WO2020121639A1 - Composition de cristaux liquides contenant un composé polymérisable, élément d'affichage à cristaux liquides et composé polymérisable - Google Patents

Composition de cristaux liquides contenant un composé polymérisable, élément d'affichage à cristaux liquides et composé polymérisable Download PDF

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WO2020121639A1
WO2020121639A1 PCT/JP2019/039987 JP2019039987W WO2020121639A1 WO 2020121639 A1 WO2020121639 A1 WO 2020121639A1 JP 2019039987 W JP2019039987 W JP 2019039987W WO 2020121639 A1 WO2020121639 A1 WO 2020121639A1
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group
formula
liquid crystal
mass
crystal composition
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Japanese (ja)
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麻里奈 後藤
雄一 井ノ上
雅弘 堀口
青木　良夫
卓央 林
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Dic株式会社
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Priority to JP2020524255A priority Critical patent/JP6849151B2/ja
Priority to CN201980064232.4A priority patent/CN112789344A/zh
Publication of WO2020121639A1 publication Critical patent/WO2020121639A1/fr

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    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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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
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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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    • C09K19/10—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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    • C09K19/08—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
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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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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
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    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a liquid crystal composition containing a polymerizable compound, a liquid crystal display device using the same, and a polymerizable compound.
  • a liquid crystal composition containing a polymerizable compound is referred to as a polymerizable compound-containing liquid crystal composition.
  • the polymerizable compound means a compound having a polymerizable group.
  • a PSA (Polymer Sustained Alignment) type liquid crystal display element has a structure in which a polymer structure is formed in the cell to control the pretilt angle of liquid crystal molecules, and is used as a liquid crystal display element because of its high-speed response and high contrast. Has been transformed.
  • a PSA type liquid crystal display device is manufactured by injecting a liquid crystal composition containing a polymerizable compound between substrates, irradiating ultraviolet rays in a state in which a voltage is applied to align liquid crystal molecules to polymerize the polymerizable compound. This is done by fixing the orientation of liquid crystal molecules.
  • a polymerizable compound-containing liquid crystal composition suitable for this in Patent Documents 1 to 3, the following compound (A) having a biphenyl skeleton or a compound (B) having a terphenyl skeleton as a polymerizable compound is described. , A liquid crystal composition containing a compound (C) having a cinnamic acid skeleton is disclosed.
  • the problem to be solved by the present invention is that the precipitation of a polymerizable compound is suppressed, sufficient polymerization can be performed at a high speed, and a high voltage holding ratio (VHR) and high tilt stability can be achieved at the same time. It is to provide a liquid crystal composition, a liquid crystal display device using the same, and a polymerizable compound suitable for preparation of the polymerizable compound-containing liquid crystal composition.
  • a i1 and A i2 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-.) (B) 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced by —N ⁇ ) and (c).
  • P i3 —S i3 —, P i1 , P i2, and P i3 are each independently the formula (R-1) to the formula (R-9).
  • R 11 , R 12 , R 13 , R 14 and R 15 each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • m r5 , m r7 , n r5 and n r7 each independently represent a group selected from 0, 1, or 2
  • S i1 , S i2 and S i3 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH 2 — in the alkylene group or two or more not adjacent to each other.
  • -CH 2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other
  • R i1 represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • n i1 represents 1, 2 or 3
  • a i2 , S i2 , P i3 and/or S i3 they may be the same or different.
  • the liquid crystal composition containing 1 type or 2 types or more of the polymeric compound represented by these.
  • the present invention also provides a liquid crystal display device, a liquid crystal display device for active matrix driving, a PSA mode, a PSVA mode, which uses a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i).
  • a liquid crystal display device for PS-IPS mode or PS-FFS mode is provided.
  • the present invention provides a polymerizable compound represented by the above general formula (i).
  • a low viscosity ( ⁇ ), a small rotational viscosity ( ⁇ 1) and a large value are obtained without decreasing the refractive index anisotropy ( ⁇ n) and the nematic phase-isotropic liquid phase transition temperature (Tni).
  • ⁇ refractive index anisotropy
  • Tni nematic phase-isotropic liquid phase transition temperature
  • the liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention has a small residual amount of unreacted polymerizable compound, high voltage holding ratio (VHR), high-speed response, and high tilt stability. It is possible to exhibit excellent display quality in which there is no display defect such as alignment defect due to change in pretilt angle or display defect such as burn-in.
  • total amount means “total mass”
  • unit “%” of the content of each compound means “% by mass”.
  • the polymerizable compound-containing liquid crystal composition of the present invention has the general formula (i):
  • a i1 and A i2 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-.) (B) 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced by —N ⁇ ) and (c).
  • P i3 —S i3 —, P i1 , P i2, and P i3 are each independently the formula (R-1) to the formula (R-9).
  • R 11 , R 12 , R 13 , R 14 and R 15 each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • m r5 , m r7 , n r5 and n r7 each independently represent a group selected from 0, 1, or 2
  • S i1 , S i2 and S i3 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH 2 — in the alkylene group or two or more not adjacent to each other.
  • -CH 2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other
  • R i1 represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • n i1 represents 1, 2 or 3
  • a liquid crystal composition containing one or more polymerizable compounds represented by the formula (1) When there are a plurality of A i2 , S i2 , P i3 and/or S i3 , they may be the same or different.
  • the precipitation of the polymerizable compound represented by the general formula (i) is small, the polymerization rate of the polymerization compound is sufficiently high, and the polymerization reaction proceeds sufficiently.
  • a liquid crystal composition containing a polymerizable compound having a small residual amount of the compound can be obtained.
  • the polymerizable compound-containing liquid crystal composition of the present invention can have the above-mentioned characteristics while satisfying various characteristics required for a liquid crystal display device such as high-speed response, high contrast, and low power consumption. Further, by using the polymerizable compound-containing liquid crystal composition of the present invention, it is possible to suppress the occurrence of display defects (burn-in) due to changes in the pretilt angle, and to simultaneously achieve high voltage holding ratio (VHR) and high tilt stability. An achievable liquid crystal display device can be manufactured.
  • the polymerizable compound-containing liquid crystal composition of the present invention is useful for producing a PSA-type or PSVA-type liquid crystal display device having excellent reliability after the ultraviolet irradiation step. Further, according to the polymerizable compound-containing liquid crystal composition of the present invention, it is possible to control the tilt angle and the residual amount of the polymerizable compound, so that the energy cost for manufacturing a liquid crystal display device can be optimized and reduced. Therefore, the production efficiency of the liquid crystal display device can be easily improved. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal display device using the same are very useful.
  • Polymerizable compound The polymerizable compound essentially contained in the present invention is represented by the above general formula (i).
  • a i1 and A i2 are (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-.) (B) 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced by —N ⁇ ) and (c).
  • the naphthalenediyl group which A i1 and A i2 can take is one of two positions selected from the 1 to 8 positions, which is bonded to S i1 or S i2 and, on the other hand, in the above general formula (i). It is a group that binds to a structural site represented by the following formula (hereinafter referred to as a specific structural site).
  • naphthalenediyl group examples include naphthalene-1,2-diyl group, naphthalene-1,3-diyl group, naphthalene-1,4-diyl group, naphthalene-1,5-diyl group, naphthalene-1,6-diyl group.
  • the 1,2,3,4-tetrahydronaphthalenediyl group which A i1 and A i2 can have is a bond with S i1 or S i2 at one of two positions selected from 1 to 8 and the other. It is a group that binds to the above-mentioned specific structural site in the general formula (i).
  • Examples of the 1,2,3,4-tetrahydronaphthalenediyl group include a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and 1,2,3,4-tetrahydronaphthalene-1,4-diyl group. Group, 1,2,3,4-tetrahydronaphthalene-1,5-diyl group and the like.
  • the decahydronaphthalenediyl group which A i1 and A i2 can take is one of two positions selected from the 1 to 10 positions, which is bonded to S i1 or S i2, and the other is a general formula (i). It is a group that binds to the above-mentioned specific structure site.
  • Examples of the decahydronaphthalenediyl group include a decahydronaphthalene-2,6-diyl group.
  • group (a), group (b) and group (c) are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen, a cyano group or a nitro group. Alternatively, it may be substituted with P i3 ⁇ S i3 ⁇ .
  • a i1 and A i2 each independently represent one of the following structures.
  • R i2 and R i3 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a fluorine atom or P i3 —S i3 —)
  • a i1 and A i2 are each independently 1,4-phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, 2-methoxy-1,4- More preferably, it is a phenylene group, 3-methoxy-1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group or naphthalene-2,6-diyl group. , 1,4-phenylene group, 2-fluoro-1,4-phenylene group or 3-fluoro-1,4-phenylene group is more preferable, and 1,4-phenylene group is particularly preferable.
  • the number of rings represented by A i1 is one.
  • the number of rings represented by A i2 is one or two or more depending on the number of n i1 .
  • the polymerizable compound represented by the general formula (i) has such a structure, so that the ring represented by A i1 in the general formula (i) such as the compound (C) described above has 2 rings. It is presumed that the solubility is improved as compared with one or more polymerizable compounds, and as a result, precipitation is less likely to occur. If the A i2 is more, all the plurality of A i2 may be the same group or may be different groups.
  • P i1 , P i2 and P i3 each independently represent a group selected from the above formulas (R-1) to (R-9).
  • P i1 , P i2 and P i3 may all be the same polymerizable group (formula (R-1) to (R-9)) or at least one group may be different. , All may be different polymerizable groups.
  • Both P i1 and P i2 may be the same polymerizable group or different polymerizable groups, but when P i1 and P i2 are the same polymerizable group, the compound represented by the general formula (i) It has an advantage that the compound represented by is easy to synthesize.
  • the P i3 there are multiple all of the plurality of P i3 may be the same group or may be different groups.
  • P i1 , P i2 and P i3 are each independently a formula (R-1), a formula (R-2), a formula (R-3) and a formula (R-4).
