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
  • C09K19/06—Non-steroidal liquid crystal compounds
• • 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
• • 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
  • C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
• • 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
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
• • 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
  • G02F1/139—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 based on orientation effects in which the liquid crystal remains transparent

Definitions

• the present invention relates to a liquid crystal composition, and more particularly to a liquid crystal composition having suitable optical anisotropy, suitable dielectric anisotropy, high clearing point, and good UV stability, and a liquid crystal composition comprising the same Liquid crystal display device.
• Liquid crystals are mainly used as dielectrics in liquid crystal display elements because the optical properties of such materials can be affected by the applied voltage.
• the liquid crystal display elements are classified into phase change (PC), twisted phase (TN), super twisted phase (STN), electrically controlled birefringence (ECB), and optically compensated bend (OCB) according to the operation mode. ), lateral electric field switching, vertical alignment (VA), polymer stable alignment (PSA) mode, etc.
• the liquid crystal display elements currently used are mainly those of the TN type liquid crystal display elements. However, they have a strong contrast angle dependence defect.
• a so-called VA type liquid crystal display element having a wider viewing angle is known.
• the liquid crystal cell of the VA type liquid crystal display element contains a liquid crystal dielectric layer between two transparent electrodes, wherein the liquid crystal medium generally has a negative dielectric anisotropy value.
• the molecules of the liquid crystal layer In the de-energized state, the molecules of the liquid crystal layer are oriented perpendicular to the surface of the electrode (vertically) or have an orientation of the inclined vertical plane. When a voltage is applied to the electrodes, a vertical orientation of the liquid crystal molecules parallel to the electrode faces occurs.
• an OCB type liquid crystal display element which is based on a birefringence effect and has a liquid crystal layer having a so-called "bending" orientation and generally positive dielectric anisotropy is known. When a voltage is applied, reorientation of the liquid crystal molecules perpendicular to the electrode faces occurs.
• OCB type liquid crystal display elements typically contain one or more birefringent optical retardation films to prevent undesired optical transparency of the box from being bent in the dark state.
• the OCB type liquid crystal display element has a wider viewing angle and a shorter response time than the TN type liquid crystal display element.
• a PSA liquid crystal display element In a state in which a polymerizable liquid crystal composition formed of a liquid crystal composition and a polymerizable compound is disposed between substrates, a PSA liquid crystal display element is applied with a voltage between the substrates to orient the liquid crystal molecules, and is oriented. In the state of being irradiated with ultraviolet rays or the like, the polymerizable compound is polymerized to store the alignment state of the liquid crystal as a cured product.
• the PSA principle is being used in various conventional liquid crystal display elements.
• PSA-VA, PSA-OCB, PS-IPS/FFS-, and PS-TN-display elements are known.
• liquid crystal compositions and polymerizable compounds are suitable for PSA display elements. This is because, for example, tilting or sufficient tilting cannot be adjusted, or because, for example, the so-called "voltage holding ratio" (VHR) is insufficient for TFT display applications.
• VHR voltage holding ratio
• liquid crystal compositions and polymerizable compounds known from the prior art still have some drawbacks when used in PSA display elements. Therefore, not every known polymerizable compound which is soluble in a liquid crystal composition is suitable for a PSA display. Selected liquid crystal composition and group of polymerizable compounds It should have as good electrical properties as possible, in particular, it should have the highest possible VHR.
• a high VHR after irradiation with UV light is particularly required.
• An object of the present invention is to provide a novel material suitable for a PSA liquid crystal display element, particularly a combination of a liquid crystal composition and a polymerizable compound, which are suitable for solving the above problems, and can overcome the above disadvantages when applied to a PSA type liquid crystal display element.
• the combination of the liquid crystal composition and the polymerizable compound provided by the present invention has a large operating temperature range, and also has suitable dielectric anisotropy, suitable optical anisotropy, and high VHR after UV exposure. value.
• the liquid crystal composition of the present invention When used in combination with a polymerizable compound, it has good UV resistance and characteristics of being able to produce a pretilt angle faster than the prior art.
• the technical problem to be solved by the present invention is to provide a liquid crystal composition having suitable optical anisotropy, suitable dielectric anisotropy, high clearing point, good UV stability, and a liquid crystal combination capable of forming a pretilt angle. Things.
