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WO2018192474A1 - Composition de cristaux liquides et son dispositif d'affichage - Google Patents

Composition de cristaux liquides et son dispositif d'affichage Download PDF

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Publication number
WO2018192474A1
WO2018192474A1 PCT/CN2018/083327 CN2018083327W WO2018192474A1 WO 2018192474 A1 WO2018192474 A1 WO 2018192474A1 CN 2018083327 W CN2018083327 W CN 2018083327W WO 2018192474 A1 WO2018192474 A1 WO 2018192474A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
crystal composition
group
formula
carbon atoms
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/CN2018/083327
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English (en)
Chinese (zh)
Inventor
韩文明
徐海彬
徐爽
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.)
Jiangsu Hecheng Display Technology Co Ltd
Original Assignee
Jiangsu Hecheng Display Technology 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
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Application filed by Jiangsu Hecheng Display Technology Co Ltd filed Critical Jiangsu Hecheng Display Technology Co Ltd
Publication of WO2018192474A1 publication Critical patent/WO2018192474A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • 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-)
    • C09K2019/123—Ph-Ph-Ph
    • 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
    • G02F1/13712—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 the liquid crystal having negative dielectric anisotropy

Definitions

  • the present invention relates to the field of liquid crystal materials, and in particular to a liquid crystal composition having negative dielectric anisotropy and a display device 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.
  • the type of display mode it is divided into PC (phase change), TN (twist nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment).
  • PM passive matrix
  • AM active matrix
  • 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 differ from the conventional TN mode or the STN mode in that the former uses a liquid crystal material having a negative dielectric anisotropy.
  • the VA mode has a very dark contrast ratio compared to the conventional TN mode, and the contrast is less dependent on the birefringence of the liquid crystal, the thickness of the liquid crystal layer, and the wavelength of the incident light, and the VA mode is The wide viewing angle also has a good performance.
  • the VA mode can also omit the rubbing process, resulting in an increase in yield.
  • the liquid crystal composition is often required to have a large negative value of negative dielectric anisotropy, and also requires a higher clearing point, a lower threshold voltage, and a faster response time, in addition to Has good low temperature stability.
  • liquid crystal composition which has large optical anisotropy, large absolute value of negative dielectric anisotropy, good low temperature stability, and fast response.
  • a liquid crystal composition having a large absolute value of dielectric anisotropy has a high critical voltage, high power consumption, and a relatively slow response speed. Therefore, in order to meet the increasing demand for applications, there is a need in the art for liquid crystal compounds that continuously improve negative dielectric anisotropy.
  • an object of the present invention is to provide a liquid crystal composition having large optical anisotropy, large absolute value of negative dielectric anisotropy, low temperature stability, and rapid response. Its display device.
  • a liquid crystal composition comprising:
  • R 1 and R 2 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the compound of formula I comprises from 1 to 35 wt% of the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 5 to 30% by weight based on the total weight of the liquid crystal composition.
  • R 2 represents an alkoxy group having 1 to 12 carbon atoms or an alkenyloxy group having 2 to 12 carbon atoms, and the alkane having 1 to 12 carbon atoms
  • One or more non-adjacent -CH 2 - of the oxy group or the alkenyloxy group having 2 to 12 carbon atoms may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the liquid crystal composition comprises at least two of the compounds of Formula I.
  • the compound of formula I is selected from the group consisting of compounds of formula I-a:
  • R 3 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms
  • n an integer of 2-6.
  • the compound of Formula I-a comprises from 1 to 35 wt% of the total weight of the liquid crystal composition.
  • the compound of Formula I is selected from the group consisting of:
  • R 3 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms
  • n an integer of 2-6.
  • the compound of Formula I is selected from the group consisting of the above Formulas I-1 to I-12, and the compound of Formula I occupies the liquid crystal composition
  • the total weight is 1-35 wt%.
  • the compound of Formula I is selected from the group consisting of the above Formulas I-1 to I-12, and the compound of Formula I occupies the liquid crystal composition 5-30% by weight of the total weight.
  • R 4 and R 5 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected;
  • ring Express Said One or more of -CH 2 - may be replaced by -O-
  • One or more H's may be replaced by F;
  • Z 1 represents a single bond, -CH 2 O-, -CF 2 O- or -COO-;
  • n 0 or 1.
  • R 41 and R 51 each independently represent an alkyl group or alkoxy group having 1 to 7 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 7 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the compound of the formula II-1 is selected from the group consisting of:
  • the compound of formula II-2 is selected from the group consisting of:
  • the compound of formula II-3 is selected from the group consisting of:
  • the compound of formula II-4 is selected from the group consisting of:
  • the compound of formula II-5 is selected from the group consisting of:
  • the compound of formula II-6 is selected from the group consisting of:
  • At least one compound of Formula III is further included
  • R 6 and R 7 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected;
  • Z 2 represents a single bond, -CH 2 O-, -CF 2 O- or -COO-;
  • p 0 or 1.
  • the compound of the formula III is selected from the group consisting of the following compounds:
  • R 61 and R 71 each independently represent an alkyl or alkoxy group having 1 to 7 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 7 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the compound of formula III-1 is selected from the group consisting of:
  • the compound of formula III-2 is selected from the group consisting of:
  • the compound of formula III-3 is selected from the group consisting of:
  • the compound of formula III-4 is selected from the group consisting of:
  • a liquid crystal display device comprising the above liquid crystal composition.
  • liquid crystal composition further comprises one or more additives known to those skilled in the art and described in the literature.
  • Stabilizers which can be added, for example, to the mixture according to the invention are mentioned below.
  • the stabilizer is selected from the group consisting of stabilizers as shown below.
  • the stabilizer accounts for 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1 wt% of the total weight of the liquid crystal composition. As a particularly preferred embodiment, the stabilizer accounts for 0.01 to 0.1% by weight based on the total weight of the liquid crystal composition.
  • Another aspect of the present invention also provides a liquid crystal display comprising the liquid crystal composition provided by the present invention.
  • the liquid crystal composition provided by the invention has the characteristics of high absolute value of negative dielectric anisotropy, high optical anisotropy, good low temperature stability and fast response speed, and liquid crystal comprising the liquid crystal composition of the invention.
  • the display can meet the needs of low voltage drive and fast response.
  • the ratios are all by weight, and all temperatures are in degrees Celsius.
  • nCCGF The structural formula is expressed by the code listed in Table 1, and can be expressed as: nCCGF, where n in the code represents the number of C atoms of the left-end alkyl group, for example, n is "3", that is, the alkyl group is -C 3 H 7 ; C in the code represents a cyclohexane group, G represents 2-fluoro-1,4-phenylene, and F represents fluorine.
  • Optical anisotropy was measured using an Abbe refractometer under a sodium light (589 nm) light source at 25 °C.
  • ⁇ ⁇ ⁇ - ⁇ ⁇ , where ⁇ ⁇ is the dielectric constant parallel to the molecular axis, ⁇ ⁇ is the dielectric constant perpendicular to the molecular axis, test conditions: 25 ° C, 1 KHz, test box is TN90 type, box thickness 7 ⁇ m.
  • ⁇ 1 was tested using a TOYO6254 liquid crystal physical property evaluation system; the test temperature was 25 ° C, and the test voltage was 90V.
  • the components used in the following examples can be synthesized by a known method or obtained commercially. These synthetic techniques are conventional, and each of the obtained liquid crystal compounds has been tested to meet the standards of electronic compounds.
  • a liquid crystal composition was prepared in accordance with the ratio of each liquid crystal composition specified in the following examples.
  • the preparation of the liquid crystal composition is carried out in accordance with a conventional method in the art, such as heating, ultrasonication, suspension, or the like in a predetermined ratio.
  • liquid crystal composition given in the following examples was prepared and studied.
  • the composition of each liquid crystal composition and the test results of its performance parameters are shown below.
  • the liquid crystal compositions of Comparative Example 1 were prepared according to the respective compounds and weight percentages listed in Table 2, and were filled in the performance test between the two substrates of the liquid crystal display.
  • the test data are shown in the following table:
  • Example 1 The liquid crystal composition of Example 1 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 as shown in the following table:
  • Example 2 The liquid crystal composition of Example 2 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 are shown in the following table:
  • Example 3 The liquid crystal composition of Example 3 was formulated according to each compound and weight percentage listed in Table 5, and was filled between the two substrates of the liquid crystal display for performance test.
  • the test data are 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 6, 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:
  • Example 5 The liquid crystal composition of Example 5 was prepared according to each compound and weight percentage listed in Table 7, 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:
  • the liquid crystal composition provided by the present invention has the characteristics of high absolute value of negative dielectric anisotropy, high optical anisotropy, good low temperature stability, and fast response speed.
  • the liquid crystal display comprising the liquid crystal composition of the present invention can satisfy the demand of low voltage driving and fast response.
  • liquid crystal composition according to the present invention can be applied to the field of liquid crystals.

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

Abstract

La présente invention concerne une composition de cristaux liquides et son dispositif d'affichage à cristaux liquides comprenant ladite composition de cristaux liquides, ladite composition de cristaux liquides contenant au moins l'un des composés de la formule générale (I). La composition de cristaux liquides présente des caractéristiques telles qu'une valeur absolue élevée d'anisotropie diélectrique négative, une anisotropie optique élevée, une bonne stabilité aux faibles températures, et une vitesse de réponse rapide. Le dispositif d'affichage à cristaux liquides satisfait les exigences d'entraînement à basse tension et de réponse rapide.
PCT/CN2018/083327 2017-04-18 2018-04-17 Composition de cristaux liquides et son dispositif d'affichage Ceased WO2018192474A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201710254496.9 2017-04-18
CN201710254496.9A CN108728117B (zh) 2017-04-18 2017-04-18 一种液晶组合物及其显示器件

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TW (1) TWI662110B (fr)
WO (1) WO2018192474A1 (fr)

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CN109207164B (zh) * 2017-06-30 2021-08-06 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN109575943B (zh) * 2017-09-28 2022-01-07 江苏和成显示科技有限公司 液晶组合物及其液晶显示器件
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TWI662110B (zh) 2019-06-11

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