  • P i1 , P i2 and P i3 at least one of P i1 and P i2 is preferably the formula (R-1), more preferably an acryloxy group or a methacryloxy group, A methacryloxy group is more preferred, and it is particularly preferred that both P i1 and P i2 are methacryloxy groups. This is because when both P i1 and P i2 are methacryloxy groups, display defects due to changes in the pretilt angle are less likely to occur when used in a liquid crystal display element. Also, the degree of polymerization of the polymerizable compound can be increased as compared with the case where both P i1 and P i2 are acryloxy groups.
  • R 11 , R 12 , R 13 , R 14 and R 15 in the formulas (R-1) to (R-9) each independently have 1 to 5 carbon atoms. Represents either an alkyl group, a fluorine atom or a hydrogen atom.
  • R 11 , R 12 , R 13 , R 14 and R 15 are each independently preferably a methyl group or a hydrogen atom, and are hydrogen atoms when the polymerization rate of the polymerizable compound is important. Is preferred, and a methyl group is preferred when importance is attached to reduction of display defects due to changes in the pretilt angle.
  • n r5 , n r5 and n r7 in formulas (R-1) to (R-9) each independently represent 0, 1 or 2.
  • S i1 , S i2 and S i3 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms.
  • S i1 , S i2 and S i3 are each independently preferably a single bond or an alkylene group having 1 to 5 carbon atoms, and particularly preferably a single bond.
  • S i1 , S i2, and S i3 are single bonds, the residual amount of the polymerizable compound after the irradiation of ultraviolet rays is sufficiently small, and display defects due to changes in the pretilt angle are less likely to occur. If S i2 have multiple all of the plurality of S i2 may be the same or different all S i2 or at least one S i2.
  • ni1 represents 1, 2 or 3, but it is more preferably 1 or 2 since the solubility in the liquid crystal composition is good, and the solubility in the liquid crystal composition is more preferable. It is particularly preferable that it is 1, since it is more favorable.
  • R i1 represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and among them, R i1 is a methyl group, an ethyl group, a fluorine atom or a hydrogen atom. Is preferred, and a hydrogen atom is more preferred.
  • the lower limit of the content of the polymerizable compound represented by the general formula (i) is preferably 0.01%, preferably 0.02%, and 0.03%.
  • 0.04% is preferable, 0.05% is preferable, 0.06% is preferable, 0.07% is preferable, 0.08% is preferable, 0.09% is preferable, 0.1% is preferable.
  • the upper limit of the content of the polymerizable compound represented by formula (i) is preferably 5%, 4.5%, preferably 4%, 3.5.
  • % Is preferred 3% is preferred, 2.5% is preferred, 2% is preferred, 1.5% is preferred, 1% is preferred, 0.95% is preferred, 0.9% is preferred, 0.85 % Is preferred, 0.8% is preferred, 0.75% is preferred, 0.7% is preferred, 0.65% is preferred, 0.6% is preferred, 0.55% is preferred, 0.5% Is preferable, 0.45% is preferable, and 0.4% is preferable.
  • the content of the polymerizable compound represented by the general formula (i) in the polymerizable compound-containing liquid crystal composition is 0. It is preferably within the range of 0.2% to 1.5%.
  • the content of the polymerizable compound represented by the general formula (i) in the polymerizable compound-containing liquid crystal composition is 0.01% to 1.0%. It is preferably within the range of %.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains a plurality of polymerizable compounds represented by the general formula (i), the content of each is within the range of 0.01% to 0.6%. Is preferred. Therefore, in order to solve all of these problems, it is particularly desirable to adjust the polymerizable compound represented by the general formula (i) in the range of 0.1% to 1.0%.
  • polymerizable compound represented by the general formula (i) specifically, compounds represented by the general formulas (i-1) to (i-33) are preferable.
  • R i4 and R i5 each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom.
  • R i4 and R i5 are each independently an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and among them, a methyl group or a hydrogen atom is preferable.
  • the compounds represented by the above general formulas (i-1) to (i-33) are more preferable, and in addition to the above-mentioned viewpoints, the compounds represented by the general formula (i-1) from the viewpoint of good tilt stability (hard to cause seizure)
  • the compounds represented by general formula (i-12), general formula (i-23) to general formula (i-26), or general formula (i-28) to general formula (i-33) are more preferable, and
  • the compounds of the general formula (i-1) to the general formula (i-5) is more preferable, and the compound represented by the general formula (i-25), the general formula (i-26), or the general formula (i-28) to the general formula (i-33) is more preferable, and the compound represented by the general formula (i-1).
  • the liquid crystal composition is a host liquid crystal to which the polymerizable compound represented by the general formula (i) is added, and contains at least the liquid crystal compound.
  • the liquid crystal composition preferably contains one kind or two or more kinds of compounds selected from the compounds represented by the general formulas (N-1), (N-2) and (N-3). These compounds correspond to dielectrically negative compounds (the sign of ⁇ is negative and the absolute value thereof is larger than 2).
  • each of R N11 , R N12 , R N21 , R N22 , R N31, and R N32 independently represents an alkyl group having 1 to 8 carbon atoms, and one of the alkyl groups or a non-adjacent group is present.
  • Two or more —CH 2 — of each may independently be 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 — present in this group or adjacent Two or more —CH 2 — which are not present may be replaced by —O—.)
  • (B) 1,4-phenylene group one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced with —N ⁇ ).
  • (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups, wherein the groups (a), (b), (c) and (d) are each independently cyano.
  • X N21 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, and n N11 +n N12 , n N21 +n N22 and n N31 +
  • the compounds represented by the general formulas (N-1), (N-2) and (N-3) are preferably compounds having a negative ⁇ and an absolute value larger than 3.
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 each independently have 1 to 10 carbon atoms.
  • 8 represents an alkyl group, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, —C ⁇ C—, —O—, —CO— , -COO- or -OCO-.
  • R N11 , R N12 , R N21 , R N22 , R N31, and R N32 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or 2 to 8 carbon atoms.
  • An alkenyl group having 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms is preferable, and 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 a carbon atom.
  • 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 2 to 3 carbon atoms. Is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 each have a linear carbon number of 1 to 5 when the ring structure to which they are bonded is a phenyl group (aromatic).
  • the alkyl group, the straight-chain alkoxy group having 1 to 4 carbon atoms and the alkenyl group having 4 to 5 carbon atoms are preferable.
  • RN11 , RN12 , RN21 , RN21 , RN22 , RN31 and RN32 are linear carbon atoms when the ring structure to which they are bonded is a saturated ring structure such as cyclohexane, pyran and dioxane.
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 preferably have a total of carbon atoms and oxygen atoms, if any, of 5 or less, and a straight chain. It is preferably in the form of a circle.
  • the alkenyl group is preferably selected from the 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 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-.)
  • B) 1,4-phenylene group one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced with —N ⁇ ).
  • (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups.
  • the above group (a), group (b), group (c) and group (d) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom.
  • a N11 , A N12 , A N21 , A N22 , A N31 and A N32 are preferably aromatic when it is required to independently increase ⁇ n, and fat is used to improve the response speed. It is preferably a family.
  • the above-mentioned group (a), group (b), group (c) and group (d) are trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group.
  • Z N11 , Z N12 , Z N21 , Z N22 , Z N31 and Z N32 are each independently a single bond or —CH 2.
  • X N21 represents a hydrogen atom or a fluorine atom, and among them, a fluorine atom is preferable.
  • T N31 represents —CH 2 — or an oxygen atom, and among them, an oxygen atom is preferable.
  • n N11 , n N12 , n N21 , n N22 , n N31 and n N32 are each independently an integer of 0 to 3. Represents.
  • n N11 +n N12 , n N21 +n N22, and n N31 +n N32 are 1, 2 or 3 independently.
  • n N11 +n N12 , n N21 +n N22, and n N31 +n N32 are preferably 1 or 2, and at this time, a combination in which n N11 is 1 and n N12 is 0, n N11 is 2 and n N12 is 0.
  • the lower limit of the preferred content of the compound represented by formula (N-1) based on the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.
  • the lower limit of the preferred content of the compound represented by formula (N-2) based on the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.
  • the lower limit of the preferred content of the compound represented by formula (N-3) based on the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.
  • the lower limit value and the upper limit value are low.
  • the lower limit value is low and the upper limit value is low.
  • the lower limit value is high and the upper limit value is high.
  • Examples of the compound represented by the general formula (N-1) include compounds represented by the following general formulas (N-1a) to (N-1g).
  • R N11 and R N12 are as defined R N11 and R N12 in the general formula (N-1), n Na11 represents 0 or 1, n NB11 is 1 or 2, n NC11 is 0 or 1, n Nd11 represents 1 or 2, n Ne11 represents 1 or 2, n Nf12 represents 1 or 2, n Ng11 represents 1 or 2, and A Ne11 represents trans-1,4.
  • a Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group
  • n Nd11 Is 2 at least one of A Ng11 represents a 1,4-cyclohexenylene group
  • Z Ne11 represents a single bond or ethylene, but at least one existing in the molecule represents ethylene, and a plurality of them in the molecule.
  • the existing A Ne11 , Z Ne11 , and/or A Ng11 may be the same or different.
  • the compound represented by the general formula (N-1) is a compound selected from the group of compounds represented by the general formulas (N-1-1) to (N-1-21). Is preferred.
  • the compound represented by the general formula (N-1-1) is the following compound.
  • R N111 and R N112 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group, pentyl group or vinyl group.
  • R N112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-1) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the formula (N-1-1) is preferably set higher when the improvement of ⁇ is important, and is higher when the solubility at low temperature is important.
  • the effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-1) with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%.
  • the preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.
  • the compound represented by the general formula (N-1-1) is a compound selected from the group of compounds represented by the formulas (N-1-1.1) to (N-1-1.25). Are preferred, and compounds represented by formulas (N-1-1.1) to (N-1-1.4) are preferred, and formulas (N-1-1.1) and (N-1) Compounds represented by -1.3) are preferred.
  • the compounds represented by the formulas (N-1-1.1) to (N-1-1.25) can be used alone or in combination.
  • the lower limit of the preferable content of the compound alone or with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, 15%, 17%, 20%. Yes, 23%, 25%, 27%, 30%, 33%, 35%.
  • the preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.
