WO2022001866A1 - 一种包含二苯并衍生物的液晶组合物及其液晶显示器件 - Google Patents

一种包含二苯并衍生物的液晶组合物及其液晶显示器件 Download PDF

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WO2022001866A1
WO2022001866A1 PCT/CN2021/102342 CN2021102342W WO2022001866A1 WO 2022001866 A1 WO2022001866 A1 WO 2022001866A1 CN 2021102342 W CN2021102342 W CN 2021102342W WO 2022001866 A1 WO2022001866 A1 WO 2022001866A1
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general formula
liquid crystal
crystal composition
compound
ring
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PCT/CN2021/102342
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French (fr)
Chinese (zh)
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刘云云
姚利芳
徐爽
贺笛
丁文全
徐海彬
杨亚非
潘帝可
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江苏和成显示科技有限公司
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Priority to KR1020227046140A priority Critical patent/KR20230017306A/ko
Priority to JP2022580230A priority patent/JP7498807B2/ja
Publication of WO2022001866A1 publication Critical patent/WO2022001866A1/zh

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    • 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
    • C09K19/44Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL 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
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/13Devices 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
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods

Definitions

  • the present application belongs to the technical field of liquid crystal, and relates to a liquid crystal composition comprising a dibenzo derivative and a liquid crystal display device thereof.
  • the liquid crystal material is a mixture of organic rod-shaped small molecular compounds with both liquid fluidity and crystal anisotropy at a certain temperature.
  • the liquid crystal display device utilizes the optical anisotropy and dielectric anisotropy of the liquid crystal material itself to work, and has been widely used at present.
  • the operation mode of liquid crystal display elements based on liquid crystal molecules is divided into: PC (phase change, phase change), TN (twist nematic, twisted nematic), STN (super twisted nematic, super twisted nematic), DS (dynamic scattering, dynamic scattering) ), FLC (ferroelectric liquid crystal, FLC), GH (guest-host, guest-host), ECB (electrically controlled birefringence, electronically controlled birefringence), OCB (optically compensated bend, optically compensated bending), IPS (in-plane) switching, coplanar transition), VA (vertical alignment, vertical alignment), FFS (fringe field switching, fringe field switching) FPA (field-induced photo-reactive alignment, electric field-induced photoreactive alignment) and other types.
  • contrast In the application of liquid crystal display devices, the impact of contrast on the visual effect is very critical. Generally speaking, the larger the contrast, the clearer and more eye-catching the image, and the brighter and brighter the color; and the smaller the contrast, the whole picture will be gray. High contrast is very helpful for image clarity, detail performance, and grayscale performance. High-contrast products have advantages in black and white contrast, sharpness, and integrity. Contrast also has a great influence on the display effect of dynamic video. Since the light and dark transition in dynamic images is relatively fast, the higher the contrast, the easier it is for human eyes to distinguish such a transition process.
  • d represents the pitch of the liquid crystal cell
  • n e represents the extraordinary refractive index
  • n o is the ordinary refractive index
  • contrast ratio (CR) and brightness (L) are as follows:
  • L 255 is the on-state brightness
  • L 0 is the off-state brightness.
  • significant changes should influence CR of L 0.
  • L 0 has nothing to do with the dielectric properties of the liquid crystal molecules, but is related to the LC Scattering of the liquid crystal material itself; the smaller the LC Scattering, the smaller the L 0 , and the CR will also be significantly improved.
  • Patent application CN107973766A discloses a liquid crystal compound containing the oxyfluorene derivative of cycloalkyl, the structure is as follows:
  • H represents one of cyclopropyl, cyclobutyl, cyclopentyl or 2-tetrahydrofuranyl
  • Z represents single bond, -CH 2 -, -O-, -CH 2 CH 2 - or -CH 2 O
  • X represents a hydrogen atom, a fluorine atom, an alkyl group having 1-7 carbon atoms or an alkoxy group having 1-7 carbon atoms.
  • liquid crystal compound of the oxofluorene derivative having a cycloalkyl group has good compatibility with other liquid crystal compounds, and the low temperature stability is also improved accordingly.
  • the transmittance of liquid crystal compositions containing such compounds needs to be further improved.
