WO2019062700A1 - 液晶组合物及其液晶显示器件 - Google Patents

液晶组合物及其液晶显示器件 Download PDF

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WO2019062700A1
WO2019062700A1 PCT/CN2018/107280 CN2018107280W WO2019062700A1 WO 2019062700 A1 WO2019062700 A1 WO 2019062700A1 CN 2018107280 W CN2018107280 W CN 2018107280W WO 2019062700 A1 WO2019062700 A1 WO 2019062700A1
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group
liquid crystal
carbon atoms
compound
crystal composition
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PCT/CN2018/107280
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English (en)
French (fr)
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王莉
徐海彬
李鹏飞
贺笛
金睿
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江苏和成显示科技有限公司
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Priority to US16/632,677 priority Critical patent/US11634640B2/en
Publication of WO2019062700A1 publication Critical patent/WO2019062700A1/zh

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    • 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
    • C09K19/3001—Cyclohexane rings
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    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • 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
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    • 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-)
    • C09K2019/122—Ph-Ph
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    • 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
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    • 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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
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    • 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
    • C09K19/3001—Cyclohexane rings
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    • 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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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    • 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
    • C09K19/3001—Cyclohexane rings
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    • C09K2019/3013—Cy-Ph-Cy
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    • 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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
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    • 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
    • C09K19/3001—Cyclohexane rings
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    • 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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • C09K2019/3037—Cy-Cy-C2H4-Ph
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    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C09K2019/3078—Cy-Cy-COO-Ph-Cy

Definitions

  • the present invention relates to the field of liquid crystal display materials, and in particular to liquid crystal compositions and liquid crystal display devices thereof.
  • the classification based on the operation mode of the liquid crystal molecules is: phase change (PC), twisted nematic (TN), super twisted nematic (STN), electronically controlled birefringence. (electrically controlled birefringence, ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (VA), fringe field switching (FFS) , field-induced photo-reactive alignment (FPA) and other modes.
  • the component-based driving methods are classified into a passive matrix (PM) and an active matrix (AM).
  • the PM is classified into a static type, a multiplex type, etc.
  • the AM is classified into a thin film transistor (TFT), a metal insulator metal (MIM), or the like.
  • the classification of TFTs is amorphous silicon and polycrystalline silicon. The latter are classified into a high temperature type and a low temperature type according to the manufacturing steps.
  • the classification based on the light source is a reflection type using natural light, a transmission type using a backlight, and a semi-transmissive type using both natural light and a backlight.
  • the liquid crystal display element contains a liquid crystal composition having a nematic phase.
  • the composition has suitable characteristics. By improving the characteristics of the composition, an AM device having good characteristics can be obtained. The correlation among the characteristics of the two is summarized in Table 1 below. The characteristics of the composition are further described based on commercially available AM elements.
  • the temperature range of the nematic phase is related to the temperature range over which the component can be used.
  • the preferred upper limit temperature of the nematic phase is about 70 ° C or higher, and the preferred lower limit temperature of the nematic phase is about -10 ° C or lower.
  • the viscosity of the composition is related to the response time of the component. In order to display a moving image as a component, it is preferable that the response time is short. Ideally a response time shorter than 1 millisecond. Therefore, it is preferred that the viscosity in the composition is small. More preferably, the viscosity at a low temperature is small.
  • AM components 1 Wide range of nematic phase temperatures Wide temperature range available 2 Low viscosity Short response time 3 Optical anisotropy is appropriate Large contrast 4 Positive or negative dielectric anisotropy Low threshold voltage, low power consumption, large contrast 5 High resistivity Large voltage retention and large contrast 6 UV and heat stable long life 7 Large elastic constant Short response time and large contrast
  • the prior art discloses a liquid crystal composition having low power consumption and fast response, such as the patent document CN102858918A, but there are environmental problems in the prior art (such as the use of chlorine-containing compounds) and short service life (such as poor UV or thermal stability). Low contrast (such as white screen display in daylight), and the inability to balance the dielectric anisotropy, high optical anisotropy, high clearing point, and high contrast ratio on LCD TVs, tablets, etc. And the performance balance problem of good mutual solubility, can not meet all aspects of the indicators at the same time.
  • the liquid crystal composition can make the liquid crystal display device comprising the liquid crystal composition of the present invention have a good display effect, such as relatively large elastic constants K 11 and K 33 , high contrast and the like.
  • Another object of the present invention is to provide a liquid crystal display device comprising the liquid crystal composition.
  • liquid crystal composition comprising:
  • R 1 and R 2 each independently represent -H, -F, a linear or branched alkyl or alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 An alkenyl or alkenyloxy group of -12 carbon atoms, -OR 1 'OR 2 ', wherein one or more of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be replaced by F
  • R 1 ' represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms
  • R 2 ' represents an alkyl group having 1 to 12 carbon atoms or 2 to 12 carbons.
  • R 3 and R 4 each independently represent -H, -F, a linear or branched alkyl or alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 An alkenyl or alkenyloxy group of -12 carbon atoms, -OR 3 'OR 4 ', wherein one or more of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be replaced by F
  • R 3 ' represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group having 2 to 12 carbon atoms
  • R 4 ' represents an alkyl group having 1 to 12 carbon atoms or contains 2 to 12 Alkenyl of one carbon atom;
  • R 5 and R 6 each independently represent -H, -F, a linear or branched alkyl or alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 An alkenyl or alkenyloxy group of -12 carbon atoms;
  • Z 1 , Z 2 , Z 3 and Z 4 each independently represent a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2 - or -CH 2 CH 2 -;
  • L 1 and L 2 each independently represent -H, -F, -Cl, -CN or -NCS;
  • L 3 and L 4 each independently represent -F, -Cl, -CN or -NCS;
  • One or more -CH 2 - may be replaced by -O-, One or more H may be replaced by a halogen;
  • a 0, 1, 2 or 3
  • the Z 1 may be the same or different
  • the ring May be the same or different
  • at least one Z 1 represents a single bond, then at least one ring Express
  • b, c, and d each independently represent 0 or 1.
  • R 1 and R 2 each independently represent a straight or branched alkyl or alkoxy group having from 1 to 10 carbon atoms, and contains from 3 to 6 carbons.
  • the liquid crystal composition comprises at least one liquid crystal compound having a terminal group of -OR 1 'OR 2 ' or -OR 3 'OR 4 '.
