WO2017071575A1 - Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée - Google Patents

Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée Download PDF

Info

Publication number
WO2017071575A1
WO2017071575A1 PCT/CN2016/103328 CN2016103328W WO2017071575A1 WO 2017071575 A1 WO2017071575 A1 WO 2017071575A1 CN 2016103328 W CN2016103328 W CN 2016103328W WO 2017071575 A1 WO2017071575 A1 WO 2017071575A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
compound
dielectric anisotropy
negative dielectric
crystal composition
Prior art date
Application number
PCT/CN2016/103328
Other languages
English (en)
Chinese (zh)
Inventor
韩文明
徐爽
王盼盼
徐海彬
Original Assignee
江苏和成显示科技股份有限公司
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 江苏和成显示科技股份有限公司 filed Critical 江苏和成显示科技股份有限公司
Publication of WO2017071575A1 publication Critical patent/WO2017071575A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • 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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering

Definitions

  • the present invention relates to a liquid crystal compound, particularly a liquid crystal compound having negative dielectric anisotropy, a method for synthesizing the same, and an application thereof.
  • the liquid crystal display element can be used in various household electric appliances, measurement equipment, automobile panels, word processors, computers, printers, televisions, and the like represented by watches and clocks and electronic calculators.
  • PC phase change
  • TN tunnel nematic
  • STN super twisted nematic
  • ECB electrically controlled
  • Birefringence electronically controlled birefringence
  • OCB optical compensated bend
  • IPS in-plane switching
  • VA vertical alignment
  • CSH color super homeotropic
  • the PM is divided into static (static) and multiplex (multiplex) types.
  • the AM is classified into a TFT (thin film transistor), a MIM (metal insulator metal), and the like.
  • the types of TFTs are amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to a manufacturing process.
  • the liquid crystal display element is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmissive type using both natural light and backlight depending on the type of the light source.
  • the IPS mode, the ECB mode, the VA mode, or the CSH mode are different from the conventional TN mode or the STN mode in that the former uses a liquid crystal material having a negative dielectric anisotropy.
  • an AM-driven VA-type display is used in a display element requiring a high-speed and wide viewing angle, and among them, the most desirable one is application to a liquid crystal element such as a television.
  • the liquid crystal material used is required to have a low driving voltage, a high response speed, a wide operating temperature range, a large absolute value of negative dielectric anisotropy, a high phase transition temperature, and good mutual solubility.
  • a highly conjugated molecular structure has a tendency to be inferior in compatibility with other liquid crystal materials, and is difficult to be used as a constituent element of a liquid crystal composition having good electrical characteristics.
  • a liquid crystal compound used as a constituent element of a liquid crystal composition requiring light stability such as a liquid crystal display device of a thin film transistor type is required to have high stability.
  • a liquid crystal display element containing a liquid crystal composition having a large absolute value of dielectric anisotropy can lower the basic voltage value, lower the driving voltage, and further reduce the power consumption.
  • a large number of hydrogen-substituted liquid crystal compounds on a benzene ring have been studied for a long time as a component of a liquid crystal composition having negative dielectric anisotropy which can be used for a liquid crystal display element.
  • the side fluorine-containing negative compounds such as Ref.2 and Ref.3 avoid the disadvantages of the bis-cyano-negative compound, the negative dielectric anisotropy value is too small (Ref. 2 dielectric anisotropy literature). The value is -4.1, and the Ref. 3 dielectric anisotropy literature value is -6.0). Therefore, compounds with large negative dielectric side fluorine species still need to be explored.
  • low temperature stable liquid crystal compound such that the composition containing the liquid crystal compound has large dielectric anisotropy, low threshold voltage, fast response speed, high contrast, good mutual solubility, and good light stability And low temperature stability.
  • Another object of the present invention is to provide a method of synthesizing the above liquid crystal composition.
  • Still another object of the present invention is to provide use of the above liquid crystal compound for preparing a liquid crystal composition and a display containing the same.
  • the present invention provides a compound having a negative dielectric anisotropy, the compound having the structure of Formula I:
  • R 1 and R 2 are the same or different and each independently represents an alkyl group of 1 to 10 carbon atoms;
  • X 1 and X 2 are each different and independently represent -O- or -CH 2 -;
  • R 1 and R 2 are the same or different and each independently represents an alkyl group of 1 to 6 carbon atoms.
  • the Z represents a single bond, -CH 2 O- or -CH 2 CH 2 -.
  • the Z represents a single bond or -CH 2 CH 2 -.
  • the compound of Formula I is selected from the group consisting of one or more of the following Formulae I-A through I-F:
  • the R1 and R2 are the same or different and each independently represents an alkyl group of 1 to 6 carbon atoms.
  • the compound of Formula I is preferably selected from the group consisting of one or more of the following formulae:
  • the R1 and R2 are the same or different and each independently represents an alkyl group of 1 to 6 carbon atoms.