  • the compound represented by the general formula (N-1-2) is the following compound.
  • R N121 and R N122 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group or a pentyl group.
  • R N122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group. preferable.
  • the compound represented by the general formula (N-1-2) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-2) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important.
  • the effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-2) with respect to the total amount of the liquid crystal composition is 5%, 7%, 10%, and 13%. , 15%, 17%, 20%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37% , 40% and 42%.
  • the preferable upper limit of the content is 50%, 48%, 45%, 43%, 40%, 38%, 35% with respect to the total amount of the liquid crystal composition. Yes, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10% Yes, 8%, 7%, 6%, 5%.
  • the compound represented by the general formula (N-1-2) is a compound selected from the group of compounds represented by the formula (N-1-2.1) to the formula (N-1-2.25). Are preferred, and formula (N-1-2.3) to formula (N-1-2.7), formula (N-1-2.10), formula (N-1-2.11), formula (N -1-2.13) and the compound represented by the formula (N-1-2.20) are preferable, and when the improvement in ⁇ is emphasized, the compounds represented by the formula (N-1-2.3)
  • the compound represented by (N-1-2.7) is preferable, and when importance is attached to the improvement of Tni, the formula (N-1-2.10), the formula (N-1-2.11) and the formula (N-1-2.11)
  • the compound represented by formula (N-1-2.13) is preferable, and the compound represented by formula (N-1-2.20) is preferable when the improvement in response speed is emphasized.
  • the compounds represented by formulas (N-1-2.1) to (N-1-2.25) can be used alone or in combination, but the total amount of the liquid crystal composition is
  • the lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20% and 23%. Yes, 25%, 27%, 30%, 33%, 35%.
  • the preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.
  • the compound represented by the general formula (N-1-3) is the following compound.
  • R N131 and R N132 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group. ..
  • the compound represented by the general formula (N-1-3) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the formula (N-1-3) is preferably set higher when the improvement of ⁇ is important, and is higher when the solubility at low temperature is important.
  • the effect is high when the content is set high, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-3) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.21). Are preferably the compounds represented by the formulas (N-1-3.1) to (N-1-3.7) and the formula (N-1-3.21), and the compounds represented by the formula (N-1 -3.1), formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and formula (N-1-3.6) The compounds represented by the formulas (N-1-3.3), (N-1-3.4) and (N-1-3.6) are preferred.
  • the compounds represented by the formula (N-1-3.1) to the formula (N-1-3.4), the formula (N-1-3.6) and the formula (N-1-3.21) are independent. Although they can be used in combination with each other or in combination, the combination of formula (N-1-3.1) and formula (N-1-3.2), formula (N-1-3.3) ), the formula (N-1-3.4) and the formula (N-1-3.6), and a combination of two or three kinds thereof is preferable, and the formula (N-1-3.3) and the formula (N ⁇ 1-3.4) and the formula (N-1-3.6) are preferably used in combination.
  • the lower limit of the preferable content of the compound alone or with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, 15%, 17%, 20%. is there.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-4) is the following compound.
  • R N141 and R N142 each independently represents the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N141 and R N142 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 4-5 preferably a methyl group, a propyl group, an ethoxy A group or butoxy group is preferred.
  • the compound represented by the general formula (N-1-4) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-4) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important, the content is preferably set higher.
  • the effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-4) based on the total amount of the liquid crystal composition is 3%, 5%, 7%, and 10%. , 13%, 15%, 17%, 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 11%, 10%, 8%.
  • the compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formulas (N-1-4.1) to (N-1-4.24). Are preferred, and compounds represented by formulas (N-1-4.1) to (N-1-4.4) are preferred. Formulas (N-1-4.1) and (N-1) -4.2) and compounds represented by the formula (N-1-4.4) are preferred.
  • the compounds represented by the formulas (N-1-4.1) to (N-1-4.24) can be used alone or in combination, but the amount is not limited to the total amount of the liquid crystal composition.
  • the lower limit of the preferable content of the compound alone or these compounds is 3%, 5%, 7%, 10%, 13%, 15%, 17%. , 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 11%, 10%, 8%.
  • the compound represented by the general formula (N-1-5) is the following compound.
  • R N151 and R N152 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N151 and R N152 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. Is preferred.
  • the compound represented by the general formula (N-1-5) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-5) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important.
  • the effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-5) based on the total amount of the liquid crystal composition is 5%, 8%, 10%, and 13%. , 15%, 17% and 20%.
  • the upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, 20% with respect to the total amount of the liquid crystal composition. Yes, 18%, 15%, 13%.
  • the compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formulas (N-1-5.1) to (N-1-5.12). Are preferred, and compounds represented by formula (N-1-5.1), formula (N-1-5.2) and formula (N-1-5.4) are preferred.
  • the compounds represented by formula (N-1-5.1), formula (N-1-5.2) and formula (N-1-5.4) may be used alone or in combination.
  • the lower limit of the preferable content of the compound alone or in the total amount of the liquid crystal composition is 5%, 8%, 10%, 13%, 15% with respect to the total amount of the liquid crystal composition. And 17% and 20%.
  • the upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, 20% with respect to the total amount of the liquid crystal composition. Yes, 18%, 15%, 13%.
  • the compound represented by the general formula (N-1-10) is the following compound.
  • R N1101 and R N1102 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • R N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-10) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-10) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important.
  • the effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-10) is 5%, 10%, 13%, and 15% with respect to the total amount of the liquid crystal composition. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-10) is a compound selected from the group of compounds represented by the formulas (N-1-10.1) to (N-1-10.14).
  • Compounds represented by Formulas (N-1-10.1) to (N-1-10.5) are preferred, and Formulas (N-1-10.1) and (N-1) are preferred.
  • Compounds represented by -10.2) are preferable.
  • the compounds represented by formula (N-1-10.1) and formula (N-1-10.2) can be used alone or in combination, but the total amount of the liquid crystal composition is not limited.
  • the lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-11) is the following compound.
  • R N1111 and R N1112 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • R N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-11) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-11) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important.
  • the effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-11) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-11) is a compound selected from the group of compounds represented by the formulas (N-1-11.1) to (N-1-11.14). Are preferred, and compounds represented by formulas (N-1-11.1) to (N-1-11.14) are preferred. Formulas (N-1-11.2) and (N-1) -11.4) is preferred.
  • the compounds represented by formula (N-1-11.2) and formula (N-1-11.4) can be used alone or in combination, but the total amount of the liquid crystal composition is not limited.
  • the lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compounds represented by the general formula (N-1-12) are the following compounds.
  • R N1121 and R N1122 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-12) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-12) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important.
  • the effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-12) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compounds represented by the general formula (N-1-13) are the following compounds.
  • R N1131 and R N1132 each independently have the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-13) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-13) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important, the content is preferably set higher. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-13) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-14) is the following compound.
  • R N1141 and R N1142 each independently have the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a methyl group, an ethyl group, a propyl group or a butyl group.
  • R N1142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-14) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-14) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-14) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-14) is a compound selected from the group of compounds represented by the formulas (N-1-14. 1) to (N-1-14.5). Are preferred, and compounds represented by formulas (N-1-14.1) to (N-1-14.3.) are preferred, and formulas (N-1-14.2) and (N-1) are preferred.
  • the compound represented by -14.3) is preferable.
  • the compound represented by the general formula (N-1-20) is the following compound.
  • R N1201 and R N1202 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1201 and R N1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-20) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-20) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-20) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-21) is the following compound.
  • R N1211 and R N1212 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1211 and R N1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-21) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-21) is preferably set higher when the improvement in ⁇ is important, and is included when the solubility at low temperature is important.
  • the effect is high when the amount is set high, and the effect is high when the content is set high when Tni is important. Furthermore, in the case of improving the drop mark and the seizure property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-21) with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.
  • the compound represented by the general formula (N-1-22) is the following compound.
  • R N1221 and R N1222 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N1221 and R N1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-22) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (N-1-22) is preferably set higher when the improvement of ⁇ is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (N-1-22) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%.
  • the preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 10%, 5%.
  • the compound represented by the general formula (N-1-22) is a compound selected from the group of compounds represented by the formula (N-1-22.12) to the formula (N-1-22.12). Are preferred, and compounds represented by formulas (N-1-22.1) to (N-1-22.5) are preferred, and compounds represented by formulas (N-1-22.1) to (N-1-) are preferred.
  • the compound represented by 22.4) is preferable.
  • the liquid crystal composition preferably contains one kind or two or more kinds of compounds represented by the general formula (L).
  • the compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound ( ⁇ value is ⁇ 2 to ⁇ 2). Therefore, the number of polar groups such as halogens in the molecule is preferably 2 or less, more preferably 1 or less, and preferably not.
  • R L1 and R L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — groups in the alkyl group are independent of each other. And may be substituted with —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO—, n L1 represents 0, 1, 2 or 3,
  • a L1 , A L2 and A L3 are each independently (a) a 1,4-cyclohexylene group (one —CH 2 — present in this group or two or more —CH 2 which are not adjacent to each other).
  • n L1 is 2 or 3 and a plurality of A L2 are present, they may be the same or different, and when n L1 is 2 or 3 and Z L2 is present a plurality of them. May be the same or different. However, compounds represented by formulas (N-1), (N-2) and (N-3) are excluded. )
  • the compounds represented by the general formula (L) may be used alone or in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the type of compound used is, for example, one type in one embodiment of the present invention. Alternatively, in another embodiment of the present invention, there are two types, three types, four types, five types, six types, seven types, eight types, nine types, and ten types. More than type.
  • the content of the compound represented by the general formula (L) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the drop mark, the burn-in, the dielectric constant. It is necessary to appropriately adjust according to required performance such as anisotropy.
  • the lower limit of the preferred content of the compound represented by formula (L) with respect to the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, and 40%. Yes, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.
  • the content of the compound represented by the formula (L) has a high lower limit and a high upper limit.
  • the lower limit of the content of the compound represented by formula (L) is preferably high and the upper limit thereof is preferably high.
  • the lower limit of the content of the compound represented by the formula (L) is low and the upper limit thereof is low.