  • the compound of Formula I comprises at least one liquid crystal compound having a terminal group of -OR 1 'OR 2 '.
  • the compound of formula I comprises from 1 to 50% by weight of the total weight of the liquid crystal composition
  • the compound of formula II comprises from 1 to 80% by weight of the total weight of the liquid crystal composition
  • the compound of the formula III accounts for from 1 to 85% by weight based on the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 1% to 40% by weight of the total weight of the liquid crystal composition
  • the compound of Formula II comprises from 15% to 80% by weight of the total weight of the liquid crystal composition
  • the compound of the formula III accounts for from 15 to 80% by weight based on the total weight of the liquid crystal composition.
  • the compound of formula I comprises from 1 to 30% by weight of the total weight of the liquid crystal composition
  • the compound of formula II comprises from 20 to 70% by weight of the total weight of the liquid crystal composition
  • the compound of the formula III accounts for 20-75% of the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 1 to 30% by weight of the total weight of the liquid crystal composition
  • the compound of Formula II comprises from 25 to 70% by weight of the total weight of the liquid crystal composition.
  • the compound of the formula III accounts for 25-70% of the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 1 to 30% by weight of the total weight of the liquid crystal composition
  • the compound of Formula II comprises from 25 to 65% by weight based on the total weight of the liquid crystal composition.
  • the compound of the formula III accounts for 25-68% of the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 1 to 30% by weight of the total weight of the liquid crystal composition
  • the compound of Formula II comprises from 25 to 60% by weight of the total weight of the liquid crystal composition
  • the compound of the formula III accounts for 25-65% by weight of the total weight of the liquid crystal composition.
  • the compound of Formula I comprises from 1 to 30% by weight of the total weight of the liquid crystal composition
  • the compound of Formula II comprises from 30% to 60% by weight based on the total weight of the liquid crystal composition.
  • the compound of the formula III accounts for 30-65% by weight of the total weight of the liquid crystal composition.
  • the compound of Formula I is selected from the group consisting of:
  • the compound of formula 1-1 is selected from the group consisting of:
  • R 11 and R 21 each independently represent a linear or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 to 10 carbon atoms.
  • R 1 ' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms
  • R 2 ' represents an alkyl group having 1 to 10 carbon atoms or 2 to 10 carbon atoms. Alkenyl.
  • the compound of formula 1-2 is selected from the group consisting of:
  • R 12 and R 22 each independently represent a straight or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 to 10 carbon atoms.
  • R 1 ' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms
  • R 2 ' represents an alkyl group having 1 to 10 carbon atoms or 2 to 10 carbon atoms. Alkenyl.
  • the compound of formula I-1-1 is selected from the group consisting of:
  • the compound of formula I-1-2 is selected from the group consisting of:
  • the compound of formula I-1-3 is selected from the group consisting of:
  • the compound of formula I-2-1 is selected from the group consisting of the following compounds:
  • the compound of formula I-2-2 is selected from the group consisting of:
  • the compound of formula I-2-3 is selected from the group consisting of:
  • the R 2 ' is preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
  • the compounds of the formula I have a large optical anisotropy and a high clearing point, so that the liquid crystal composition comprising the compound of the formula I has a high contrast and a high clearing point.
  • the compound of Formula II is selected from the group consisting of:
  • R 3 and R 4 each independently represent a straight or branched alkyl or alkoxy group having from 1 to 6 carbon atoms, and a cycloalkyl group having from 3 to 6 carbon atoms.
  • An alkenyl or alkenyloxy group having 2 to 6 carbon atoms, -OR 3 'OR 4 ', wherein one or more of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may Substituted by F, wherein R 3 ' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms, and R 4 ' represents an alkyl group having 1 to 10 carbon atoms or contains An alkenyl group of 2 to 10 carbon atoms.
  • the compound of Formula II comprises at least one liquid crystal compound having a terminal group of -OR 3 'OR 4 '.
  • R 3 ' is preferably an alkylene group having 2 to 10 carbon atoms or an alkenylene group having 2 to 6 carbon atoms, particularly preferably an alkylene group having 2 to 10 carbon atoms. base.
  • R 3 each independently preferably has the following groups:
  • R 4 each independently preferably has a linear or branched alkyl or alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms. Or an alkenyloxy group, wherein R 4 ' is preferably an alkyl group having 2 to 10 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, and particularly preferably an alkyl group having 2 to 10 carbon atoms.
  • R 4 each independently preferably has the following groups:
  • R 3 each independently preferably has a linear or branched alkyl or alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms.
  • R 4 ' is preferably an alkyl group having 2 to 10 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, and particularly preferably an alkyl group having 2 to 10 carbon atoms.
  • R 3 and R 4 each independently preferably have a linear chain of 1 to 6 carbon atoms. Or a branched alkyl or alkoxy group, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or an alkenyloxy group.
  • the compound of Formula III is selected from the group consisting of:
  • R 51 , R 52 , R 53 , R 61 , R 62 and R 63 each independently represent -H, -F, an alkyl or alkoxy group having 1 to 12 carbon atoms, and 2 to 12 carbon atoms.
  • Alkenyl or alkenyloxy Wherein one or more of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be substituted by F;
  • Z 2 , Z 3 and Z 4 each independently represent a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2 - or -CH 2 CH 2 -;
  • 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:
  • R 51 , R 52 , R 53 , R 61 , R 62 and R 63 each independently represent H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl group or alkene having 2 to 7 carbon atoms. Oxygen.
  • the compound of Formula III-1-1 is selected from the group consisting of:
  • the compound of Formula III-1-2 is selected from the group consisting of:
  • the compound of Formula III-1-3 is selected from the group consisting of:
  • the compound of Formulas III-1-4 is selected from the group consisting of:
  • the compound of Formula III-2-1 is selected from the group consisting of:
  • the compound of formula III-2-2 is selected from the group consisting of:
  • the compound of Formula III-2-3 is selected from the group consisting of:
  • the compound of Formula III-2-4 is selected from the group consisting of:
  • the compound of Formula III-2-5 is selected from the group consisting of:
  • the compound of Formula III-3-1 is selected from the group consisting of:
  • the compound of Formula III-3-2 is selected from the group consisting of:
  • the compound of Formula III-3-3 is selected from the group consisting of:
  • the compound of Formula III-3-4 is selected from the group consisting of:
  • the compound of Formula III-3-5 is selected from the group consisting of:
  • the compound of Formula I is preferably selected from the group consisting of I-1-1-11, I-1-1-3, I-1-1-10, I- 1-1-2, I-1-1-4, I-1-1-1, I-1-1-5, I-1-1-9, I-1-1-6, I-1- 1-7, I-2-2-9, I-2-2-10, I-2-2-6, I-2-2-1, I-2-2-7, I-2-1- 9. I-2-1-10, I-2-1-2, I-2-1-6 and I-1-2-10.