  • the compound of Formula I-A is preferably selected from the group consisting of one or more of the following structures:
  • the compound of Formula I-B is preferably selected from the group consisting of one or more of the following structures:
  • the compound of Formulas I-C is preferably selected from the group consisting of one or more of the following structures:
  • the compound of Formulas I-D is preferably selected from the group consisting of one or more of the following structures:
  • the compound of Formulas I-E is preferably selected from the group consisting of one or more of the following structures:
  • the compound of Formulas I-F is preferably selected from the group consisting of one or more of the following structures:
  • Another aspect of the present invention provides a liquid crystal composition comprising the liquid crystal compound of the formula I of the present invention.
  • the liquid crystal composition further comprises a group consisting of one or more of Formulas II, III, and/or IV:
  • the R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and each independently represents a substituted or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms. a substituted or unsubstituted linear or branched alkenyl or alkenyloxy group of 2 to 10 carbon atoms, wherein one or more -CH 2 - may be substituted by -O-, provided that the oxygen atom is not Directly connected;
  • the m and n are the same or different and each independently represents 0 or 1.
  • Another aspect of the present invention provides a display device comprising the liquid crystal composition of the present invention.
  • Another aspect of the present invention provides an application comprising the liquid crystal composition of the present invention in VA, FFS, IPS, PSVA display modes.
  • the liquid crystal compound of the formula I provided by the present invention and other negative liquid crystal compounds of the prior art Compared with a larger absolute value of dielectric anisotropy, a low viscosity, and a high voltage holding ratio, the composition containing the liquid crystal compound has large dielectric anisotropy, low threshold voltage, and fast response speed. High contrast, good mutual solubility and good light stability and low temperature stability; and the preparation process of the liquid crystal compound of the formula I of the invention, the raw materials are easy to obtain, the synthesis route is simple and easy, and it is suitable for large-scale industrial production.
  • the refractive index anisotropy was measured at 25 ° C under a sodium light (589 nm) light source using an Abbe refractometer; the dielectric test box was a TN90 type, and the cell thickness was 7 ⁇ m.
  • ⁇ ⁇ - ⁇ , where ⁇ is the dielectric constant parallel to the molecular axis, ⁇ is the dielectric constant perpendicular to the molecular axis, test conditions: 25°C, 1KHz, test box is TN90 type, box thickness 7 ⁇ m.
  • VHR (initial) is tested using TOY06254 liquid crystal physical property evaluation system; pulse voltage: 5V 6HZ, test temperature is 60 ° C, test unit period is 166.7 ms;
  • liquid crystal compounds of the general formula I prepared by the following examples were tested for optical anisotropy and clearing points and the extrapolation parameters were determined as follows:
  • the commercial liquid crystal No. TS023 produced by Jiangsu Hecheng Display Technology Co., Ltd. was selected as the precursor, and the liquid crystal compound represented by Formula I was dissolved in the parent liquid crystal (10% by weight) to test the optical anisotropy of the mixture. Clearing point and dielectric anisotropy, and liquid crystal performance data of the liquid crystal compound represented by Formula I was extrapolated according to a linear relationship according to the ratio added in the matrix.
  • the parent liquid crystal (host) is obtained by mixing the following compounds in a ratio of 20%:40%:40%:
  • the compound represented by the following Table 1 can be converted by the compound C and the compound A to obtain other target compounds:
  • liquid crystal properties of the above target compounds are as follows:
  • Example 1 Representative compound data of the formulae I-A, I-B, I-C and I-D are provided in Example 1, by the liquid crystal compounds I-A-9, I-A-11 of Example 1, The data of I-B-9, I-B-10, I-C-19 and I-D-19 can be seen that the liquid crystals contained in the formulae I-A, I-B, I-C and I-D The compounds all have large absolute values of dielectric anisotropy.
  • T -10 ° C indicates the storage stability of the mixture of the compounds I-A-9, I-A-11, I-B-9, V and the parent liquid crystal host in a ratio of 10:90 at -10 °C.
  • the compound of the invention Compared with the prior art compound V, the compound of the invention has a larger absolute value of dielectric anisotropy and higher Voltage retention and stable low temperature stability.
  • Example 3 The liquid crystal composition of Example 3 was prepared according to each compound and weight percentage listed in Table 3, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is shown in the following table:
  • Example 4 The liquid crystal composition of Example 4 was prepared according to each compound and weight percentage listed in Table 4, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is shown in the following table:
  • Example 5 The liquid crystal composition of Example 5 was prepared according to each compound and weight percentage listed in Table 5, and was filled in the performance test between the two substrates of the liquid crystal display. The test data are shown in the following table:
  • the liquid crystal composition has good liquid crystal properties, and the compound of the present invention has achieved very good technical effects.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