  • both R L1 and R L2 are preferably alkyl groups when importance is placed on reliability, and alkoxy groups when importance is placed on reducing the volatility of the compound. Is preferred, and when importance is attached to the reduction of viscosity, at least one is preferably an alkenyl group.
  • the number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, and 0 or 1 is preferable, and 1 is preferable when the compatibility with other liquid crystal molecules is important. ..
  • R L1 and R L2 are a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group when the ring structure to which it is bonded is a phenyl group (aromatic). Preferred are an alkoxy group having 1 to 4 carbon atoms and an alkenyl group having 4 to 5 carbon atoms.
  • R L1 and R L2 are each a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group having a saturated ring structure such as cyclohexane, pyran or dioxane to which it is bonded.
  • each of R L1 and R L2 preferably has a total of 5 or less carbon atoms and oxygen atoms, if any, and is preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • n L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferable for improving the maximum temperature of the nematic phase, and 1 is preferable for achieving a balance between them. preferable. Further, in order to satisfy the properties required for the composition, it is preferable to combine compounds having different values of n L1 .
  • a L1 , A L2, and A L3 are preferably aromatic when it is required to increase ⁇ n, and are aliphatic in order to improve the response speed.
  • a L1 , A L2 and A L3 are each independently 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, 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-1,4-diyl group, naphthalene It is preferable to represent a -2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and it is more preferable to represent the following structure
  • Z L1 and Z L2 are preferably single bonds when the response speed is important.
  • the compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.
  • the compound represented by the general formula (L) is preferably a compound selected from the group of compounds represented by the general formulas (L-1) to (L-7).
  • the compound represented by the general formula (L-1) is the following compound.
  • R L11 and R L12 each independently represent the same meaning as R L1 and R L2 in the general formula (L).
  • 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.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the lower limit of the preferred content of the compound represented by formula (L-1) is 1%, 2%, 3%, or 5% with respect to the total amount of the liquid crystal composition. 7%, 10%, 15%, 20%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%.
  • the upper limit of the preferable content of the compound represented by the general formula (L-1) is 95%, 90%, 85%, and 80% with respect to the total amount of the liquid crystal composition. Yes, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% Yes, 25%.
  • the content of the compound represented by the general formula (L-1) has a high lower limit and a high upper limit.
  • the lower limit of the content of the compound represented by formula (L-1) is moderate and the upper limit thereof is moderate. Is preferred.
  • the lower limit and the upper limit of the content of the compound represented by the general formula (L-1) are preferably low.
  • 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-1-1).
  • R L12 has the same meaning as in the general formula (L-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-1-1.1) to the formula (L-1-1.3). Is preferably a compound represented by the formula (L-1-1.2) and/or the formula (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3) It is preferably a compound represented.
  • the lower limit of the preferred content of the compound represented by formula (L-1-1.3) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, and 5%. , 7%, and 10%.
  • the preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.
  • 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-1-2).
  • R L12 has the same meaning as in the general formula (L-1).
  • the lower limit of the preferred content of the compound represented by formula (L-1-2) with respect to the total amount of the liquid crystal composition is 1%, 5%, 10%, and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 35%.
  • the preferable upper limit of the content is 60%, 55%, 50%, 45%, 42%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 33%, 30%.
  • 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-1-2.4). Are preferred, and compounds represented by formula (L-1-2.2) to formula (L-1-2.4) are preferred. In particular, the compound represented by the formula (L-1-2.2) is preferable because it improves the response speed of the liquid crystal composition. Further, when obtaining a Tni higher than the response speed, it is preferable to use the compound represented by the formula (L-1-2.3) and/or the formula (L-1-2.4).
  • the content of the compound represented by the formula (L-1-2.3) or the formula (L-1-2.4) is not preferably 30% or more in order to improve the solubility at low temperature.
  • the lower limit of the preferred content of the compound represented by formula (L-1-2.2) with respect to the total amount of the liquid crystal composition is 10%, 15%, 18%, and 20%. , 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40%.
  • the preferable upper limit of the content is 60%, 55%, 50%, 45%, 43%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 32%, 30%, 27%, 25%, 22%.
  • the lower limit of the preferred total content of the compound represented by formula (L-1-1.3) and the compound represented by formula (L-1-2.2) is based on the total amount of the liquid crystal composition. 10%, 15%, 20%, 25%, 27%, 30%, 35%, 40%.
  • the preferable upper limit of the content is 60%, 55%, 50%, 45%, 43%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 32%, 30%, 27%, 25%, 22%.
  • 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).
  • R L13 and R L14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • R L13 and R L14 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 lower limit of the preferred content of the compound represented by formula (L-1-3) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17%, 20%, 23%, 25%, 30%.
  • the preferable upper limit of the content is 60%, 55%, 50%, 45%, 40%, 37%, 35% with respect to the total amount of the liquid crystal composition. Yes, 33%, 30%, 27%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10% is there.
  • the compound represented by the general formula (L-1-3) is a compound selected from the compound group represented by the formulas (L-1-3.1) to (L-1-3.13). Is preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) and/or the formula (L-1-3.4), It is preferably a compound represented by L-1-3.1) and/or a formula (L-1-3.3). In particular, the compound represented by the formula (L-1-3.1) is preferable because it improves the response speed of the liquid crystal composition.
  • the total of the compounds represented by the formula (L-1-3.3), the formula (L-1-3.4), the formula (L-1-3.11) and the formula (L-1-3.13) The content of is not preferably 20% or more in order to improve the solubility at low temperature.
  • the lower limit of the preferred content of the compound represented by formula (L-1-3.1) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, and 5%. , 7%, 10%, 13%, 15%, 18%, 20%.
  • the preferable upper limit of the content is 20%, 17%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition. Yes, 6%.
  • 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-1-4) and/or (L-1-5).
  • R L15 and R L16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • R L15 and R L16 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 lower limit of the preferred content of the compound represented by formula (L-1-4) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%.
  • the preferable upper limit of the content is 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the liquid crystal composition. is there.
  • the lower limit of the preferred content of the compound represented by formula (L-1-5) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%.
  • the preferable upper limit of the content is 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the liquid crystal composition. is there.
  • the compounds represented by the general formulas (L-1-4) and (L-1-5) are the compounds represented by the formulas (L-1-4.1) to (L-1-5.3).
  • a compound selected from the group is preferable, and a compound represented by the formula (L-1-4.2) and/or the formula (L-1-5.2) is preferable.
  • the lower limit of the preferred content of the compound represented by formula (L-1-4.2) is 1%, 2%, 3%, and 5% with respect to the total amount of the liquid crystal composition. , 7%, 10%, 13%, 15%, 18%, 20%.
  • the preferable upper limit of the content is 20%, 17%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition. Yes, 6%.
  • Formula (L-1-1.3), Formula (L-1-2.2), Formula (L-1-3.1), Formula (L-1-3.3), Formula (L-1- It is preferable to combine two or more compounds selected from the compounds represented by formula (3.4), formula (L-1-3.11) and formula (L-1-3.12), and formula (L-1 -1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4) and It is preferable to combine two or more compounds selected from the compounds represented by formula (L-1-4.2).
  • the preferred lower limit of the total content of these compounds is 1%, 2%, 3%, 5%, 7% with respect to the total amount of the liquid crystal composition.
  • the reliability of the composition is emphasized, it is represented by the formula (L-1-3.1), the formula (L-1-3.3) and the formula (L-1-3.4)). It is preferable to combine two or more compounds selected from the following compounds. When importance is attached to the response speed of the composition, the formula (L-1-1.3) and the formula (L-1-2.2) are used. It is preferable to combine two or more compounds selected from the compounds shown.
  • the compound represented by formula (L-1) is preferably a compound selected from the group of compounds represented by formula (L-1-6).
  • R L17 and R L18 each independently represent a methyl group or a hydrogen atom.
  • the lower limit of the preferred content of the compound represented by formula (L-1-6) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 35%.
  • the preferable upper limit of the content is 60%, 55%, 50%, 45%, 42%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 33%, 30%.
  • the compound represented by the general formula (L-1-6) is a compound selected from the compound group represented by the formulas (L-1-6.1) to (L-1-6.3). Is preferred.
  • the compound represented by the general formula (L-2) is the following compound.
  • R L21 and R L22 each independently represent the same meaning as R L1 and R L2 in the general formula (L).
  • R L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L22 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom. Alkoxy groups of the numbers 1 to 4 are preferred.
  • the compound represented by the general formula (L-2) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the solubility at low temperature when the solubility at low temperature is important, the effect is high when the content is set high, and conversely, when the response speed is important.
  • the effect is high when the content is set low. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the lower limit of the preferred content of the compound represented by formula (L-2) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 % And 10%.
  • the preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.
  • the compound represented by formula (L-2) is preferably a compound selected from the group of compounds represented by formula (L-2.1) to formula (L-2.6), Compounds represented by -2.1), formula (L-2.3), formula (L-2.4) and formula (L-2.6) are preferred.
  • the compound represented by the general formula (L-3) is the following compound.
  • R L31 and R L32 each independently represent the same meaning as R L1 and R L2 in the general formula (L).
  • R L31 and R L32 are preferably each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
  • the compound represented by the general formula (L-3) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the lower limit of the preferred content of the compound represented by formula (L-3) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 % And 10%.
  • the preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.
  • the content of the compound represented by the general formula (L-3) when a high birefringence is to be obtained, it is highly effective to set the content higher. On the contrary, when a high Tni is important, The effect is high when the content is set low. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.
  • the compound represented by formula (L-3) is preferably a compound selected from the group of compounds represented by formula (L-3.1) to formula (L-3.7), It is preferably a compound represented by the formula (L-3.5) from -3.2).
  • the compound represented by the general formula (L-4) is the following compound.
  • R L41 and R L42 each independently represent the same meaning as R L1 and R L2 in the general formula (L).
  • R L41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L42 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom Alkoxy groups of the numbers 1 to 4 are preferred.
  • the compound represented by the general formula (L-4) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-4) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the seizure, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferred content of the compound represented by formula (L-4) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%.
  • the upper limit of the preferred content of the compound represented by formula (L-4) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%.