  • the compound of Formula II is preferably selected from the group consisting of: II-2, II-3, II-5, II-7, II-4, II-10, II- 11, II-8 and II-12.
  • the compound of Formula III is preferably selected from the group consisting of: III-1-1-6, III-1-1-8, III-1-1-10, III- 1-2-2, III-2-1-2, III-2-1-4, III-2-1-6, III-1-1-15, III-1-3-18, III-1- 1-19, III-1-3-33, III-2-2-5, III-2-2-2, III-2-2-4, III-1-3-4, III-3-1- 5. III-3-1-7, III-3-2-6 and III-2-2-7.
  • liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature.
  • a multicolor dye and/or a chiral dopant may be added in an amount of from 0 to 15% by weight based on the total weight of the liquid crystal composition.
  • the dopant accounts for 0-5% of the total weight of the liquid crystal composition; more preferably, the dopant accounts for 0% of the total weight of the liquid crystal composition. -1%.
  • Stabilizers which can be added, for example, to the composition according to the invention are mentioned below.
  • the stabilizer is selected from the group consisting of stabilizers as shown below.
  • n is a positive integer from 1-20.
  • the stabilizer accounts for 0 to 5% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1 of the total weight of the liquid crystal composition. %; as a particularly preferred embodiment, the stabilizer comprises from 0 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 device comprising the above liquid crystal composition.
  • the liquid crystal composition of the compound of the formula II has, in addition to having a lower viscosity, a faster response speed, a higher clearing point, in particular, a larger optical anisotropy and a higher contrast, so that inclusion
  • the liquid crystal display device of the liquid crystal composition exhibits a good display effect.
  • the liquid crystal composition provided by the invention has high optical anisotropy, and has a relatively high clearing point, appropriate dielectric anisotropy and good low-temperature mutual solubility, and has The relatively large elastic constants K 11 and K 33 , the liquid crystal display device comprising the liquid crystal composition of the invention can have the advantages of fast response, high contrast, large temperature range, etc., thereby having good display effect and large application. range.
  • 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.
  • V10 threshold voltage normally white mode, the relative contrast is 10% of the characteristic voltage
  • 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.
  • K 11 and K 33 were calculated using a LCR meter and an anti-parallel friction box to test the CV curve of the liquid crystal.
  • 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.
  • 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 composition of Comparative 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 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 4, and was filled between two substrates of the liquid crystal display for performance test.
  • the test data are 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 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:
  • Example 3 The liquid crystal composition 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 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 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:
  • Example 5 The liquid crystal composition 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 shown in the following table:
  • Example 6 The liquid crystal composition of Example 6 was prepared according to each compound and weight percentage listed in Table 9, 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 7 The liquid crystal composition of Example 7 was prepared according to each compound and weight percentage listed in Table 10, 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 8 The liquid crystal composition of Example 8 was prepared according to each compound and weight percentage listed in Table 11, and was filled between two substrates of the liquid crystal display for performance test.
  • the test data are shown in the following table:
  • Example 9 The liquid crystal composition of Example 9 was prepared according to each compound and weight percentage listed in Table 12, 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 10 The liquid crystal composition of Example 10 was prepared according to the respective compounds and weight percentages listed in Table 13, 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 11 The liquid crystal composition of Example 11 was prepared according to each compound and weight percentage listed in Table 14, and was filled between two substrates of the liquid crystal display for performance test.
  • the test data are shown in the following table:
  • Example 12 The liquid crystal composition of Example 12 was prepared according to each compound and weight percentage listed in Table 15 and filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is as follows:
  • Example 13 The liquid crystal composition of Example 13 was prepared according to each compound and weight percentage listed in Table 16, and was filled between two substrates of the liquid crystal display for performance test.
  • the test data are shown in the following table:
  • Example 14 The liquid crystal composition of Example 14 was prepared according to each compound and weight percentage listed in Table 17, 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 15 The liquid crystal composition of Example 15 was prepared according to each compound and weight percentage listed in Table 18, 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 16 The liquid crystal composition of Example 16 was prepared according to each compound and weight percentage listed in Table 19, and was filled between two substrates of the liquid crystal display for performance test.
  • the test data are shown in the following table:
  • Example 17 The liquid crystal composition of Example 17 was prepared according to each compound and weight percentage listed in Table 20, 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 of the present invention has high optical anisotropy, high clearing point, appropriate dielectric anisotropy, and good low temperature mutual interaction. At the same time of solubility, it also has relatively large elastic constants K 11 and K 33 , so that the liquid crystal display device comprising the liquid crystal composition of the invention can have the advantages of fast response, high contrast, large temperature range and the like, and thus has good advantages. Display performance and a large range of applications.
  • liquid crystal composition according to the present invention can be applied to the field of liquid crystals.