  • the purpose of the present application is to provide a device with a larger absolute value of dielectric anisotropy, a larger vertical dielectric, and a larger vertical dielectric under the condition of maintaining a proper clearing point and proper optical anisotropy.
  • the present application provides a liquid crystal composition comprising a dibenzo derivative, the liquid crystal composition comprising:
  • X 1 represents -O-, -S-, -CO-, -CF 2 -, -NH- or -NF-;
  • Y 1 and Y 2 each independently represent -H, halogen, halogenated or unhalogenated alkyl group containing 1-3 carbon atoms, halogenated or unhalogenated alkoxy group containing 1-3 carbon atoms ;
  • Z represents -(CH 2 ) a O- or -(CH 2 ) a S-, wherein a represents an integer from 0 to 7, such as 1, 2, 3, 4, 5, etc.;
  • L N1 and L N2 each independently represent -H, an alkyl group containing 1-3 carbon atoms or a halogen
  • n N1 0, 1, 2 or 3
  • n N2 represents 0 or 1
  • the short straight lines on one or both sides of the group structure represent access bonds, not methyl groups, such as The short straight line on the right, Short straight lines on both sides.
  • the number of carbons in the straight-chain or branched-chain alkyl group containing 1-12 carbon atoms includes, but is not limited to, 2, 4, 6, 8, 10, and the like.
  • halogen includes, but is not limited to, fluorine, chlorine, bromine or iodine, and the like.
  • the present application provides a novel liquid crystal composition, which introduces a negative liquid crystal compound represented by formula I, and cooperates with the compound of formula N, which can maintain a proper clearing point and proper optical anisotropy.
  • the ratio of the absolute value of the absolute value of dielectric anisotropy, a large dielectric vertical, greater vertical dielectric and the dielectric, the larger the value of K ave is preferably low transmittance and longer storage time , so that the liquid crystal display device comprising it has lower threshold voltage, better contrast ratio, shorter response time, better transmittance and better low temperature storage stability.
  • the compound of general formula I of the present application is a structure of oxa five-membered ring or thia five-membered ring. Compared with the five-membered carbocyclic structure, the compound of general formula I is added to the liquid crystal composition, which is more conducive to maintaining proper clearing point and proper optical properties.
  • anisotropy it has a larger absolute value of dielectric anisotropy, a larger vertical dielectric, a larger ratio of the vertical dielectric to the absolute value of the dielectric, a larger Kave value, and better penetration. permeability and longer storage time at low temperature.
  • the present application also surprisingly found that, in the compound of the general formula I, Z is the structure of an alkyleneoxy group or an alkylenethio group.
  • Z represents a straight-chain alkyl group
  • the compound of the general formula I reflects the overall The conjugation effect is stronger, and the absolute value of dielectric anisotropy, vertical dielectric, ratio of vertical dielectric to absolute value of dielectric, Kave value, penetration rate and low temperature storage time are all after the synergistic effect of intramolecular groups.
  • the obvious improvement effect is more conducive to realizing the effects of low threshold voltage, high contrast ratio, short response time, high transmittance and good low temperature storage stability of the present application.
  • the ring and ring represent independently
  • X 1 represents -O-, -S- or -CO-; optionally X 1 represents -O- or -S-.
  • Y 1 and Y 2 each independently represent -H, -F, -Cl, -CN, -CH 3 , -OCH 3 , -CF 3 or -OCF 3 ; alternatively, Y 1 and Y 2 each independently represent -H, -F or -Cl; alternatively, both Y 1 and Y 2 represent -F.
  • the present application can optionally substitute -F on the benzene ring of the dibenzo derivative, which is more conducive to improving the absolute value of dielectric anisotropy, vertical dielectric, vertical dielectric and dielectric properties of the liquid crystal composition compared with other substituents.
  • absolute power ratio, K ave value, penetration, and cryogenic storage time In some embodiments of the present application, X 1 represents -O-, -S- or -CO-, and both Y 1 and Y 2 represent -F. In some embodiments of the present application, a represents an integer from 0 to 3; alternatively, a represents 1 or 2.
  • n 1 and n 2 each independently represent 0 or 1; alternatively, n 1 represents 0, and n 2 represents 0 or 1; alternatively, n 1 and n 2 each independently represent means 0.