  • the compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formula (L-4.1) to the formula (L-4.3).
  • the liquid crystal composition contains the compound represented by the formula (L-4.1) according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. Or may contain a compound represented by the formula (L-4.2), represented by a compound represented by the formula (L-4.1) and a compound represented by the formula (L-4.2). It may contain both the compound and the compound represented by the formula (L-4.1) to the formula (L-4.3).
  • the lower limit of the preferred content of the compound represented by formula (L-4.1) or formula (L-4.2) is 3% or 5%, based on the total amount of the liquid crystal composition. 7%, 9%, 11%, 12%, 12%, 13%, 18%, 21%, preferred upper limit values are 45, 40%, 35 %, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%.
  • both compounds are preferably contained in the total amount of the liquid crystal composition.
  • the lower limit of the amount is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%.
  • the compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formula (L-4.4) to the formula (L-4.6), and the compound represented by the formula (L-4.4): It is preferable that it is a compound represented by these.
  • the liquid crystal composition contains the compound represented by the formula (L-4.4) according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. Also contains a compound represented by the formula (L-4.5), a compound represented by the formula (L-4.4) and a compound represented by the formula (L-4.5) Both may be included.
  • the lower limit of the preferred content of the compound represented by formula (L-4.4) or formula (L-4.5) is 3% or 5%, based on the total amount of the liquid crystal composition. 7%, 9%, 11%, 12%, 13%, 18%, 21%. Preferred upper limits are 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13 %, 10%, 8%.
  • the both compounds are preferably contained in the total amount of the liquid crystal composition.
  • the lower limit of the amount is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%.
  • the compound represented by the general formula (L-4) is preferably a compound represented by the formula (L-4.7) to the formula (L-4.10), and particularly, the compound represented by the formula (L-4.
  • the compound represented by 9) is preferable.
  • the compound represented by the general formula (L-5) is the following compound.
  • R L51 and R L52 each independently represent the same meaning as R L1 and R L2 in the general formula (L).
  • R L51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L52 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom Alkoxy groups of the numbers 1 to 4 are preferred.
  • the compound represented by the general formula (L-5) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-5) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the seizure, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferred content of the compound represented by formula (L-5) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%.
  • the upper limit of the preferred content of the compound represented by formula (L-5) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%
  • the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) and/or the formula (L-5.2), and particularly, the compound represented by the formula (L- It is preferably a compound represented by 5.1).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%.
  • the upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.
  • the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) and/or the formula (L-5.4).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%.
  • the upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.
  • the compound represented by the general formula (L-5) is preferably a compound selected from the group of compounds represented by the formulas (L-5.5) to (L-5.7), and particularly preferably the compound represented by the formula (L-5.5) It is preferably a compound represented by L-5.7).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%.
  • the upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.
  • the compound represented by the general formula (L-6) is the following compound.
  • R L61 and R L62 each independently represent the same meaning as R L1 and R L2 in the general formula (L), and X L61 and X L62 each independently represent a hydrogen atom or a fluorine atom.
  • R L61 and R L62 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of X L61 and X L62 is a fluorine atom and the other is a hydrogen atom. Preferably.
  • the compound represented by the general formula (L-6) can be used alone, or two or more compounds can be used in combination.
  • the kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.
  • the lower limit of the preferred content of the compound represented by formula (L-6) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%.
  • the upper limit of the preferred content of the compound represented by formula (L-6) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%.
  • the compound represented by the general formula (L-6) is preferably a compound represented by the formula (L-6.1) to the formula (L-6.9).
  • the types of compounds that can be combined are not particularly limited, but it is preferable to contain 1 to 3 types of these compounds, and more preferably 1 to 4 types. Further, the fact that the selected compound has a wide molecular weight distribution is also effective for solubility. Therefore, for example, one kind of the compounds represented by the formulas (L-6.1) and (L-6.2) or the formula (L- 6.4) and (L-6.5), one type, compounds represented by formula (L-6.6) and (L-6.7), one type, formula (L It is preferable to select one kind of compound from the compounds represented by -6.8) and (L-6.9) and to combine these appropriately. Among them, it is represented by formula (L-6.1), formula (L-6.3), formula (L-6.4), formula (L-6.6) and formula (L-6.9). It is preferable to include a compound.
  • the compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formula (L-6.10) to the formula (L-6.17), and among them, the compound represented by the formula (L- The compound represented by 6.11) is preferable.
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5% and 7%.
  • the upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.
  • the compound represented by the general formula (L-7) is the following compound.
  • R L71 and R L72 each independently represent the same meaning as R L1 and R L2 in the general formula (L), and A L71 and A L72 are each independently A L2 in the general formula (L) and It has the same meaning as A L3 , but the hydrogen atoms on A L71 and A L72 may each independently be replaced by a fluorine atom, and Z L71 has the same meaning as Z L2 in formula (L), (X L71 and X L72 each independently represent a fluorine atom or a hydrogen atom.)
  • R L71 and R L72 are each independently preferably 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, and A L71 and A L72 Are each independently preferably a 1,4-cyclohexylene group or a 1,4-phenylene group, hydrogen atoms on A L71 and A L72 may be each independently substituted by a fluorine atom, and Z L71 is a single group. A bond or COO- is preferred, a single bond is preferred, and X L71 and X L72 are preferably hydrogen atoms.
  • the types of compounds that can be combined are, for example, one type, two types, three types, and four types in one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-7) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the burn-in, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferred content of the compound represented by formula (L-7) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%.
  • the upper limit of the preferred amount of the compound represented by formula (L-7) based on the total amount of the liquid crystal composition is 30%, 25%, 23%, 20%, 18 %, 15%, 10%, 5%.
  • the liquid crystal composition preferably contains a large amount of the compound represented by the formula (L-7) when an embodiment having a high Tni is desired, and when an embodiment having a low viscosity is desired, the content thereof is preferably increased. It is preferable to use a small amount.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.1) to the formula (L-7.4), and the compound represented by the formula (L-7.2) The compound represented by is preferable.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.11) to the formula (L-7.13), and the compound represented by the formula (L-7.11) The compound represented by is preferable.
  • the compound represented by the general formula (L-7) is a compound represented by the formula (L-7.21) to the formula (L-7.23). It is preferably a compound represented by the formula (L-7.21).
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.31) to the formula (L-7.34), and a compound represented by the formula (L-7.31) And/or a compound represented by the formula (L-7.32) are preferred.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.41) to the formula (L-7.44), and a compound represented by the formula (L-7.41) And/or a compound represented by the formula (L-7.42) is preferable.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.51) to the formula (L-7.53).
  • the polymerizable compound-containing liquid crystal composition of the present invention may contain a polymerization initiator in order to promote the polymerization, although the polymerization proceeds even when the polymerization initiator is not present.
  • a polymerization initiator examples include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides and the like.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains the polymerizable compound represented by the general formula (i), but other polymerizable compounds may be used in combination.
  • Examples of the other polymerizable compound include compounds represented by the following general formula (P).
  • R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or —Sp p2 —P p2 , and one of the alkyl group or non- Two or more adjacent —CH 2 — may be independently substituted by —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO—, One or two or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom, P p1 and P p2 are each independently a general formula (P p1 -1) to a formula (P p1 -9)
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms
  • W p11 is a single bond
  • t p11 represents 0, 1 or 2, but when a plurality of R p11 , R p12 , W p11 and/or t p11 are present in the molecule, they are the same.
  • Sp p1 and Sp p2 each independently represent a single bond or a spacer group
  • R ZP1 is Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, but when a plurality of R ZP1's are present in the molecule, they may be the same or different).
  • a p1 , A p2 and A p3 are each independently (A p) 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-.) (B p ) 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced with —N ⁇ ) and (c).
  • a p represents a group, the above groups (a p), 1 or 2 or more hydrogen atoms present in the radical (b p) and group (c p) are each independently a halogen atom, a cyano group, a carbon atom It may be substituted with an alkyl group of the formulas 1 to 8 or —Sp p2 —P p2 , and one or two or more non-adjacent —CH 2 — in the alkyl group are independently —CH ⁇ CH.
  • m p1 represents 0, 1, 2 or 3
  • a p3 represents a single bond when m p1 is 0 and A p1 is a phenanthrene-2,7-diyl group or anthracene-2,6-diyl group.
  • the compound represented by the general formula (i) is excluded.
  • the compound represented by the general formula (P) is preferably contained in one kind or two or more kinds.
  • R p1 is preferably —Sp p2 —P p2 .
  • P p1 and P p2 each independently represent one of formulas (P p1 -1) to (P p1 -3), and preferably (P p1 -1).
  • R p11 and R p12 are preferably each independently a hydrogen atom or a methyl group.
  • 0 or 1 is preferable for tp11 .
  • W p11 is preferably a single bond, a methylene group or an ethylene group.
  • m p1 is preferably 0, 1 or 2, and preferably 0 or 1.
  • Z p1 and Z p2 are each independently a single bond, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —COOC 2 H 4 —.
  • Z p1 and Z p2 existing in the molecule is —CH ⁇ CH—COO—, —COO—CH ⁇ CH—, —(CH 2 ) 2 —COO—, —(CH 2 ) 2 It is preferably a linking group selected from the group consisting of —OCO—, —O—CO—(CH 2 ) 2 —, and —COO—(CH 2 ) 2 —, and the others are preferably single bonds.
  • a p1 , A p2 and A p3 are each independently preferably a 1,4-phenylene group or a 1,4-cyclohexylene group, more preferably a 1,4-phenylene group.
  • the 1,4-phenylene group is preferably substituted with one fluorine atom, one methyl group or one methoxy group in order to improve the compatibility with the liquid crystal compound.
  • the total content of the compounds represented by the general formula (P) is 0.05 to 10 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). %, preferably 0.1 to 8%, more preferably 0.1 to 5%, and 0.1 to 3%. It is preferably in the range of 0.2 to 2%, preferably in the range of 0.2 to 1.3%, and in the range of 0.2 to 1%. It is preferably in the range of 0.2 to 0.56%.
  • the preferable lower limit of the total content of the compounds represented by the general formula (P) is 0 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0. 25% and 0.3%.