• the liquid crystal composition can be applied to a liquid crystal display, and the liquid crystal display has characteristics such as high reliability and normal operation after UV illumination.
• the liquid crystal composition provided by the invention has better ability to form a pretilt angle, enables a polymer-stabilized vertical alignment display element to have a better optical effect, and the liquid crystal composition of the invention has a better VHR after UV illumination. Numerical values, the liquid crystal display device using the liquid composition of the present invention has better stability.
• a liquid crystal composition having negative dielectric anisotropy which comprises:
• R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , R 10 , R 11 and R 13 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms;
• R 6 , R 12 and R 14 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms;
• R 7 and R 8 are the same or different and each independently represents H or an alkyl group having 1 to 10 carbon atoms, wherein one or more of the non-adjacent CH 2 groups may be -O-, -CO-, - a COO-, -OCO-O-, -OCO-substitution in which an oxygen atom is not directly bonded, and wherein one or more H atoms may be substituted by fluorine;
• L 1 represents H or F
• Z 1 and Z 2 are the same or different and each independently represents -CH 2 O-, -OCH 2 -, -O-, -CH 2 CH 2 - or a single bond, and at least one of Z 1 and Z 2 is -CH 2 O-, -OCH 2 - or -O-;
• a and B are the same or different and each independently represents a 1,4-cyclohexylene group or a 1,3-cyclopentylene group, wherein one or more non-adjacent CH 2 groups may be replaced by -O-;
• n and n are the same or different and each independently represents 0, 1, or 2, and n + m ⁇ 2.
• the compound of formula I is preferably one or more compounds of the group consisting of:
• the compound of the formula II is preferably one or more compounds of the group consisting of:
• the compound of the formula III is preferably one or more compounds of the group consisting of:
• the compound of the formula III is especially preferably a compound of III-4, III-5, III-7, III-8, III-9, particularly preferably a compound of III-7, III-8, III-9.
• the compound of the formula IV is preferably one or more compounds of the group consisting of:
• R 7 and R 8 are the same or different and each independently independently has an alkyl group having 1 to 10 carbon atoms, wherein one or more H atoms may be substituted by fluorine;
• L 1 represents H or F
• Z 3 , Z 4 , Z 5 , Z 6 and Z 7 are the same or different and each independently represents —CH 2 O—, —OCH 2 —, —O—, —CH 2 CH 2 — or a single bond;
• p, q, r, s, and t are the same or different, each independently representing 0 or 1, and p+q ⁇ 1.
• the compound of the formula IV-1 is particularly preferably one or more compounds of the group consisting of:
• R 7 and R 8 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms, and particularly preferably a compound of the formula IV-1-c.
• the compound of the formula IV-2 is particularly preferably one or more compounds of the group consisting of:
• R 7 and R 8 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms, and particularly preferably a compound of the formulae IV-2-d and IV-2-c.
• the compound of the formula IV-3 is particularly preferably one or more compounds of the group consisting of:
• R 8 is the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms, and particularly preferably a compound of the formula IV-3-d.
• the compound of the formula IV-4 is particularly preferably one or more compounds of the group consisting of:
• R 7 and R 8 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms.
• the compound of the formula IV-5 is particularly preferably one or more compounds of the group consisting of:
• R 7 and R 8 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms.
• the compound of the formula V-1 is preferably one or more compounds of the group consisting of:
• the compound of the formula V-2 is preferably one or more compounds of the group consisting of:
• the compound of the formula VI is preferably one or more compounds of the group consisting of:
• R 15 and R 16 are the same or different and each independently represents an alkyl group having 1 to 5 carbon atoms.
• the compound of the formula III accounts for 10-30% by weight of the total weight of the liquid crystal composition
• the compound of the formula IV accounts for the total weight of the liquid crystal composition.
• the compound of the formula V-1 and/or the formula V-2 accounts for 12-30% by weight of the total weight of the liquid crystal composition
• the compound of the formula VI-1 accounts for the liquid crystal combination
• the total weight of the object is 3-18%.
• the compound of the formula VI-1 accounts for 5 to 15% by weight based on the total weight of the liquid crystal composition.