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Abstract

本发明提供了一种液晶组合物，所述液晶组合物包含：至少一种通式Ⅰ的化合物；至少一种通式Ⅱ的化合物以及至少一种通式Ⅲ的化合物，所述液晶组合物具有较高的光学各向异性，在维持相对高的清亮点、适当的介电各向异性以及较好的低温互溶性的同时，还具有相对大的弹性常数K 11和K 33，本发明还提供了一种包含本发明所述液晶组合物的液晶显示器件，所述显示器件具有响应快、对比度高、温宽范围大等优点，从而具有良好的显示效果以及较大的适用范围。

Description

液晶组合物及其液晶显示器件 技术领域
本发明涉及液晶显示材料领域，具体涉及液晶组合物及其液晶显示器件。
背景技术
液晶显示元件中，基于液晶分子的运作模式的分类为：相变(phase change，PC)、扭转向列(twisted nematic，TN)、超扭转向列(super twisted nematic，STN)、电控双折射(electrically controlled birefringence，ECB)、光学补偿弯曲(optically compensated bend，OCB)、共面切换(in-plane switching，IPS)、垂直配向(vertical alignment，VA)、边缘场切换(fringe field switching，FFS)、电场感应光反应配向(field-induced photo-reactive alignment，FPA)等模式。基于元件的驱动方式的分类为：被动矩阵(passive matrix，PM)与主动矩阵(active matrix，AM)。PM被分类为静态式(static)、多工式(multiplex)等，AM被分类为薄膜电晶体(thin film transistor，TFT)、金属-绝缘体-金属(metal insulator metal，MIM)等。TFT的分类为非晶矽(amorphous silicon)及多晶矽(polycrystal silicon)。后者根据制造步骤而分类为高温型及低温型。基于光源的分类为利用自然光的反射型、利用背光的透过型、以及利用自然光及背光此两者的半透过型。
液晶显示元件含有具有向列相的液晶组合物。该组合物具有适当的特性。借由提高该组合物的特性，可获得具有良好特性的AM元件。将所述两者的特性中的关联归纳于下述表1中。基于市售的AM元件来对组合物的特性进行进一步的说明。向列相的温度范围与元件可使用的温度范围相关联。向列相的较佳上限温度为约70℃以上，而且向列相的较佳下限温度为约-10℃以下。组合物的粘度与元件的响应时间相关联。为了以元件显示动态影像，较佳为响应时间短。理想为短于1毫秒的响应时间。因此，较佳为组合物中的粘度小。更佳为低温下的粘度小。
表1组合物与AM元件的特性
编号 组合物的特性 AM元件的特性
1 向列相的温度范围广 可使用的温度范围广
2 粘度小 响应时间短
3 光学各向异性适当 对比度大
4 正或负的介电各向异性大 阈值电压低，消耗电量小，对比度大
5 电阻率大 电压保持率大，对比度大
6 对紫外线及热稳定 寿命长
7 弹性常数大 响应时间短，对比度大
现有技术公开了具有低功耗、快响应的液晶组合物，如专利文献CN102858918A，但现有技术中存在环保问题(如含氯化合物的使用)、使用寿命短(如UV或热稳定性差)、对比度低(如日光下显示屏幕泛白)，以及无法兼顾在液晶电视、平板电脑等要求适当的介电各向异性、较高的光学各向异性、较高的清亮点、高的对比度，以及良好互溶性的等性能均衡问题，不能同时满足各方面指标。
从液晶材料的制备角度出发，液晶材料的各项性能是互相牵制影响的，某项性能指标的提升可能会使其它性能发生变化。因此，制备各方面性能都合适的液晶材料往往需要创造性劳动。
发明内容
本发明的目的是提供一种液晶组合物，所述液晶组合物具有适当的介电各向异性、较高的清亮点、较高的光学各向异性、良好的低温互溶性、快的响应速度、相对大的弹性常数K 11和K 33、较高的对比度等特性，所述液晶组合物可以使得包含本发明的液晶组合物的液晶显示器件具有良好的显示效果。
本发明的另一目的是提供一种包含所述液晶组合物的液晶显示器件。
为了完成上述发明目的，本发明提供了一种液晶组合物，所述液晶组合物包含：
至少一种通式Ⅰ的化合物
Figure PCTCN2018107280-appb-000001
至少一种通式Ⅱ的化合物
Figure PCTCN2018107280-appb-000002
以及
至少一种通式Ⅲ的化合物
Figure PCTCN2018107280-appb-000003
其中，
R 1和R 2各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基、-OR 1’OR 2’，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R 1’表示含有1-12个碳原子的亚烷基或2-12个碳原子的亚烯基，R 2’表示含有1-12个碳原子的烷基或2-12个碳原子的烯基；
R 3和R 4各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基、-OR 3’OR 4’，其中所述 烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R 3’表示含有1-12个碳原子的亚烷基或含有2-12个碳原子的亚烯基，R 4’表示含有1-12个碳原子的烷基或含有2-12个碳原子的烯基；
R 5和R 6各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基；
Z 1、Z 2、Z 3和Z 4各自独立地表示单键、-COO-、-OCO-、-CH 2O-、-OCH 2-或-CH 2CH 2-；
L 1和L 2各自独立地表示-H、-F、-Cl、-CN或-NCS；
L 3和L 4各自独立地表示-F、-Cl、-CN或-NCS；
环
Figure PCTCN2018107280-appb-000004
表示
Figure PCTCN2018107280-appb-000005
其中，
Figure PCTCN2018107280-appb-000006
中一个或多个-CH 2-可被-O-替代，
Figure PCTCN2018107280-appb-000007
中一个或多个H可以被卤素取代；
环
Figure PCTCN2018107280-appb-000008
环
Figure PCTCN2018107280-appb-000009
环
Figure PCTCN2018107280-appb-000010
和环
Figure PCTCN2018107280-appb-000011
各自独立地表示
Figure PCTCN2018107280-appb-000012
a表示0、1、2或3，当a为2或3时，所述Z 1可以相同或不同，所述环
Figure PCTCN2018107280-appb-000013
可以相同或不同，且当至少一个Z 1表示单键时，则至少一个环
Figure PCTCN2018107280-appb-000014
表示
Figure PCTCN2018107280-appb-000015
b、c、d各自独立地表示0或1。
在本发明的一些实施方案中，优选地，所述R 1和R 2各自独立地表示含有1-10个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-10个碳原子的烯基或烯氧基、-OR 1’OR 2’，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R 1’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 2’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
在本发明的一些实施方案中，所述液晶组合物中至少包含一种端基基团为-OR 1’OR 2’或-OR 3’OR 4’的液晶化合物。
在本发明的一些实施方案中，所述通式Ⅰ的化合物包含至少一种端基基团为-OR 1’OR 2’的液晶化合物。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-50％，所述通式Ⅱ的化合物占所述液晶组合物总重量的1-80％，所述通式Ⅲ的化合物占所述液晶组合物总重量的1-85％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-40％，所述通式Ⅱ的化合物占所述液晶组合物总重量的15-80％，所述通式Ⅲ的化合物占所述液晶组合物总重量的15-80％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-30％，所述通式Ⅱ的化合物占所述液晶组合物总重量的20-70％，所述通式Ⅲ的化合物占所述液晶组合物总重量的20-75％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-30％，所述通式Ⅱ的化合物占所述液晶组合物总重量的25-70％，所述通式Ⅲ的化合物占所述液晶组合物总重量的25-70％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-30％，所述通式Ⅱ的化合物占所述液晶组合物总重量的25-65％，所述通式Ⅲ的化合物占所述液晶组合物总重量的25-68％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-30％，所述通式Ⅱ的化合物占所述液晶组合物总重量的25-60％，所述通式Ⅲ的化合物占所述液晶组合物总重量的25-65％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-30％，所述通式Ⅱ的化合物占所述液晶组合物总重量的30-60％，所述通式Ⅲ的化合物占所述液晶组合物总重量的30-65％。