  • the preferable upper limit of the total content of the compounds represented by the general formula (P) is 10 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). %, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% is there.
  • the content of the compound represented by the general formula (P) contained in the polymerizable compound-containing liquid crystal composition of the present invention is small, the effect of adding the compound represented by the general formula (P) is difficult to appear and the liquid crystal composition
  • the content is set in consideration of these balances.
  • Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-1-1) to (P-1-46).
  • P p11 , P p12 , Sp p11, and Sp p12 have the same meanings as P p1 , P p2 , Sp p1, and Sp p2 in the general formula (P).
  • Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-2-1) to (P-2-9).
  • P p21 , P p22 , Sp p21, and Sp p22 have the same meanings as P p1 , P p2 , Sp p1, and Sp p2 in the general formula (P).
  • Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-3-1) to (P-3-15).
  • P p31 , P p32 , Sp p31, and Sp p32 have the same meanings as P p1 , P p2 , Sp p1, and Sp p2 in the general formula (P).
  • Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-19).
  • P p41 , P p42 , Sp p41, and Sp p42 have the same meanings as P p1 , P p2 , Sp p1, and Sp p2 in the general formula (P-4).
  • the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained.
  • the amount is preferably in the range of 0.05 to 10%, preferably 0.1 to 8%, and 0.1 to the total amount of the polymerizable compound-containing liquid crystal composition. Is preferably in the range of 5% to 5%, more preferably in the range of 0.1% to 3%, preferably in the range of 0.2% to 2%, and 0.2% to 1.3%. Is preferably in the range of 0.2 to 1%, more preferably 0.2 to 0.56%.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained.
  • the preferred lower limit of the amount is 0.01%, 0.03%, 0.05%, 0.08%, and 0.1% with respect to the polymerizable compound-containing liquid crystal composition. %, 0.15%, 0.2%, 0.25%, 0.3%.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained.
  • the preferable upper limit of the amount is 10%, 8%, 5%, 3%, 1.5%, 1.2% with respect to the polymerizable compound-containing liquid crystal composition. , 1%, 0.8%, 0.5%.
  • the polymerizable compound-containing liquid crystal composition of the present invention may further contain a compound represented by the general formula (Q).
  • R Q represents a straight chain alkyl group or a branched chain alkyl group having 1 to 22 carbon atoms, and one or more CH 2 groups in the alkyl group are such that oxygen atoms are not directly adjacent to each other. May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O—, —OCF 2 —, and M Q is trans. Represents a 1,4-cyclohexylene group, a 1,4-phenylene group or a single bond.
  • a branched chain alkyl group in which one CH 2 group is replaced by —OCO— or —COO— is preferable, a straight chain alkyl group having 1 to 20 carbon atoms, and one CH 2 group is replaced by —OCO— or —COO—
  • a straight chain alkyl group, a branched chain alkyl group, a branched alkoxy group, and a branched chain alkyl group in which one CH 2 group is replaced with —OCO— or —COO— are more preferable.
  • M Q represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a single bond, but a trans-1,4-cyclohexylene group or a 1,4-cyclohexylene group.
  • a phenylene group is preferred.
  • the compound represented by the general formula (Q) is preferably a compound represented by the following general formula (Qa) to general formula (Qd).
  • R Q1 is preferably a straight chain alkyl group or a branched chain alkyl group having 1 to 10 carbon atoms
  • R Q2 is preferably a straight chain alkyl group or a branched chain alkyl group having 1 to 20 carbon atoms
  • R Q3 is A linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group, a linear alkoxy group or a branched alkoxy group is preferable
  • L Q is preferably a linear alkylene group having 1 to 8 carbon atoms or a branched alkylene group. ..
  • the compound represented by the general formula (Q) is a compound represented by the general formula (Qc) and the general formula (Qd) among the compounds represented by the general formula (Qa) to the general formula (Qd). More preferably, it is the compound represented.
  • the polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds represented by formula (Q), and more preferably one to five compounds.
  • the content of the compound represented by the general formula (Q) relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 0.001 to 1%, and 0.001 to 0.1%. % Is more preferable, and 0.001 to 0.05% is particularly preferable.
  • the polymerizable compound-containing liquid crystal composition of the present invention may contain a usual nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, an antioxidant, an ultraviolet absorber, a light stabilizer or an infrared absorber in addition to the above compounds. good.
  • n represents an integer of 0 to 20.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains one or more compounds represented by the general formula (Q) or compounds selected from the general formulas (III-1) to (III-40). It is more preferable to contain 1 to 5 types, and the content is preferably 0.001 to 1%, more preferably 0.001 to 0.1%, and 0.001 to 0.05. % Is particularly preferred.
  • the dielectric constant anisotropy ( ⁇ ) of the polymerizable compound-containing liquid crystal composition of the present invention at 20° C. is preferably ⁇ 2.0 to ⁇ 8.0, more preferably ⁇ 2.0 to ⁇ 5.0, 2.5 to -5.0 is particularly preferred.
  • the refractive index anisotropy ( ⁇ n) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, and 0.09 to 0. .12 is particularly preferred. More specifically, it is preferably 0.10 to 0.13 when it corresponds to a thin cell gap and 0.08 to 0.10 when it corresponds to a thick cell gap.
  • the viscosity ( ⁇ ) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 10 to 50 mPa ⁇ s, preferably 10 to 40 mPa ⁇ s, and 10 to 35 mPa ⁇ s. Is preferable, 10 to 30 mPa ⁇ s is preferable, 10 to 25 mPa ⁇ s is more preferable, and 10 to 22 mPa ⁇ s is particularly preferable.
  • the rotational viscosity ( ⁇ 1 ) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 50 to 160 mPa ⁇ s, preferably 60 to 160 mPa ⁇ s, and 60 to 150 mPa ⁇ s. Is preferably 60 to 140 mPa ⁇ s, preferably 60 to 130 mPa ⁇ s, more preferably 60 to 125 mPa ⁇ s, and even more preferably 60 to 120 mPa ⁇ s, It is more preferably 60 to 115 mPa ⁇ s, more preferably 60 to 110 mPa ⁇ s, and particularly preferably 60 to 100 mPa ⁇ s.
  • the nematic phase-isotropic liquid phase transition temperature (Tni) of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 60° C. to 120° C., more preferably 70° C. to 100° C., and particularly 70° C. to 85° C. preferable.
  • the compound represented by the general formula (i), the general formula (N-1), the general formula (N-2), the general formula (N-3) and the general formula (L) The upper limit of the proportion occupied by the components composed only of the represented compounds is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, It is preferably 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, and 84% by mass.
  • the lower limit of the proportion of the components composed only of the compound is 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass% %, 89 mass %, 90 mass %, 91 mass %, 92 mass %, 93 mass %, 94 mass %, 95 mass %, 96 mass %, 97 mass %, 98 mass %, 99 mass %. ..
  • the entire polymerizable compound-containing liquid crystal composition of the present invention is composed of only the compounds represented by the general formula (i), the general formula (N-1c), the general formula (N-1d), and the general formula (L).
  • the lower limit value of the proportion occupied by the components is 50 mass %, 61 mass %, 63 mass %, 65 mass %, 66 mass %, 67 mass %, 68 mass %, 70 mass %, 71 mass %, 73 mass %.
  • the lower limit values of the proportions of the components composed only of the compounds represented by (N-1d), the general formula (N-1e) and the general formula (L) are 78% by mass, 80% by mass, 81% by mass, 83% by mass, 85% by mass, 86% by mass, 87% by mass, 88% by mass, 89% by mass, 90% by mass, 91% by mass, 92% by mass, 93% by mass, 94% by mass, 95% by mass, 96% by mass %, 97% by mass, 98% by mass, and 99% by mass are preferable.
  • general formula (i), general formula (N-1a), general formula (N-1b), general formula (N-1c), and general formula (N-1d) general formula (N-1e), general formula (L-1), general formula (L-3), general formula (L-4), general formula (L-5) and general formula (L-6).
  • the upper limit of the proportion occupied by the components composed only of the represented compounds is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass %, 83 mass %, 82 mass %, 81 mass %, 80 mass % Is preferable.
  • general formula (i), general formula (N-1a), general formula (L-1), general formula (L-3), and general formula (L -4), the lower limit of the proportion occupied by the components composed only of the compounds represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass% %, 74 mass %, 76 mass %, 78 mass %, 80 mass %, 82 mass %, 84 mass %, 86 mass %, 88 mass %, 90 mass %, and 92 mass %.
  • the lower limit of the proportion occupied by the components composed only of the compounds represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass% %, 74 mass %, 76 mass %, 78 mass %, 80 mass %, 82 mass %, 84 mass %, 86 mass %, 88 mass %, 90 mass %, and 92 mass %.
  • general formula (i), general formula (N-1c), general formula (N-1d), general formula (L-1), and general formula (L-3 ), and the lower limit of the proportion occupied by the component composed only of the compound represented by the general formula (L-5) is 38% by mass, 40% by mass, 41% by mass, 43% by mass, 45% by mass, 48% by mass.
  • Mass% 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass% , 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 It is preferably mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
  • general formula (i), general formula (N-1c), general formula (N-1d), general formula (L-1), and general formula (L -3), and the upper limit of the proportion of the components composed only of the compound represented by the general formula (L-5) is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass.
  • the polymerizable compound-containing liquid crystal composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are bonded to each other such as a peracid (—CO—OO—) structure in the molecule.
  • the content of the compound having a carbonyl group contained in the polymerizable compound-containing liquid crystal composition of the present invention is the total amount of the polymerizable compound-containing liquid crystal composition. Is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially not contained.
  • the content of the compound substituted with a chlorine atom is 15% with respect to the total amount of the polymerizable compound-containing liquid crystal composition. It is preferably not more than 10%, preferably not more than 10%, more preferably not more than 8%, more preferably not more than 5%, preferably not more than 3%, and not substantially contained. Is more preferable.
  • the polymerizable compound-containing liquid crystal composition of the present invention preferably contains a large amount of a compound in which all the ring structures in the molecule are 6-membered rings.