  • the liquid crystal composition comprises at least two compounds of formula I.
  • the liquid crystal composition comprises at least one compound of general formula I wherein X 2 is -O- and/or one compound of general formula I wherein X 2 is -S-; optional Typically, the liquid crystal composition comprises at least two compounds of the general formula I wherein X 2 is -O-.
  • at least two compounds of the general formula I where X 2 is -O- can be selected to cooperate with each other to further improve the absolute value of dielectric anisotropy, the vertical dielectric, and the ratio of the vertical dielectric to the absolute value of the dielectric of the liquid crystal composition. , Kave value, penetration rate and low temperature storage time.
  • X 1 when X 2 is -O-, X 1 is -O- or -S-; optionally, when X 2 is -O-, X 1 is -O-. In some embodiments of the present application, when X 2 is -S-, X 1 is -O- or -S-; optionally, when X 2 is -S-, X 1 is -S-.
  • R 1 can be optionally a linear or branched alkyl group containing 1-10 carbon atoms, a linear or branched alkoxy group containing 1-9 carbon atoms, a A straight-chain or branched alkylthio group of 1-9 carbon atoms, or a straight-chain or branched alkenyl group containing 2-10 carbon atoms; R 1 can be further optionally a straight-chain or branched alkenyl group containing 1-8 carbon atoms Chain or branched alkyl, straight or branched alkoxy containing 1-7 carbon atoms, straight or branched alkylthio containing 1-7 carbon atoms, or 2-8 carbon atoms Straight-chain or branched alkenyl of carbon atoms; R 1 can be further optionally a straight-chain or branched alkyl group containing 1-5 carbon atoms, a straight-chain or branched alkyl group containing 1-4 carbon atoms Alkoxy,
  • R x represents -H or a straight chain alkyl group containing 1-6 carbon atoms.
  • the compound of formula I accounts for 0.1%-40% by weight of the liquid crystal composition, such as 0.1%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, etc.; optionally, The compound of formula I accounts for 0.1%-30% by weight of the liquid crystal composition; optionally, the compound of formula I accounts for 0.5%-30% by weight of the liquid crystal composition.
  • the ring and ring represent independently
  • the compound of general formula N is selected from any one or a combination of at least two of the following compounds:
  • R N1 is not alkenyl.
  • the compound of general formula N comprises general formula N-1, general formula N-2, general formula N-3, general formula N-4, general formula N-5, general formula N -6, general formula N-8, general formula N-9, general formula N-10, general formula N-11, general formula N-12, general formula N-13, general formula N-17, general formula N-18 , any one of the compounds of general formula N-19 and general formula N-21 or a combination of at least two; optionally, the compound of general formula N comprises general formula N-2, general formula N-3, general formula N-3 Any one or a combination of at least two of the compounds of formula N-5, general formula N-6, general formula N-11, general formula N-12 and general formula N-13.
  • the compounds of the general formula N with the above-mentioned specific structures can be selected, and these compounds are used in combination with the compounds of the formula I, which can further improve the absolute value of dielectric anisotropy, vertical dielectric, vertical dielectric and absolute value of dielectric of the liquid crystal composition.
  • ratio, Kave value, penetration rate and low temperature storage time can be selected, and these compounds are used in combination with the compounds of the formula I, which can further improve the absolute value of dielectric anisotropy, vertical dielectric, vertical dielectric and absolute value of dielectric of the liquid crystal composition. ratio, Kave value, penetration rate and low temperature storage time.
  • the compound of general formula N comprises at least one compound of general formula N-3 and/or general formula N-6. In some embodiments of the present application, the compound of general formula N comprises at least one compound of general formula N-12, general formula N-13, general formula N-17. In some embodiments of the present application, the compound of general formula N comprises at least one compound of general formula N-3 and/or general formula N-6, and at least one compound of general formula N-12 and/or general formula Compounds of N-13. In some embodiments of the present application, the compound of general formula N comprises at least one compound of general formula N-10 and/or general formula N-11.