在本发明的一些实施方案中，所述通式Ⅰ的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000016
以及
Figure PCTCN2018107280-appb-000017
在本发明的一些实施方案中，进一步优选地，所述通式Ⅰ-1的化合物选自如下化合物中组成的组：
Figure PCTCN2018107280-appb-000018
Figure PCTCN2018107280-appb-000019
以及
Figure PCTCN2018107280-appb-000020
其中，
R 11和R 21各自独立地表示含有1-10个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-10个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
R 1’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 2’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
在本发明的一些实施方案中，进一步优选地，所述通式Ⅰ-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000021
Figure PCTCN2018107280-appb-000022
以及
Figure PCTCN2018107280-appb-000023
其中，
R 12和R 22各自独立地表示含有1-10个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-10个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
R 1’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 2’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-1-1的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000024
Figure PCTCN2018107280-appb-000025
Figure PCTCN2018107280-appb-000026
以及
Figure PCTCN2018107280-appb-000027
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-1-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000028
Figure PCTCN2018107280-appb-000029
Figure PCTCN2018107280-appb-000030
以及
Figure PCTCN2018107280-appb-000031
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-1-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000032
Figure PCTCN2018107280-appb-000033
以及
Figure PCTCN2018107280-appb-000034
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-2-1的化合物选自如下化 合物组成的组：
Figure PCTCN2018107280-appb-000035
Figure PCTCN2018107280-appb-000036
以及
Figure PCTCN2018107280-appb-000037
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-2-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000038
Figure PCTCN2018107280-appb-000039
Figure PCTCN2018107280-appb-000040
以及
Figure PCTCN2018107280-appb-000041
在本发明的一些实施方案中，再进一步优选地，所述通式Ⅰ-2-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000042
Figure PCTCN2018107280-appb-000043
Figure PCTCN2018107280-appb-000044
以及
Figure PCTCN2018107280-appb-000045
在本发明的一些实施方案中，所述R 2’优选为含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
所述通式Ⅰ的化合物具有较大的光学各向异性、较高的清亮点，使得包含通式Ⅰ的化合物的液晶组合物具有较高的对比度以及较高的清亮点。
在本发明的一些实施方案中，所述通式Ⅱ的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000046
Figure PCTCN2018107280-appb-000047
Figure PCTCN2018107280-appb-000048
以及
Figure PCTCN2018107280-appb-000049
在本发明的一些实施方案中，R 3和R 4各自独立地表示含有1-6个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-6个碳原子的烯基或烯氧基、-OR 3’OR 4’，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R 3’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 4’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
在本发明的一些实施方案中，所述通式Ⅱ的化合物包含至少一种端基基团为-OR 3’OR 4’的液晶化合物。
在本发明的一些实施方案中，R 3’优选为含有2-10个碳原子的亚烷基或含有2-6个碳原子的亚烯基，特别优选为2-10个碳原子的亚烷基。
在本发明的一些实施方案中，所述通式Ⅱ-1、Ⅱ-2、Ⅱ-3、Ⅱ-4、Ⅱ-5、Ⅱ-6、Ⅱ-7、Ⅱ-8、Ⅱ-9、Ⅱ-10、Ⅱ-11、Ⅱ-12、Ⅱ-13、Ⅱ-14、Ⅱ-15以及Ⅱ-16的化合物中，R 3各自独立地分别优选如下基团：
Figure PCTCN2018107280-appb-000050
Figure PCTCN2018107280-appb-000051
R 4各自独立地分别优选含有1-6个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-6个碳原子的烯基或烯氧基，其中，R 4’优选为含有2-10个碳原子的烷基或含有2-6个碳原子的烯基，特别优选为含有2-10个碳原子的烷基。
在本发明的一些实施方案中，所述通式Ⅱ-1、Ⅱ-2、Ⅱ-3、Ⅱ-4、Ⅱ-5、Ⅱ-6、Ⅱ-7、Ⅱ-8、Ⅱ-9、Ⅱ-10、Ⅱ-11、Ⅱ-12、Ⅱ-13、Ⅱ-14、Ⅱ-15以及Ⅱ-16的化合物中，R 4各自独立地分别优选如下基团：
Figure PCTCN2018107280-appb-000052
Figure PCTCN2018107280-appb-000053
R 3各自独立地分别优选含有1-6个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-6个碳原子的烯基或烯氧基，其中，R 4’优选为含有2-10个碳原子的烷基或含有2-6个碳原子的烯基，特别优选为含有2-10个碳原子的烷基。
在本发明的一些实施方案中，所述通式Ⅱ-1、Ⅱ-2、Ⅱ-3、Ⅱ-4、Ⅱ-5、Ⅱ-6、Ⅱ-7、Ⅱ-8、Ⅱ-9、Ⅱ-10、Ⅱ-11、Ⅱ-12、Ⅱ-13、Ⅱ-14、Ⅱ-15以及Ⅱ-16的化合物中，R 3和R 4各自独立地分别优选含有1-6个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-6个碳原子的烯基或烯氧基。
在本发明的一些实施方案中，所述通式Ⅲ的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000054
Figure PCTCN2018107280-appb-000055
以及
Figure PCTCN2018107280-appb-000056
其中，
R 51、R 52、R 53、R 61、R 62和R 63各自独立地表示-H、-F、含有1-12个碳原子的烷基或烷氧基、含有2-12个碳原子的烯基或烯氧基、
Figure PCTCN2018107280-appb-000057
其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
Z 2、Z 3和Z 4各自独立地表示单键、-COO-、-OCO-、-CH 2O-、-OCH 2-或-CH 2CH 2-；
环
Figure PCTCN2018107280-appb-000058
环
Figure PCTCN2018107280-appb-000059
环
Figure PCTCN2018107280-appb-000060
和环
Figure PCTCN2018107280-appb-000061
各自独立地表示
Figure PCTCN2018107280-appb-000062