  • the content of compounds in which all ring structures in the molecule are 6-membered rings is 80% or more based on the total amount of the polymerizable compound-containing liquid crystal composition. It is preferably 90% or more, more preferably 95% or more, and the polymerizable compound-containing liquid crystal composition is a compound in which the ring structure in the molecule is substantially all 6-membered ring. Most preferably it is configured.
  • the polymerizable compound-containing liquid crystal composition of the present invention preferably contains a small amount of a compound having a cyclohexenylene group as a ring structure.
  • the content of the compound having a cyclohexenylene group is preferably 10% or less with respect to the total amount of the polymerizable compound-containing liquid crystal composition, and 8% or less. It is preferable that the content is 5% or less, more preferably 3% or less, and further preferably substantially not contained.
  • the polymerizable compound-containing liquid crystal composition of the present invention contains a molecule of 2-methylbenzene-1,4-diyl group in which a hydrogen atom may be substituted with halogen. It is preferable that the content of the compound contained therein is small.
  • the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is 10% or less based on the total amount of the polymerizable compound-containing liquid crystal composition. Is preferable, 8% or less is preferable, 5% or less is more preferable, 3% or less is preferable, and it is more preferable not to contain substantially.
  • substantially free from means not including except an unintended inclusion.
  • the liquid crystal display device of the present invention is a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i), in other words, the above-mentioned item "I. Polymerizable compound-containing liquid crystal composition".
  • the liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention has a remarkable feature of high-speed response. In addition, a tilt angle is sufficiently obtained, and there is no unreacted polymerizable compound.
  • VHR voltage holding ratio
  • the liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention is particularly useful as an active matrix driving liquid crystal display device, and has a PSA mode, a PSVA mode, a VA mode, a PS-IPS mode or a PS-FFS mode. It can be used for a liquid crystal display device.
  • the liquid crystal display element of the present invention includes a first substrate and a second substrate which are arranged to face each other, a common electrode provided on the first substrate or the second substrate, and the first substrate or the first substrate. It is preferable to have a pixel electrode provided on the second substrate and having a thin film transistor, and a liquid crystal layer containing the polymerizable compound-containing liquid crystal composition provided between the first substrate and the second substrate. If necessary, an alignment film for controlling the alignment direction of the liquid crystal molecules may be provided on the facing surface side of at least one of the first substrate and the second substrate so as to come into contact with the liquid crystal layer. The alignment film may not be provided on both the second substrate and the second substrate.
  • a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a rubbing alignment film (eg, polyimide alignment film) or a photo alignment film (eg, decomposition type).
  • a rubbing alignment film eg, polyimide alignment film
  • a photo alignment film eg, decomposition type
  • a known alignment film such as a polyimide alignment film
  • a color filter may be appropriately provided on the first substrate or the second substrate, and a color filter can be provided on the pixel electrode or the common electrode.
  • the two substrates of the liquid crystal cell used in the liquid crystal display device of the present invention can be made of a transparent transparent material such as glass or plastic, and one of them may be an opaque material such as silicon.
  • the transparent substrate having the transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like.
  • the method for producing a color filter by the pigment dispersion method will be described as an example.
  • a curable colored composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this step for each of the three colors of red, green, and blue, a pixel portion for a color filter can be created.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.
  • the first substrate and the second substrate are preferably opposed to each other so that the common electrode and the pixel electrode layer are inside.
  • the distance between the first substrate and the second substrate may be adjusted via a spacer.
  • the thickness of the obtained liquid crystal layer is preferably adjusted to 1 to 100 ⁇ m, more preferably 1.5 to 10 ⁇ m.
  • a polarizing plate it is preferable to adjust the product of the refractive index anisotropy ⁇ n of the liquid crystal and the cell thickness d so as to maximize the contrast.
  • the spacer include glass particles, plastic particles, alumina particles, and photoresist material.
  • a usual vacuum injection method or ODF method can be used as a method for sandwiching the polymerizable compound-containing liquid crystal composition between the two substrates.
  • an appropriate polymerization rate is desirable, so that an active energy ray such as an ultraviolet ray or an electron beam is used.
  • a method of polymerizing by irradiating a single type or a combination or sequential irradiation is preferable.
  • ultraviolet rays When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used.
  • the polymerization is carried out in a state where the polymerizable compound-containing liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency to active energy rays.
  • the orientation state of the unpolymerized part is changed by changing the conditions such as electric field, magnetic field or temperature, and further irradiation with active energy rays is performed. It is also possible to use a means of polymerizing the polymer.
  • a means of polymerizing the polymer In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the polymerizable compound-containing liquid crystal composition.
  • the AC electric field to be applied is preferably AC having a frequency of 10 Hz to 10 kHz, more preferably 60 Hz to 10 kHz, and the voltage is selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the PSVA mode liquid crystal display element, it is preferable to control the pretilt angle from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.
  • the temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron rays used when polymerizing the polymerizable compound contained in the polymerizable compound-containing liquid crystal composition is not particularly limited.
  • active energy rays such as ultraviolet rays or electron rays used when polymerizing the polymerizable compound contained in the polymerizable compound-containing liquid crystal composition
  • it is preferably within a temperature range in which the liquid crystal state of the polymerizable compound-containing liquid crystal composition is maintained. .. It is preferable to polymerize at a temperature close to room temperature, that is, typically at 15 to 35°C.
  • the polymerizable compound-containing liquid crystal composition when applied to a liquid crystal display device provided with a substrate having no alignment film, when applied to a liquid crystal display device provided with a substrate having the above alignment film A wider temperature range than the above temperature range may be used.
  • a metal halide lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, or the like can be used as the lamp that generates ultraviolet rays.
  • the wavelength of the ultraviolet rays to be irradiated it is preferable to irradiate the ultraviolet rays in a wavelength range other than the absorption wavelength range of the polymerizable compound-containing liquid crystal composition, and it is preferable to use the ultraviolet rays after cutting the ultraviolet rays if necessary.
  • the intensity of the ultraviolet rays applied is preferably 0.1 mW/cm 2 to 100 W/cm 2, and more preferably 2 mW/cm 2 to 50 W/cm 2 .
  • the amount of energy of the ultraviolet rays to be irradiated can be appropriately adjusted, but is preferably 10 mJ/cm 2 to 500 J/cm 2, and more preferably 100 mJ/cm 2 to 200 J/cm 2 .
  • the intensity may be changed when the ultraviolet rays are irradiated.
  • the time for irradiating with ultraviolet rays is appropriately selected depending on the intensity of ultraviolet rays for irradiation, but is preferably 10 seconds to 3600 seconds, more preferably 10 seconds to 600 seconds.
  • polymerizable compound of the present invention is a compound represented by the general formula (i).
  • a i1 and A i2 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-.) (B) 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced by —N ⁇ ) and (c).
  • P i3 —S i3 —, P i1 , P i2, and P i3 are each independently the formula (R-1) to the formula (R-9).
  • R 11 , R 12 , R 13 , R 14 and R 15 each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • m r5 , m r7 , n r5 and n r7 each independently represent a group selected from 0, 1, or 2
  • S i1 , S i2 and S i3 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH 2 — in the alkylene group or two or more not adjacent to each other.
  • -CH 2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other
  • R i1 represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom
  • n i1 represents 1, 2 or 3
  • a i2 , S i2 , P i3 and/or S i3 they may be the same or different.
  • the polymerizable compound of the present invention when the polymerizable compound-containing liquid crystal composition is added to the liquid crystal composition, it is difficult to precipitate from the polymerizable compound-containing liquid crystal composition, the polymerization rate is fast, and the ultraviolet rays are short. Since sufficient polymerization is possible even by irradiation, the amount of unreacted polymerizable compound remaining can be reduced. Further, according to the polymerizable compound of the present invention, it is possible to suppress display failure (burn-in) due to a large change in the pretilt angle in the liquid crystal display element.
  • the present invention is not limited to the above embodiment.
  • the above-described embodiment is merely an example, and the invention having substantially the same configuration as the technical idea described in the scope of claims of the present invention and exhibiting the same action and effect is the present invention It is included in the technical scope of.
  • Tni Nematic phase-isotropic liquid phase transition temperature (°C) ⁇ n: refractive index anisotropy at 20°C ⁇ : viscosity at 20°C (mPa ⁇ s) ⁇ 1 : rotational viscosity at 20°C (mPa ⁇ s) ⁇ : Dielectric anisotropy at 20° C.
  • a polymerizable compound-containing liquid crystal composition to be described later was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 ⁇ m and including a substrate with ITO, which was coated with a polyimide alignment film that induces vertical alignment and rubbed. Then, the liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for an arbitrary time using a fluorescent UV lamp to obtain a liquid crystal display element. At this time, the fluorescent UV lamp was adjusted so that the illuminance measured under the condition of the central wavelength of 313 nm was 3 mW/cm 2 .
  • VHR evaluation method The liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for 60 minutes under the above irradiation conditions, and VHR was measured.
  • the measurement conditions of VHR were 1 V, 0.6 Hz, and 60°C.
  • the liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for 60 minutes under the above irradiation conditions, and then the display defect (burn-in) was evaluated due to the change in the pretilt angle.
  • the pretilt angle of the liquid crystal display element was measured and used as the pretilt angle (initial).
  • a backlight was irradiated for 3 hours while applying a voltage of 30 V at a frequency of 100 Hz to this liquid crystal display element. Then, the pretilt angle was measured and used as the pretilt angle (after the test).
  • pretilt angle change amount absolute value of pretilt angle change
  • the pretilt angle was measured using OPTIPRO manufactured by Shintech. The closer the pretilt angle change amount is to 0[°], the lower the possibility of display failure due to the change of the pretilt angle becomes, and when it becomes 0.5[°] or more, the display failure due to the change of the pretilt angle occurs. More likely.
  • phase transition temperature (temperature rise 5°C/min): C 161 I 1 H NMR (CDCl 3 ) ⁇ 2.08 (m, 6H), 5.78 (d, 2H), 6.37 (d, 2H), 6.59 (d, 1H), 7.16-7 .22 (m, 6H), 7.63 (d, 2H), 7.86 (d, 1H) ppm ⁇ LC-MS: 393 [M+1]
  • phase transition temperature (temperature increase 5° C./min): C 179 N >220
  • I 1 H NMR (CDCl 3 ) ⁇ 1.54-1.67 (m, 4H), 1.95-2.01 (m, 5H), 2.07 (s, 3H), 2.14-2.