  • R N1 and R N2 can each independently be a linear or branched alkyl group containing 1-10 carbon atoms, a linear or branched chain containing 1-9 carbon atoms alkoxy, or straight-chain or branched alkenyl containing 2-10 carbon atoms; R N1 and R N2 are further optionally each independently a straight-chain or branched alkane containing 1-8 carbon atoms group, a straight-chain or branched alkoxy group containing 1-7 carbon atoms, or a straight-chain or branched alkenyl group containing 2-8 carbon atoms; R N1 and R N2 can be independently selected to contain Linear or branched alkyl of 1 to 5 carbon atoms, linear or branched alkoxy of 1 to 4 carbon atoms, or linear or branched alkene of 2 to 5 carbon atoms base.
  • the compound of general formula N accounts for 0.1%-60% by weight of the liquid crystal composition, such as 0.1%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44% , 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, etc.; optionally, the compound of general formula N accounts for 0.1%-50% by weight of the liquid crystal composition; Optionally, the compound of general formula N accounts for 5%-50% by weight of the liquid crystal composition.
  • the liquid crystal composition comprises at least one compound of general formula M:
  • ring ring and ring represent independently in, One or at least two of the -CH 2 - may be replaced by -O-, and one or at least two of the single bonds in the ring may be replaced by a double bond, wherein, At most one of the -Hs may be substituted by halogen;
  • the alkenyl group in the present application can be optionally selected from the groups represented by any one of formula (V1) to formula (V9), and particularly can be selected from formula (V1), formula (V2), formula (V8) or (V9).
  • the groups represented by formula (V1) to formula (V9) are as follows:
  • * represents a carbon atom in the bonded ring structure.
  • the alkenyloxy group in this application can be optionally selected from the groups represented by any one of formula (OV1) to formula (OV9), and particularly can be selected from formula (OV1), formula (OV2), formula (OV8) or (OV9).
  • the groups represented by formula (OV1) to formula (OV9) are as follows:
  • * represents a carbon atom in the bonded ring structure.
  • the compound of general formula M is selected from any one or a combination of at least two of the following compounds:
  • the content of the compound of general formula M must depend on solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drip marks, burn-in, dielectric anisotropy Make appropriate adjustments according to the required performance.
  • R M1 and R M2 can each independently be a straight-chain alkyl group containing 1-10 carbon atoms, a straight-chain alkoxy group containing 1-9 carbon atoms, or A straight-chain alkenyl group containing 2-10 carbon atoms; R M1 and R M2 can be further optionally independently a straight-chain alkyl group containing 1-8 carbon atoms, a straight-chain alkyl group containing 1-7 carbon atoms alkoxy, or straight-chain alkenyl containing 2-8 carbon atoms; R M1 and R M2 can be further optionally independently a straight-chain alkyl group containing 1-5 carbon atoms, containing 1- A straight-chain alkoxy group having 4 carbon atoms, or a straight-chain alkenyl group having 2-5 carbon atoms.
  • R M1 and R M2 may each independently be a straight chain alkenyl group containing 2-8 carbon atoms, and may each independently be a straight chain containing 2-5 carbon atoms alkenyl.
  • either one of R M1 and R M2 is a straight-chain alkenyl group containing 2-5 carbon atoms, and the other is a straight-chain alkenyl group containing 1-5 carbon atoms alkyl.
  • R M1 and R M2 can each independently be a straight-chain alkyl group containing 1-8 carbon atoms, or a straight-chain alkoxy group containing 1-7 carbon atoms; Each can be independently a straight-chain alkyl group containing 1-5 carbon atoms, or a straight-chain alkoxy group containing 1-4 carbon atoms.
  • either one of R M1 and R M2 is a straight-chain alkyl group containing 1-5 carbon atoms, and the other is a straight-chain alkyl group containing 1-5 carbon atoms Alkyl, or a straight-chain alkoxy group containing 1-4 carbon atoms; alternatively, both R M1 and R M2 are each independently a straight-chain alkyl group containing 1-5 carbon atoms.
  • both optional R M1 and R M2 are alkyl; when attention is paid to reducing the volatility of the compound, optional R M1 and R M2 are both alkoxy ; When emphasis is placed on viscosity reduction , at least one of R M1 and R M2 may be an alkenyl group.
  • the compound of general formula M comprises general formula M-1, general formula M-2, general formula M-4, general formula M-6, general formula M-9, general formula M -11, general formula M-12, general formula M-13, general formula M-14, general formula M-15, general formula M-16, general formula M-19, general formula M-21, general formula M-26 , any one or a combination of at least two compounds of the general formula M-28, the general formula M-29 and the general formula M-30.