在本发明的一些实施方案中，所述通式Ⅲ-1的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000063
Figure PCTCN2018107280-appb-000064
以及
Figure PCTCN2018107280-appb-000065
在本发明的一些实施方案中，所述通式Ⅲ-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000066
Figure PCTCN2018107280-appb-000067
以及
Figure PCTCN2018107280-appb-000068
在本发明的一些实施方案中，所述通式Ⅲ-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000069
Figure PCTCN2018107280-appb-000070
以及
Figure PCTCN2018107280-appb-000071
其中，
R 51、R 52、R 53、R 61、R 62和R 63各自独立地表示H、含有1-7个碳原子的烷基或烷氧基、含有2-7个碳原子的烯基或烯氧基。
在本发明的一些实施方案中，所述通式Ⅲ-1-1的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000072
Figure PCTCN2018107280-appb-000073
以及
Figure PCTCN2018107280-appb-000074
在本发明的一些实施方案中，所述通式Ⅲ-1-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000075
Figure PCTCN2018107280-appb-000076
以及
Figure PCTCN2018107280-appb-000077
在本发明的一些实施方案中，所述通式Ⅲ-1-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000078
Figure PCTCN2018107280-appb-000079
Figure PCTCN2018107280-appb-000080
以及
Figure PCTCN2018107280-appb-000081
在本发明的一些实施方案中，所述通式Ⅲ-1-4的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000082
Figure PCTCN2018107280-appb-000083
Figure PCTCN2018107280-appb-000084
以及
Figure PCTCN2018107280-appb-000085
在本发明的一些实施方案中，所述通式Ⅲ-2-1的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000086
Figure PCTCN2018107280-appb-000087
Figure PCTCN2018107280-appb-000088
以及
Figure PCTCN2018107280-appb-000089
在本发明的一些实施方案中，所述通式Ⅲ-2-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000090
Figure PCTCN2018107280-appb-000091
以及
Figure PCTCN2018107280-appb-000092
在本发明的一些实施方案中，所述通式Ⅲ-2-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000093
Figure PCTCN2018107280-appb-000094
Figure PCTCN2018107280-appb-000095
以及
Figure PCTCN2018107280-appb-000096
在本发明的一些实施方案中，所述通式Ⅲ-2-4的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000097
Figure PCTCN2018107280-appb-000098
以及
Figure PCTCN2018107280-appb-000099
在本发明的一些实施方案中，所述通式Ⅲ-2-5的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000100
Figure PCTCN2018107280-appb-000101
Figure PCTCN2018107280-appb-000102
以及
Figure PCTCN2018107280-appb-000103
在本发明的一些实施方案中，所述通式Ⅲ-3-1的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000104
Figure PCTCN2018107280-appb-000105
Figure PCTCN2018107280-appb-000106
以及
Figure PCTCN2018107280-appb-000107
在本发明的一些实施方案中，所述通式Ⅲ-3-2的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000108
Figure PCTCN2018107280-appb-000109
Figure PCTCN2018107280-appb-000110
以及
Figure PCTCN2018107280-appb-000111
在本发明的一些实施方案中，所述通式Ⅲ-3-3的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000112
Figure PCTCN2018107280-appb-000113
Figure PCTCN2018107280-appb-000114
以及
Figure PCTCN2018107280-appb-000115
在本发明的一些实施方案中，所述通式Ⅲ-3-4的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000116
Figure PCTCN2018107280-appb-000117
Figure PCTCN2018107280-appb-000118
以及
Figure PCTCN2018107280-appb-000119
在本发明的一些实施方案中，所述通式Ⅲ-3-5的化合物选自如下化合物组成的组：
Figure PCTCN2018107280-appb-000120
Figure PCTCN2018107280-appb-000121
以及
Figure PCTCN2018107280-appb-000122
在本发明的一些实施方案中，所述通式I的化合物优选自如下化合物组成的组：Ⅰ-1-1-11、Ⅰ-1-1-3、Ⅰ-1-1-10、Ⅰ-1-1-2、Ⅰ-1-1-4、Ⅰ-1-1-1、Ⅰ-1-1-5、Ⅰ-1-1-9、Ⅰ-1-1-6、Ⅰ-1-1-7、Ⅰ-2-2-9、Ⅰ-2-2-10、Ⅰ-2-2-6、Ⅰ-2-2-11、Ⅰ-2-2-7、Ⅰ-2-1-9、Ⅰ-2-1-10、Ⅰ-2-1-2、Ⅰ-2-1-6和Ⅰ-1-2-10。
在本发明的一些实施方案中，所述通式II的化合物优选自如下化合物组成的组：Ⅱ-2、Ⅱ-3、Ⅱ-5、Ⅱ-7、Ⅱ-4、Ⅱ-10、Ⅱ-11、Ⅱ-8和Ⅱ-12。
在本发明的一些实施方案中，所述通式III的化合物优选自如下化合物组成的组：Ⅲ-1-1-6、Ⅲ-1-1-8、Ⅲ-1-1-10、Ⅲ-1-2-2、Ⅲ-2-1-2、Ⅲ-2-1-4、Ⅲ-2-1-6、Ⅲ-1-1-15、Ⅲ-1-3-18、Ⅲ-1-1-19、Ⅲ-1-3-33、Ⅲ-2-2-5、Ⅲ-2-2-2、Ⅲ-2-2-4、Ⅲ-1-3-4、Ⅲ-3-1-5、Ⅲ-3-1-7、Ⅲ-3-2-6和Ⅲ-2-2-7。
本发明另一方面提供一种液晶组合物，还包含本领域技术人员已知和文献中描述的一种或多种添加剂。例如，可以加入占所述液晶组合物总重量的0-15％的多色染料和/或手性掺杂剂。
如下显示优选加入到根据本发明的组合物中的可能掺杂剂。
Figure PCTCN2018107280-appb-000123
Figure PCTCN2018107280-appb-000124
Figure PCTCN2018107280-appb-000125
以及
Figure PCTCN2018107280-appb-000126
在本发明的一些实施方案中，优选地，所述掺杂剂占所述液晶组合物总重量的0-5％；更优选地，所述掺杂剂占所述液晶组合物总重量的0-1％。
如下提及例如可以加入到根据本发明的组合物中的稳定剂。
Figure PCTCN2018107280-appb-000127
Figure PCTCN2018107280-appb-000128
优选地，所述稳定剂选自如下所示的稳定剂。
Figure PCTCN2018107280-appb-000129
其中，n为1-20的正整数。
在本发明的一些实施方案中，优选地，所述稳定剂占所述液晶组合物总重量的0-5％；更优选地，所述稳定剂占所述液晶组合物总重量的0-1％；作为特别优选方案，所述稳定剂占所述液晶组合物总重量的0-0.1％。
本发明另一方面还提供一种包含上述液晶组合物的液晶显示器件。
本发明所述通式Ⅰ的化合物具有-OR 1’OR 2’基团和\或通式Ⅱ的化合物具有–OR 3’OR 4’基团时，包含所述通式Ⅰ的化合物或所述通式Ⅱ的化合物的液晶组合物除了具有较低的粘度、较快的响应速度、较高的清亮点之外，特别地，还具有较大的光学各向异性、较高的对比度，使得包含所述液晶组合物的液晶显示器件表现出良好的显示效果。