La présente invention concerne un composé à cristaux liquides de formule générale I présentant une anisotropie diélectrique négative. Le composé à cristaux liquides présente une grande valeur absolue d'anisotropie diélectrique, un rapport de maintien de tension élevé, une bonne intersolubilité et une bonne photostabilité et une stabilité à basse température ; de plus, le procédé de préparation du composé à cristaux liquides de formule générale I de la présente invention utilise des matières premières facilement disponibles et une voie de synthèse simple et réalisable, et est approprié pour une production industrielle à grande échelle. L'invention concerne en outre une composition de cristaux liquides comprenant ledit composé à cristaux liquides. Ladite composition de cristaux liquides présente de bonnes propriétés de cristaux liquides.
PCT/CN2016/103328 2015-10-28 2016-10-26 Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée WO2017071575A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201510712026.3 2015-10-28
CN201510712026.3A CN106635052A (zh) 2015-10-28 2015-10-28 具有负介电各向异性的液晶化合物及其应用

Publications (1)

Publication Number Publication Date
WO2017071575A1 true WO2017071575A1 (fr) 2017-05-04

Family

ID=58629875

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2016/103328 WO2017071575A1 (fr) 2015-10-28 2016-10-26 Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée

Country Status (3)

Country Link
CN (1) CN106635052A (fr)
TW (1) TWI608085B (fr)
WO (1) WO2017071575A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101519594A (zh) * 2009-04-01 2009-09-02 晶宝液晶有限公司 液晶混合物和含所述液晶混合物的液晶显示器件
WO2010095506A1 (fr) * 2009-02-19 2010-08-26 チッソ株式会社 Composé cristallin liquide tétracyclique ayant du tétrahydropyrane et du 2,2',3,3'-tétrafluorobiphényle, composition cristalline liquide, et élément d'écran à cristaux liquides
CN103666485A (zh) * 2013-12-04 2014-03-26 石家庄诚志永华显示材料有限公司 一种负介电各向异性液晶组合物
WO2015079797A1 (fr) * 2013-11-29 2015-06-04 Jnc株式会社 Composition à cristaux liquides et élément d'affichage à cristaux liquides