  • the compound of general formula M comprises at least one compound of general formula M-12 and/or general formula M-16, and the general formula M-12 and/or general formula M At least one of R M1 and R M2 in -16 is an alkenyl group.
  • the compound of general formula M accounts for 0.1%-80% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46% , 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 70%, 72%, 74%, 76%, 78%, etc.;
  • the compound of general formula M accounts for 1%-60% by weight of the liquid crystal composition; optionally, the compound of general formula M accounts for 5%-60% by weight of the liquid crystal composition.
  • the lower limit value and the upper limit value can be selected to be higher;
  • the lower limit value and the upper limit value of the liquid crystal composition can be selected to be high;
  • the lower limit value can be selected to be lower and the upper limit value to be lower.
  • the liquid crystal composition comprises at least one compound of formula A-1 and/or any one or a combination of at least two compounds of formula A-2:
  • R A1 and R A2 each independently represent a straight or branched chain alkyl group containing 1 to 12 carbon atoms,
  • One or at least two of the -Hs may be independently replaced by -F or -Cl;
  • L A11 , L A12 , L A13 , L A21 and L A22 each independently represent -H, an alkyl group containing 1-3 carbon atoms or a halogen;
  • X A1 and X A2 each independently represent halogen, haloalkyl or haloalkoxy containing 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy containing 2 to 5 carbon atoms;
  • the compound of general formula A-1 is selected from any one or a combination of at least two of the following compounds:
  • R A1 represents a straight or branched chain alkyl group containing 1-8 carbon atoms
  • R v and R w independently represent -CH 2 - or -O-; each of L A11 , L A12 , L A11 ′, L A12 ′, L A14 , L A15 and L A16 independently represent -H or -F;
  • L A13 and L A13 ' each independently represent -H or -CH 3 ;
  • the compound of general formula A-1 accounts for 0.1%-50% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12% %, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, etc.
  • the compound of general formula A-2 is selected from any one or a combination of at least two of the following compounds:
  • R A2 represents a straight-chain or branched alkyl group containing 1-8 carbon atoms, and one of the straight-chain or branched alkyl groups containing 1-8 carbon atoms or two non-adjacent ones
  • One or at least two -Hs may be independently substituted by -F or -Cl, respectively;
  • LA21 , LA22 , LA23 , LA24 and LA25 each independently represent -H, -F or -Cl;
  • the compound of general formula A-2 accounts for 0.1%-50% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12% %, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, etc.
  • liquid crystal composition of the present application may also contain usual nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers, light stabilizers, and the like .
  • the dopant accounts for 0%-5% by weight of the liquid crystal composition; optionally, the dopant accounts for 0.01%-1% by weight of the liquid crystal composition.
  • additives such as antioxidants and light stabilizers used in the liquid crystal composition of the present application can be selected from the following substances:
  • n represents a positive integer from 1 to 12, such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and so on.
  • the light stabilizer is selected from the following light stabilizers:
  • the light stabilizer accounts for 0%-5% of the total weight of the liquid crystal composition; optionally, the light stabilizer accounts for 0.01%-1% of the total weight of the liquid crystal composition; more Optionally, the light stabilizer accounts for 0.01%-0.1% of the total weight of the liquid crystal composition.
  • the present application provides a liquid crystal display device comprising the liquid crystal composition of the first aspect.
  • the present application has the following beneficial effects: the liquid crystal composition of the present application has a larger absolute value of dielectric anisotropy and a higher absolute value of dielectric anisotropy under the condition of maintaining a proper clearing point and proper optical anisotropy.
  • the large vertical dielectric, the ratio of the vertical dielectric to the absolute value of the dielectric, the large Kave value, the better transmittance and the longer low temperature storage time make the liquid crystal display device containing it have a relatively high performance.
  • Low threshold voltage, better contrast ratio, shorter response time, better transmittance and better low temperature storage stability have high application value in IPS mode, FFS mode and VA mode liquid crystal display.