与现有技术相比，本发明提供的液晶组合物具有较高的光学各向异性，在维持相对高的清亮点、适当的介电各向异性以及较好的低温互溶性的同时，还具有相对大的弹性常数K 11和K 33，包含本发明所述液晶组合物的液晶显示器件，可以具有响应快、对比度高、温宽范围大等优点，从而具有良好的显示效果以及较大的适用范围。
具体实施方式
以下将结合具体实施方案来说明本发明。需要说明的是，下面的实施例为本发明的示例，仅用来说明本发明，而不用来限制本发明。在不偏离本发明主旨或范围的情况下，可进行本发明构思内的其他组合和各种改良。
为便于表达，以下各实施例中，液晶组合物的基团结构用表2所列的代码表示：
表2液晶化合物的基团结构代码
Figure PCTCN2018107280-appb-000130
Figure PCTCN2018107280-appb-000131
以如下结构式的化合物为例：
Figure PCTCN2018107280-appb-000132
该结构式如用表1所列代码表示，则可表达为：nCCGF，代码中的n表示左端烷基的C原子数，例如n为“3”，即表示该烷基为-C 3H 7；代码中的C代表环己烷基，G代表2-氟-1,4-亚苯基，F代表氟。
以下实施例中测试项目的简写代号如下：
Cp(℃)            清亮点(向列-各向同性相转变温度)
Δn               光学各向异性(589nm，25℃)
Δε              介电各向异性(1KHz，25℃)
V10               阈值电压(常白模式下，相对对比度为10％的特征电压)
K 11               展曲弹性常数
K 33               弯曲弹性常数
t -40℃            低温储存时间(在-40℃下)
其中，
光学各向异性使用阿贝折光仪在钠光灯(589nm)光源下、25℃测试得到；
Δε＝ε ‖-ε ⊥，其中，ε ‖为平行于分子轴的介电常数，ε ⊥为垂直于分子轴的介电常数，测试条件：25℃、1KHz、测试盒为TN90型，盒厚7μm。
K 11、K 33是使用LCR仪和反平行摩擦盒，测试液晶的C-V曲线计算所得，测试条件：7μm反平行摩擦盒，V＝0.1～20V。
在以下的实施例中所采用的各成分，均可以通过公知的方法进行合成，或者通过商业途径获得。这些合成技术是常规的，所得到各液晶化合物经测试符合电子类化合物标准。
按照以下实施例规定的各液晶组合物的配比，制备液晶组合物。所述液晶组合物的制备是按照本领域的常规方法进行的，如采取加热、超声波、悬浮等方式按照规定比例混合制得。
制备并研究下列实施例中给出的液晶组合物。下面显示了各液晶组合物的组成和其性能参数测试结果。
对比例1
按表3中所列的各化合物及重量百分数配制成对比例1的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表3液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000133
实施例1
按表4中所列的各化合物及重量百分数配制成实施例1的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表4液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000134
Figure PCTCN2018107280-appb-000135
实施例2
按表5中所列的各化合物及重量百分数配制成实施例2的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表5液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000136
Figure PCTCN2018107280-appb-000137
实施例3
按表6中所列的各化合物及重量百分数配制成实施例3的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表6液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000138
实施例4
按表7中所列的各化合物及重量百分数配制成实施例4的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表7液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000139
Figure PCTCN2018107280-appb-000140
实施例5
按表8中所列的各化合物及重量百分数配制成实施例5的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表8液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000141
实施例6
按表9中所列的各化合物及重量百分数配制成实施例6的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表9液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000142
实施例7
按表10中所列的各化合物及重量百分数配制成实施例7的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表10液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000143
Figure PCTCN2018107280-appb-000144
实施例8
按表11中所列的各化合物及重量百分数配制成实施例8的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表11液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000145
实施例9
按表12中所列的各化合物及重量百分数配制成实施例9的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表12液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000146
实施例10
按表13中所列的各化合物及重量百分数配制成实施例10的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表13液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000147
Figure PCTCN2018107280-appb-000148
实施例11
按表14中所列的各化合物及重量百分数配制成实施例11的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表14液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000149
实施例12
按表15中所列的各化合物及重量百分数配制成实施例12的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表15液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000150
实施例13
按表16中所列的各化合物及重量百分数配制成实施例13的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表16液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000151
Figure PCTCN2018107280-appb-000152
实施例14
按表17中所列的各化合物及重量百分数配制成实施例14的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表17液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000153
实施例15
按表18中所列的各化合物及重量百分数配制成实施例15的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表18液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000154
实施例16
按表19中所列的各化合物及重量百分数配制成实施例16的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表19液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000155
Figure PCTCN2018107280-appb-000156
实施例17
按表20中所列的各化合物及重量百分数配制成实施例17的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表20液晶组合物配方及其测试性能
Figure PCTCN2018107280-appb-000157
Figure PCTCN2018107280-appb-000158
通过对比例1和实施例1-17可以看出，本发明所述的液晶组合物具有较高的光学各向异性、较高的清亮点、适当的介电各向异性以及较好的低温互溶性的同时，还具有相对大的弹性常数K 11和K 33，使得包含本发明所述液晶组合物的液晶显示器件，可以具有响应快、对比度高、温宽范围大等优点，从而具有良好的显示效果以及较大的适用范围。
工业实用性
本发明所涉及的液晶组合物可以应用于液晶领域。

Claims (12)

  1. 一种液晶组合物，所述液晶组合物包含：
    至少一种通式Ⅰ的化合物