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3839213A1 (de) * 1988-11-19 1990-05-23 Merck Patent Gmbh Bis-(difluorphenylen)-derivate
JP4320824B2 (ja) * 1998-06-02 2009-08-26 チッソ株式会社 Δεが負の値を有するアルケニル化合物、液晶組成物および液晶表示素子
DE19927627B4 (de) * 1998-06-30 2008-01-31 Merck Patent Gmbh Flüssigkristallines Medium
JP4547742B2 (ja) * 1999-10-13 2010-09-22 チッソ株式会社 液晶組成物および液晶表示素子
WO2014094965A2 (fr) * 2012-12-18 2014-06-26 Merck Patent Gmbh Émetteur comprenant un système cyclique condensé
CN106278812B (zh) * 2015-06-24 2019-03-19 江苏和成显示科技有限公司 一种具有负介电各向异性的液晶化合物及其组合物和其应用
CN106324883B (zh) * 2015-07-03 2019-04-23 北京大学 紫外光-加热分步聚合制备胆甾相液晶功能薄膜的方法
CN106338854B (zh) * 2015-07-07 2019-04-23 北京大学 加热-紫外光分步聚合制备胆甾相液晶功能薄膜的方法
CN106336875B (zh) * 2015-07-07 2018-10-02 北京大学 一种反式聚合物分散液晶薄膜的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010095506A1 (fr) * 2009-02-19 2010-08-26 チッソ株式会社 Composé cristallin liquide tétracyclique ayant du tétrahydropyrane et du 2,2',3,3'-tétrafluorobiphényle, composition cristalline liquide, et élément d'écran à cristaux liquides
CN101519594A (zh) * 2009-04-01 2009-09-02 晶宝液晶有限公司 液晶混合物和含所述液晶混合物的液晶显示器件
WO2015079797A1 (fr) * 2013-11-29 2015-06-04 Jnc株式会社 Composition à cristaux liquides et élément d'affichage à cristaux liquides
CN103666485A (zh) * 2013-12-04 2014-03-26 石家庄诚志永华显示材料有限公司 一种负介电各向异性液晶组合物

Also Published As

Publication number Publication date
CN106635052A (zh) 2017-05-10
TWI608085B (zh) 2017-12-11
TW201716553A (zh) 2017-05-16

Similar Documents

Publication Publication Date Title
TWI662110B (zh) Liquid crystal composition and display device thereof
TWI711690B (zh) 具有負介電各向異性的液晶化合物及其應用
KR102190145B1 (ko) 액정조성물 및 액정표시장치
CN106318403B (zh) 具有负介电各向异性的液晶化合物及其合成方法与应用
TWI683892B (zh) 一種液晶組合物及其顯示器件
TWI759641B (zh) 液晶組合物及其顯示器件
TWI711691B (zh) 液晶組合物及其顯示器件
JP2004307810A (ja) 超高速応答特性を有する液晶組成物及びこれを利用した液晶表示装置
WO2018107911A1 (fr) Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée
CN112538357B (zh) 液晶组合物及其液晶显示器件
CN111117655B (zh) 液晶组合物及其显示器件
TWI762826B (zh) 液晶組合物及其顯示器件
WO2017071575A1 (fr) Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée
CN108659859B (zh) 具有正介电各向异性的液晶组合物及其显示器件
CN106635051B (zh) 具有负介电各向异性的液晶化合物及其应用
TWI761716B (zh) 液晶組合物及其顯示器件
CN112048319B (zh) 液晶组合物及其显示器件
CN112048320B (zh) 液晶组合物及其显示器件
CN112048314B (zh) 液晶组合物及其显示器件
CN111117652B (zh) 液晶组合物及其显示器件
CN111117648B (zh) 液晶组合物及其显示器件
CN108239538B (zh) 一种介电各向异性为负的液晶组合物及其应用
JP2010083938A (ja) 液晶組成物、及び液晶表示素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16859010

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16859010

Country of ref document: EP

Kind code of ref document: A1