• the present invention also provides a mixture comprising the aforementioned liquid crystal composition and one or more of the following formula RM Polymeric liquid crystal compound:
• P 1 and P 2 are the same or different and each independently represents
• L 2 represents H or F.
• the polymerizable compound of the formula RM is preferably one or more compounds of the group consisting of:
• the present invention also provides a liquid crystal display comprising the liquid crystal composition provided by the present invention or a mixture provided by the present invention.
• the present invention adopts the above technical solutions, and the technological progress obtained compared with the prior art includes:
• the liquid crystal composition provided by the invention has suitable optical anisotropy, suitable dielectric anisotropy, high clearing point, wide nematic phase temperature range, good UV stability and ability to form pretilt angle. Strong, suitable for use in liquid crystal display devices, so that the liquid crystal display device has the characteristics of being able to display well under the irradiation of UV light. Moreover, the liquid crystal composition provided by the present invention has a better ability to form a pretilt angle, enables a polymer-stabilized vertical alignment display element to have a better optical effect, and the liquid crystal composition of the present invention has better after UV illumination. The VHR value, the liquid crystal display device using the liquid crystal composition of the present invention has better stability.
• the ratios are all by weight, all temperatures are in degrees Celsius, and the thickness of the test for the response time data is 7 ⁇ m.
• the structural formula is expressed by the code listed in Table 1, and can be expressed as: C(5)PPOn, where n in the code represents the number of C atoms of the right-end alkyl group, for example, n is "3", that is, the alkyl group is -C. 3 H 7 : C(5) in the code represents a cyclopentyl group; P in the code represents a 1,4-phenylene group; and O in the code represents an oxygen substituent.
• VHR Voltage retention after UV lamp exposure for 15 minutes (%)
• the refractive index anisotropy was measured by an Abbe refractometer under a sodium light (589 nm) light source at 20 ° C; the dielectric test box was a TN90 type, and the cell thickness was 7 ⁇ m.
• ⁇ ⁇
• VHR (initial) was tested using TOY06254 liquid crystal physical property evaluation system; test temperature was 60 ° C, test voltage was 5 V, test time was 166.7 ms; VHR (UV) was UV light with intensity of 5.8 mw/cm 2 , 365 nm Irradiation, after 15 min, was tested using the TOY06254 liquid crystal physical property evaluation system; the test temperature was 60 ° C, the test voltage was 5 V, and the test time was 166.7 ms.
• 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 according to a conventional method in the art, such as heating, ultrasonic wave, suspension, etc., in a predetermined ratio.
• the liquid crystal composition M1 of Comparative Example 1 was prepared according to each compound and weight percentage listed in Table 2, 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 M2 of Comparative Example 2 was prepared according to the respective compounds and weight percentages listed in Table 3, 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 N1 of Example 1 was prepared according to each compound and weight percentage listed in Table 4, and was filled between two substrates of the liquid crystal display for performance test.
• the test data are as follows:
• the liquid crystal composition N2 of Example 2 was formulated according to each compound and weight percentage listed in Table 5, and was filled in The performance test is performed between the two substrates of the liquid crystal display.
• the test data is shown in the following table:
• the liquid crystal composition N3 of Example 3 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 is shown in the following table:
• the liquid crystal composition N4 of Example 4 was prepared according to the respective compounds and weight percentages listed in Table 7, 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 N5 of Example 5 was prepared according to each compound and weight percentage listed in Table 8, 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:
• the liquid crystal composition N6 of Example 6 was prepared according to the respective compounds and weight percentages listed in Table 9, 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 provided by the invention has suitable optical anisotropy, suitable dielectric anisotropy, wide nematic phase temperature range, high clearing point, and can be applied to liquid crystal.
• the liquid crystal composition provided by the present invention has better UV stability and has achieved remarkable skill improved.
• the data of the above examples show that the liquid crystal composition provided by the present invention has better ability to form a pretilt angle than the prior art, and the polymer-stabilized vertical alignment display element has better optical effects, and
• the liquid crystal composition of the invention has a better VHR value after UV illumination, and the liquid crystal display device using the liquid crystal composition of the invention has better stability and has achieved very good technical progress.

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• 2014
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