  • nCCGF n in the code represents the number of C atoms of the left-terminal alkyl group, for example, n is "3", which means that the alkyl group is -C 3 H 7 ;
  • C in the code represents cyclohexyl, G represents 2-fluoro-1,4-phenylene, and F represents fluorine.
  • Cp obtained by melting point apparatus test.
  • ⁇ n measured using an Abbe refractometer under a sodium lamp (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, 1KHz and VA type test box (cell thickness 6 ⁇ m ).
  • K 11 , K 22 , K 33 are obtained by testing the CV curves of liquid crystal materials using LCR instrument and VA test box and calculated, test conditions: 6 ⁇ m VA test box,
  • nematic liquid crystal medium was placed in a glass bottle, stored at -30°C, and the time recorded when precipitation of crystals was observed.
  • the components used in the following examples can be synthesized by known methods or obtained through commercial channels. These synthesis techniques are conventional, and each of the resulting liquid crystal compounds has been tested to meet electronic compound standards.
  • liquid crystal compositions were prepared according to the proportions of the liquid crystal compositions specified in the following examples.
  • the preparation of the liquid crystal composition is carried out according to conventional methods in the art, such as heating, ultrasonic waves, suspension, etc., by mixing in a prescribed ratio.
  • liquid crystal compositions given in the following examples were prepared and studied.
  • the composition of each liquid crystal composition and the test results of its performance parameters are shown below.
  • the liquid crystal composition of Comparative Example 1 was formulated according to the compounds listed in Table 2 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 1 The liquid crystal composition of Example 1 was prepared according to the compounds listed in Table 3 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • the liquid crystal composition of Comparative Example 2 was prepared according to each compound listed in Table 4 and its weight percentage, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 2 The liquid crystal composition of Example 2 was prepared according to the compounds listed in Table 5 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • the liquid crystal composition of Comparative Example 3 was prepared according to the compounds listed in Table 6 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 3 The liquid crystal composition of Example 3 was prepared according to the compounds listed in Table 7 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 4 The liquid crystal composition of Example 4 was prepared according to the compounds listed in Table 8 and their weight percentages, and was filled between the two substrates of the liquid crystal display for performance testing.
  • Example 5 The liquid crystal composition of Example 5 was prepared according to the compounds listed in Table 9 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 6 The liquid crystal composition of Example 6 was prepared according to the compounds listed in Table 10 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 7 The liquid crystal composition of Example 7 was prepared according to the compounds listed in Table 11 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Example 8 The liquid crystal composition of Example 8 was prepared according to the compounds listed in Table 12 and their weight percentages, and was filled between two substrates of a liquid crystal display for performance testing.
  • Comparative Example 2 It can be known from Comparative Example 2 and Comparative Example 2 that the present application contains the compound of the general formula I (Example 2) of an oxa five-membered ring or a thia five-membered ring structure, compared to the structure of the five-membered carbocyclic ring in the prior art (Example 2). Comparative example 2), can improve the absolute value of dielectric anisotropy, vertical dielectric, vertical dielectric and absolute value of dielectric ratio of liquid crystal composition under the condition of maintaining proper clearing point and proper optical anisotropy , Kave value, penetration rate and low temperature storage time.
  • Comparing Example 3 and Comparative Example 3 it can be seen that the compound of general formula I (Example 3) introduced into the liquid crystal composition, compared with no introduction (Comparative Example 3), can maintain a proper clearing point and proper optical isotropy.
  • anisotropy the absolute value of dielectric anisotropy, vertical dielectric, ratio of vertical dielectric to absolute value of dielectric, Kave value, transmittance and low temperature storage time of the liquid crystal composition are improved.
  • the liquid crystal composition of the present application has larger absolute value of dielectric anisotropy, larger vertical dielectric, larger vertical dielectric under the condition of maintaining appropriate clearing point and appropriate optical anisotropy.
  • the ratio of the absolute value of electricity to dielectric larger Kave value, better transmittance and longer low temperature storage time, make the liquid crystal display device containing it have smaller threshold voltage, better contrast, better Short response time, good transmittance and good low-temperature storage stability have high application value in IPS mode, FFS mode and VA mode liquid crystal displays.

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PCT/CN2021/102342 2020-06-28 2021-06-25 一种包含二苯并衍生物的液晶组合物及其液晶显示器件 WO2022001866A1 (zh)

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