WO2018212059A1 - Composition de cristaux liquides et élément d'affichage à cristaux liquides utilisant ladite composition - Google Patents

Composition de cristaux liquides et élément d'affichage à cristaux liquides utilisant ladite composition Download PDF

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WO2018212059A1
WO2018212059A1 PCT/JP2018/018075 JP2018018075W WO2018212059A1 WO 2018212059 A1 WO2018212059 A1 WO 2018212059A1 JP 2018018075 W JP2018018075 W JP 2018018075W WO 2018212059 A1 WO2018212059 A1 WO 2018212059A1
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group
general formula
liquid crystal
carbon atoms
crystal composition
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淳子 山本
原　智章
須藤　豪
松崎　進
豊 門本
青木　良夫
礼貴 細野
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Dic株式会社
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    • 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
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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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
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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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
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    • 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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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    • 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
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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    • 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
    • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
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    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • 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

Definitions

  • the present invention relates to a liquid crystal composition useful as an electro-optical liquid crystal display material.
  • Liquid crystal display elements are used in various measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, etc., including clocks and calculators.
  • Typical examples of liquid crystal display systems include TN (twisted nematic) type, STN (super twisted nematic) type, and VA (vertucallyucaligned) type characterized by vertical alignment using TFT (thin film transistor: transistor).
  • IPS in-plane switching
  • FFS far field switching
  • IPS type, ECB type (Electrically Controlled Birefringence), VA type, CSH (color super homeotropic) type, etc. use a liquid crystal material having a negative dielectric anisotropy ( ⁇ ).
  • ⁇ dielectric anisotropy
  • a liquid crystal composition having a positive ⁇ is used in a horizontal alignment type display such as a TN type, STN type, or IPS type.
  • driving method in which a liquid crystal composition having a positive ⁇ is vertically aligned when no voltage is applied and an IPS type / FFS type electric field is applied to display. All these driving methods require low voltage driving, high-speed response, and a wide operating temperature range.
  • the absolute value of ⁇ is large, the viscosity ( ⁇ ) is small, and a high nematic phase-isotropic liquid phase transition temperature (T ni ) is required.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • ⁇ n ⁇ d which is the product of refractive index anisotropy ( ⁇ n) and cell gap (d)
  • ⁇ n refractive index anisotropy
  • d cell gap
  • a liquid crystal composition having a small ⁇ 1 is required.
  • the liquid crystal composition is generally composed of several to several tens of compounds.
  • the liquid crystal compositions used for liquid crystal display elements are required to be stable against external stimuli such as moisture, air, heat, and light. If the stability against external stimuli is impaired, display defects such as image sticking and display unevenness occur in the liquid crystal display element. In order to suppress display defects such as image sticking and display unevenness, it is generally considered that a high voltage holding ratio (VHR) is essential. For this reason, for example, an antioxidant, an ultraviolet absorber, or light It is known to use a liquid crystal composition in which a stabilizer and a specific compound are combined (Patent Document 1 and Patent Document 2). This stability to external stimuli is regarded as important in every application, and further development of a liquid crystal composition capable of realizing a high VHR has been demanded.
  • VHR voltage holding ratio
  • ⁇ is sufficiently small, ⁇ 1 is sufficiently small, and an elastic constant (K 33 ) is large without reducing ⁇ n and T ni.
  • K 33 an elastic constant
  • the problem to be solved by the present invention is to provide a liquid crystal composition that is stable against heat and light and can maintain a high voltage holding ratio, and further, there is no display defect such as image sticking or display unevenness by using this composition.
  • An object of the present invention is to provide a liquid crystal display element that is suppressed and has excellent display quality.
  • the present inventor has studied various liquid crystal compounds and various chemical substances, and found that the above problems can be solved by using a specific compound, and has completed the present invention. That is, the present invention relates to the general formula (I)
  • R I11 , R I12 , R I13 , R I14 , R I15 , R I21 , R I22 , R I23 , R I24 and R I25 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, chlorine Atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, isocyano group, amino group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano Group or an alkyl group having 1 to 20 carbon atoms, and one or more of —CH 2 — present in the alkyl group is each independently —O—, —S—, —CO—, — CO—O—, —O—CO—, —CO—S—, —S—CO
  • R II1 represents an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, — Optionally substituted by C ⁇ C—, —O—, —CO—, —COO— or —OCO—
  • a II1 and A II2 each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - is -O
  • Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group naphthalene-2,6-diyl group or One —CH ⁇ present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH ⁇ may be replaced by —N ⁇ .
  • the group (a), the group (b) and the group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom, Z II1 represents a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—.
  • the atom may be substituted with a fluorine atom
  • m II1 each represents 1, 2, 3 or 4, if m II1 is representative of the 2, 3 or 4,
  • a II1 and Z II1 there is a plurality may be the same or different.
  • the liquid crystal composition of the present invention is stable against heat and light and can maintain a high voltage holding ratio, display defects such as image sticking and display unevenness are not caused or suppressed by using this liquid crystal display element. Thus, a liquid crystal display element having excellent display quality can be obtained.
  • the liquid crystal composition in the present invention contains one or more compounds represented by the general formula (I).
  • R I11 , R I12 , R I13 , R I14 , R I15 , R I21 , R I22 , R I23 , R I24 and R I25 are hydrogen atoms from the viewpoint of compatibility with the liquid crystal composition.
  • the alkyl group or alkenyl group is preferably linear or branched, and is preferably linear.
  • a fluorine atom, a hydrogen atom, or a linear alkyl group having 1 to 5 carbon atoms is particularly preferable.
  • one to eight of R I11 , R I12 , R I13 , R I14 , R I15 , R I21 , R I22 , R I23 , R I24 and R I25 are hydroxyl groups.
  • 1 to 6 are hydroxyl groups, preferably 1 to 4 are hydroxyl groups, preferably 1 to 2 are hydroxyl groups, and particularly preferably 2 are hydroxyl groups.
  • one or more groups represent an alkyl group having 4 to 20 carbon atoms.
  • the alkyl group is preferably linear or branched, and is preferably linear.
  • the alkyl group preferably has 4 to 15 carbon atoms, preferably 4 to 10 carbon atoms, and preferably 4 to 8 carbon atoms.
  • the compounds represented by general formula (I) are specifically compounds represented by general formula (I-1) to general formula (I-7) from the viewpoint of ease of synthesis and ability to prevent photodegradation. It is preferable that
  • n in C n H (2n + 1) represents an integer of 1 to 8.
  • the compounds represented by the general formula (I) are specifically represented by the general formulas (I-8) to (I-10) from the viewpoint of ease of synthesis and compatibility with the liquid crystal composition. It is preferable that it is a compound represented by these.
  • the composition containing one or more compounds represented by the general formula (I) preferably has a liquid crystal phase at room temperature.
  • the compound represented by the general formula (I) preferably contains 0.001% by mass or more, preferably 0.005% by mass or more, as a lower limit with respect to the total mass of the composition. It is preferably contained in an amount of 01% by mass or more, preferably 0.02% by mass or more, preferably 0.03% by mass or more, preferably 0.05% by mass or more, and 0.07% by mass. %, Preferably 0.1% by weight or more, preferably 0.15% by weight or more, preferably 0.2% by weight or more, preferably 0.25% by weight or more.
  • the content is preferably 0.01 to 5% by mass, preferably 0.01 to 0.3% by mass, more preferably 0.02 to 0.3% by mass, Particularly preferred is 0.05 to 0.25% by mass. More specifically, when emphasizing the suppression of precipitation at low temperatures, the content is preferably 0.01 to 0.1% by mass.
  • composition containing the compound represented by the general formula (I) may contain a compound having a liquid crystal phase in addition to the compound represented by the general formula (I), or a compound having no liquid crystal phase. It may contain.
  • the liquid crystal composition of the present invention contains one or more compounds represented by the general formula (II).
  • R II1 represents an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, — Optionally substituted by C ⁇ C—, —O—, —CO—, —COO— or —OCO—
  • a II1 and A II2 each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - is -O
  • Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group naphthalene-2,6-diyl group or One —CH ⁇ present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH ⁇ may be replaced by —N ⁇ .
  • the group (a), the group (b) and the group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom, Z II1 represents a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—.
  • the atom may be substituted with a fluorine atom
  • m II1 each represents 1, 2, 3 or 4, if m II1 is representative of the 2, 3 or 4,
  • a II1 and Z II1 there is a plurality may be the same or different.
  • the compound represented by the general formula (II) is a so-called p-type liquid crystal compound having a positive dielectric anisotropy, and examples thereof include compounds represented by the following general formula (J).
  • the compound represented by the general formula (II) contains one or more compounds represented by the general formula (J). These compounds correspond to dielectrically positive compounds ( ⁇ is greater than 2).
  • R J1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, — Optionally substituted by C ⁇ C—, —O—, —CO—, —COO— or —OCO—, n J1 represents 0, 1, 2, 3 or 4;
  • a J1 , A J2 and A J3 are each independently (A) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O-.)
  • the group (a), the group (b) and the group (c) are each independently selected from the group consisting of cyano group, fluorine atom, chlorine atom, methyl group, trifluoromethyl group or trifluoro May be substituted with a methoxy group
  • Z J1 and Z J2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, Represents —COO—, —OCO— or —C ⁇ C—
  • n J1 is 2, 3 or 4 and a plurality of A J2 are present, they may be the same or different, and n J1 is 2, 3 or 4 and a plurality of Z J1 is present.
  • X J1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group.
  • R J1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or alkenyloxy having 2 to 8 carbon atoms.
  • a group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable.
  • An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.
  • R J1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane
  • a straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dot in each formula represents the carbon atom in the ring structure to which the alkenyl group is bonded.)
  • a J1 , A J2 and A J3 are preferably aromatic when it is required to independently increase ⁇ n, and are preferably aliphatic to improve the response speed.
  • Z J1 and Z J2 each independently preferably represent —CH 2 O—, —OCH 2 —, —CF 2 O—, —CH 2 CH 2 —, —CF 2 CF 2 — or a single bond, OCH 2 —, —CF 2 O—, —CH 2 CH 2 — or a single bond is more preferred, and —OCH 2 —, —CF 2 O— or a single bond is particularly preferred.
  • X J1 is preferably a fluorine atom or a trifluoromethoxy group, and more preferably a fluorine atom.
  • n J1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of ⁇ , and preferably 1 or 2 when emphasizing Tni .
  • the types of compounds that can be combined are used in combination according to desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the content of the compound represented by the general formula (J) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the general formula (J) with respect to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferable content is, for example, 95%, 85%, 75%, 65%, and 55% with respect to the total amount of the composition of the present invention. Yes, 45%, 35%, 25%.
  • the composition of the present invention keeps the viscosity low and a composition having a high response speed is required, it is preferable to lower the lower limit and lower the upper limit. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, it is preferable to lower the lower limit and lower the upper limit. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the upper limit value while increasing the lower limit value.
  • R J1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.
  • composition of the present invention preferably contains one or more compounds represented by the general formula (M). These compounds correspond to dielectrically positive compounds ( ⁇ is greater than 2).
  • R M1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, — Optionally substituted by C ⁇ C—, —O—, —CO—, —COO— or —OCO—, n M1 represents 0, 1, 2, 3 or 4;
  • a M1 and A M2 are each independently (A) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O- or -S- And (b) a 1,4-phenylene group (one —CH ⁇ present in this group or two or more non-adjacent —CH ⁇ may be replaced by —N ⁇ ).
  • a hydrogen atom on the group (a) and the group (b) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • Z M1 and Z M2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, Represents —COO—, —OCO— or —C ⁇ C—
  • n M1 is 2, 3 or 4 and a plurality of A M2 are present, they may be the same or different, and n M1 is 2, 3 or 4 and a plurality of Z M1 is present
  • X M1 and X M3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom
  • X M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a
  • R M1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy having 2 to 8 carbon atoms.
  • a group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable.
  • An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.
  • R M1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane
  • a straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dot in each formula represents the carbon atom in the ring structure to which the alkenyl group is bonded.)
  • a M1 and A M2 are preferably aromatic when it is required to independently increase ⁇ n, and are preferably aliphatic for improving the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It preferably represents a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:
  • Z M1 and Z M2 each independently -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CF 2 O-, —CH 2 CH 2 — or a single bond is more preferable, and —CF 2 O— or a single bond is particularly preferable.
  • n M1 is preferably 0, 1, 2, or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of ⁇ , and preferably 1 or 2 when emphasizing Tni .
  • the types of compounds that can be combined are used in combination according to desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the content of the compound represented by the general formula (M) is low-temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (M) with respect to the total amount of the composition of the present invention is 0%, 1%, 10%, 20%, 30 %, 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%.
  • the upper limit of the preferable content is, for example, 95%, 85%, 75%, 65%, and 55% with respect to the total amount of the composition of the present invention. Yes, 45%, 35%, 25%.
  • the composition of the present invention keeps the viscosity low and a composition having a high response speed is required, it is preferable to lower the lower limit and lower the upper limit. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, it is preferable to lower the lower limit and lower the upper limit. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the upper limit value while increasing the lower limit value.
  • the liquid crystal compound represented by the general formula (M) preferably has the following general formula (M-1) and general formula (M-2).
  • R 31 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X 31 and X 32 are each independently hydrogen.
  • An atom or a fluorine atom Y 31 represents a fluorine atom or OCF 3
  • M 31 to M 33 each independently represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group, One or two —CH 2 — in the trans-1,4-cyclohexylene group may be substituted with —O— so that the oxygen atom is not directly adjacent to one another.
  • the liquid crystal compound represented by the general formula (M-1) is preferably a compound represented by the following general formula (M-1-a) to general formula (M-1-f).
  • the liquid crystal compound represented by the general formula (M-2) is preferably a compound represented by the following general formula (M-2-a) to general formula (M-2-n).
  • R 31, X 31, X 32 and Y 31 are as defined R 31, X 31, X 32 and Y 31 in the general formula (M), X 34 ⁇ X 39 are each independently Represents a hydrogen atom or a fluorine atom.
  • the liquid crystal compound represented by the general formula (M) is preferably from the following general formula (M-3) to general formula (M-26).
  • R 31, X 31, X 32 and Y 31 are as defined R 31, X 31, X 32 and Y 31 in the general formula (M), X 34 ⁇ X 39 are each independently Represents a hydrogen atom or a fluorine atom.
  • the composition of this invention contains 1 type, or 2 or more types of compounds represented by general formula (K). These compounds correspond to dielectrically positive compounds ( ⁇ is greater than 2).
  • R K1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, — Optionally substituted by C ⁇ C—, —O—, —CO—, —COO— or —OCO—, n K1 represents 0, 1, 2, 3 or 4;
  • a K1 and A K2 are each independently (A) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O- or -S- And (b) a 1,4-phenylene group (one —CH ⁇ present in this group or two or more non-adjacent —CH ⁇ may be replaced by —N ⁇ ).
  • a hydrogen atom on the group (a) and the group (b) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • Z K1 and Z K2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, Represents —COO—, —OCO— or —C ⁇ C—
  • n K1 is 2, 3 or 4 and a plurality of A K2 are present, they may be the same or different, and n K1 is 2, 3 or 4 and a plurality of Z K1 is present
  • X K1 and X K3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom
  • X K2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a
  • R K1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or alkenyloxy having 2 to 8 carbon atoms.
  • a group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable.
  • An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.
  • RK1 is preferably an alkyl group when importance is placed on reliability, and an alkenyl group is preferred when importance is placed on lowering viscosity.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane
  • a straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dot in each formula represents the carbon atom in the ring structure to which the alkenyl group is bonded.)
  • a K1 and A K2 are preferably aromatic when it is required to independently increase ⁇ n, and are preferably aliphatic for improving the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It preferably represents a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:
  • Z K1 and Z K2 are each independently -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CF 2 O-, —CH 2 CH 2 — or a single bond is more preferable, and —CF 2 O— or a single bond is particularly preferable.
  • n K1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of ⁇ , and preferably 1 or 2 when emphasizing Tni. .
  • the types of compounds that can be combined are used in combination according to desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the content of the compound represented by the general formula (K) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (K) with respect to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40% %, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferable content is, for example, 95%, 85%, 75%, 65%, and 55% with respect to the total amount of the composition of the present invention. Yes, 45%, 35%, 25%.
  • the composition of the present invention keeps the viscosity low and a composition having a high response speed is required, it is preferable to lower the lower limit and lower the upper limit. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, it is preferable to lower the lower limit and lower the upper limit. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the upper limit value while increasing the lower limit value.
  • the liquid crystal compound represented by the general formula (K) preferably has the following general formula (K-1) and general formula (K-2).
  • R 41 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X 41 and X 42 are each independently hydrogen.
  • Y 41 represents an atom or a fluorine atom
  • Y 41 represents a fluorine atom or OCF 3
  • M 41 to M 43 each independently represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group
  • One or two —CH 2 — in the trans-1,4-cyclohexylene group may be substituted with —O— so that the oxygen atom is not directly adjacent to one another.
  • the liquid crystal compound represented by the general formula (K-1) is preferably a compound represented by the following general formula (K-1-a) to general formula (K-1-d).
  • the liquid crystal compound represented by the general formula (K-2) is preferably a compound represented by the following general formula (K-2-a) to general formula (K-2-g).
  • R 41, X 41, X 42 and Y 41 are as defined R 41, X 41, X 42 and Y 41 in the general formula (K), X 44 ⁇ X 49 are each independently Represents a hydrogen atom or a fluorine atom.
  • the liquid crystal compound represented by the general formula (K) is preferably the following general formula (K-3) to general formula (K-5).
  • R 41, X 41, X 42 and Y 41 are as defined R 41, X 41, X 42 and Y 41 in the general formula (K), X 44 ⁇ X 49 are each independently Represents a hydrogen atom or a fluorine atom.
  • the compound represented by the general formula (II) is a so-called n-type liquid crystal compound having a negative dielectric anisotropy and includes compounds represented by the following general formula (LC1) and general formula (LC2). it can.
  • the compound represented by the general formula (II) preferably contains one or more compounds selected from the compound group represented by the general formula (N-1) to the general formula (N-3).
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 each independently represents an alkyl group having 1 to 8 carbon atoms, and one or non-adjacent 2 in the alkyl group
  • Two or more —CH 2 — may be each independently substituted by —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO—
  • a N11 , A N12 , A N21 , A N22 , A N31, and A N32 are each independently (a) a 1,4-cyclohexylene group (one —CH 2 — or adjacent to each other in this group).
  • —CH 2 — Two or more —CH 2 — that are not present may be replaced by —O—.
  • the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom, Z N11 , Z N12 , Z N21 , Z N22 , Z N31 and Z N32 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—.
  • XN21 represents a hydrogen atom or a fluorine atom
  • T N31 represents —CH 2 — or an oxygen atom
  • n N11 , n N12 , n N21 , n N22 , n N31, and n N32 each independently represent an integer of 0 to 3, but n N11 + n N12 , n N21 + n N22, and n N31 + n N32 are each independently When there are a plurality of A N11 to A N32 and Z N11 to Z N32 , they may be the same or different.
  • the compound represented by the general formula (N-1) is excluded, and in the general formula (N-3), the general formula (N-2) The compound represented by is excluded.
  • the compounds represented by the general formulas (N-1), (N-2), and (N-3) are dielectrically negative compounds (the sign of ⁇ is negative and the absolute value thereof is greater than 2). Although applicable, it is preferable that ⁇ is negative and the absolute value thereof is larger than 3.
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 each independently represent 1 to 8 carbon atoms.
  • An alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms preferably an alkyl group having 1 to 5 carbon atoms.
  • An alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable.
  • an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
  • a decrease in voltage holding ratio (VHR) is remarkably suppressed. be able to.
  • a decrease in voltage holding ratio (VHR) is remarkably suppressed.
  • the voltage holding ratio (VHR) is decreased. Can be remarkably suppressed.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane
  • a straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • a N11 , A N12 , A N21 , A N22 , A N31, and A N32 are preferably aromatic when it is required to increase ⁇ n independently, and in order to improve the response speed, fat
  • fat Preferably a trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 , 4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group Preferred, it is more preferable that represents the following
  • it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
  • Z N11, Z N12, Z N21 , Z N22, Z N31 and Z N32 -CH 2 each independently O -, - CF 2 O - , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents an, -CH 2 O -, - CH 2 CH 2 - or a single bond is more preferable, -CH 2 O-or a single bond is particularly preferred.
  • XN21 is preferably a fluorine atom.
  • T N31 is preferably an oxygen atom.
  • n N11 + n N12 , n N21 + n N22 and n N31 + n N32 are preferably 1 or 2, a combination in which n N11 is 1 and n N12 is 0, a combination in which n N11 is 2 and n N12 is 0, n A combination in which N11 is 1 and n N12 is 1, a combination in which n N11 is 2 and n N12 is 1, a combination in which n N21 is 1 and n N22 is 0, n N21 is 2 and n N22 is n A combination in which n N31 is 1 and n N32 is 0, and a combination in which n N31 is 2 and n N32 is 0 are preferable.
  • the lower limit of the preferable content of the compound represented by the formula (N-1) with respect to the total amount of the composition of the present invention is 0%, 1%, 10%, 20% 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the lower limit of the preferable content of the compound represented by the formula (N-2) with respect to the total amount of the composition of the present invention is 0%, 1%, 10%, 20% 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the lower limit of the preferable content of the compound represented by the formula (N-3) with respect to the total amount of the composition of the present invention is 0%, 1%, 10%, 20% 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the above lower limit value is preferably low and the upper limit value is preferably low. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, the above lower limit value is preferably low and the upper limit value is preferably low. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above lower limit value is increased and the upper limit value is high.
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (i-1) as general formula (N-1).
  • a i11 , A i12 and A i13 each independently represents a 1,4-cyclohexylene group or a 1,4-phenylene group, but one existing in the 1,4-cyclohexylene group) of -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O- or -S-, it is one of the hydrogen atoms present in the 1,4-phenylene group, respectively Independently substituted with a fluorine atom or a chlorine atom
  • Z i1 represents —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 — or —CF 2 CF 2 - represents, m i11 and m i12 are each independently 0 or 1, R N11, R N12 and Z N12 is, R N11, R N12 and in the general formula (N-1) each independently Z represents the same meaning as N12 .
  • R N11 , R N12 , A i11 and Z i1 each independently represent the same meaning as R N11 , R N12 , A i11 and Z i1 in formula (i-1)).
  • R N11, R N12, A i11 , A i12 and Z i1 are the same meaning as R N11, R N12, A i11 , A i12 and Z i1 in the general formula (i1) independently To express.
  • m i13 represents 1, and R N11 , R N12 , A i11 , A i12 , A i13 , Z i1 , Z i2 and m i11 are each independently R N11 in the general formula (i-1). , R N12 , A i11 , A i12 , A i13 , Z i1 , Z i2 and m i11 represent the same meaning.
  • compounds represented by the general formula (i-1A) compounds represented by the following general formula (i-1A-1) to general formula (i-1A-4) are preferable.
  • R N11 and R N12 each independently represent the same meaning as R N11 and R N12 in formula (i-1)).
  • the compound represented by the general formula (i-1B) is preferably a compound represented by the following general formula (i-1B-1) to general formula (i-1B-7).
  • R N11 and R N122 each independently represent the same meaning as R N11 and R N12 in formula (i-1).
  • the compound represented by the general formula (i-1C) is preferably a compound represented by the following general formula (i-1C-1) to general formula (i-1C-4). -1C-1) and a compound represented by the general formula (i-1C-2) are more preferable.
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (i), but the general formula (i-1A), the general formula (i-1B) or the general formula One or more compounds selected from the group of compounds represented by (i-1C) may be contained, or represented by the general formula (i-1A), general formula (i-1B), or general formula (i One or more compounds each represented by -1C) may be contained.
  • One or more compounds represented by general formula (i-1A) and general formula (i-1B) are preferably contained, and more preferably 2 to 10 compounds are contained.
  • general formula (i-1A), general formula (i-1B) and general formula (i-1C) are represented by general formula (i-1A-1), general formula (i-1B-1) and general formula (i-1B-1). It is preferable to contain one or more compounds selected from the compound group represented by the formula (i-1C-1), and the compound represented by the general formula (i-1A-1) and the general formula (i The combination of the compounds represented by -1B-1) is more preferable.
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (ii) as general formula (LC3).
  • a ii1 and A ii2 each independently represent 1,4-cyclohexylene group or 1,4-phenylene group, but one —CH existing in 1,4-cyclohexylene group) 2 — or two or more non-adjacent —CH 2 — may be replaced by —O— or —S—, and one hydrogen atom present in the 1,4-phenylene group is each independently may be substituted by a fluorine atom or a chlorine atom, m ii1 and m ii2 independently represents 1 or 2, R N11 and R N12 is, R N11 and in the general formula (N-1) each independently represent the same meaning as R N12.) As general formula (ii-1), it is preferable to contain one or more compounds represented by general formula (ii-1).
  • the compound represented by the general formula (ii-1) is preferably a compound represented by the general formula (II-2A) or the general formula (II-2B).
  • R N11, R N12 and A ii1 have the same meanings as R N11, R N12 and A ii1 in formula (ii).
  • a ii11 and A ii11 each independently represents a 1,4-cyclohexylene group or a 1,4-phenylene group, but one —CH existing in the 1,4-cyclohexylene group) 2 — or two or more non-adjacent —CH 2 — may be replaced by —O— or —S—, and one hydrogen atom present in the 1,4-phenylene group is each independently (It may be substituted with a fluorine atom or a chlorine atom, and R N11 and R N12 represent the same meaning as R N11 and R N12 in formula (ii).)
  • compounds represented by the following general formula (ii-1A-1) and general formula (ii-1A-2) are preferable.
  • the compound represented by the general formula (ii-1B) is preferably a compound represented by the following general formula (ii-1B-1) to general formula (ii-1B-3).
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (ii), but is represented by general formula (ii-1A) and general formula (ii-1B). 1 or 2 or more types of compounds selected from the group of compounds described above may be included, or each of the compounds represented by general formula (ii-1A) and general formula (ii-1B) may be included. Also good. It is preferable to contain 2 to 10 compounds represented by general formula (ii-1A) and general formula (ii-1B).
  • the general formula (ii-1A) preferably contains one or more compounds selected from the compound group represented by the general formula (ii-1A-1).
  • 1B) preferably contains one or more compounds selected from the group of compounds represented by general formula (ii-1B-1) and general formula (ii-1B-2).
  • a combination of the compounds represented by 1A-1) and the general formula (ii-1B-1) is more preferable.
  • R N11 , R N12 , A N11 , A N12 and Z N11 are each independently the same meaning as R N11 , R N12 , A N11 , A N12 and Z N11 in the general formula (N-1).
  • X LC3b1 to X LC3b4 each represent a hydrogen atom or a fluorine atom, but at least one of X LC3b1 and X LC3b2 , or at least one of X LC3b3 and X LC3b4 represents a fluorine atom, and m LC3b1 represents 0 or 1 (However, in general formula (LC3-b), the compounds represented by general formula (i-1) and general formula (ii) are excluded.)
  • the general formula (LC3-b) preferably represents the following general formula (LC3-b1) to general formula (LC3-b10).
  • R N11 and R N12 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • the combination of R N11 and R N12 is not particularly limited, but both represent an alkyl group, both represent an alkenyl group, one represents an alkyl group, the other represents an alkenyl group, and either one represents It is preferable that one represents an alkyl group, the other represents alkoxy, and one represents an alkyl group and the other represents an alkenyloxy group, both represent an alkyl group, and both represent an alkenyl group. It is more preferable that it represents.
  • the general formula (LC3-b) preferably represents the following general formula (LC3-c).
  • R N11 and R N12 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • the compound represented by the general formula (N-2) is preferably a compound selected from the group of compounds represented by the general formulas (N-2-1) to (N-2-3).
  • R N211 and R N22 each independently represent the same meaning as R N211 and R N22 in formula (N-2).
  • the compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formulas (N-3-1) and (N-3-2).
  • the compound represented by the general formula (N-3-1) is the following compound.
  • the fourth component is a so-called nonpolar liquid crystal compound having a dielectric anisotropy of about 0, and examples thereof include compounds represented by the following general formula (L).
  • composition of the present invention preferably contains one or more compounds represented by the general formula (L).
  • the compound represented by the general formula (L) corresponds to a dielectrically neutral compound ( ⁇ value is ⁇ 2 to 2).
  • R L1 and R L2 each independently represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently Optionally substituted by —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO—, n L1 represents 0, 1, 2 or 3,
  • a L1 , A L2 and A L3 each independently represent (a) a 1,4-cyclohexylene group (one —CH 2 — present in the group or two or more —CH 2 — not adjacent to each other).
  • the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • n L1 is 2 or 3
  • a plurality of A L2 are present, they may be the same or different, and when n L1 is 2 or 3, and a plurality of Z L3 are present, May be the same or different, but excludes compounds represented by general formula (J), general formula (N-1), general formula (N-2) and general formula (N-3).
  • the compound represented by general formula (L) may be used independently, it can also be used in combination.
  • the types of compounds that can be combined but they are used in appropriate combinations according to desired properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention.
  • the content of the compound represented by the general formula (L) is low-temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L) with respect to the total amount of the composition of the present invention is 0%, 1%, 10%, 20%, 30 %, 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%.
  • the upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, and 25%.
  • the above lower limit value is preferably high and the upper limit value is preferably high. Furthermore, when the composition of the present invention maintains a high Tni and requires a composition having good temperature stability, the above lower limit value is preferably high and the upper limit value is preferably high. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above lower limit value is lowered and the upper limit value is low.
  • R L1 and R L2 are preferably both alkyl groups, and when importance is placed on reducing the volatility of the compound, it is preferably an alkoxy group, and importance is placed on viscosity reduction. In this case, at least one is preferably an alkenyl group.
  • R L1 and R L2 are each a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group having 1 to 4 carbon atoms when the ring structure to which R L1 is bonded is a phenyl group (aromatic).
  • a phenyl group aromatic
  • Alkyl groups, linear alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • VHR voltage holding ratio
  • n L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferred for improving the upper limit temperature of the nematic phase, and 1 is preferred for balancing these. In order to satisfy the properties required for the composition, it is preferable to combine compounds having different values.
  • a L1 , A L2, and A L3 are preferably aromatic when it is required to increase ⁇ n, and are preferably aliphatic for improving the response speed, and are each independently trans- 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -It preferably represents a diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:
  • it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
  • Z L1 and Z L2 are preferably single bonds when the response speed is important.
  • the number of halogen atoms in the molecule is preferably 0 or 1.
  • the compound represented by the general formula (L) is preferably a compound selected from the compounds represented by the general formula (L-1).
  • R L11 and R L12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms.
  • the compound represented by the general formula (L-1) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content is 1%, 2%, 3%, 5%, 7%, 10%, and 15% with respect to the total amount of the composition of the present invention. %, 20%, 25%, 30%, 35%, 40%, 45%, 50%, and 55%.
  • the upper limit of the preferable content is 95%, 90%, 85%, 80%, 75%, 70%, 65%, based on the total amount of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.
  • the above lower limit value is preferably high and the upper limit value is preferably high. Furthermore, when the composition of the present invention requires a high Tni and a composition having good temperature stability, it is preferable that the lower limit value is moderate and the upper limit value is moderate. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value is low and the upper limit value is low.
  • the compound represented by the general formula (L-1) is preferably a compound represented by the general formula (L-1-1).
  • the compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.11) to the formula (L-1-1.13). And is preferably a compound represented by formula (L-1-1.12) or formula (L-1-1.13), and particularly represented by formula (L-1-1.13). It is preferable that it is a compound.
  • the compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.21) to the formula (L-1-1.24). It is preferable that the compound be a compound represented by the formula (L-1-1.22) to the formula (L-1-1.24). In particular, the compound represented by the formula (L-1-1.22) is preferable because the response speed of the composition of the present invention is particularly improved. When obtaining Tni higher than the response speed, it is preferable to use a compound represented by formula (L-1-1.23) or formula (L-1-1.24).
  • the compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.31) and the formula (L-1-1.41). Preferably there is.
  • the compound represented by the general formula (L-1) is preferably a compound represented by the general formula (L-1-2).
  • the compound represented by the general formula (L-1-2) is a compound selected from the group of compounds represented by the formula (L-1-2.1) to the formula (L-1-2.12). Are preferred, and compounds represented by formula (L-1-2.1), formula (L-1-2.3) or formula (L-1-2.4) are preferred. In particular, the compound represented by the formula (L-1-2.1) is preferable because the response speed of the composition of the present invention is particularly improved.
  • a compound represented by 1-2.12 Sum of compounds represented by formula (L-1-2.3), formula (L-1-2.4), formula (L-1-2.11) and formula (L-1-2.12)
  • the content of is not preferably 20% or more in order to improve the solubility at low temperatures.
  • the compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-3) and / or (L-1-4). .
  • R ii31 and R ii41 each independently represent the same meaning as R ii2 in the general formula (L).
  • the compound represented by the general formula (L) is preferably a compound represented by the following general formula (L-2) to general formula (L-11).
  • the liquid crystal composition of the present invention contains one or more compounds represented by general formula (L-2) to general formula (L-11) as the compound represented by general formula (L). Is preferred.
  • R L31 and R L32 are an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R L32 is an alkyl group having 1 to 5 carbon atoms, and 1 to C atoms
  • 5 represents an alkoxyl group, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms.
  • the compound represented by general formula (L) is a compound selected from general formula (L-4), general formula (L-6), general formula (L-7), and general formula (L-8).
  • the compound is selected from the general formula (L-6), the general formula (L-7), and the general formula (L-8), and the general formula (L-7) and the general formula (L-
  • the compound selected from 8) is more preferable, and the compound selected from General Formula (L-6) and General Formula (L-8) is also preferable. More specifically, when a large ⁇ n is required, a compound selected from general formula (L-6), general formula (L-8), and general formula (L-11) is preferable.
  • R L31 represents an alkyl group having 1 to 5 carbon atoms or 2 carbon atoms.
  • R L32 is an alkoxy group having 5 alkyl group or a carbon number of 1 1 to 5 carbon atoms
  • R L31 is an alkenyl group having 2 to 5 carbon atoms More preferably, it is more preferably an alkenyl group having 2 or 3 carbon atoms.
  • R L31 and R L32 each independently represent 1 to 5 carbon atoms. And an alkenyl group having 2 to 5 carbon atoms.
  • the compound represented by the general formula (L) contains one or more compounds represented by the general formula (L-12), the general formula (L-13), or the general formula (L-14). It is also preferable to do.
  • R L51 and R L52 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 2 to 5
  • X L51 and X L52 each independently represents a fluorine atom or a hydrogen atom, and one of X L51 and X L52 is a fluorine atom, and the other is a hydrogen atom.
  • the compound represented by the general formula (L) may contain one or more compounds represented by the general formula (L-16.1) to the general formula (L-16.3). .
  • the compound represented by the general formula (L) may contain one or more compounds represented by the general formula (N-001).
  • R N1 and R N2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or 2 to 8 carbon atoms.
  • L 1 and L 2 each independently represents a hydrogen atom, a fluorine atom, CH 3 or CF 3 (except that both L 1 and L 2 represent a fluorine atom).
  • R N1 and R N2 preferably represent an alkyl group having 1 to 5 carbon atoms.
  • the liquid crystal composition of the present invention preferably has a positive dielectric anisotropy ( ⁇ ) at 25 ° C., and the dielectric anisotropy ( ⁇ ) at 25 ° C. is 1.5 to 20.0.
  • ⁇ dielectric anisotropy
  • 1.5 to 18.0 is more preferable
  • 1.5 to 15.0 is more preferable
  • 1.5 to 11 is more preferable
  • 1.5 to 8 is particularly preferable.
  • the liquid crystal composition having a positive value preferably contains a compound represented by the general formula (J) and a compound represented by the general formula (L).
  • it preferably contains a compound represented by the general formula (M) and a compound represented by the general formula (L-1), and the general formula (M-1) and / or the general formula (M -2) and a compound represented by the general formula (L-1-1).
  • the total content of the compound represented by the general formula (I), the compound represented by the general formula (J), and the compound represented by the general formula (L) The lower limit is preferably 5% or more, preferably 80% or more, preferably 85% or more, preferably 88% or more, preferably 90% or more, It is preferable to contain 92% or more, preferably 95% or more, preferably 97% or more, preferably 98% or more, preferably 99% or more. It is preferable not to contain a compound. Further, the upper limit value is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not. Substantially, it means to exclude compounds that are unintentionally contained such as impurities inevitably generated during production.
  • the total content of the compound represented by the general formula (I), the compound represented by the general formula (M) and the compound represented by the general formula (L) The lower limit is preferably 5% or more, preferably 80% or more, preferably 85% or more, preferably 88% or more, preferably 90% or more, It is preferable to contain 92% or more, preferably 95% or more, preferably 97% or more, preferably 98% or more, preferably 99% or more. It is preferable not to contain a compound. Further, the upper limit value is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not.
  • the liquid crystal composition of the present invention has a total content of the compound represented by the general formula (I), the compound represented by the general formula (J) and the compound represented by the general formula (L-1).
  • the lower limit of the content is preferably 5% or more, preferably 10% or more, preferably 13% or more, preferably 15% or more, and 18% or more.
  • 20% or more is contained, preferably 23% or more, preferably 25% or more, preferably 28% or more, preferably 30% or more, 33% or more It is preferable to contain, it is preferable to contain 35% or more, it is preferable to contain 38% or more, and it is preferable to contain 40% or more.
  • the upper limit value is preferably 95% or less, preferably 90% or less, preferably 88% or less, preferably 85% or less, and preferably 83% or less. 80% or less, preferably 78% or less, preferably 75% or less, preferably 73% or less, preferably 70% or less, preferably 68% or less Preferably 65% or less, preferably 63% or less, preferably 60% or less, preferably 55% or less, preferably 50% or less, It is preferable to contain 40% or less.
  • the liquid crystal composition of the present invention preferably has a negative dielectric anisotropy ( ⁇ ) at 25 ° C., and the dielectric anisotropy ( ⁇ ) at 25 ° C. is from ⁇ 2.0 to ⁇ 8.0. -2.0 to -6.0 is preferred, -2.0 to -5.0 is more preferred, and -2.5 to -4.0 is particularly preferred.
  • Liquid crystal compositions having a negative dielectric anisotropy include compounds represented by general formulas (N-1) to (N-3) and compounds represented by general formula (L). It is preferable to contain. More specifically, it preferably contains a compound represented by the general formula (N-1) and a compound represented by the general formula (L-1), and the compound represented by the general formula (N-1) And a compound represented by the general formula (L-1-1).
  • the liquid crystal composition of the present invention includes a compound represented by general formula (I), a compound represented by general formula (N-1) to general formula (N-3), and a compound represented by general formula (L).
  • the total content is preferably 5% or more, preferably 80% or more, preferably 85% or more, and preferably 88% or more as the lower limit in the composition.
  • the upper limit value is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds.
  • the upper limit value is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds.
  • the liquid crystal composition of the present invention has a total content of the compound represented by the general formula (I), the compound represented by the general formula (N-1) and the compound represented by the general formula (L).
  • the lower limit is preferably 5% or more, preferably 80% or more, preferably 85% or more, preferably 88% or more, and 90% or more.
  • it contains 92% or more, preferably 95% or more, preferably 97% or more, preferably 98% or more, preferably 99% or more, substantially It is preferable not to contain other compounds.
  • the upper limit value is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds.
  • the liquid crystal composition of the present invention has a total content of the compound represented by the general formula (I), the compound represented by the general formula (J) and the compound represented by the general formula (L-1).
  • the lower limit of the content is preferably 5% or more, preferably 10% or more, preferably 13% or more, preferably 15% or more, and 18% or more.
  • 20% or more is contained, preferably 23% or more, preferably 25% or more, preferably 28% or more, preferably 30% or more, 33% or more It is preferable to contain, it is preferable to contain 35% or more, it is preferable to contain 38% or more, and it is preferable to contain 40% or more.
  • the upper limit value is preferably 95% or less, preferably 90% or less, preferably 88% or less, preferably 85% or less, and preferably 83% or less. 80% or less, preferably 78% or less, preferably 75% or less, preferably 73% or less, preferably 70% or less, preferably 68% or less Preferably 65% or less, preferably 63% or less, preferably 60% or less, preferably 55% or less, preferably 50% or less, It is preferable to contain 40% or less.
  • the liquid crystal composition of the present invention has a refractive index anisotropy ( ⁇ n) at 25 ° C. of 0.08 to 0.14, more preferably 0.09 to 0.13, and 0.09 to 0.12. Particularly preferred. More specifically, it is preferably 0.10 to 0.13 when dealing with a thin cell gap, and preferably 0.08 to 0.10 when dealing with a thick cell gap.
  • the liquid crystal composition of the present invention has a viscosity ( ⁇ ) at 25 ° C. of 10 to 50 mPa ⁇ s, more preferably 10 to 40 mPa ⁇ s, and particularly preferably 10 to 35 mPa ⁇ s.
  • the liquid crystal composition of the present invention has a rotational viscosity ( ⁇ 1 ) at 25 ° C. of 60 to 130 mPa ⁇ s, more preferably 60 to 110 mPa ⁇ s, and particularly preferably 60 to 100 mPa ⁇ s. .
  • the liquid crystal composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T ni ) of 60 ° C. to 120 ° C., more preferably 70 ° C. to 100 ° C., and particularly preferably 70 ° C. to 85 ° C.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • the liquid crystal composition of the present invention may be an ordinary nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, or other light stabilizer (HALS). ) And the like.
  • the liquid crystal composition of the present invention may contain a liquid crystal compound having a dielectric anisotropy ( ⁇ ) at 25 ° C. of +2.0 to +50.0 as a normal nematic liquid crystal or smectic liquid crystal.
  • the content is 0% to 50% by mass, preferably 1% to 30% by mass, preferably 3% to 30% by mass, and 5% to 20% by mass. Is preferred.
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (i) and general formula (ii).
  • R i0 represents a hydrogen atom, a hydroxyl group, —O., Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent —CH 2 present in the alkyl group
  • R i0 represents a hydrogen atom, a hydroxyl group, —O., Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent —CH 2 present in the alkyl group
  • R i1 , R i2 , R i3 and R i4 each independently represents an alkyl group having 1 to 12 carbon atoms, and R i1 and R i2 and / or R i3 and R i4 are bonded to each other to form a ring.
  • R i5, R i6, R i7 and R i8 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, when R II5 and R II6 and / or the R II7 and R II8 represents an alkyl group , wherein R II5 and R II6 and / or R II7 and R II8 may be bonded to each other to form a ring, n i represents 0 or 1, m i represents an integer of 1-6, M i represents 1 to hexavalent organic group, the valence of M i is the same number as the number represented by m i, R i0, R i1 , R i2, When there are a plurality of R i3 , R i4 , R i5 , R i6 , R i7 , R i8 and n i , they may be the same or different. )
  • R ii0 represents a hydrogen atom, a hydroxyl group, —O ⁇ , or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent —CH 2 present in the alkyl group
  • R ii0 1 or 2 a trans 1,4-cyclohexylene group, a 1,4-phenylene group or a naphthalene-2,6-diyl group may be substituted in R ii0 1 or 2 or more hydrogen atoms are each independently substituted with a fluorine atom, a chlorine atom or a cyano group It may be, R ii1 , R ii2 , R ii3 and R ii4 each independently represent an alkyl group having 1 to 12 carbon atoms, and R ii1 and R ii2 and / or R ii3 and R ii4 are bonded to each other to form a ring
  • n ii represents 0 or 1
  • t represents 1 to 4
  • U represents a 2 ⁇ t-valent organic group forming a ring structure, R ii0 , R ii1 , R ii2 , R ii3 , R ii4 , R ii5 , R ii6 , R ii7 , R If ii8 and n ii there are a plurality, they may be different even in the same.
  • R i0 and R ii0 are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms from the viewpoint of compatibility with the liquid crystal composition. It is preferably an alkoxy group or an alkenyl group having 2 to 20 carbon atoms, and is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 3 to 12 carbon atoms. Is more preferable.
  • the alkyl group, alkoxy group or alkenyl group is preferably linear or molecular, and preferably linear.
  • a hydrogen atom or a linear alkyl group having 1 to 5 carbon atoms is particularly preferable.
  • a hydrogen atom or a hydroxyl group is preferable, and a hydrogen atom is particularly preferable.
  • R i1 , R i2 , R i3 , R i4 , R ii1 , R ii2 , R ii3 and R ii4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, A methyl group is particularly preferred from the viewpoint of the stability of the compound.
  • R i1 and R i2 and / or R i3 and R i4 are preferably bonded to each other to form a ring structure.
  • R ii1 and R ii2 and / or R ii3 and R ii4 are preferably bonded to each other to form a ring structure.
  • R i5 , R i6 , R i7 , R i8 , R ii5 , R ii6 , R ii7 and R ii8 are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, An alkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom or a methyl group is particularly preferable from the viewpoint of availability of raw materials and stability of the compound.
  • m i is an integer of 1-6
  • M i represents 1 to hexavalent organic group
  • many valence of M i is represented by n i although, m i is 3
  • M i is preferably a trivalent organic group.
  • M i represents the general formula (i ⁇ M)
  • Z 1 , Z 2 and Z 3 are each independently —O—, —S—, —CH ⁇ CH—, —C ⁇ C—, —CO—, —CO—O—, —O It represents —CO—, —OCF 2 —, —CF 2 O—, —NH— or a single bond.
  • Sp 1 , Sp 2 and Sp 3 each independently represent a single bond or an alkylene group having 1 to 10 carbon atoms, and one or more —CH 2 — present in the alkylene group is independently Substituted with —O—, —S—, —CH ⁇ CH—, —C ⁇ C—, —CO—, —CO—O—, —O—CO—, —OCF 2 — or —CF 2 O—. May be.
  • A is
  • R 8 represents a hydrogen atom, —OH or an alkyl group having 1 to 10 carbon atoms, and one or two or more —CH 2 — present in the alkyl group are each independently —O—, —S—, —CH ⁇ CH—, —C ⁇ C—, —CO—O—, —O—CO— may be substituted, and the hydrogen atom in the cyclic structure is a halogen atom or (It may be substituted with a cyano group.) Represents a group selected from: ) In order to improve the compatibility with the liquid crystal composition and the storage stability, it is preferable.
  • At least one of Z 1 , Z 2 and Z 3 preferably represents —O—, —CO—O— or a single bond, and Z 1 , It is particularly preferred that all of Z 2 and Z 3 represent —O—, —CO—O— or a single bond.
  • Sp 1 , Sp 2 and Sp 3 preferably represent a single bond or an alkylene group having 1 to 10 carbon atoms, preferably a single bond or an alkylene group having 1 to 8 carbon atoms, Alternatively, it is more preferably an alkylene group having 1 to 4 carbon atoms.
  • the alkylene group is unsubstituted, or one or more —CH 2 — present in the alkylene group is each independently —O—, —CO—, —CO—O— or —O—. It is preferably substituted with CO-, more preferably unsubstituted.
  • Sp 1, Sp 2 and Sp 3 are, -CO -, - CH 2 -CO -, - CH 2 -CH 2 -CO -, - CH 2 -O -, - CH 2 -CH 2 - O -, - CH 2 -CH 2 -CH 2 -O -, - CH 2 -O-CO -, - CH 2 -CH 2 -O-CO -, - CH 2 -CH 2 -CH 2 -O-CO -, - CH 2 -CH 2 -CH 2 -O-CO
  • Particularly preferred is an unsubstituted alkylene group having 1 to 4 carbon atoms or a single bond.
  • —Sp 1 —Z 1 —, —Sp 2 —Z 2 —, and —Sp 2 —Z 2 — are each independently —CO—O—, —CH 2 —CO—O—, —CH 2 —.
  • CH 2 -CO-O - - CH 2 -CH 2 --CH 2 -CO-O -, - CH 2 -O -, - CH 2 -CH 2 -O -, - CH 2 -CH 2 -CH 2 -O -, - CH 2 -O- CO-O -, - preferably CH 2 -CH 2 -O-CO- O- or -CH 2 -CH 2 -CH 2 -O- CO-O- in which , -CO-O -, - CH 2 -CO-O- or more preferably -CH 2 -CH 2 -CO-O- and which.
  • R 8 represents a hydrogen atom, —OH or an alkyl group having 1 to 10 carbon atoms, and one or two or more —CH 2 — present in the alkyl group are each independently A liquid crystal having a structure represented by —O—, —S—, —CH ⁇ CH—, —C ⁇ C—, —CO—O— or —O—CO—. It is more preferable to improve the compatibility with the composition and the storage stability.
  • R 8 is a hydrogen atom, —OH, an alkyl group having 2 to 10 carbon atoms, —O—CO—R 9 (R 9 is 1 carbon atom) because of the ease of production and the availability of raw materials.
  • compounds n i is 3 as a general formula (i) is a compound represented by the general formula (i-a1) ⁇ (i -a14) are particularly preferred.
  • the compound represented by the general formula (i) is preferably a compound represented by the following general formula (i-1).
  • R is each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is particularly preferably a hydrogen atom.
  • it is an alkyl group, it preferably has 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and 1 carbon atom. Further preferred.
  • RHS may be the same or different.
  • M iS represents an alkyl group having 1 to 15 carbon atoms when m iS represents 1, and represents an alkylene group having 1 to 15 carbon atoms when m iS represents an integer of 2 to 6, and is present in M iS
  • One or more —CH 2 — represents —O—, —CH ⁇ CH—, —C ⁇ C—, —CO—, —OCO—, —COO—, trans-1,4-cyclohexylene group, 1 , 4-phenylene group and naphthalene-2,6-diyl group may be substituted, but considering the viscosity given to the liquid crystal composition and its volatility, M iS is an alkyl group having 2 to 10 carbon atoms or An alkylene group is preferable, an alkyl group or alkylene group having 2 to 8 carbon atoms is preferable, an alkyl group or alkylene group having 4 to 8 carbon atoms is preferable, and an alkyl group or alkylene group having 6
  • m iS represents an integer of 1 to 6, and preferably 2 to 4.
  • the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-11) or the general formula (i-12).
  • R H11 independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • M represents an alkylene group having 1 to 13 carbon atoms.
  • R is and R i11 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • miS represents 2
  • the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-2).
  • R H1 and R H2 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • M represents an alkylene group having 1 to 15 carbon atoms.
  • One or more —CH 2 — is —O—, —CH ⁇ CH—, —C ⁇ C—, —CO—, —OCO—, —COO—, trans-1,4-cyclohexylene group, 1, (It may be substituted with a 4-phenylene group or a naphthalene-2,6-diyl group.)
  • R H1 and R H2 are particularly preferably hydrogen atoms.
  • M represents an alkylene group having 1 to 15 carbon atoms.
  • M is an alkylene group having 2 to 10 carbon atoms.
  • alkylene having 4 to 8 carbon atoms is preferable, and alkylene having 6 or 8 carbon atoms is preferable.
  • Specific examples include compounds represented by general formula (i-24), general formula (i-26), and general formula (i-28).
  • R H1 and R H2 in these formulas are as described above.
  • the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-3).
  • R H3 , R H4 and R H5 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • N H1 and n H2 each independently represent 0 or 1 n.
  • H3 represents an integer of 1 to 4.
  • n H3 is 2, 3 or 4, and a plurality of R H5 are present, they may be the same or different.
  • R H3 , R H4 and R H5 are particularly preferably hydrogen atoms.
  • it is an alkyl group, it preferably has 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and 1 carbon atom. Further preferred.
  • n H3 when n H3 represents 1, it is preferable to represent the above general formula (i-a1) to general formula (i-a3).
  • n H3 when n H3 represents 2, compounds represented by the following general formula (i-31) and general formula (i-32) are preferable.
  • R H3 , R H4 and R H5 in these formulas are as described above.
  • n i 0 in the compound represented by the general formula (i), the following compounds are preferred.
  • the compound represented by the general formula (ii) is preferably a compound represented by the following general formula (ii-1) or general formula (ii-2).
  • R ii10 represents a hydrogen atom or a hydroxyl group
  • R ii12 represents a hydrogen atom or a monovalent organic group
  • Sp ii1 represents a single bond or an alkylene group having a carbon number of from 12, one -CH 2 present in the alkylene group - or nonadjacent two or more -CH 2 - is -O -, - May be replaced by COO—, —OCO—, —CH ⁇ CH— or —C ⁇ C—
  • a ii1 each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - is replaced by -O- May be.)
  • R ii11 may be a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a general formula ( ie )
  • R e1 represents a hydrogen atom or a hydroxyl group
  • Sp ie1 represents a single bond or an alkylene group having 1 to 12 carbon atoms, and one —CH 2 — present in the alkylene group or adjacent thereto.
  • —CH 2 — may be replaced by —O—, —COO—, —OCO—, —CH ⁇ CH— or —C ⁇ C—, and s1 represents 0 or 1.
  • s1 represents 0 or 1.
  • R ii10 and R ii21 each represent a hydrogen atom or a hydroxyl group, and n ii2 , l, o, and r each independently represent 0 or 1
  • the following general formulas (ii-1-1) to (ii-1-20) and (ii-2-1) are particularly preferable.
  • R a02 , R a92 , A a12 and Sp a12 represent the same meaning as R ii10 , R ii11 , A ii1 and Sp ii1 in general formula (ii-1), and Sp a13 represents a single bond or a carbon atom
  • It represents an alkylene group having 1 8, one -CH 2 present in the alkylene group - or nonadjacent two or more -CH 2 - is -O -, - COO -, - OCO -, - It may be replaced by CH ⁇ CH— or —C ⁇ C—, pa1 represents 1 or 2, and when a plurality of Sp a13 and A a12 are present, they may be the same or different.
  • R a02 and R a03 each independently represent the same meaning as R ii10 in general formula (ii-1)
  • a a13 represents the same meaning as A ii1 in general formula (ii-1)
  • Sp a14 and Sp a15 each represent the same meaning as Sp ii1 in formula (ii-1)
  • Sp a16 and Sp a17 each independently represent a single bond or an alkylene group having 1 to 8 carbon atoms, One —CH 2 — or two or more non-adjacent —CH 2 — present in the group is replaced by —O—, —COO—, —OCO—, —CH ⁇ CH— or —C ⁇ C—.
  • the composition containing the compound represented by general formula (I) further contains one or more antioxidants.
  • an antioxidant it is preferable to contain a hindered phenol compound.
  • the hindered phenol compound is preferably a compound represented by the general formula (H1).
  • X y represents a hydrocarbon having 1 to 25 carbon atoms (one or more —CH 2 — in the hydrocarbon is —O—, —CO— , -COO-, or -OCO- may be substituted.)
  • M y is -CH 2 1, two or more of the alkylene group (the alkylene group having from 1 to 15 carbon atoms - as the oxygen atoms are not directly adjacent, -O -, - CO -, - COO- , it may be substituted in -OCO-), -.
  • a 4-phenylene group and a trans-1,4-cyclohexylene group are represented.
  • an arbitrary hydrogen atom may be substituted with a fluorine atom, and l represents an integer of 2 to 6.
  • Examples of the antioxidant represented by the general formula (H1) include the following general formula (H1-I)
  • M x is a hydrocarbon having 1 to 25 carbon atoms (one or two or more —CH 2 — in the hydrocarbon is —O—, —CO— X represents an alkylene group having 1 to 15 carbon atoms (one or more of —CH 2 — in the alkylene group represents oxygen, and —COO— may be substituted with —OCO—).
  • M x is a hydrocarbon having 2 to 15 carbon atoms (one or more —CH 2 — in the hydrocarbon is —O—, —CO—, —COO— so that oxygen atoms are not directly adjacent to each other).
  • X may be an alkylene group having 2 to 15 carbon atoms (one or more of —CH 2 — in the alkylene group is directly adjacent to an oxygen atom) May be substituted with —O—, —CO—, —COO—, —OCO—), preferably a single bond, 1,4-phenylene group, or trans-1,4-cyclohexylene group.
  • a + b + c + d is more preferably 2 to 4, and 2 is particularly preferable.
  • M x is more preferably an alkylene group having 1 to 15 carbon atoms. In consideration of volatility, a large carbon number is preferable, and in consideration of viscosity, the carbon number is not too large. Is preferred. From the above, M x has more preferably 2 to 15 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • the compound B2 is preferably a compound represented by the general formula (H2).
  • R H21 represents a straight-chain alkyl group or a branched-chain alkyl group having 1 to 22 carbon atoms, and one or more —CH 2 — in the alkyl group represents an oxygen atom. May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 — so that they are not directly adjacent to each other.
  • a H2 represents 0, 1 or 2
  • M H21 represents (a) a trans-1,4-cyclohexylene group (one —CH 2 — present in this group or two or more non-adjacent —CH 2 — represents —O— or —S—).
  • R H1 represents an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or It represents an alkenyloxy group having 2 to 10 carbon atoms, one -CH 2 present in the radical - or non-adjacent two or more -CH 2 - are each independently -O- or -S- In addition, one or two or more hydrogen atoms present in the group may be each independently substituted with a fluorine atom or a chlorine atom.
  • alkyl group having 2 to 7 carbon atoms an alkoxyl group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms.
  • An alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms is more preferable.
  • M H4 is -CH 2 1, two or more of the alkylene group (the alkylene group having from 1 to 15 carbon atoms - as the oxygen atoms are not directly adjacent, - O—, —CO—, —COO—, —OCO— may be substituted.), —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, — OCF 2 —, —CF 2 CF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, — C ⁇ C—, a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted with a fluorine atom) or a trans-1,4-cyclohexylene group.
  • an alkylene group having 1 to 14 carbon atoms In consideration of the viscosity, a large number of carbon atoms is preferable, but in consideration of the viscosity, the number of carbon atoms is preferably not too large. Therefore, the number of carbon atoms is more preferably 2 to 12, more preferably 3 to 10. 4 to 10 carbon atoms are more preferred, 5 to 10 carbon atoms are more preferred, and 6 to 10 carbon atoms are more preferred.
  • one or more non-adjacent —CH ⁇ in the 1,4-phenylene group may be substituted by —N ⁇ .
  • each hydrogen atom in the 1,4-phenylene group may be independently substituted with a fluorine atom or a chlorine atom.
  • general formula (H-1) to general formula (H-4) one or more non-adjacent —CH 2 — in the 1,4-cyclohexylene group is replaced by —O— or —S—. May be.
  • each hydrogen atom in the 1,4-cyclohexylene group may be independently substituted with a fluorine atom or a chlorine atom. More specifically, for example, the formulas (H-11) to (H-15) can be given.
  • the liquid crystal composition of the present invention may contain 1 ppm by mass or more of an antioxidant, preferably 10 ppm by mass or more, preferably 20 ppm by mass or more, and more preferably 50 ppm by mass or more.
  • an antioxidant preferably 10 ppm by mass or more, preferably 20 ppm by mass or more, and more preferably 50 ppm by mass or more.
  • the upper limit of content of antioxidant is 10000 mass ppm, 1000 mass ppm is preferable, 500 mass ppm is preferable, and 100 mass ppm is preferable.
  • the total amount of the compounds represented by the general formula (i), the general formula (ii), and the general formula (H1) is 0.001% as a lower limit with respect to the total mass of the composition
  • it is contained 0.002% or more, preferably 0.003% or more, preferably 0.004% or more, and preferably 0.005% or more.
  • the upper limit is preferably 5% or less, preferably 3% or less, preferably 2% or less, preferably 1.5% or less, and preferably 1% or less.
  • 0.9% or less preferably 0.8% or less, preferably 0.7% or less, preferably 0.6% or less, 0.5% It is preferably contained below, preferably 0.45% or below, preferably 0.4% or below, preferably 0.35% or below, preferably 0.3% or below. , 0.25% or less, preferably 0.2% or less, preferably 0.15% or less, preferably 0.1% or less, 0.07 Preferably contains less, preferably it contains more than 0.05%, and preferably 0.03% or less.
  • the content is preferably 0.01 to 2% by mass, more preferably 0.01 to 1% by mass, still more preferably 0.01 to 0.2% by mass. It is particularly preferably from 01 to 0.15% by weight. More specifically, when emphasizing the suppression of precipitation at low temperatures, the content is preferably 0.01 to 0.1% by mass.
  • the ratio of the total content of the compounds represented by the general formula (I) to the total content of the compounds represented by the general formulas (i) and (ii) is 100.
  • Is preferably in the range of 1: 1 to 1: 10000, more preferably in the range of 100: 1 to 1: 1000, in the range of 10: 1 to 1: 100, and 1: 1 to 1. : 100, preferably 1: 1 to 1:50, and preferably 1: 1 to 1:10.
  • the total amount of the compound represented by the general formula (I) and the content of the compound represented by the general formula (i), the general formula (ii), and the general formula (H1) Is preferably in the range of 1: 100 to 10000: 1, more preferably in the range of 1:10 to 1000: 1, 1: 1 to 1: 500, The ratio is preferably 1 to 1: 100.
  • the liquid crystal composition of the present invention preferably further contains one or more polymerizable compounds.
  • the liquid crystal composition may contain 0.01 to 2% by mass of a polymerizable compound such as a biphenyl derivative or a terphenyl derivative as a polymerizable monomer.
  • polymerizable monomer one or two kinds of monofunctional polymerizable compounds having one reactive group and polyfunctional polymerizable compounds having two or more reactive groups such as bifunctional or trifunctional You may contain above.
  • the polymerizable compound having a reactive group may or may not contain a mesogenic moiety.
  • the reactive group is preferably a substituent having photopolymerizability.
  • X 3 represents a hydrogen atom or a methyl group
  • Sp 3 represents a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH 2 ) t — (wherein t is 2 to And an oxygen atom is bonded to an aromatic ring.
  • V represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic group having 5 to 30 carbon atoms.
  • the alkylene group in the polyvalent alkylene group may be substituted with an oxygen atom in the range where the oxygen atom is not adjacent to each other, and the alkyl group having 5 to 20 carbon atoms (the alkylene group in the group is an oxygen atom) May be substituted with an oxygen atom in a range not adjacent to each other)) or may be substituted with a cyclic substituent, and W represents a hydrogen atom, a halogen atom or an alkylene group having 1 to 8 carbon atoms).
  • the polymerizable compound represented is preferred.
  • X 3 represents a hydrogen atom or a methyl group.
  • a hydrogen atom is preferred, and when importance is placed on reducing the residual amount of reaction, a methyl group is preferred. preferable.
  • Sp 3 represents a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH 2 ) t — (wherein t represents an integer of 2 to 7, Represents a bond to an aromatic ring, but the carbon chain is preferably not so long, a single bond or an alkylene group having 1 to 5 carbon atoms is preferable, and a single bond or 1 to 3 carbon atoms is preferable.
  • An alkylene group is more preferred.
  • Sp 3 represents —O— (CH 2 ) t —
  • t is preferably 1 to 5, and more preferably 1 to 3.
  • V represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic substituent having 5 to 30 carbon atoms, and an alkylene group in the polyvalent alkylene group. May be substituted with an oxygen atom in the range where the oxygen atom is not adjacent, and an alkyl group having 5 to 20 carbon atoms (the alkylene group in the group may be substituted with an oxygen atom within the range where the oxygen atom is not adjacent) .) Or may be substituted with a cyclic substituent, and is preferably substituted with two or more cyclic substituents.
  • polymerizable compound represented by the general formula (VI) is represented by the general formula (X1a).
  • a 1 represents a hydrogen atom or a methyl group
  • a 2 represents a single bond or an alkylene group having 1 to 8 carbon atoms (one or two or more methylene groups in the alkylene group are each independently an oxygen atom, assuming that oxygen atoms are not directly bonded to each other, -CO-, -COO- or -OCO- may be substituted, and one or more hydrogen atoms in the alkylene group are each independently substituted with a fluorine atom, a methyl group or an ethyl group.
  • a 3 and A 6 are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms (one or two or more methylene groups in the alkyl group are such that oxygen atoms are not directly bonded to each other) And each independently may be substituted with an oxygen atom, —CO—, —COO— or —OCO—, and one or more hydrogen atoms in the alkyl group are each independently a halogen atom. Which may be substituted with an atom or an alkyl group having 1 to 17 carbon atoms).
  • a 4 and A 7 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms (one or two or more methylene groups in the alkyl group are such that oxygen atoms are not directly bonded to each other) And each independently may be substituted with an oxygen atom, —CO—, —COO— or —OCO—, and one or more hydrogen atoms in the alkyl group are each independently a halogen atom. Which may be substituted with an atom or an alkyl group having 1 to 9 carbon atoms).
  • B 1 , B 2 and B 3 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms (one or two or more methylene groups in the alkyl group are
  • each may be independently substituted with an oxygen atom, —CO—, —COO— or —OCO—, and one or more of the alkyl groups may be substituted.
  • each of the hydrogen atoms may be independently substituted with a halogen atom or a trialkoxysilyl group having 3 to 6 carbon atoms.
  • polymerizable compound represented by the general formula (VI) is specifically the general formula (X1b).
  • T 1 , T 2 and T 3 are each independently
  • polymerizable compound represented by the general formula (VI) is specifically the general formula (X1c).
  • R 70 represents a hydrogen atom or a methyl group
  • R 71 represents a hydrocarbon group having a condensed ring
  • the polymerizable compound having a polyfunctional reactive group is represented by the following general formula (VII).
  • X 1 and X 2 each independently represent a hydrogen atom or a methyl group
  • Sp 1 and Sp 2 each independently represent a single bond
  • U is a linear or branched chain having 2 to 20 carbon atoms
  • X 1 and X 2 each independently represent a hydrogen atom or a methyl group. However, when importance is attached to the reaction rate, a hydrogen atom is preferable, and importance is placed on reducing the reaction residual amount. In this case, a methyl group is preferred.
  • Sp 1 and Sp 2 are each independently a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH 2 ) s — (wherein s is 2 to 7 Wherein the oxygen atom is bonded to the aromatic ring), the carbon chain is preferably not so long, a single bond or an alkylene group having 1 to 5 carbon atoms is preferable, and a single bond or An alkylene group having 1 to 3 carbon atoms is more preferred.
  • Sp 1 and Sp 2 represent —O— (CH 2 ) s —
  • s is preferably 1 to 5, more preferably 1 to 3, and at least one of Sp 1 and Sp 2 is a single bond. More preferably, it is particularly preferable that both are single bonds.
  • U represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic substituent having 5 to 30 carbon atoms
  • an alkylene group in the polyvalent alkylene group May be substituted with an oxygen atom in the range where the oxygen atom is not adjacent, and an alkyl group having 5 to 20 carbon atoms (the alkylene group in the group may be substituted with an oxygen atom within the range where the oxygen atom is not adjacent) ), May be substituted with a cyclic substituent, and is preferably substituted with two or more cyclic substituents.
  • U specifically preferably represents the following formulas (VII-1) to (VII-5), and the formulas (VII-1) to (VII-3) It is more preferable to represent, and it is particularly preferable to represent the formula (VII-1).
  • both ends shall be bonded to Sp 1 or Sp 2.
  • at least one of the Sp 1 and Sp 2 preferably represents a single bond, and it is also preferable that both are single bonds.
  • k represents an integer of 1 to 5, and k is preferably a bifunctional compound having 1 or a trifunctional compound having k being 2, and more preferably a bifunctional compound.
  • X 201 and X 202 each independently represent a hydrogen atom, a methyl group, or a —CF 3 group.
  • X 201 and X 202 are each preferably a diacrylate derivative that is a hydrogen atom, and a dimethacrylate derivative that is both a methyl group, and a compound in which one is a hydrogen atom and the other is a methyl group.
  • a preferred compound can be used depending on the application, but in the PSA display element, the polymerizable compound represented by the general formula (P) preferably has at least one methacrylate derivative, and preferably has two.
  • Sp 201 and Sp 202 each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms or —O— (CH 2 ) s — (wherein s is 2 to 7 And an oxygen atom is bonded to the ring.
  • Sp 201 and Sp 202 are preferably at least one is a single bond in a PSA type liquid crystal display device, either a single bond compound or one is a single bond and the other is an alkylene having 1 to 8 carbon atoms.
  • M 201 , M 202 and M 203 each independently represents a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH 2 — in the group represents Optionally substituted by —O— or —S—), 1,4-phenylene group (one or two or more non-adjacent —CH ⁇ in the group may be substituted by —N ⁇ ) 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene- Represents a 2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and each hydrogen atom in the group independently represents a fluorine atom, a —CF 3 group, or a carbon atom number. 1 to 10 al
  • Z 201 and Z 202 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, — CH 2 CH 2 —, —CF 2 CF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO —, —CH 2 —OCO—, —CY 1 ⁇ CY 2 — (wherein Y 1 and Y 2 each independently represents a fluorine atom or a hydrogen atom), —C ⁇ C— or a single bond
  • n 201 represents 0, 1 or 2, and 0 or 1 is preferable. However, when there are a plurality of M 202 and Z 202 , they may be different or the same.
  • It may contain at least one polymerizable compound represented by formula (P), preferably 1 to 5 types, more preferably 1 to 3 types.
  • the content of the general formula (P) is preferably 0.01 to 2.00% by mass, more preferably 0.05 to 1.00% by mass, and 0.10 to 0.50% by mass. It is particularly preferred.
  • the ring structure between Sp 201 and Sp 202 is preferably a formula (XXa-1) to a formula (XXa-5),
  • the formula (XXa-1) to the formula (XXa-3) are more preferable, and the formula (XXa-1) or the formula (XXa-2) is particularly preferable.
  • both ends of the equation shall be connected to Sp 201 or Sp 202 .
  • the polymerizable compound represented by the general formula (P) containing these skeletons is suitable for a PSA type liquid crystal display element because of its alignment regulating power after polymerization, and a good alignment state is obtained, thereby suppressing display unevenness. There is an effect that does not occur at all.
  • the polymerizable monomer is preferably a compound represented by the formula (XX-1) to the general formula (XX-10), more preferably the formula (XX-1) to the formula (XX-4).
  • Sp xx represents an alkylene group having 1 to 8 carbon atoms or —O— (CH 2 ) s — (wherein s represents an integer of 2 to 7) And an oxygen atom is bonded to the ring).
  • the hydrogen atom in the 1,4-phenylene group is further —F, —Cl, —CF 3 , —CH 3 , formula (R-1) To optionally substituted by any of formulas (R-15).
  • n 201 is 1, for example, a polymerizable compound such as the formula (P31) to the formula (P48) is preferable.
  • the hydrogen atoms in the 1,4-phenylene group and the naphthalene group in the formula (P31) to the formula (P48) are further represented by —F, —Cl, —CF 3 , —CH 3 , and a formula from the formula (R-1). It may be substituted by any of (R-15).
  • the polymerizable compound represented by the general formula (P) containing these skeletons is suitable for a PSA type liquid crystal display element because of its alignment regulating power after polymerization, and a good alignment state is obtained, thereby suppressing display unevenness. There is an effect that does not occur at all.
  • n 201 is 1 and there are a plurality of formulas (R-1) or (R-2), for example, a polymerizable compound such as formula (P301) to formula (P316) preferable.
  • the hydrogen atoms in the 1,4-phenylene group and naphthalene group in the formulas (P301) to (P316) may be further substituted with —F, —Cl, —CF 3 , or —CH 3 .
  • polymerizable compounds represented by the general formula (P) for example, polymerizable compounds such as formula (Ia-1) to formula (Ia-31) are also preferable.
  • the liquid crystal display element using the liquid crystal composition of the present invention has no display defects or is suppressed and has excellent display quality and high response speed.
  • an active matrix liquid crystal display element for example, a TN type , OCB type, VA type, VA-IPS type, PSVA type, PSA type, FFS type, IPS type or ECB type.
  • the PSVA type and the PSA type are substantially synonymous.
  • the liquid crystal composition of the present invention containing a polymerizable compound is a polymer-stabilized VA type prepared by polymerizing a polymerizable compound contained in the liquid crystal composition with or without voltage application,
  • a liquid crystal display element such as a PSA type, a TN type, an OCB type, an ECB type, an IPS type, an FFS type, or a VA-IPS type can be provided.
  • T ni Nematic phase-isotropic liquid phase transition temperature (° C.) ⁇ n: Refractive index anisotropy at 25 ° C. ⁇ : Dielectric anisotropy at 25 ° C. ⁇ 1 : Rotational viscosity at 25 ° C. (mPa ⁇ s) VHR (UV): A 180 UV high pressure mercury lamp (J) Voltage holding ratio with respect to the initial applied voltage after irradiation (%), measurement conditions 1V, 60 Hz, 60 ° C., illuminance 100 mW / cm 2 at 365nm The cell thickness of the test panel is 3.5 ⁇ m, the alignment film for vertical alignment is JALS2096, and the alignment film for horizontal alignment is AL1051.
  • VHR Voltage holding ratio (%) with respect to the initial applied voltage after heating at 100 ° C. for 26 hours, measurement conditions are 1 V, 60 Hz, 60 ° C., test panel cell thickness is 3.5 ⁇ m, vertical alignment
  • the alignment film for use is JALS2096, and the alignment film for horizontal alignment is AL1051.
  • the following LC-A liquid crystal composition was prepared, and its physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 1 a liquid crystal composition LC-1 prepared by adding 0.20 parts by weight of the compound represented by the formula (I-1) to 100 parts by weight of the liquid crystal composition LC-A was prepared.
  • Example 2 a liquid crystal composition LC-2 in which 0.10 parts by weight of the compound represented by the formula (I-1) was added to 100 parts by weight of the liquid crystal composition LC-A was prepared.
  • Example 3 a liquid crystal composition LC-3 in which 0.05 part by weight of the compound represented by the formula (I-1) was added to 100 parts by weight of the liquid crystal composition LC-A was prepared.
  • a liquid crystal composition containing 100 parts by weight of LC-A was used as Comparative Example 1. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 1 to 3 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 1. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-1, LC-2, and LC-3 were the same as the values of the liquid crystal composition LC-A.
  • Comparative Example 2 Examples 4 to 6
  • the following LC-B liquid crystal composition was prepared, and its physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 4 a liquid crystal composition LC-4 was prepared by adding 0.05 parts by weight of the compound represented by (I-8) to 100 parts by weight of the liquid crystal composition LC-B.
  • Example 5 a liquid crystal composition LC-5 was prepared by adding 0.05 parts by weight of the compound represented by the formula (I-2-1) to 100 parts by weight of the liquid crystal composition LC-B.
  • Example 6 a liquid crystal composition LC-6 in which 0.05 part by weight of the compound represented by the formula (I-6) was added to 100 parts by weight of the liquid crystal composition LC-B was prepared.
  • a liquid crystal composition containing 100 parts by weight of LC-B was used as Comparative Example 2. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Example 7 with respect to 100 parts by weight of the liquid crystal composition LC-C, 0.12 parts by weight of the compound represented by the formula (I-1) and 0% of the compound represented by the formula (I-6) A liquid crystal composition LC-7 added with 0.08 parts by weight was prepared.
  • Example 8 with respect to 100 parts by weight of the liquid crystal composition LC-C, 0.12 parts by weight of the compound represented by the formula (I-6) and 0% of the compound represented by the formula (I-5) A liquid crystal composition LC-8 added with 0.08 parts by weight was prepared.
  • Example 9 with respect to 100 parts by weight of the liquid crystal composition LC-C, 0.08 parts by weight of the compound represented by the formula (I-1) and 0% of the compound represented by the formula (I-5) A liquid crystal composition LC-9 added with 12 parts by weight was prepared. A liquid crystal composition containing 100 parts by weight of LC-C was used as Comparative Example 3. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 7 to 9 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 3. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-7, LC-8, and LC-9 were the same as the values of the liquid crystal composition LC-C.
  • the following LC-D liquid crystal composition was prepared and measured for physical properties. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 10 a liquid crystal composition LC-10 in which 0.30 parts by weight of the compound represented by the formula (I-1) was added to 100 parts by weight of the liquid crystal composition LC-D was prepared.
  • Example 11 with respect to 100 parts by weight of the liquid crystal composition LC-D, 0.30 parts by weight of the compound represented by the formula (I-1) and the compound represented by the formula (i-28-1) A liquid crystal composition LC-11 added with 0.10 parts by weight of was prepared.
  • Example 12 with respect to 100 parts by weight of the liquid crystal composition LC-D, 0.30 parts by weight of the compound represented by the formula (I-1) and the compound represented by the formula (i-31-1) A liquid crystal composition LC-12 containing 0.10 parts by weight of was prepared.
  • a liquid crystal composition having 100 parts by weight of LC-D was used as Comparative Example 4. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 10 to 12 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 4. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-10, LC-11, and LC-12 were the same as those of the liquid crystal composition LC-D.
  • the following LC-E liquid crystal composition was prepared, and its physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 13 a liquid crystal composition LC-13 was prepared by adding 0.10 parts by weight of the compound represented by the formula (I-8) to 100 parts by weight of the liquid crystal composition LC-E.
  • Example 14 for 100 parts by weight of the liquid crystal composition LC-E, 0.05 part by weight of the compound represented by the formula (I-8) and the compound represented by the formula (i-2-C1) A liquid crystal composition LC-15 added with 0.05 part by weight of was prepared.
  • a liquid crystal composition containing 100 parts by weight of LC-E was used as Comparative Example 5.
  • liquid crystal composition LC-E-2 was prepared by adding 0.10 parts by weight of the compound represented by formula (i-2-C1) to 100 parts by weight of liquid crystal composition LC-E. did.
  • the results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 13 to 14 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 5.
  • both VHR (UV) and VHR (HEAT) were better than Comparative Examples 5 and 6. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-13 and LC-14 were the same as the values of the liquid crystal composition LC-E.
  • the following LC-F liquid crystal composition was prepared, and its physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 15 a liquid crystal composition LC-15 in which 0.20 parts by weight of the compound represented by the formula (I-6) was added to 100 parts by weight of the liquid crystal composition LC-F was prepared.
  • Example 16 with respect to 100 parts by weight of the liquid crystal composition LC-F, 0.10 parts by weight of the compound represented by the formula (I-6) and 0% of the compound represented by the formula (ia-2) Liquid crystal composition LC-16 added with 10 parts by weight was prepared.
  • Example 17 with respect to 100 parts by weight of the liquid crystal composition LC-F, 0.20 parts by weight of the compound represented by the formula (I-6) and 0% of the compound represented by the formula (ia-2) Liquid crystal composition LC-17 added with 10 parts by weight was prepared.
  • a liquid crystal composition containing 100 parts by weight of LC-F was used as Comparative Example 7. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 15 to 17 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 7. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-15, LC-16, and LC-17 were the same as the values of the liquid crystal composition LC-F. (Examination of response speed) When the response speeds of the liquid crystal display elements using the liquid crystal compositions LC-1 to LC-17 were measured, the response speed was sufficiently high for television applications.
  • the cell thickness was 3.5 ⁇ m
  • the alignment film was JALS2096
  • the response speed measurement conditions were Von 6 V, Voff 1 V, measurement temperature 25 ° C.
  • DTS703 from AUTRONIC-MELCHERS.
  • a PSVA liquid crystal display device was manufactured using a liquid crystal composition prepared with 99.6% by mass of LC-1 and 0.4% by mass of formula (XX-4) as a polymerizable monomer. It was confirmed that there was no defect and the response was sufficiently fast. Further, when a PSVA liquid crystal display element was manufactured using a liquid crystal composition in which LC-1 was replaced with LC-2 to LC17, it was confirmed that there was no display defect and the response was sufficiently fast. Further, a composition in which 20 ppm of (H-14) was added as an antioxidant to a liquid crystal composition prepared with 99.7% of LC-1 and 0.3% of (XX-4) as a polymerizable monomer.
  • a PSVA type liquid crystal display element was fabricated using the same, and it was confirmed that there was no display defect and the response was sufficiently fast. Further, when a PSVA liquid crystal display element was manufactured using a liquid crystal composition in which LC-1 was replaced with LC-2 to LC17, it was confirmed that there was no display defect and the response was sufficiently fast.
  • a PSVA liquid crystal display device was produced using a liquid crystal composition prepared with 99.6% by mass of LC-1 and 0.4% by mass of the formula (P-302) as a polymerizable monomer. It was confirmed that there was no defect and the response was sufficiently fast.
  • Example 19 a liquid crystal composition LC-19 was prepared by adding 0.10 parts by weight of the compound represented by the formula (I-1) to 100 parts by weight of the liquid crystal composition LC-G.
  • Example 20 a liquid crystal composition LC-20 was prepared by adding 0.05 parts by weight of the compound represented by formula (I-1) to 100 parts by weight of the liquid crystal composition LC-G.
  • Example 21 a liquid crystal composition LC-21 in which 0.02 parts by weight of the compound represented by the formula (I-1) was added to 100 parts by weight of the liquid crystal composition LC-G was prepared.
  • Example 22 with respect to 100 parts by weight of the liquid crystal composition LC-G, 0.10 parts by weight of the compound represented by the formula (I-1) and the formula (i-28-1) A liquid crystal composition LC-22 added with 0.10 parts by weight of the compound was prepared.
  • Example 23 with respect to 100 parts by weight of the liquid crystal composition LC-G, 0.05 part by weight of the compound represented by the formula (I-1) and the formula (i-28-1) A liquid crystal composition LC-23 to which 0.05 part by weight of the compound was added was prepared.
  • Example 24 with respect to 100 parts by weight of the liquid crystal composition LC-G, 0.02 parts by weight of the compound represented by the formula (I-1) and the formula (i-28-1) A liquid crystal composition LC-24 to which 0.02 part by weight of the compound was added was prepared. A liquid crystal composition containing 100 parts by weight of LC-G was used as Comparative Example 9. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 19 to 24 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 8. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-19 to LC-24 were the same as the values of the liquid crystal composition LC-G.
  • Examples 22 to 24 were confirmed to have higher VHR (UV) and VHR (HEAT) than when the compound represented by formula (I-1) was used alone.
  • Comparative Example 9, Examples 25 to 27 The following LC-H liquid crystal compositions were prepared and their physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • liquid crystal composition LC-25 was prepared by adding 0.02 part by weight of the compound represented by formula (I-5) to 100 parts by weight of liquid crystal composition LC-H.
  • liquid crystal composition LC-25 was prepared by adding 0.05 part by weight of the compound represented by formula (I-5) to 100 parts by weight of liquid crystal composition LC-H.
  • a liquid crystal composition LC-27 was prepared by adding 0.10 parts by weight of the compound represented by the formula (I-5) to 100 parts by weight of the liquid crystal composition LC-H.
  • a liquid crystal composition containing 100 parts by weight of LC-H was used as Comparative Example 9. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 25 to 27 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 9. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-25, LC-26, and LC-27 were the same as the values of the liquid crystal composition LC-H.
  • the following LC-I liquid crystal composition was prepared, and its physical properties were measured. The composition of the liquid crystal composition and the results of its physical properties were as shown in the table.
  • Example 28 with respect to 100 parts by weight of the liquid crystal composition LC-I, 0.05 part by weight of the compound represented by the formula (I-8) and the compound represented by the formula (I-2-1) A liquid crystal composition LC-28 containing 0.03 part by weight of was prepared.
  • Example 29 with respect to 100 parts by weight of the liquid crystal composition LC-I, 0.03 parts by weight of the compound represented by the formula (I-8) and the compound represented by the formula (I-2-1) A liquid crystal composition LC-29 added with 0.05 part by weight of was adjusted.
  • Example 30 for 100 parts by weight of the liquid crystal composition LC-I, 0.02 parts by weight of the compound represented by the formula (I-8) and the compound represented by the formula (I-2-1) A liquid crystal composition LC-30 was prepared by adding 0.02 part by weight of the compound represented by formula (ii-1-21a) and 0.04 part by weight of the compound represented by formula (ii-1-21a). A liquid crystal composition having 100 parts by weight of LC-I was used as Comparative Example 10. The results of VHR (UV) and VHR (HEAT) are shown in the table.
  • Examples 28 to 30 had VHR (UV) and VHR (HEAT) sufficiently higher than those of Comparative Example 10. It was also confirmed that there was no display unevenness.
  • the values of T ni , ⁇ n, ⁇ , and ⁇ 1 of the liquid crystal compositions LC-28, LC-29, and LC-30 were the same as the values of the liquid crystal composition LC-K.
  • no drop mark was generated when a drop injection (ODF) method was performed when the liquid crystal composition was injected into the substrate. Further, no alignment unevenness occurred in these liquid crystal display elements. Furthermore, it was confirmed that no seizure occurred during driving.
  • ODF drop injection
  • the liquid crystal composition of the present invention has sufficient rotational viscosity ( ⁇ 1 ) without lowering the refractive index anisotropy ( ⁇ n) and nematic phase-isotropic liquid phase transition temperature (T ni ). It was found that sufficiently high VHR (UV) and VHR (HEAT) can be obtained without causing drop marks and alignment unevenness. It was confirmed that the liquid crystal display element using the liquid crystal composition of the present invention has no display defect or is suppressed and has an excellent display quality and a high response speed.

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Abstract

La présente invention concerne une composition de cristaux liquides qui comprend un ou plusieurs composés représentés par la formule générale (I) et un ou plusieurs composés représentés par la formule générale (II). Les composés représentés par la formule générale (I) sont des composés ayant chacun une structure présentant un groupe hydroxy en leur sein. Grâce à l'inclusion d'un ou de plusieurs composés représentés par la formule générale (I) et d'un ou de plusieurs composés représentés par la formule générale (II), cette composition de cristaux liquides peut présenter une anisotropie diélectrique améliorée et une faible viscosité. L'utilisation de ladite composition de cristaux liquides permet d'offrir un élément d'affichage à cristaux liquides qui présente un contraste élevé, une réactivité à grande vitesse, une résistance élevée à la lumière, et une excellente qualité d'affichage sans rémanence d'image ni ruptures d'affichage. Ladite composition de cristaux liquides est extrêmement pratique à utiliser comme composition de cristaux liquides pour les affichages à cristaux liquides et est efficace pour obtenir un contraste élevé, une réactivité à grande vitesse, et une fiabilité élevée de la qualité.
PCT/JP2018/018075 2017-05-18 2018-05-10 Composition de cristaux liquides et élément d'affichage à cristaux liquides utilisant ladite composition WO2018212059A1 (fr)

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CN112824491A (zh) * 2019-11-21 2021-05-21 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824495A (zh) * 2019-11-21 2021-05-21 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112852444A (zh) * 2019-11-27 2021-05-28 Dic株式会社 液晶组合物和使用其的液晶显示元件
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CN112824495B (zh) * 2019-11-21 2023-01-24 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824495A (zh) * 2019-11-21 2021-05-21 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824491B (zh) * 2019-11-21 2022-12-30 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824498B (zh) * 2019-11-21 2022-12-30 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824491A (zh) * 2019-11-21 2021-05-21 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112824498A (zh) * 2019-11-21 2021-05-21 江苏和成显示科技有限公司 一种液晶组合物及其应用
CN112852444A (zh) * 2019-11-27 2021-05-28 Dic株式会社 液晶组合物和使用其的液晶显示元件
JP2021084949A (ja) * 2019-11-27 2021-06-03 Dic株式会社 液晶組成物およびそれを用いた液晶表示素子
JP2021084870A (ja) * 2019-11-27 2021-06-03 Dic株式会社 安定剤化合物、液晶組成物および表示素子
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