    Figure PCTCN2018107280-appb-100001
    至少一种通式Ⅱ的化合物
    Figure PCTCN2018107280-appb-100002
    以及
    至少一种通式Ⅲ的化合物
    Figure PCTCN2018107280-appb-100003
    其中，
    R 1和R 2各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基、-OR’ 1OR’ 2，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R’ 1表示含有1-12个碳原子的亚烷基或含有2-12个碳原子的亚烯基，R’ 2表示含有1-12个碳原子的烷基或含有2-12个碳原子的烯基；
    R 3和R 4各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基、-OR’ 3OR’ 4，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代，其中，R’ 3表示含有1-12个碳原子的亚烷基或含有2-12个碳原子的亚烯基，R’ 4表示含有1-12个碳原子的烷基或含有2-12个碳原子的烯基；
    R 5和R 6各自独立地表示-H、-F、含有1-12个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-12个碳原子的烯基或烯氧基；
    Z 1、Z 2、Z 3和Z 4各自独立地表示单键、-COO-、-OCO-、-CH 2O-、-OCH 2-或-CH 2CH 2-；
    L 1和L 2各自独立地表示-H、-F、-Cl、-CN或-NCS；
    L 3和L 4各自独立地表示-F、-Cl、-CN或-NCS；
    环
    Figure PCTCN2018107280-appb-100004
    表示
    Figure PCTCN2018107280-appb-100005
    其中，
    Figure PCTCN2018107280-appb-100006
    中一个或多个-CH 2-可被-O-替代，
    Figure PCTCN2018107280-appb-100007
    中一个或多个H可以被卤素取代；
    环
    Figure PCTCN2018107280-appb-100008
    环
    Figure PCTCN2018107280-appb-100009
    环
    Figure PCTCN2018107280-appb-100010
    和环
    Figure PCTCN2018107280-appb-100011
    各自独立地表示
    Figure PCTCN2018107280-appb-100012
    a表示0、1、2或3，当a为2或3时，所述Z 1可以相同或不同，所述环
    Figure PCTCN2018107280-appb-100013
    可以相同或不同，且当至少一个Z 1表示单键时，则至少一个环
    Figure PCTCN2018107280-appb-100014
    表示
    Figure PCTCN2018107280-appb-100015
    b、c、d各自独立地表示0或1。
  2. 根据权利要求1所述的液晶组合物，其特征在于，所述液晶组合物中至少包含一种端基基团为-OR’ 1OR’ 2或-OR’ 3OR’ 4的液晶化合物。
  3. 根据权利要求1所述的液晶组合物，其特征在于，所述通式Ⅰ的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100016
    以及
    Figure PCTCN2018107280-appb-100017
  4. 根据权利要求3所述的液晶组合物，其特征在于，所述通式Ⅰ-1的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100018
    Figure PCTCN2018107280-appb-100019
    以及
    Figure PCTCN2018107280-appb-100020
    其中，
    R 11和R 21各自独立地表示含有1-10个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-10个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
    R 1’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 2’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
  5. 根据权利要求3所述的液晶组合物，其特征在于，所述通式Ⅰ-2的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100021
    Figure PCTCN2018107280-appb-100022
    以及
    Figure PCTCN2018107280-appb-100023
    其中，
    R 12和R 22各自独立地表示含有1-10个碳原子的直链或支链的烷基或烷氧基、含有3-6个碳原子的环烷基、含有2-10个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
    R 1’表示含有1-10个碳原子的亚烷基或含有2-10个碳原子的亚烯基，R 2’表示含有1-10个碳原子的烷基或含有2-10个碳原子的烯基。
  6. 根据权利要求1所述的液晶组合物，其特征在于，所述通式Ⅱ的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100024
    Figure PCTCN2018107280-appb-100025
    Figure PCTCN2018107280-appb-100026
    以及
    Figure PCTCN2018107280-appb-100027
  7. 根据权利要求6所述的液晶组合物，其特征在于，所述通式Ⅱ的化合物包含至少一种端基基团为-OR’ 3OR’ 4的液晶化合物。
  8. 根据权利要求1所述的液晶组合物，其特征在于，所述通式Ⅲ的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100028
    Figure PCTCN2018107280-appb-100029
    以及
    Figure PCTCN2018107280-appb-100030
    其中，
    R 51、R 52、R 53、R 61、R 62和R 63各自独立地表示-H、-F、含有1-12个碳原子的烷基或烷氧基、含有2-12个碳原子的烯基或烯氧基、
    Figure PCTCN2018107280-appb-100031
    其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个H可以被F取代；
    Z 2、Z 3和Z 4各自独立地表示单键、-COO-、-OCO-、-CH 2O-、-OCH 2-或-CH 2CH 2-；
    环
    Figure PCTCN2018107280-appb-100032
    环
    Figure PCTCN2018107280-appb-100033
    环
    Figure PCTCN2018107280-appb-100034
    和环
    Figure PCTCN2018107280-appb-100035
    各自独立地表示
    Figure PCTCN2018107280-appb-100036
  9. 根据权利要求8所述的液晶组合物，其特征在于，所述通式Ⅲ-1的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100037
    Figure PCTCN2018107280-appb-100038
    以及
    Figure PCTCN2018107280-appb-100039
    其中，
    R 51和R 61各自独立的表示H、含有1-7个碳原子的烷基或烷氧基、含有2-7个碳原子的烯基或烯氧基。
  10. 根据权利要求8所述的液晶组合物，其特征在于，所述通式Ⅲ-2的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100040
    Figure PCTCN2018107280-appb-100041
    以及
    Figure PCTCN2018107280-appb-100042
    其中，
    R 52和R 62各自独立地表示H、含有1-7个碳原子的烷基或烷氧基、含有2-7个碳原子的烯基或烯氧基。
  11. 根据权利要求8所述的液晶组合物，其特征在于，所述通式Ⅲ-3的化合物选自如下化合物组成的组：
    Figure PCTCN2018107280-appb-100043
    Figure PCTCN2018107280-appb-100044
    以及
    Figure PCTCN2018107280-appb-100045
    其中，
    R 53和R 63各自独立地表示H、含有1-7个碳原子的烷基或烷氧基、含有2-7个碳原子的烯基或烯氧基。
  12. 一种包含权利要求1-11中任一项所述的液晶组合物的液晶显示器件。
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