  • phase transition temperature (temperature increase 5°C/min): C160N>220I ⁇ 1 H NMR (CDCl 3) ⁇ 2.08 (s, 3H), 2.09 (s, 3H), 2.29 (s, 3H), 5.79 (dt, 2H), 6.38 (d , 2H), 6.62 (d, 1H), 7.06 (m, 2H), 7.16-7.35 (m, 7H), 7.64 (d, 2H), 7.87 (d, 1H) ppm.
  • ⁇ LC-MS 483 [M+1]
  • phase transition temperature (temperature increase 5° C./min): C 165 N 200 poly ⁇ 1 H NMR (CDCl 3) ⁇ 2.08 (s, 6H), 2.29 (s, 3H), 5.78 (dt, 2H), 6.37 (dt, 2H), 6.63 (d , 1H), 7.01 (m, 2H), 7.22 (m, 5H), 7.35 (m, 2H), 7.64 (d, 2H), 7.88 (d, 1H) ppm.
  • ⁇ LC-MS 483 [M+1]
  • Example 5A Synthesis of Polymerizable Compounds Represented by Formulas (i-2a) and (i-18a) Represented by formulas (i-2a) and (i-18a) according to the method of Example 1A.
  • the respective polymerizable compounds were synthesized.
  • Liquid Crystal Composition Containing Polymerizable Compound and Evaluation Results Preparation of Liquid Crystal Composition and Physical Properties
  • Liquid crystal compositions LC-001 to LC-005 before adding the polymerizable compound were prepared, and the physical properties thereof were measured.
  • Table 1 shows the configurations of the liquid crystal compositions LC-001 to LC-005 and the results of their physical properties.
  • Comparative Examples 1 and 2 A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the following formula (A) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was designated as Comparative Example 1. did.
  • a polymerizable compound-containing liquid crystal composition prepared by adding 0.3 part by mass of a compound represented by the following formula (B) as a polymerizable compound to Comparative Example 2 was added to Liquid Crystal Composition LC-001 as 99.7 parts by mass. did.
  • Example 1B to 4B A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was used as Example 1B. And
  • the composition was Example 2B.
  • the composition was Example 3B.
  • the composition was Example 4B.
  • the residual amount of the polymerizable compound after irradiation with ultraviolet rays for a predetermined time, VHR after irradiation with ultraviolet rays for 60 minutes, and pretilt angle change amount are as follows. Table 2 below.
  • the physical properties of the polymerizable compound-containing liquid crystal compositions of Comparative Examples 1 to 2 and Examples 1B to 4B were the same as those of the liquid crystal composition LC-001.
  • the pretilt angle change amount was a sufficiently small value, but the amount of the polymerizable compound remaining after irradiation with ultraviolet rays for 60 minutes was large.
  • the residual amount of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, but the amount of change in pretilt angle was large.
  • Examples 1B to 4B which are the polymerizable compound-containing liquid crystal compositions of the present invention
  • the residual amount of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, and the amount was significantly smaller than that in Comparative Example 1. Indicated. From this, it was found that the polymerization rate of the polymerizable compound in Examples 1B to 4B was sufficiently higher than that in Comparative Example 1. It was also confirmed that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Furthermore, in Examples 1B to 4B, the VHR after irradiation with ultraviolet rays for 60 minutes was a sufficiently high value as compared with Comparative Examples 1 and 2.
  • the polymerization rate of the polymerizable compound represented by the general formula (i) is sufficiently high, and the residual amount of the unreacted polymerizable compound is suppressed. It was confirmed that the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently high and that a display defect due to a change in the pretilt angle was unlikely to occur.
  • Comparative example 3 Comparative Example 3 was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (C) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. ..
  • the residual amount and VHR of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes and the result of the pretilt angle change amount were the same as those in Examples 1B to 4B, but at room temperature.
  • the precipitation of the polymerizable compound was confirmed.
  • the polymerizable compound-containing liquid crystal compositions of Examples 1B to 4B retained a uniform nematic liquid crystal phase even after being stored at room temperature for 240 hours, and precipitation of the polymerizable compound was not confirmed.
  • the polymerizable compound represented by the formula (C) used in Comparative Example 3 corresponds to the case where the number of A i1 in the general formula (i) is two. From the results of Comparative Example 3, when A i1 in the general formula (i) is 2 or more, the solubility is lowered and the compound is easily precipitated, and in the compound represented by the general formula (i) in the present invention, There was one A i1 in the general formula (i), which suggests that the solubility is improved and precipitation is less likely to occur.
  • Example 5B to 8B A polymerizable compound-containing liquid crystal composition obtained by adding 0.4 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to Example 9B was obtained based on 99.6 parts by mass of the liquid crystal composition LC-001.
  • a polymerizable compound-containing liquid crystal composition obtained by adding 0.6 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.4 parts by mass of the liquid crystal composition LC-001 was prepared as Example 6B.
  • Example 7B A polymerizable compound-containing liquid crystal composition obtained by adding 50 ppm of the antioxidant represented by the formula (H-1) to Example 1 was used as Example 7B.
  • Example 8B was a liquid crystal composition containing a polymerizable compound in which 50 ppm of the antioxidant represented by the formula (H-2) was further added to Example 1.
  • the polymerizable compound-containing liquid crystal compositions of Examples 5B to 8B were evaluated in the same manner as in Example 1B.
  • Example 1B the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, and the polymerization rate was higher than that in Comparative Example 1, The amount of change in pretilt angle was sufficiently smaller than in Example 2.
  • the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2.
  • precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 5B to 8B also solved the problems of the present invention.
  • Example 9B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002.
  • Example 10B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003.
  • a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004 was used as Example 11B.
  • Example 12B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005.
  • Example 9B to 12B The polymerizable compound-containing liquid crystal compositions of Examples 9B to 12B were evaluated in the same manner as in Example 1B. As a result, in all of Examples 9B to 12B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 1B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 9B to 12B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 1B. Therefore, it was suggested that Examples 9B to 12B had a higher polymerization rate than Comparative Example 1.
  • Examples 9B to 12B all showed the same amount of change in pretilt angle as Example 1B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2.
  • the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 1B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than those in Comparative Examples 1 and 2.
  • precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 9B to 12B solved the problems of the present invention.
  • Example 13B to 16B A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-31a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002 was used as Example 13B.
  • Example 14B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-31a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003.
  • a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-31a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004 was used as Example 15B.
  • Example 16B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-31a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005.
  • Example 13B to 16B The polymerizable compound-containing liquid crystal compositions of Examples 13B to 16B were evaluated in the same manner as in Example 3B. As a result, in all of Examples 13B to 16B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 3B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 13B to 16B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 3B. Therefore, it was suggested that Examples 13B to 16B had a higher polymerization rate than Comparative Example 1.
  • Examples 13B to 16B all showed the same amount of change in pretilt angle as Example 3B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2.
  • the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 3B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2.
  • precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 13B to 16B solved the problem of the present invention.
  • Example 17B to 20B A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002 was used as Example 17B. And
  • a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003 was used as Example 18B.
  • Example 19B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-33a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004.
  • a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005 was used as Example 20B.
  • Example 17B to 20B The polymerizable compound-containing liquid crystal compositions of Examples 17B to 20B were evaluated in the same manner as in Example 4B. As a result, in each of Examples 17B to 20B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 4B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 17B to 20B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 4B. Therefore, it was suggested that Examples 17B to 20B had a higher polymerization rate than Comparative Example 1.
  • Examples 17B to 20B all showed the same amount of change in pretilt angle as Example 4B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Further, in Examples 17B to 20B, the VHR after irradiation with ultraviolet rays for 60 minutes was the same as that of Example 4B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than those in Comparative Examples 1 and 2. Furthermore, in Examples 17B to 20B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 17B to 20B solved the problems of the present invention.
  • Example 21B to 22B A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-2a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was used as Example 21B. And
  • Example 22B was a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by formula (i-18a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001.
  • Example 21B to 22B The polymerizable compound-containing liquid crystal compositions of Examples 21B to 22B were evaluated in the same manner as in Example 1B. As a result, in each of Examples 21B to 22B, the residual amount of the unreacted polymerizable compound after the irradiation of the ultraviolet rays for 150 seconds and the irradiation of the ultraviolet rays for 15 minutes was the same as that of Example 1B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 21B to 22B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 1B. Therefore, it was suggested that Examples 21B to 22B had a higher polymerization rate than Comparative Example 1.
  • Examples 21B to 22B all showed the same amount of change in pretilt angle as Example 1B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Further, in Examples 21B to 22B, the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 1B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2. Furthermore, in Examples 21B to 22B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 21B to 22B solved the problem of the present invention.

Abstract

La présente invention vise à fournir : une composition de cristaux liquides contenant un composé polymérisable dans lequel la précipitation d'un composé polymérisable est supprimée et avec laquelle une vitesse de polymérisation rapide, une quantité résiduelle réduite d'un composé polymérisable n'ayant pas réagi, un rapport de maintien de tension élevée (VHR)), et une stabilité d'inclinaison élevée peuvent être obtenus en même temps ; un dispositif d'affichage à cristaux liquides utilisant ladite composition de cristaux liquides ; et un composé polymérisable approprié pour la préparation de la composition de cristaux liquides contenant un composé polymérisable. La présente invention résout ledit problème en fournissant une composition de cristaux liquides qui contient un ou deux composés polymérisables ou plus représentés par la formule générale (i).
PCT/JP2019/039987 2018-12-12 2019-10-10 Composition de cristaux liquides contenant un composé polymérisable, élément d'affichage à cristaux liquides et composé polymérisable WO2020121639A1 (fr)

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CN201980064232.4A CN112789344A (zh) 2018-12-12 2019-10-10 含聚合性化合物的液晶组合物、及液晶显示元件以及聚合性化合物

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