mouth reagent, and the like can be suitably used.
  • FIG. 1 is a diagram showing response times of the compositions of Examples and Comparative Examples.
  • the phase transition temperature was measured by placing the sample on a slide glass, placing the sample covered with a cover glass on a hot plate, and raising the temperature at 1 ° 0 min under a polarizing microscope.
  • the melting point was measured by differential scanning calorimetry (DSC) at a temperature of 1 ° CZmin.
  • Stage 2 N— (4-octyl benzoyl) -N′—Preparation of butyl dihydrazide 9.0 g of 4-octyl benzohydrazide obtained in stage 1 and 40 ml of pyridine are added, and octanoyl is added. 5.9 g of chloride was added dropwise, and the mixture was heated under reflux for 3 hours. After allowing to cool, the reaction product was poured into water, and the precipitated crystals were collected by filtration and air-dried. The solid was washed with hot ethanol to obtain 10.3 g of the desired product.
  • compositions (mixtureA) composed of the following six compounds were prepared. ⁇ The respective concentrations are 30.2010, 10 and 20.10 wt% in order from the top.
  • the phase transition temperature of this composition A was Cr4SC65SA79N90ISO.
  • Example 2 The compound of the present invention (50 wt%) obtained in Example 1 was mixed with the above (m i X t urea
  • a ferroelectric liquid crystal composition consisting of (45 wt. And optically active compound (Ch ra 1.A) (5 wt.%) was prepared. It was as follows.
  • Example 2 Each of the compositions of Example 2 and Comparative Example 1 was sealed in a cell having a thickness of 2 m, and the response time of each was measured. The response time at each measurement temperature was as follows. C These data are shown in FIG.
  • liquid crystal compound which can be used as a basic substance of a ferroelectric liquid crystal composition, has a low viscosity and exhibits a liquid crystal phase and has a low temperature range, and a ferroelectric liquid crystal composition containing this compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

L'invention a trait à des composés de cristaux liquides utiles en tant que substance de base de compositions de cristaux liquides ferro-électriques, qui présentent une viscosité faible, et une phase de cristaux liquides dans une zone à basse température, et à des compositions de cristaux liquides ferro-électriques qui les contiennent. Ces composés sont des 2-(4-alkylphényl)-5-alkylthiadiazoles représentés par la formule générale (1), dans laquelle Ra est un C5-C15 alkyle; et Rb est un C5-C15 alkyle.
PCT/JP1997/003896 1996-11-01 1997-10-27 2-(4-alkylphenyl)-5-alkylthiadiazoles Ceased WO1998020004A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47245/97A AU4724597A (en) 1996-11-01 1997-10-27 2-(4-alkylphenyl)-5-alkylthiadiazoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/307279 1996-11-01
JP30727996 1996-11-01

Publications (1)

Publication Number Publication Date
WO1998020004A1 true WO1998020004A1 (fr) 1998-05-14

Family

ID=17967223

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/003896 Ceased WO1998020004A1 (fr) 1996-11-01 1997-10-27 2-(4-alkylphenyl)-5-alkylthiadiazoles

Country Status (2)

Country Link
AU (1) AU4724597A (fr)
WO (1) WO1998020004A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003027061A (ja) * 2001-07-12 2003-01-29 Mitsui Chemicals Inc 液晶組成物および液晶素子

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH021482A (ja) * 1988-02-25 1990-01-05 Toshiba Corp ヘテロ環化合物およびこれを含有する液晶材料を用いた液晶素子
EP0418922A2 (fr) * 1989-09-22 1991-03-27 Canon Kabushiki Kaisha Composé mésomorphe, composition de cristaux liquides contenant ledit composé et dispositif à cristaux liquides utilisant ledit composé
JPH0428787A (ja) * 1990-05-23 1992-01-31 Canon Inc 液晶組成物およびこれを含む液晶素子

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH021482A (ja) * 1988-02-25 1990-01-05 Toshiba Corp ヘテロ環化合物およびこれを含有する液晶材料を用いた液晶素子
EP0418922A2 (fr) * 1989-09-22 1991-03-27 Canon Kabushiki Kaisha Composé mésomorphe, composition de cristaux liquides contenant ledit composé et dispositif à cristaux liquides utilisant ledit composé
JPH0428787A (ja) * 1990-05-23 1992-01-31 Canon Inc 液晶組成物およびこれを含む液晶素子

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003027061A (ja) * 2001-07-12 2003-01-29 Mitsui Chemicals Inc 液晶組成物および液晶素子

Also Published As

Publication number Publication date
AU4724597A (en) 1998-05-29

Similar Documents

Publication Publication Date Title
EP0667385B1 (fr) Composé mésomorphe, composition liquido-cristallique le contenant, dispositif liquido-cristallique utilisant cette composition et appareil indicateur
US5116530A (en) Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same
EP0415256B1 (fr) Composé mésomorphe, composition de cristaux liquides contenant ledit composé et dispositif à cristaux liquides utilisant ledit composé
US5462694A (en) Mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method
EP0498277B1 (fr) Benzthiazoles optiquement actifs, composition de cristaux liquides, appareil pour affichage et méthode d'affichage
US5268123A (en) Liquid crystal composition, liquid crystal device, display apparatus and display method
EP0476567B1 (fr) Composé mésomorphe, composition de cristaux liquides, dispositif à cristaux liquides, appareil de visualisation et méthode de visualisation
EP0622359B1 (fr) Composé de guinoxaline, composition liquide cristalline le contenant, dispositif d'affichage l'utilisant
US5830386A (en) Optically active compound, liquid crystal composition, device, display apparatus and display method
EP0500072B1 (fr) Composition liquide cristalline, dispositif à cristal liquide, appareil et méthode d'affichage
EP0467260B1 (fr) Composé mésomorphe et composition liquide cristalline le contenant, utilisation dans un dispositif à cristaux liquides et dispositif d'affichage
JP3308626B2 (ja) 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法、および表示装置
US5217644A (en) Mesomorphic compound, liquid crystal composition containing same, liquid crystal device using same and display apparatus
US5238601A (en) Ferroelectric chiral smectic liquid crystal composition and liquid crystal device using same
WO1998020004A1 (fr) 2-(4-alkylphenyl)-5-alkylthiadiazoles
US5318720A (en) Liquid crystal composition, liquid crystal device, display apparatus and display method
EP0461620B1 (fr) Composé mésomorphe, composition cristal liquide, dispositif, dispositif indicateur et méthode d'affichage
US5281362A (en) Optically active compound, liquid crystal composition, liquid crystal device, display apparatus and display method
US5424004A (en) Chiral smectic liquid crystal composition, liquid crystal device, display apparatus and display method
US5624600A (en) Optically active compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method
EP0418922A2 (fr) Composé mésomorphe, composition de cristaux liquides contenant ledit composé et dispositif à cristaux liquides utilisant ledit composé
EP0439170A2 (fr) Composé mésomorphe, composition liquide cristalline le contenant, dispositif et système d'affichage l'utilisant
EP0460624A2 (fr) Composition liquide cristalline, dispositif à cristal liquide, dispositif d'affichage et procédé d'affichage
JP4151087B2 (ja) スルフェニルチアジアゾール誘導体およびチアジアゾールチオエステル誘導体
JPH01121244A (ja) 光学活性な液晶性化合物、それを含有する液晶組成物およびそれを使用した液晶素子

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AU BA BB BG BR CA CN CU CZ EE GE HU ID IL IS JP KR LC LK LR LT LV MG MK MN MX NO NZ PL RO SG SI SK SL TR TT UA US UZ VN YU AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 09284014

Country of ref document: US

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA