WO2020230480A1 - Composition de cristaux liquides polymérisables et élément d'affichage à cristaux liquides, ainsi que composé - Google Patents

Composition de cristaux liquides polymérisables et élément d'affichage à cristaux liquides, ainsi que composé Download PDF

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WO2020230480A1
WO2020230480A1 PCT/JP2020/015723 JP2020015723W WO2020230480A1 WO 2020230480 A1 WO2020230480 A1 WO 2020230480A1 JP 2020015723 W JP2020015723 W JP 2020015723W WO 2020230480 A1 WO2020230480 A1 WO 2020230480A1
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group
mass
carbon atoms
liquid crystal
general formula
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Japanese (ja)
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正臣 木村
雄一 井ノ上
大樹 野呂
僚 神田
林　正直
豊 門本
学 高地
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Dic株式会社
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Priority to JP2020542671A priority Critical patent/JP6870784B2/ja
Priority to CN202080028144.1A priority patent/CN113677657A/zh
Publication of WO2020230480A1 publication Critical patent/WO2020230480A1/fr

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
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    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/14—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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    • C09K19/08—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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    • C09K19/10—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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    • C09K19/08—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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    • C09K19/34—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 polymerizable liquid crystal composition, a liquid crystal display element, and a compound.
  • Liquid crystal display elements typified by the VA type, PSA type, and PSVA type exhibit a black display associated with vertical orientation when no voltage is applied, while exhibiting a white display associated with horizontally tilted uniformly when a voltage is applied.
  • a special layer called a polyimide alignment film (hereinafter referred to as PI layer) may be provided on the electrode at present. It was mandatory. However, in recent years, panel makers have merits such as cost reduction, environmental consideration, and narrowing of the frame of the PI layer, so that various methods can be used to realize the orientation of the liquid crystal molecules while omitting the PI layer. Method is being considered.
  • Patent Document 1 describes a self-oriented polymerizable mesogen having a negative or positive dielectric anisotropy, a low molecular weight component which is a component constituting a liquid crystal composition such as a liquid crystal molecule, and a polar anchor group (spontaneous).
  • a liquid crystal medium containing a polymerizable component containing an orientation additive is disclosed.
  • the liquid crystal medium contains a self-orientation polymerizable mesogen, it is possible to achieve homeotropic (vertical) orientation of the LC medium on the surface or cell wall of the liquid crystal display (LC display). It is disclosed that an LC display having a homeotropic orientation of an LC medium can be obtained without an alignment film.
  • liquid crystal molecules depend on the number of polymerizable groups and polar groups of the spontaneous orientation additive added to the liquid crystal composition, and the positions of those groups in the molecular structure. It was found that the stability of vertical orientation and the stability of pre-tilt angle were inferior. Further, the spontaneously oriented additive has a problem that the compatibility with the hydrophobic liquid crystal molecules is lowered depending on the structure, and it is easy to precipitate from the polymerizable liquid crystal composition.
  • an object of the present invention is that uniform vertical orientation of the liquid crystal compound is possible without providing a PI layer, dripping marks and uneven orientation are less likely to occur, and long-term stability of vertical orientation and pretilt angle is high.
  • An object of the present invention is to provide a polymerizable liquid crystal composition having excellent solubility, and to provide a liquid crystal display element using the liquid crystal composition.
  • Another object of the present invention is to provide a compound for enabling the above-mentioned liquid crystal composition.
  • the present invention provides a polymerizable liquid crystal composition containing one or more compounds represented by the general formula (i).
  • R i1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a linear or branched alkyl halide having 1 to 20 carbon atoms, and is contained in the alkyl group or the alkyl halide group.
  • a i1 and A i2 independently represent a divalent aromatic group, a divalent ring-aliphatic group, a divalent heterocyclic compound group, a divalent fused ring, or a divalent fused polycycle.
  • R i2 , R i3 and R i4 are independently hydrogen atom, halogen atom, linear or branched alkyl group having 1 to 20 carbon atoms, and linear or branched alkyl halide having 1 to 20 carbon atoms.
  • Represents a group, or Xi4 , and -CH 2- in the alkyl group or alkyl halide group may be substituted with -CH CH-, -C ⁇ C- or -O-, but two or more-. O-is not adjacent, X i1 , X i2 , X i3 and X i4 independently represent -Sp i1- P i1 or -Sp i2- K i1 respectively. Ki1 is independently represented by the general formula (K-1) or (K-2).
  • T k1 are independently from the general formulas (T-1) to (T-7).
  • -Or- may be replaced with -OCO-
  • R T2 and R T3 independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R k1 independently represents a hydrogen atom and a linear or branched alkyl having 1 to 6 carbon atoms, respectively. Representing a group, one or two or more non-adjacent -CH 2- in the alkyl group may be substituted with -O-.
  • T k2 are independently from the general formulas (T-8) to (T-17).
  • the black dot represents the bond.
  • Z K1 independently represents an oxygen atom or a sulfur atom, respectively.
  • W K1 , UK1 , V K1 and SK1 each independently represent a methine group or a nitrogen atom, and here hydrogen atoms in the groups represented by the general formulas (T-8) to (T-17).
  • the black dot represents the bond.
  • mi1 and mi2 each independently represent an integer of 1 to 4.
  • ni1 represents an integer of 0 to 2
  • ni1 is an integer of 1 or 2
  • one or two hydrogen atoms in the ring structure of A i2 is substituted by X i1, ki1, ki2 and ki3 each independently represent an integer of 0 to 3, where the sum of ki1, ki2 and ki3 is 3.
  • the general formula (i) includes one or more groups selected from the group consisting of Pi 1 , Pi 2 and Pi 3 , and one group selected from the group consisting of T k1 and T k 2. The total number of groups included as described above and selected from the group consisting of Pi 1 , Pi 2 , Pi 3 , T k1 and T k 2 is 5 or more.
  • the present invention provides a liquid crystal display device having two substrates and a resin component in which the compound represented by the general formula (i) in the above-mentioned polymerizable liquid crystal composition is cured between the two substrates. provide.
  • the present invention also provides a compound represented by the above general formula (i).
  • the polymerizable liquid crystal composition according to the present invention enables uniform vertical orientation of the liquid crystal compound without providing a PI layer, is less likely to cause dripping marks and uneven orientation, and has long-term stability of vertical orientation and pretilt angle. It has the effect of being highly compatible and having excellent compatibility.
  • the liquid crystal display element according to the present invention can have uniform vertical orientation of liquid crystal molecules, has no dripping marks or uneven orientation, or is reduced to an allowable level, and has excellent long-term display characteristics in which afterimages are less likely to occur. It has the effect of being able to do it.
  • the compound according to the present invention has a desired structure represented by the general formula (i), so that the compatibility with the liquid crystal composition is good, and the liquid crystal molecules in the liquid crystal composition are uniformly vertical. It has the effect of making it possible to provide orientation and a stable pre-tilt angle.
  • the polymerizable liquid crystal composition according to one embodiment of the present invention contains one or two compounds represented by the general formula (i). Contains more than seeds.
  • the compound represented by the general formula (i) may be referred to as a compound (i) or a compound of the formula (i).
  • R i1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a linear or branched alkyl halide having 1 to 20 carbon atoms, and is contained in the alkyl group or the alkyl halide group.
  • a i1 and A i2 independently represent a divalent aromatic group, a divalent ring-aliphatic group, a divalent heterocyclic compound group, a divalent fused ring, or a divalent fused polycycle.
  • R i2 , R i3 and R i4 are independently hydrogen atom, halogen atom, linear or branched alkyl group having 1 to 20 carbon atoms, and linear or branched alkyl halide having 1 to 20 carbon atoms.
  • Represents a group, or Xi4 , and -CH 2- in the alkyl group or alkyl halide group may be substituted with -CH CH-, -C ⁇ C- or -O-, but two or more-. O-is not adjacent, X i1 , X i2 , X i3 and X i4 independently represent -Sp i1- P i1 or -Sp i2- K i1 respectively. Ki1 is independently represented by the general formula (K-1) or (K-2).
  • T k1 are independently from the general formulas (T-1) to (T-7).
  • -Or- may be replaced with -OCO-
  • R T2 and R T3 independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R k1 independently represents a hydrogen atom and a linear or branched alkyl having 1 to 6 carbon atoms, respectively. Representing a group, one or two or more non-adjacent -CH 2- in the alkyl group may be substituted with -O-.
  • T k2 are independently from the general formulas (T-8) to (T-17).
  • the black dot represents the bond.
  • Z K1 independently represents an oxygen atom or a sulfur atom, respectively.
  • W K1 , UK1 , V K1 and SK1 each independently represent a methine group or a nitrogen atom, and here hydrogen atoms in the groups represented by the general formulas (T-8) to (T-17).
  • the black dot represents the bond.
  • mi1 and mi2 each independently represent an integer of 1 to 4.
  • ni1 represents an integer of 0 to 2
  • ni1 is an integer of 1 or 2
  • one or two hydrogen atoms in the ring structure of A i2 is substituted by X i1, ki1, ki2 and ki3 each independently represent an integer of 0 to 3, where the sum of ki1, ki2 and ki3 is 3.
  • the general formula (i) includes one or more groups selected from the group consisting of Pi 1 , Pi 2 and Pi 3 , and one group selected from the group consisting of T k1 and T k 2. The total number of groups included as described above and selected from the group consisting of Pi 1 , Pi 2 , Pi 3 , T k1 and T k 2 is 5 or more.
  • the polymerizable liquid crystal composition refers to one or more polymerizable compounds having a polymerizable group and one or more non-polymerizable liquid crystal compounds (liquid crystal materials). It refers to a liquid crystal composition containing and a composition containing.
  • the compound represented by the general formula (i) corresponds to a polymerizable compound because it has a polymerizable group.
  • the compound represented by the general formula (i) has a mesogen skeleton composed of a plurality of ring structures, and the mesogen skeleton has a polymerizable group and a polar group via a spacer group, and is spontaneously oriented. Functions as an additive.
  • the polymerizable liquid crystal composition of the present invention comprise the formula (i) compound represented by the general formula (i), P i1, P i2 and one or more groups selected from the group consisting of P i3 and T a group selected from the group consisting of k1 and T k2 comprise one or more, and P i1, P i2, P i3 , T k1 and total number of groups selected from the group consisting of T k2 5 It is characterized by the above.
  • the group selected from the group consisting of Pi1 , Pi2, and Pi3 represents a polymerizable group, and has a function of forming a polymer at the interface in the liquid crystal display element by an external stimulus such as heat or light and unevenly distributing the polymer.
  • the group selected from the group consisting of T k1 and T k2 represents a polar group, and contributes to the vertical orientation of the liquid crystal molecules by adsorbing to the substrate interface in the liquid crystal display element.
  • the compound represented by the general formula (i) is the total number of groups selected from the group consisting of Pi 1 , Pi 2 , Pi 3 , T k1 and T k 2 (hereinafter, the total number of polymerizable groups and polar groups).
  • the probability of being first adsorbed on the substrate when the polymerizable liquid crystal composition is sealed in the panel is dramatically increased as compared with the case of 4 or less. It is possible to maintain good vertical orientation.
  • the other polar groups in compound (i) are asymmetrically adjacent to one side of the molecule as in compound (i)
  • the other polar groups can be adsorbed to the substrate at more points by thermal motion. Therefore, as a result, it is possible to maintain good vertical orientation.
  • the polymerizable group is not as strong as the polar group, but functions as an assist for orientation.
  • the compound represented by the general formula (i) is located at a desired position in the general formula (i), Pi 1 , Pi 2 , Pi 3 , T k 1 and T k 2. It is characterized by having a group selected from the group consisting of.
  • the compound represented by the general formula (i) is at least on one side of the molecular structure in the major axis direction, specifically, on the benzene ring located at one end in the major axis direction. It has a characteristic structure in which X i2 and X i3 are unevenly distributed.
  • X i2 and X i3 include a partial structure represented by P i1 , P i2 and P i3, and T k1 and T k2 and have polarity, they are adsorbed to the substrate at multiple points as described above. can do. Therefore, in the liquid crystal display element using the polymerizable liquid crystal composition of the present invention, the compound represented by the general formula (i) can be adsorbed on the substrate sandwiching the liquid crystal composition (liquid crystal layer) with an appropriate strength. It is estimated that it can be done. Further, since the compound represented by the general formula (i) has a partial structure represented by T k1 and T k2 at the end, it is considered that the liquid crystal molecules can be held in a vertically oriented state. ..
  • the liquid crystal molecules are uniformly and vertically oriented without providing the PI layer (the vertical orientation of the liquid crystal molecules is induced when no voltage is applied, and the liquid crystal molecules are horizontally oriented when the voltage is applied. Orientation) is possible.
  • the compound represented by the general formula (i) has a function of assisting the vertical orientation of the liquid crystal molecules in the liquid crystal composition.
  • the polymerizable liquid crystal composition of the present invention is represented by the general formula (i) because the compound represented by the general formula (i) has the above-mentioned characteristic structure. It has been found that the compatibility between the compound and the liquid crystal composition is high and low temperature stability can be ensured. Although the reason for this is not certain, the binding of polymerizable or alkyl groups from the linear and lateral sides of the mesogen exerts a relative improvement in overall molecular flexibility and thus inhibition of crystallization packing. It is presumed that it is due to being done.
  • the polymerizable liquid crystal composition of the present invention enables uniform vertical orientation of the liquid crystal compound without providing a PI layer, and can cause dripping marks and dripping marks. Orientation unevenness is unlikely to occur, vertical orientation and long-term stability of the pretilt angle are high, and excellent compatibility can be exhibited.
  • the compound represented by general formula (i) is a polymerizable compound, and a compound having a function of spontaneously orienting liquid crystal molecules (spontaneous orientation). Additive).
  • the compound represented by the general formula (i) has a total number of groups selected from the group consisting of Pi 1 , Pi 2 , Pi 3 , T k 1 and T k 2 of 5 or more, and , At one end in the major axis direction in the molecular structure, preferably at one end of the main chain of the molecule, has a partial structure represented by one of Pi 1 , Pi 2 and Pi 3 and T k 1 and T k 2.
  • the chemical structure of the bond destination to which the above partial structure is bonded is not particularly limited as long as it does not interfere with the function of the liquid crystal composition.
  • the total number of groups selected from the group consisting of Pi 1 , Pi 2 , Pi 3 , T k1 and T k 2 may be 5 or more, but the polymerizable group and the polar group may be used.
  • the total number of the groups is preferably 8 or less and 7 or less in order to secure the synthesis cost and crystallinity.
  • the number of groups selected from the group consisting of Pi 1 , Pi 2 and Pi 3 is 1 or more, but 3 or more is preferable, and 4 or more is particularly preferable. preferable.
  • the number of the groups is preferably 6 or less, and more preferably 5 or less.
  • the number of groups selected from the group consisting of T k1 and T k2 is 1 or more, preferably 3 or more, and particularly preferably 4 or more.
  • the number of the groups is preferably 7 or less, more preferably 6 or less. This is because the vertical orientation of the liquid crystal molecules can be enhanced by setting the number of groups selected from the group consisting of T k1 and T k 2 within the above range.
  • Z i1 and Z i2 are independently single-bonded, -COO-, -OCO-, -OCH 2 CH 2 O-, or an alkylene group having 2 carbon atoms (ethylene group (-CH 2 CH)). 2- )) Or one of the -CH 2- in the ethylene group is replaced by -O- (-CH 2 O-, -OCH 2- ), or one of the -CH 2- in the ethylene group. Represents a group substituted with -COO-, -OCO-.
  • a i1 and A i2 in the general formula (i) are independently divalent ring aromatic groups, divalent ring complex aromatic groups, divalent ring aliphatic groups, or divalent ring complex fats, respectively.
  • Group groups are preferred, divalent 6-membered ring aromatic groups, divalent 6-membered ring heteroaromatic groups, divalent 6-membered ring aliphatic groups, divalent 6-membered ring heterolipid group, More preferably, it is a divalent 5-membered ring aromatic group, a divalent 5-membered ring heteroaromatic group, a divalent 5-membered ring aliphatic group, or a divalent 5-membered ring heterolipid group.
  • the hydrogen atoms in these ring structures may be substituted with Li1 .
  • Ai1 and Ai2 are 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5.
  • -Diyl group pyrimidin-2,5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, chroman-3,7-diyl, 1,2,3,4-tetrahydronaphthalene-
  • a 2,6-diyl group or a 1,3-dioxane-2,5-diyl group is preferable, and the ring structure in these groups is preferably unsubstituted or the hydrogen atom is preferably substituted with Li1 .
  • Li1 is an alkyl group having 1 to 12 carbon atoms, an alkyl halide group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, or a halogen. Atoms are preferable, and alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or halogen atoms are more preferable. Examples of the halogen atom include a fluorine atom and a chlorine atom, and among them, a fluorine atom is preferable.
  • the alkyl group, the halogenated alkyl group, and the alkoxy group may be linear or branched.
  • Ai1 is a divalent unsubstituted 6-membered ring aromatic group, or a divalent unsubstituted 6-membered ring aliphatic group, or hydrogen atoms in these ring structures having 1 to 12 carbon atoms. It represents an alkyl group, an alkyl halide group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, or a group substituted with a halogen atom.
  • the hydrogen atom in the ring structure is an alkyl group having 1 to 6 carbon atoms, an alkyl halide group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
  • the halogen atom is preferably a fluorine atom.
  • a i2 preferably represents a 1,4-phenylene group.
  • At least one hydrogen atom in the ring structure may be substituted with X i1 .
  • the number of X i1 that is, ni1 in the general formula (i) represents an integer of 0 to 2, but for reasons of cryopreservation stability and orientation, it preferably represents an integer of 1 to 2, with 1 being more. preferable.
  • ni1 represents 0, hydrogen atom of the ring structure of A i2 is not substituted in the X i1, when representing an integer of ni1 is 1 or 2, the ring structure of A i2
  • One or two hydrogen atoms in the above are replaced by X i1 . If more hydrogen atoms in the ring structure of A i2 is replaced with X i1, the plurality of X i1 may be the same or may be different.
  • the position of the X i1 is not particularly limited in the ring structure of A i2, A i2 of the case inter alia described above, the following formula (a i2 -1) from (a i2 -4) is preferably represented by any one of.
  • R i2 , R i3 and R i4 in the general formula (i) are preferably hydrogen atoms, halogen atoms, linear or branched alkyl groups having 1 to 18 carbon atoms, or X i4 , respectively.
  • Hydrogen atom, halogen atom, linear or branched alkyl group having 3 to 18 carbon atoms, or Xi4 is more preferable.
  • R i2 , R i3 and R i4 are independently alkyl groups
  • the number of carbon atoms in R i2 , R i3 and R i4 is preferably 3 or more from the viewpoint of improving the orientation of the liquid crystal compound. 4 or more is preferable, and 5 or more is preferable.
  • X i1 , X i2 , X i3 and X i4 in the general formula (i) independently represent -Sp i1- P i1 or -Sp i2- K i1 respectively.
  • Ki 1 is independently represented by the above-mentioned general formula (K-1) or (K-2). When a plurality of X i1 and X i4 are present, they may be the same or different.
  • X i2 and X i3 and R i2 , R i3 and R i4 are groups that replace hydrogen atoms in the ring structure of the benzene ring.
  • the position of the X i2 and X i3 and R i2, R i3 and R i4 is not particularly limited, for example, the following formulas (A i3 -1) either of (A i3 -6) Can be a position.
  • R i4 represents X i4
  • R i4 represents -Sp i1- P i1 or -Sp i2- K i1
  • the positions of X i2 , X i3 and X i4 , and R i2 and R i2 Is not particularly limited, but is preferably represented by the following formula (A i3 1-1) or (A i3 3-1).
  • T k1 in the general formula (K-1) independently represents a group represented by the above-mentioned general formulas (T-1) to (T-7), and among them, the general formula (T-1). , (T-3), (T-4) or (T-7) is preferable.
  • Formula (T-3) and (T-7) S T1 in each independently a single bond, an alkylene group or a carbon atom number of 2 to 10 carbon atoms having from 1 to 10 carbon linear or branched It is preferable to represent a number of linear or branched alkenylene groups, such as a linear or branched alkylene group having 1 to 7 carbon atoms or a linear or branched alkenylene group having 2 to 7 carbon atoms. Is preferable, and a linear alkylene group having 1 to 3 carbon atoms is preferable. Further, -CH 2- in the alkylene group or alkenylene group may be substituted with -O-, -COO-, -C ( O)-or -OCO- so that oxygen atoms are not directly adjacent to each other.
  • Each of RT1 in the general formula (T-3) independently represents an alkyl group having 1 to 5 carbon atoms.
  • the alkyl group is linear or branched.
  • RT1 is preferably a linear alkyl group having 1 to 3 carbon atoms.
  • it is preferable that at least two or more secondary carbon atoms contain ⁇ C ( O).
  • RT2 and RT3 in the general formula (T-6) independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and among them, it is preferable to represent a hydrogen atom.
  • R k1 independently represents a hydrogen atom and a linear or branched alkyl group having 1 to 6 carbon atoms, and one or two or more non-adjacent alkyl groups in the alkyl group.
  • -CH 2- may be substituted with -O-, and more preferably a hydrogen atom or a linear alkyl group having 1 to 3 carbon atoms.
  • ki1, ki2, and ki3 each independently represent an integer of 0 to 3, but the total of ki1, ki2, and ki3 is 3.
  • ki1 preferably represents an integer of 1 or 2 from the viewpoint of improving the orientation of the liquid crystal and the solubility in the liquid crystal compound.
  • ki2 preferably represents an integer of 1 or 2, and more preferably represents an integer of 1 from the viewpoint of improving orientation.
  • ki3 preferably represents an integer of 0 or 1.
  • Such a combination of ki1, ki2 and ki3 can be appropriately selected, but as a preferable combination, for example, ki1 represents an integer of 1, ki2 represents an integer of 2, and ki3 represents an integer of 0. Combination A, ki1 represents an integer of 2, ki2 represents an integer of 1, ki3 represents an integer of 0 Combination B, ki1 represents an integer of 2, ki2 represents an integer of 0, ki3 represents an integer of 1. Combination C, etc. representing the above can be mentioned.
  • the combination of ki1, ki2, and ki3 is preferably the combination A when the orientation of the liquid crystal is important, while the combination C is preferable when the solubility in the liquid crystal composition is important.
  • Preferred examples of the general formula (K-1) include the following general formulas (K-1-1) to (K-1-5). Of these, the general formulas (K-1-1), (K-1-3) or (K-1-4) are more preferable.
  • TK1s may be the same or different.
  • R T4 , R T5 and R T6 are each independently C 1 -C 3, n T1 and n T2 each independently represents 0 or 1, n T2 represents an integer of 1 to 3 independently, there exist a plurality of R T4, R T5, R T6 , n T1, n T2 and n T3, respectively It may be the same or different.
  • Each of T k2 in the general formula (K-2) independently represents a group represented by the above-mentioned general formulas (T-8) to (T-17).
  • Preferred examples of the general formulas (T-8) to (T-17) include the following formulas (T-8-1) to (T-17-1). Among them, from the viewpoint of orientation and reactivity, the formulas (T-8-1), (T-8-3), (T-10-1), (T-13-1), (T-15-1) ) And (T-18-1) are preferable, and formulas (T-8-1), (T-10-1), and (T-13-1) are particularly preferable.
  • At least one of Sp i1 , Sp i2 , Sp i3 , Sp i4 and Sp i 5 represents an alkylene group having 1 to 18 carbon atoms, and more preferably an alkylene group having 2 to 15 carbon atoms. More preferably, it represents an alkylene group having 2 to 8 carbon atoms.
  • Sp i1 and Sp i2 preferably represent the above-mentioned alkylene group having a carbon atom number. This is because the solubility in the liquid crystal composition becomes good.
  • Ki1 represents any of the above-mentioned general formulas (K-1-3), (K-1-4) or (K-1-5), the crystallinity of the compound and the pretilt when the liquid crystal display element is used. At least one of Sp i1 , Sp i2 , Sp i3 , Sp i4 and Sp i 5 may represent a single bond because of the good angle formation.
  • Pi1 , Pi2, and Pi3 independently represent groups selected from the group represented by the general formula (P-16) from the general formula (P-1) described above. Among them, from the viewpoint of ease of handling and reactivity, it is preferable that Pi1 , Pi2 and Pi3 are independently methacrylate groups or acrylate groups, and specifically, the general formula (P-1) or It is particularly preferable that the group is represented by (P-2).
  • mi1 and mi2 each independently represent an integer of 1 to 4, preferably an integer of 1 to 2, and more preferably 1. More specifically, mi1 preferably represents an integer of 1 to 3, more preferably an integer of 1 to 2, and represents an integer of 1 from the viewpoint of the balance between orientation and low temperature solution stability. Is more preferable. On the other hand, mi2 preferably represents an integer of 1 to 2, and particularly preferably an integer of 1, from the viewpoint of the balance between orientation and pretilt angle qualitative.
  • the compound represented by the general formula (i) is preferably a compound represented by the following general formula (ia).
  • R i1 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i2 , X i3 , X i4 , mi 1, mi 2 and ni 1, respectively, are general formulas (i). It has the same meaning as R i1 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i2 , X i3 , X i4 , mi1, mi2 and ni1.
  • R i2 and R i3 are independently hydrogen atoms, halogen atoms, linear or branched alkyl groups having 1 to 20 carbon atoms, or 1 to 20 carbon atoms. It is preferable to represent a linear or branched alkyl halide group.
  • the compound represented by the general formula (ia) is located at a specific position in the ring structure in the benzene ring located on one side in the major axis direction, specifically, on one side in the major axis direction in the molecular structure. It is essential that the hydrogen atom is replaced with X i2 , X i3 and X i4 , which are the groups representing -Sp i1- P i1 or -Sp i2- K i1 .
  • the polymerizable liquid crystal composition containing the compound represented by the above-mentioned general formula (i) by having a characteristic structure in which polar groups and / or polymerizable groups are unevenly distributed on one side in the major axis direction. It becomes easier to exert the effect of.
  • X i2 , X i3 and X i4 in the general formula ( ia) may be the same or different, respectively.
  • Examples of the compound represented by the general formula (ia) include compounds represented by any of the following general formulas (iA-1) to (ia-4).
  • the content of the compound represented by the general formula (i) in the polymerizable liquid crystal composition of the present invention is preferably 0.01 to 50% by mass, but the lower limit thereof more preferably orients the liquid crystal molecules. From the viewpoint of being made, preferably 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, 0.7% by mass or more, or 1% by mass based on the total amount of the polymerizable liquid crystal composition. That is all.
  • the upper limit of the content of the compound (i) is preferably 50% by mass or less, 30% by mass or less, 10% by mass or less, based on the total amount of the polymerizable liquid crystal composition, from the viewpoint of excellent response characteristics. It is 5% by mass or less, 4% by mass or less, or 3% by mass or less.
  • the polymerizable liquid crystal composition of the present invention contains a liquid crystal composition in addition to the compound represented by the general formula (i).
  • the liquid crystal composition contains one or more non-polymerizable liquid crystal compounds (liquid crystal molecules) in the composition. That is, the polymerizable liquid crystal composition of the present invention contains a non-polymerizable liquid crystal compound in addition to the compound represented by the general formula (i).
  • the liquid crystal composition and the polymerizable liquid crystal composition of the present invention containing the liquid crystal composition preferably have a negative dielectric anisotropy ( ⁇ ). Negative permittivity anisotropy ( ⁇ ) means that the sign of ⁇ is negative and its absolute value is greater than 2.
  • ⁇ at 20 ° C. is preferably in the range of ⁇ 4.0 to -2.0, and more preferably in the range of ⁇ 3.5 to ⁇ 2.3. , -3.3 to -2.5 is particularly preferable.
  • the liquid crystal composition can contain a compound selected from the compound group represented by any of the general formulas (N-1), (N-2) and (N-3) as the non-polymerizable liquid crystal compound. ..
  • a N11 , A N12 , A N21 , A N22 , A N31 and A N32 are independent of each other.
  • 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-.)
  • And (d) represent a group selected from the group consisting of 1,4-cyclohexenylene groups, and the above groups (a), group (b), group (c) and group (d) are independent of each other.
  • T N31 is, -CH 2 - represents an or an oxygen atom
  • n N11 , n N12 , n N21 , n N22 , n N31 and n N32 each independently represent an integer of 0 to 3, but n N11 + n N12 , n N21 + n N22 and n N31 + n N32 are independent of each other. And then 1, 2 or 3 When a plurality of A N11 to A N32 and Z N11 to Z N32 are present, they may be the same or different from each other. )
  • the compound represented by any of the general formulas (N-1), (N-2) and (N-3) is preferably a compound in which ⁇ is negative and its absolute value is larger than 3.
  • RN11 , RN12 , RN21 , RN22 , RN31 and RN32 are independent of each other and have 1 to 8 carbon atoms.
  • Alkyl group, alkoxy group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms or alkenyloxy group having 2 to 8 carbon atoms is preferable, and alkyl group having 1 to 5 carbon atoms and carbon atom number.
  • An alkoxy group of 1 to 5, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferable, and an alkenyl group (propenyl group) having 3 carbon atoms is particularly preferable.
  • RN11 , RN12 , RN21 , RN22 , RN31 and RN32 have linear carbon atoms of 1 to 5 when the ring structure to which they are bonded is a phenyl group (aromatic).
  • Alkyl group, linear alkoxy group with 1 to 4 carbon atoms and alkenyl group with 4 to 5 carbon atoms are preferable, and the ring structure to which they are bonded is a saturated ring structure such as cyclohexane, pyran and dioxane.
  • Is 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 total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any of the formulas (R1) to (R5) (black dots in each formula represent bonds).
  • a N11 , AN12 , A N21 , A N22 , A N31 and A N32 are preferably aromatics when it is required to increase ⁇ n independently, and fats are used to improve the response rate. It is preferably a group, and is preferably a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, 3,5.
  • Z N11, Z N12, Z N21 , Z N22, Z N31 and Z N32 -CH 2 each independently O -, - CF 2 O - , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents an, -CH 2 O -, - CH 2 CH 2 - or a single bond is more preferable, -CH 2 O-or a single bond is particularly preferred.
  • Fluorine atom is preferable for X N21 .
  • Oxygen atom is preferable for TN31 .
  • n N11 + n N12 , n N21 + n N22 and n N31 + n N32 are preferably 1 or 2, n N11 is 1 and n N12 is 0, n N11 is 2 and n N12 is 0, n A combination of N11 being 1 and nN12 being 1, a combination of nN11 being 2 and nN12 being 1, a combination of nN21 being 1 and nN22 being 0, nN21 being 2 and nN22 being A combination of 0, a combination of n N31 of 1 and n N32 of 0, and a combination of n N31 of 2 and n N32 of 0 are preferred.
  • the lower limit of the preferable content of the compound represented by the formula (N-1) with respect to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, and 20% by mass or more. 30% by mass or more, 40% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75 It is mass% or more, and is 80 mass% or more.
  • the upper limit of the preferable content is 95% by mass or less, 85% by mass or less, 75% by mass or less, 65% by mass or less, 55% by mass or less, 45% by mass or less. It is 35% by mass or less, 25% by mass or less, and 20% by mass or less.
  • the lower limit of the preferable content of the compound represented by the formula (N-2) with respect to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, 20% by mass or more. 30% by mass or more, 40% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75 It is mass% or more, and is 80 mass% or more.
  • the upper limit of the preferable content is 95% by mass or less, 85% by mass or less, 75% by mass or less, 65% by mass or less, 55% by mass or less, 45% by mass or less. It is 35% by mass or less, 25% by mass or less, and 20% by mass or less.
  • the lower limit of the preferable content of the compound represented by the formula (N-3) with respect to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, 20% by mass or more. 30% by mass or more, 40% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75 It is mass% or more, and is 80 mass% or more.
  • the upper limit of the preferable content is 95% by mass or less, 85% by mass or less, 75% by mass or less, 65% by mass or less, 55% by mass or less, 45% by mass or less. It is 35% by mass or less, 25% by mass or less, and 20% by mass or less.
  • the lower limit value of the above content is low and the upper limit value is low.
  • the lower limit of the content is low and the upper limit is low.
  • the lower limit value of the content is high and the upper limit value is high.
  • Examples of the compound represented by the general formula (N-1) include a group of 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 represents 0 or 1, n Nc11 represents 0 or 1, n Nd11 represents 0 or 1, n Ne11 represents 1 or 2, and n Nf11 represents 1 or.
  • a Ne11 represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
  • a Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, of which at least one represents a 1,4-cyclohexenylene group.
  • Z Ne 11 represents a single bond or ethylene, but at least one represents ethylene.
  • the compound represented by the general formula (N-1) is a compound selected from the compound group represented by the general formulas (N-1-1) to (N-1-22). Is preferable.
  • the compound represented by the general formula (N-1-1) is the following compound.
  • R N111 and R N112 each independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • RN111 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, a pentyl group or a vinyl group.
  • RN112 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 preferably an ethoxy group or a butoxy group.
  • the compound represented by the general formula (N-1-1) can be used alone, but can also be used in combination of two or more compounds.
  • the types 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, two types, three types, four types, and five or more types as one embodiment.
  • the content of the compound represented by the general formula (N-1-1) is preferably set high when the improvement of ⁇ is emphasized, and is increased when the solubility at low temperature is emphasized. When set to, the effect is high, and when TNI is emphasized, the effect is high when the content is set low. Further, for the compound represented by the general formula (N-1-1), it is preferable to set the content range in the middle when improving the dropping marks and the seizure characteristics.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-1) with respect to the total amount of the liquid crystal composition is 5% by mass or more, 10% by mass or more, and 13% by mass or more. Yes, 15% by mass or more, 17% by mass or more, 20% by mass or more, 23% by mass or more, 25% by mass or more, 27% by mass or more, 30% by mass or more. , 33% by mass or more, and 35% by mass or more.
  • the upper limit of the preferable content is 50% by mass or less, 40% by mass or less, 38% by mass or less, 35% by mass or less, and 33% by mass or less with respect to the total amount of the liquid crystal composition.
  • the compound represented by the general formula (N-1-1) is a compound selected from the compound group represented by the formulas (N1-1.1) to (N1-1.23). Is preferable, and the compounds represented by the formulas (N-1-1.1) to (N-1-1.4) are preferable, and the formulas (N-1-1.1) and the formula (N-1) are preferable.
  • the compound represented by ⁇ 1.3) is preferable.
  • the compounds represented by the formulas (N-1-1.1) to (N1-1.22) can be used alone or in combination, but the total amount of the liquid crystal composition may be increased.
  • the lower limit of the preferable content of the compound alone or these compounds is 5% by mass or more, and the upper limit is 50% by mass or less with respect to the total amount of the composition of the present embodiment.
  • the compound represented by the general formula (N-1-2) is the following compound.
  • R N121 and R N122 are respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group or a pentyl group.
  • the RN122 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 a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group. Is more preferable.
  • the compound represented by the general formula (N-1-2) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-2) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 7% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, 20% by mass, 23% by mass, 25% by mass, 27% by mass, and 30% by mass. %, 33% by mass, 35% by mass, 37% by mass, 40% by mass, 42% by mass.
  • the preferable upper limit values are 50% by mass, 48% by mass, 45% by mass, 43% by mass, 40% by mass, 38% by mass, 35% by mass, 33% by mass, 30% by mass, 28% by mass and 25% by mass. %, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, 6% by mass, 5% by mass.
  • the amount of the compound represented by the general formula (N-1-2) is preferably set higher, and when the solubility at low temperature is emphasized, the amount is set. If the amount is set small, the effect is high, and if Tni is emphasized, the effect is high if the amount is set large. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-2) in the middle of the above range.
  • the compounds represented by the general formula (N-1-2) are the following formulas (N-1-2.1) to (N-1-2.7) and formulas (N-1-2.10) to ( It is preferably a compound represented by N-1-2.13) or the formulas (N-1-2.20) to (N-1-2.22), and the formula (N-1-2.3).
  • ⁇ (N-1-2.7), Equation (N1-2.10), Equation (N-1-2.11), Equation (N-1-2.13) or Equation (N-1- It is more preferable that the compound is represented by 2.20).
  • the compound When emphasizing the improvement of ⁇ , it is preferable that the compound is represented by the formulas (N-1-2.3) to (N-1-2.7).
  • the compound represented by the formula (N-1-2.20) is preferable.
  • the compound represented by the general formula (N-1-3) is the following compound.
  • R N131 and R N132 are respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • the RN132 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 a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group. More preferred.
  • the compound represented by the general formula (N-1-3) one type can be used alone, but two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-3) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-3) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-3) in the middle of the above range.
  • the compounds represented by the general formula (N-1-3) are represented by the following formulas (N-1-3.1) to (N-1-3.7), formulas (N-1-3.10), and formulas. It is preferably a compound represented by (N-1-3.11), the formula (N-1-3.20) or the formula (N-1-3.21), and the compound is preferably the formula (N-1-3. It is more preferable that the compound is represented by the formulas (N-1-3.7) or (N-1-3.21) from 1) to (N-1-3.1) to (N-1). It is more preferably a compound represented by -3.4) or the formula (N-1-3.6).
  • the compound represented by the formulas (N-1-3.1) to (N-1-3.4), the formula (N-1-3.6) or the formula (N-1-3.21) is 1
  • the seeds can be used alone or in combination of two or more.
  • the combination of the compound represented by the formula (N-1-3.1) and the compound represented by the formula (N-1-3.2) is represented by the formula (N-1-3.3).
  • a combination of 2 or 3 selected from the above compounds, the compound represented by the formula (N-1-3.4) and the compound represented by the formula (N-1-3.6) is preferable.
  • the compound represented by the general formula (N-1-4) is the following compound.
  • R N141 and R N142 are respectively the same meanings 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 group or a butoxy group is more preferable.
  • the compound represented by the general formula (N-1-4) one type can be used alone, but two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-4) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 3% by mass, 5% by mass, 7% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% by mass, 11% by mass, and 10% by mass. %, 8% by mass.
  • the amount of the compound represented by the general formula (N-1-4) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a small amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-4) in the middle of the above range.
  • the compounds represented by the general formula (N-1-4) are represented by the following formulas (N-1-4.1) to (N-1-4.4) or formulas (N-1-4.11) to ( It is preferably a compound represented by N-1-4.14), and more preferably a compound represented by formulas (N-1-4.1) to (N-1-4.4).
  • the compound represented by the formula (N-1-4.1), the formula (N-1-4.2) or the formula (N-1-4.4) is more preferable.
  • the compound represented by the general formula (N-1-5) is the following compound.
  • R N151 and R N152 are respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN151 and RN152 are each independently 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 an ethyl group, a propyl group or an alkoxy group. Butyl groups are more preferred.
  • the compound represented by the general formula (N-1-5) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-5) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 33% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-5) higher, and when the solubility at low temperature is emphasized, the amount is set. If the amount is set small, the effect is high, and if Tni is emphasized, the effect is high if the amount is set large. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-5) in the middle of the above range.
  • the compound represented by the general formula (N-1-5) is preferably a compound represented by the following formulas (N-1-5.1) to (N-1-5.6), and is preferably a compound represented by the formula (N-1-5.6). It is more preferable that the compound is represented by the formula (N-1-5.1), the formula (N-1-5.2) or the formula (N-1-5.4).
  • the compound represented by the general formula (N-1-10) is the following compound.
  • RN1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • RN1102 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) one type can be used alone, or two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-10) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-10) higher, and when the solubility at low temperature is emphasized, the amount is set. If the value is set high, the effect is high, and if Tni is emphasized, the effect is high if the amount is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-10) in the middle of the above range.
  • the compounds represented by the general formula (N-1-10) are represented by the following formulas (N-1-10.1) to (N-1-10.5) or formulas (N-110.11) to ( It is preferably a compound represented by N-110.14), and more preferably a compound represented by the formulas (N-1-10.1) to (N-1-10.5).
  • the compound represented by the formula (N-1-10.1) or the formula (N-1-10.2) is more preferable.
  • the compound represented by the general formula (N-1-11) is the following compound.
  • RN1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • RN1112 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-1-11) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-11) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-11) is preferably set high, and when the solubility at low temperature is emphasized, the amount is set. If the value is set low, the effect is high, and if Tni is emphasized, the effect is high if the amount is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-11) in the middle of the above range.
  • the compounds represented by the general formula (N-1-11) are from the following formulas (N-1-11.1) to (N-1-11.5) or formulas (N-1-1.11.1) to ( It is preferably a compound represented by N-1-1.14), and more preferably a compound represented by formulas (N-1-11.1) to (N-1-11.5). ,
  • the compound represented by the formula (N-1-11.2) or the formula (N-1-11.4) is more preferable.
  • the compound represented by the general formula (N-1-12) is the following compound.
  • R N1121 and R N1122 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1122 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) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-12) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-12) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-12) in the middle of the above range.
  • the compound represented by the general formula (N-1-13) is the following compound.
  • RN1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1132 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-1-13) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-13) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-13) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-13) in the middle of the above range.
  • the compound represented by the general formula (N-1-14) is the following compound.
  • RN1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1142 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-1-14) one type can be used alone, or two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-14) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-14) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-14) in the middle of the above range.
  • the compound represented by the general formula (N-1-15) is the following compound.
  • R N1151 and R N1152 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1151 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1152 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-1-15) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-15) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-15) is preferably set high, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-15) in the middle of the above range.
  • the compound represented by the general formula (N-1-16) is the following compound.
  • R N1161 and R N1162 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1161 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1162 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-1-16) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-16) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-16) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-16) in the middle of the above range.
  • the compound represented by the general formula (N-1-17) is the following compound.
  • R N1171 and R N1172 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1171 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • RN1172 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-1-17) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-17) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-17) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-17) in the middle of the above range.
  • the compound represented by the general formula (N-1-18) is the following compound.
  • R N1181 and R N1182 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1181 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group or a butyl group.
  • RN1182 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-1-18) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-18) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the amount of the compound represented by the general formula (N-1-18) is set higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-1-18) in the middle of the above range.
  • the compound represented by the general formula (N-1-18) is preferably a compound represented by the following formulas (N-1-18.1) to (N1-18.5), and is preferably a compound represented by the formula (N-1-18.5). It is more preferable that the compounds are represented by N-1-18.1) to (N1-18.3), and the formula (N-1-18.2) or the formula (N1-18.3) is preferable. ) Is more preferable.
  • the compound represented by the general formula (N-1-20) is the following compound.
  • R N1201 and N1202 respectively the same meanings as R N11 and R N12 in the general formula (N-1).
  • RN1201 and RN1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-20) one type can be used alone, or two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-20) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the compound represented by the general formula (N-1-21) is the following compound.
  • RN1211 and RN1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-21) one type can be used alone, or two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-2-1) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the compound represented by the general formula (N-1-22) is the following compound.
  • RN1221 and RN1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.
  • the compound represented by the general formula (N-1-22) one type may be used alone, or two or more types may be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-1-22) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 35% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% by mass, 10% by mass, and 5% by mass. %.
  • the amount of the compound represented by the general formula (N-1-22) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a large amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-2-1) in the middle of the above range.
  • the compounds represented by the general formula (N-1-22) are the following formulas (N-1-22.1) to (N-1-22.6), formulas (N-1-22.11) or ( It is preferably a compound represented by N-1-22.12), and more preferably a compound represented by formulas (N-1-22.1) to (N-1-22.5). , Compounds represented by the formulas (N-1-22.1) to (N-1-22.4) are more preferable.
  • the compound represented by the general formula (N-3) is preferably a compound represented by the following general formula (N-3-2).
  • R N321 and R N322 are respectively the same meanings as R N31 and R N32 in the general formula (N-3).
  • RN321 and RN322 are preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a propyl group or a pentyl group.
  • the compound represented by the general formula (N-3-2) one type can be used alone, but two or more types can be used in combination.
  • the type of compound to be combined is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are, for example, 1 type, 2 types, 3 types, 4 types, and 5 or more types.
  • the amount of the compound represented by the general formula (N-3-2) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 3% by mass, 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, 20% by mass, 23% by mass, 25% by mass, 27% by mass, and 30% by mass. %, 33% by mass, and 35% by mass. On the other hand, the preferable upper limit values are 50% by mass, 40% by mass, 38% by mass, 35% by mass, 33% by mass, 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass and 18% by mass. %, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, 6% by mass, and 5% by mass.
  • the amount of the compound represented by the general formula (N-3-2) higher, and when the solubility at low temperature is emphasized, the amount is set. If a large amount is set, the effect is high, and if Tni is emphasized, a small amount is set to a high effect. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the amount of the compound represented by the general formula (N-3-2) in the middle of the above range.
  • the compound represented by the general formula (N-3-2) is preferably a compound represented by the following formulas (N-3-2.1) to (N-3-2.3).
  • the liquid crystal composition may further contain at least one selected from the compounds represented by the following general formula (L) as the non-polymerizable liquid crystal compound (liquid crystal molecule).
  • n L1 represents 0, 1, 2 or 3
  • a L1 , A L2 and A L3 are independent of each other.
  • A 1,4-cyclohexylene group -, (not any one or adjacent present in base two or more -CH 2 may be replaced by -O-.)
  • n L1 is 2 or 3 and there are a plurality of AL2 , they may be the same or different.
  • the compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound (the value of ⁇ is -2 to 2). Therefore, various characteristics of the liquid crystal composition can be adjusted by blending such a compound in the liquid crystal composition.
  • the compound represented by the general formula (L) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on desired performance 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.
  • the types of compounds used are 2 types, 3 types, 4 types, 5 types, 6 types, 7 types, and 8 types. There are 9 types, and there are 10 or more types.
  • the amount of the compound represented by the general formula (L) contained in the liquid crystal composition includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, seizure, and dielectric constant. It is appropriately adjusted according to the required performance such as rate anisotropy.
  • the preferable lower limit values are 1% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, and the like. It is 80% by mass.
  • the preferable upper limit values are 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, and 25% by mass.
  • the lower limit value and the upper limit value of the amount of the compound represented by the general formula (L) are high. Further, when it is necessary to keep the Tni of the liquid crystal composition high and enhance the temperature stability, it is preferable that the above lower limit value is high and the upper limit value is also high. Further, when it is desired to increase the dielectric anisotropy of the liquid crystal composition in order to keep the driving voltage low, it is preferable that the lower limit value and the upper limit value are also low.
  • both R L1 and R L2 is an alkyl group
  • reducing the volatility both R L1 and R L2 is an alkoxy group it is preferable, in the case of emphasizing a reduction in viscosity of the liquid crystal composition, it is preferable that at least one of R L1 and R L2 is an alkenyl group.
  • the number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, more preferably 0 or 1, and when compatibility with other liquid crystal molecules is important. It is more preferably one.
  • RL1 and RL2 are linear alkyl groups having 1 to 5 carbon atoms and linear carbon atoms 1 to 1 when they are bonded to a ring structure which is a benzene ring (aromatic ring). It is preferably an alkoxy group of 4 or an alkenyl group having 4 to 5 carbon atoms, and when they are bonded to a saturated ring structure such as a cyclohexane ring, a pyran ring, or a dioxane ring, a linear carbon atom. It is preferably an alkyl group having a number of 1 to 5, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.
  • the number of carbon atoms (in the case of containing oxygen atoms, the total of the number of carbon atoms and the number of oxygen atoms) is preferably 5 or less, and is linear. Is also preferable.
  • the alkenyl group is preferably selected from the groups represented by any of the following formulas (R1) to (R5).
  • n L1 is preferably 0 when the response speed is important, preferably 2 or 3 in order to improve the upper limit temperature of the nematic phase, and 1 in order to balance these. Is preferable. Further, in order to satisfy the properties required for the liquid crystal composition, it is preferable to use a plurality of kinds of compounds represented by the general formula (L) in which n L1 has a different value in combination.
  • a L1 , A L2, and A L3 are preferably aromatic when it is required to increase ⁇ n independently, and are preferably aliphatic in order to improve the response speed. .. Specifically, AL1 , AL2, and AL3 are independently trans-1,4-cyclohexylene groups, 1,4-phenylene groups, 2-fluoro-1,4-phenylene groups, and 3 -Fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 , 4-Diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, preferably as follows. It is more preferably any of the groups of Chemical formula 85, and even more preferably
  • Z L1 and Z L2 are preferably single-bonded when the response speed is important.
  • the compound represented by the general formula (L) preferably has 0 or 1 halogen atoms present in the molecule.
  • the compound represented by the general formula (L) is preferably selected from the compounds represented by the following general formulas (L-1) to (L-6).
  • the compound represented by the general formula (L-1) is the following compound.
  • R L11 and R L12 are each independently the same meaning as R L1 and R L2 in Formula (L).
  • RL11 and RL12 are independently linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or linear carbon atoms 2 to 5. It is preferably an alkenyl group of.
  • the compound represented by the general formula (L-1) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-1) contained in the liquid crystal composition is set as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 15% by mass, 20% by mass, 25% by mass, 30% by mass, and 35% by mass. %, 40% by mass, 45% by mass, 50% by mass, 55% by mass. On the other hand, the preferable upper limit values are 95% by mass, 90% by mass, 85% by mass, 80% by mass, 75% by mass, 70% by mass, 65% by mass, 60% by mass, 55% by mass, 50% by mass and 45% by mass. %, 40% by mass, 35% by mass, 30% by mass, and 25% by mass.
  • the lower limit value and the upper limit value are high. Further, when it is necessary to keep the Tni of the liquid crystal composition high and enhance the temperature stability, it is preferable that the above lower limit value is moderate and the upper limit value is moderate. Further, when it is desired to increase the dielectric anisotropy of the liquid crystal composition in order to keep the driving voltage low, it is preferable that the lower limit value and the upper limit value are also low.
  • the compound represented by the general formula (L-1) is preferably selected from the compounds represented by the general formula (L-1-1).
  • R L12 represents the same meaning as R L12 in formula (L-1).
  • the compound represented by the general formula (L-1-1) is preferably selected from the compounds represented by the formulas (L-1-1.1) to (L-1-1.3), and the compound represented by the formula (L-1-1.3) is preferably selected. It is more preferable to select from the compounds represented by L-1-1.2) and the formula (L-1-1.3), and the compound is represented by the formula (L-1-1.3). Is even more preferable.
  • the amount of the compound represented by the formula (L-1-1.3) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit value is 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, and 10% by mass. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, 6% by mass, 5% by mass, and 3% by mass.
  • the compound represented by the general formula (L-1) is preferably selected from the compounds represented by the general formula (L-1-2).
  • R L12 represents the same meaning as R L12 in formula (L-1).
  • the amount of the compound represented by the general formula (L-1-2) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 15% by mass, 17% by mass, 20% by mass, 23% by mass, 25% by mass, 27% by mass, 30% by mass, and 35% by mass. %. On the other hand, the preferable upper limit values are 60% by mass, 55% by mass, 50% by mass, 45% by mass, 42% by mass, 40% by mass, 38% by mass, 35% by mass, 33% by mass and 30% by mass.
  • the compound represented by the general formula (L-1-2) is preferably selected from the compounds represented by the formulas (L-1-2.1) to (L-1-2.4). It is more preferable to be selected from the compounds represented by the formulas (L-1-2.2) to (L-1-2.4).
  • the compound represented by the formula (L-1-2.2) is preferable because it particularly improves the response speed of the liquid crystal composition. Further, when obtaining Tni higher than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L-1-2.4).
  • the total amount of the compound represented by the formula (L-1-2.3) and the compound represented by the formula (L-1-2.4) contained in the liquid crystal composition is the solubility at a low temperature. It is not preferable that the content is 30% by mass or more in order to improve the temperature.
  • the amount of the compound represented by the formula (L-1-2.2) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 10% by mass, 15% by mass, 18% by mass, 20% by mass, 23% by mass, 25% by mass, 27% by mass, 30% by mass, 33% by mass, 35% by mass, and 38% by mass. %, 40% by mass. On the other hand, the preferable upper limit values are 60% by mass, 55% by mass, 50% by mass, 45% by mass, 43% by mass, 40% by mass, 38% by mass, 35% by mass, 32% by mass, 30% by mass and 27% by mass. %, 25% by mass, 22% by mass.
  • the total amount of the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) contained in the liquid crystal composition shall be as follows. Is preferable. That is, the preferable lower limit values are 10% by mass, 15% by mass, 20% by mass, 25% by mass, 27% by mass, 30% by mass, 35% by mass, and 40% by mass. On the other hand, the preferable upper limit values are 60% by mass, 55% by mass, 50% by mass, 45% by mass, 43% by mass, 40% by mass, 38% by mass, 35% by mass, 32% by mass, 30% by mass and 27% by mass. %, 25% by mass, 22% by mass.
  • the compound represented by the general formula (L-1) is preferably selected from the compounds represented by the general formula (L-1-3).
  • RL13 and RL14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • RL13 and RL14 are independently linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or linear carbon atoms 2 to 5. It is preferably an alkenyl group of.
  • the amount of the compound represented by the formula (L-1-3) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, 20% by mass, 23% by mass, 25% by mass, and 30% by mass. On the other hand, the preferable upper limit values are 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 37% by mass, 35% by mass, 33% by mass, 30% by mass, 27% by mass and 25% by mass. %, 23% by mass, 20% by mass, 17% by mass, 15% by mass, 13% by mass, and 10% by mass.
  • the compound represented by the general formula (L-1-3) is preferably selected from the compounds represented by the formulas (L-1-3.1) to (L-1-3.13). It is more preferable to be selected from the compounds represented by the formula (L-1-3.1), the formula (L-1-3.3) and the formula (L-1-3.4).
  • the compound represented by the formula (L-1-3.1) is preferable because it particularly improves the response speed of the liquid crystal composition. Further, when obtaining a Tni higher than the response speed, the formula (L-1-3.3), the formula (L-1-3.4), the formula (L-1-3.11) or the formula (L-) is obtained. It is preferable to use the compound represented by 1-3.12).
  • the total amount of the compound represented by .11) and the compound represented by the formula (L-1-3.13) is preferably 20% by mass or more in order to improve the solubility at low temperature. Absent.
  • the amount of the compound represented by the formula (L-1-3.1) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 20% by mass, 17% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, and 6% by mass.
  • the compound represented by the general formula (L-1) is preferably selected from the compounds represented by the general formula (L-1-4) and the general formula (L-1-5).
  • RL15 and RL16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • RL15 and RL16 are independently linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or linear carbon atoms 2 to 5. It is preferably an alkenyl group of.
  • the amount of the compound represented by the formula (L-1-4) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 25% by mass, 23% by mass, 20% by mass, 17% by mass, 15% by mass, 13% by mass, and 10% by mass.
  • the amount of the compound represented by the formula (L-1-5) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass. On the other hand, the preferable upper limit values are 25% by mass, 23% by mass, 20% by mass, 17% by mass, 15% by mass, 13% by mass, and 10% by mass.
  • the compound represented by the general formula (L-1) is preferably selected from the compounds represented by the general formula (L-1-6).
  • RL17 and RL18 each independently represent a methyl group or a hydrogen atom.
  • the amount of the compound represented by the general formula (L-1-6) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 5% by mass, 10% by mass, 15% by mass, 17% by mass, 20% by mass, 23% by mass, 25% by mass, 27% by mass, 30% by mass, and 35% by mass. %. On the other hand, the preferable upper limit values are 60% by mass, 55% by mass, 50% by mass, 45% by mass, 42% by mass, 40% by mass, 38% by mass, 35% by mass, 33% by mass and 30% by mass.
  • the compound represented by the general formula (L-2) is the following compound.
  • R L21 and R L22 are each independently the same meaning as R L1 and R L2 in Formula (L).
  • RL21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.
  • RL22 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.
  • the compound represented by the general formula (L-2) may be used alone or in combination of two or more.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-2) contained in the liquid crystal composition is highly effective when set to a high value when solubility at low temperature is important, and conversely, the response speed is emphasized. In some cases, setting it lower is more effective. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the range of the amount in the middle.
  • the preferable lower limit value is 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, and 10% by mass.
  • the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, 6% by mass, 5% by mass, and 3% by mass.
  • the compound represented by the general formula (L-2) is preferably selected from the compounds represented by the formulas (L-2.1) to (L-2.6), and the compound represented by the formula (L-2. It is more preferable to be selected from the compounds represented by 1), the formula (L-2.3), the formula (L-2.4) and the formula (L-2.6).
  • the compound represented by the general formula (L-3) is the following compound.
  • R L31 and R L32 are each independently the same meaning as R L1 and R L2 in Formula (L).
  • RL31 and RL32 are 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) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-3) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit value is 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, and 10% by mass. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, 7% by mass, 6% by mass, 5% by mass, and 3% by mass.
  • the amount of the compound represented by the general formula (L-3) contained in the liquid crystal composition is highly effective when set to a high value when obtaining a high birefringence, and conversely, when high Tni is emphasized. The effect is high when set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the range of the amount in the middle.
  • the compound represented by the general formula (L-3) is preferably selected from the compounds represented by the formulas (L-3.1) to (L-3.7), and the compound represented by the formula (L-3. It is more preferable to select from the compounds represented by 2) to (L-3.5).
  • the compound represented by the general formula (L-4) is the following compound.
  • R L41 and R L42 are each independently the same meaning as R L1 and R L2 in Formula (L).
  • RL41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.
  • RL42 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.
  • the compound represented by the general formula (L-4) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-4) contained in the liquid crystal composition includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, and seizure. , It is adjusted as appropriate according to the required performance such as dielectric anisotropy.
  • the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 14% by mass, 16% by mass, 20% by mass, 23% by mass, and 26% by mass. It is 30% by mass, 35% by mass, and 40% by mass.
  • the preferable upper limit values are 50% by mass, 40% by mass, 35% by mass, 30% by mass, 20% by mass, 15% by mass, 10% by mass, and 5% by mass.
  • the compound represented by the general formula (L-4) is preferably selected from the compounds represented by the formulas (L-4.1) to (L-4.3).
  • the liquid crystal composition may contain a compound represented by the formula (L-4.1) depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the compound represented by the formula (L-4.2) may be contained, or the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) may be contained. Both of them may be contained with the compound, or all of the compounds represented by the formulas (L-4.1) to (L-4.3) may be contained.
  • the amount of the compound represented by the formula (L-4.1) or the formula (L-4.2) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 3% by mass, 5% by mass, 7% by mass, 9% by mass, 11% by mass, 12% by mass, 13% by mass, 18% by mass, and 21% by mass. On the other hand, the preferable upper limit values are 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% by mass, and 10% by mass. %, 8% by mass.
  • the liquid crystal composition contains both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2), it is contained in those liquid crystal compositions.
  • the total amount is preferably as follows. That is, the preferable lower limit values are 15% by mass, 19% by mass, 24% by mass, and 30% by mass.
  • the preferable upper limit values are 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the compound represented by the general formula (L-4) is preferably selected from the compounds represented by the formulas (L-4.4) to (L-4.6), and the compound represented by the formula (L-4. It is more preferable that the compound is represented by 4).
  • the liquid crystal composition may contain a compound represented by the formula (L-4.4) depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. It may contain a compound represented by the formula (L-4.5), and a compound represented by the formula (L-4.4) and a compound represented by the formula (L-4.5). Both may be contained.
  • the amount of the compound represented by the formula (L-4.4) or the formula (L-4.5) in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 3% by mass, 5% by mass, 7% by mass, 9% by mass, 11% by mass, 12% by mass, 13% by mass, 18% by mass, and 21% by mass. On the other hand, the preferable upper limit values are 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% by mass, and 10% by mass. %, 8% by mass.
  • the liquid crystal composition contains both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5), it is contained in these liquid crystal compositions.
  • the total amount is preferably as follows. That is, the preferable lower limit values are 15% by mass, 19% by mass, 24% by mass, and 30% by mass.
  • the preferable upper limit values are 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass and 13% by mass.
  • the compound represented by the general formula (L-4) is preferably selected from the compounds represented by the formulas (L-4.7) to (L-4.10), and in particular, the compound represented by the formula (L-). It is preferably a compound represented by 4.9).
  • the compound represented by the general formula (L-5) is the following compound.
  • R L51 and R L52 are each independently the same meaning as R L1 and R L2 in Formula (L).
  • RL51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.
  • RL52 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.
  • the compound represented by the general formula (L-5) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-5) contained in the liquid crystal composition includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dripping marks, and seizure. , It is adjusted as appropriate according to the required performance such as dielectric anisotropy.
  • the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 14% by mass, 16% by mass, 20% by mass, 23% by mass, and 26% by mass. It is 30% by mass, 35% by mass, and 40% by mass.
  • the preferable upper limit values are 50% by mass, 40% by mass, 35% by mass, 30% by mass, 20% by mass, 15% by mass, 10% by mass, and 5% by mass.
  • the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and in particular, the compound represented by the formula (L-5.2). It is preferably a compound represented by 5.1).
  • the amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, and 7% by mass. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, and 9% by mass.
  • the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).
  • the amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, and 7% by mass. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, and 9% by mass.
  • the compound represented by the general formula (L-5) is preferably selected from the compounds represented by the formulas (L-5.5) to (L-5.7), and in particular, the compound represented by the formula (L-5.7). It is preferably a compound represented by 5.7).
  • the amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% mass%, 2 mass%, 3 mass%, 5 mass%, and 7 mass%. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, and 9% by mass.
  • 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 Formula (L)
  • X L61 and X L62 are each independently a hydrogen atom or a fluorine atom Represents.
  • RL61 and RL62 are independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.
  • one of X L61 and XL 62 is a fluorine atom and the other is a hydrogen atom.
  • the compound represented by the general formula (L-6) one type can be used alone, or two or more types can be used in combination.
  • the type of compound that can be used in combination is not particularly limited, but is appropriately selected depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
  • the types of compounds used are one type, two types, three types, four types, and five or more types.
  • the amount of the compound represented by the general formula (L-6) contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 14% by mass, 16% by mass, 20% by mass, 23% by mass, and 26% by mass. %, 30% by mass, 35% by mass, and 40% by mass. On the other hand, the preferable upper limit values are 50% by mass, 40% by mass, 35% by mass, 30% by mass, 20% by mass, 15% by mass, 10% by mass, and 5% by mass.
  • the amount of the compound represented by the general formula (L-6) is preferably large when focusing on increasing ⁇ n, and small when focusing on precipitation at low temperature. preferable.
  • the compound represented by the general formula (L-6) is preferably selected from the compounds represented by the formulas (L-6.1) to (L-6.9).
  • the types of compounds that can be used in combination are not particularly limited, but it is preferable to select 1 to 3 types from the compounds represented by the formulas (L-6.1) to (L-6.9), and 1 to 4 types. It is more preferable to select the type.
  • one of the compounds represented by the formulas (L-6.1) and (L-6.2) is used.
  • it is represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9). It preferably contains a compound.
  • the compound represented by the general formula (L-6) is preferably selected from the compounds represented by the formulas (L-6.10) to (L-6.17), and the compound represented by the formula (L-6. It is more preferable that the compound is represented by 11).
  • the amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferable lower limit values are 1% by mass, 2% by mass, 3% by mass, 5% by mass, and 7% by mass. On the other hand, the preferable upper limit values are 20% by mass, 15% by mass, 13% by mass, 10% by mass, and 9% by mass.
  • the liquid crystal composition 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 amount of the compound having a carbonyl group contained in the liquid crystal composition is preferably 5% by mass or less, and preferably 3% by mass or less. Is more preferable, and it is more preferably 1% by mass or less, and most preferably 0 (zero) mass%.
  • the amount of the compound substituted with chlorine atoms in the liquid crystal composition is preferably 15% by mass or less, and more preferably 10% by mass or less. It is preferably 8% by mass or less, more preferably 5% by mass or less, particularly preferably 3% by mass or less, and most preferably substantially 0 (zero) mass%. ..
  • the amount contained in the liquid crystal composition of the compound in which the ring structure in the molecule is all 6-membered rings specifically, it is preferably 80% by mass or more, and 90% by mass or more. It is more preferable to make it 95% by mass or more, and it is most preferable to make it substantially 100% by mass.
  • the amount of the compound having a cyclohexene ring as a ring structure in the liquid crystal composition specifically, 10% by mass or less. It is preferably 8% by mass or less, more preferably 5% by mass or less, particularly preferably 3% by mass or less, and substantially 0 (zero) mass%. Most preferred.
  • the hydrogen atom may be replaced with a halogen atom 2- It is preferable to reduce the amount contained in the liquid crystal composition of the compound having a methylbenzene-1,4-diyl group in the molecule, specifically, it is preferably 10% by mass or less, and 5% by mass or less. It is more preferable that the amount is substantially 0 (zero) mass%.
  • the number of carbon atoms of the alkenyl group is preferably 2 to 5.
  • the number of carbon atoms of the alkenyl group is preferably 4 to 5, and the alkenyl group does not have a carbon atom. It is preferable that the saturated bond and the phenylene group are not directly bonded.
  • the amount contained in the liquid crystal composition of the compound having an alkenyl group as a side chain and having a 2,3-difluorobenzene-1,4-diyl group is preferably 10% by mass or less, more preferably 5% by mass or less, and further preferably substantially 0 (zero) mass%.
  • the liquid crystal composition contains other compounds (molecules) such as ordinary nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, chiral agent, etc., in addition to the above liquid crystal molecules, depending on the application. You may.
  • the above other compounds do not have chlorine atoms in their structures.
  • the above-mentioned other compounds have a condensed ring having a long conjugated length represented by a naphthalene ring or the like and an absorption peak in the ultraviolet region in its structure. It is preferable not to have such a substance.
  • the polymerizable liquid crystal composition of the present invention contains one or two polymerizable compounds having a structure different from that of the general formula (i) (hereinafter, may be referred to as other polymerizable compounds). The above may be further contained.
  • the other polymerizable compound may be a known polymerizable compound used in a general liquid crystal composition.
  • Examples of the polymerizable compound having a structure different from the general formula (i) include a compound represented by the following general formula (P) (however, the compound represented by the general formula (i) is excluded).
  • Z p1 is an alkyl group having 1 to 15 carbon atoms in which hydrogen atoms, fluorine atoms, cyano groups, and hydrogen atoms may be substituted with halogen atoms, and hydrogen atoms are substituted with halogen atoms.
  • R p1 and R p2 independently represent any of the following formulas (RI) to (R-VIII).
  • Sp p1 and Sp p2 each independently represent a spacer group.
  • M p2 is 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5. -Diyl group, pyrimidin-2,5-diyl group, naphthalene-1,4-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene Represents a -2,6-diyl group or a 1,3-dioxane-2,5-diyl group.
  • M p2 is unsubstituted or an alkyl group having 1 to 12 carbon atoms, an alkyl halide group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and a halogenation having 1 to 12 carbon atoms. It may be substituted with an alkoxy group, a halogen atom, a cyano group, a nitro group or -R p1 .
  • M p1 represents any of the following formulas (i-11) to (ix-11).
  • M p3 represents any of the following formulas (i-13) to (ix-13).
  • m p2 to m p4 independently represent 0, 1, 2 or 3
  • m p1 and m p5 independently represent 1, 2 or 3, respectively.
  • Sp p1 and Sp p2 each independently represent a spacer group.
  • the spacer group represented by Sp p1 and Sp p2 is preferably a single bond or an alkylene group having 1 to 30 carbon atoms, and -CH 2- in the alkylene group does not have oxygen atoms directly linked to each other.
  • the hydrogen atom in the alkylene group is substituted with a halogen atom.
  • Sp p1 and Sp p2 are preferably linear alkylene groups having 1 to 10 carbon atoms or single bonds, respectively.
  • a p1 , A p2 and A p3 are each independently preferably a 1,4-phenylene group or a 1,4-cyclohexylene group, and 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 molecule (liquid crystal compound).
  • the polymerizable liquid crystal composition of the present invention preferably contains a polymerizable compound represented by the general formula (P) in addition to the compound represented by the general formula (i) to preferably set the pretilt angle of the liquid crystal molecule. Can be formed.
  • polymerizable compound represented by the general formula (P) include compounds represented by the following formulas (P-2-1) to (P-2-20).
  • the total content of the compounds represented by the general formula (P) is preferably 0.05 to 10% by mass, preferably 0.1 to 8% by mass, based on the polymerizable liquid crystal composition. More preferably, it is more preferably 0.1 to 5% by mass, further preferably 0.1 to 3% by mass, further preferably 0.2 to 2% by mass, and 0.2 to 1%. It is more preferably 3% by mass, particularly preferably 0.2 to 1% by mass, and most preferably 0.2 to 0.56% by mass.
  • the preferable lower limit of the total content of the compounds represented by the general formula (P) is 0.01% by mass, 0.03% by mass, and 0.05% by mass with respect to the polymerizable liquid crystal composition. %, 0.08% by mass, 0.1% by mass, 0.15% by mass, 0.2% by mass, 0.25% by mass, and 0.3% by mass. is there.
  • the preferable upper limit of the total content of the compounds represented by the general formula (P) is 10% by mass, 8% by mass, 5% by mass, and 3% by mass with respect to the polymerizable liquid crystal composition. %, 1.5% by mass, 1.2% by mass, 1% by mass, 0.8% by mass, and 0.5% by mass.
  • the content of the compound represented by the general formula (P) is small, the effect of adding this compound to the liquid crystal composition is unlikely to appear. For example, depending on the type of the liquid crystal molecule or the orientation aid, the orientation regulating force of the liquid crystal molecule may be increased. Problems such as weakness or weakening over time may occur. On the other hand, if the content of the compound represented by the general formula (P) is too large, the amount of the compound remaining after curing increases depending on, for example, the illuminance of the active energy ray, the curing takes time, and the liquid crystal composition. Problems such as a decrease in the reliability of the object may occur. Therefore, it is preferable to set the content in consideration of these balances.
  • polymerizable liquid crystal composition of the present invention may further contain a known spontaneous orientation aid for liquid crystal compositions in addition to the compound represented by the general formula (i).
  • the compound represented by the general formula (i), the compound represented by the general formula (L), and the compound represented by the general formula (N) are represented by the total amount of the composition used for the liquid crystal layer of the liquid crystal display element according to the present invention.
  • the lower limit of the total content of the compounds to be compounded is preferably 80%, 85%, 88%, 90%, 92%, 93%, 94%, and so on. It is 95%, 96%, 97%, 98%, 99%, and 100%.
  • the upper limit of the content is preferably 100%, 99%, 98%, and 95%.
  • the compounds represented by the general formula (i), the compounds represented by the general formulas (L-1) to (L-6), and the compounds represented by the general formulas (L-1) to the total amount of the composition used for the liquid crystal layer of the liquid crystal display element according to the present invention are preferably 80%, 85%, 88%, 90%, and so on. 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%.
  • the upper limit of the content is preferably 100%, 99%, 98%, and 95%.
  • liquid crystal display element The liquid crystal display element according to one embodiment of the present invention (hereinafter referred to as the liquid crystal display element of the present invention) is formed between two substrates and the above-mentioned "I. Polymerizable liquid crystal composition" between the two substrates.
  • the compound represented by the general formula (i) in the polymerizable liquid crystal composition described in the above section has a cured resin component.
  • the cured resin component of the compound represented by the general formula (i) can mean a polymer of the compound represented by the general formula (i). Therefore, the liquid crystal display element of the present invention is provided between the first substrate, the second substrate, the first substrate, and the second substrate, and is represented by the liquid crystal composition and the general formula (i). It has a liquid crystal layer containing at least a polymer of the compound to be used.
  • the liquid crystal layer may contain an unpolymerized compound represented by the general formula (i).
  • the liquid crystal layer contains a polymer of the compound represented by the general formula (i) and a liquid crystal composition
  • the liquid crystal molecules contained in the liquid crystal composition are of the general formula (i). It can be spontaneously oriented by the interaction between the polymer of the compound represented by i) and the non-polymerizable liquid crystal molecule. Therefore, the liquid crystal molecules in the liquid crystal composition sandwiched between the two substrates can be oriented uniformly and perpendicularly to the substrates without providing an alignment film (PI layer), and exhibit good orientation stability. be able to.
  • the polymer of the compound represented by the general formula (i) is strongly unevenly distributed on the substrate sandwiching the liquid crystal composition, so that the stability of the pretilt angle is improved by the above resin component.
  • the liquid crystal display element of the present invention can have excellent long-term display characteristics in which there are no dripping marks or uneven orientation, or the alignment is reduced to an allowable level, and afterimages are less likely to occur.
  • the liquid crystal display element of the present invention has a resin component in which the compound represented by the general formula (i) is cured between two substrates (the first substrate and the second substrate), the first substrate And it is not necessary to provide an alignment film such as a PI layer on the liquid crystal layer side of the second substrate. That is, the liquid crystal display element of the present invention can have a configuration in which at least one of the two substrates does not have an alignment film, and both substrates do not have to have an alignment film.
  • the liquid crystal display element of the present invention may be a liquid crystal display element for driving an active matrix. Further, the liquid crystal display element of the present embodiment may be a PSA type, PSVA type, VA type, IPS type, FFS type or ECB type liquid crystal display element, preferably a PSA type or PSVA type liquid crystal display element. is there.
  • the VA type liquid crystal display element may be a general VA type, a TN-VA type, or a chiral VA type having a liquid crystal layer further containing a chiral agent.
  • the liquid crystal display element of the present invention for example, a liquid crystal filled between the first substrate and the second substrate arranged to face each other and the first substrate and the second substrate. It is driven by the layer, a plurality of gate bus lines and data bus lines arranged in a matrix on the first substrate, a thin film transistor provided at an intersection of the gate bus line and the data bus line, and the thin film transistor. It is located between an electrode layer having pixel electrodes for each pixel, a common electrode formed on the first substrate or the second substrate, and the first substrate and the second substrate, and at least the above. Examples thereof include an embodiment in which the compound represented by the general formula (i) has a cured resin component.
  • the liquid crystal display element of this embodiment may not have an alignment film on the surface of at least one substrate, and may not have an alignment film on the surfaces of both the first substrate and the second substrate.
  • liquid crystal display element of the present invention there is at least a first resin component obtained by curing the compound represented by the general formula (i) between the first substrate and the second substrate.
  • a second resin component (a polymer of a polymerizable compound represented by the general formula (P)) obtained by curing the compound represented by the general formula (P) is added. You may also have more.
  • the compatibility with the liquid crystal composition is good, and the uniform vertical orientation of the liquid crystal molecules in the liquid crystal composition and It is possible to give a stable pre-tilt angle.
  • the compound (S-2) is reacted with 4-chloro-2,6-bis (hydroxypropyl) phenol in the presence of potassium carbonate in N, N-dimethylformamide to react the compound (S-3). ). Further, the compound (S-3) is reacted in tetrahydrofuran in the presence of palladium carbon in a hydrogen atmosphere to obtain the compound (S-4). Then, the compound (S-5) is obtained by subjecting the compound (S-4) to an esterification reaction using methacrylic acid chloride in the presence of triethylamine in a dichloromethane solvent.
  • the target compound (ia) can be obtained by reacting the compound (S-5) with the boron compound in the presence of potassium carbonate and tetrakis (triphenylphosphine) palladium (0) in tetrahydrofuran. ..
  • S pi3, S pi4, R i1, m i1, A i1, Z i1, A i2 and Z i2 are in the general formula (i) S pi3, S pi4 , R i1, m i1, A It has the same meaning as i1 , Z i1 , A i2 and Z i2 .)
  • the compound (S-7) and the compound (S-6) are reacted in the presence of potassium carbonate in N, N-dimethylformamide to obtain the compound (S-8). Further, the compound (S-8) is reacted in tetrahydrofuran in the presence of palladium carbon and in a hydrogen atmosphere to obtain the compound (S-9). Finally, the target compound (ib) can be obtained by subjecting the compound (S-9) to an esterification reaction with methacrylic acid chloride in the presence of triethylamine in a dichloromethane solvent.
  • S pi3, S pi4, R i1, m i1, A i1, Z i1, A i2 and Z i2 are in the general formula (i) S pi3, S pi4 , R i1, m i1, A It has the same meaning as i1 , Z i1 , A i2 and Z i2 .)
  • the compound (S-12) is subjected to an esterification reaction with methacrylic acid chloride in the presence of triethylamine in a dichloromethane solvent to obtain the compound (S-13).
  • the target compound (ic) can be obtained by reacting the compound (S-13) in the presence of concentrated hydrochloric acid in a mixed solvent of tetrahydrofuran and water.
  • R i1, m i1, A i1, Z i1, A i2 and Z i2 is, R i1, respectively in formula (i), m i1, and A i1, Z i1, A i2 and Z i2 It has the same meaning.
  • the compound (S-16) is reacted with the compound (S-17) in the presence of potassium carbonate in N, N-dimethylformamide to obtain the compound (S-18).
  • the compound (S-18) is reacted with methyl chloroglioxylate in the presence of triethylamine in dichloromethane to obtain the compound (S-19).
  • the compound (S-19) is reacted in the presence of concentrated hydrochloric acid in a mixed solvent of tetrahydrofuran and water to obtain the compound (S-20).
  • the target compound (id) can be obtained by subjecting the compound (S-20) to an esterification reaction using methacrylic acid chloride in the presence of triethylamine in a dichloromethane solvent.
  • the compound (S-24) is reacted with 4-bromo-2- (3-hydroxypropyl) phenol in the presence of potassium carbonate and tetrakis (triphenylphosphine) palladium (0) in tetrahydrofuran to form the compound.
  • (S-25) is obtained.
  • the compound (S-25) is hydrolyzed in the presence of sodium hydroxide in a mixed solvent of tetrahydrofuran and water to obtain the compound (S-26).
  • the compound (S-26) and the compound (S-6) are reacted in the presence of potassium carbonate in N, N-dimethylformamide to obtain the compound (S-27).
  • the compound (S-27) is reacted in tetrahydrofuran in the presence of palladium carbon and in a hydrogen atmosphere to obtain the compound (S-28).
  • the target compound (ie) can be obtained by subjecting the compound (S-28) to an esterification reaction with methacrylic acid chloride in the presence of triethylamine in a dichloromethane solvent.
  • S pi3, S pi4, R i1, m i1, A i1, Z i1, A i2 and Z i2 are in the general formula (i) S pi3, S pi4 , R i1, m i1, A It has the same meaning as i1 , Z i1 , A i2 and Z i2 .)
  • N in the table is a natural number.
  • N in the table is a natural number.
  • T ni Nematic phase-isotropy 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 modulus anisotropy at 20 ° C K 33 : Elastic constant at 20 ° C K 33 (pN)
  • a sealing material is drawn on the periphery of the first substrate, a polymerizable liquid crystal composition is further dropped, and the sealing material is laminated and sandwiched with the second substrate under vacuum, and the sealing material is placed at normal pressure at 110 ° C. for 1 hour.
  • the mixture was cured to obtain a liquid crystal cell having a cell gap of 3.2 ⁇ m.
  • the dropping pattern was a compulsory test in the orientation test, and as shown in FIG. 1, 5 points were dropped with 1 point as 4.2 ⁇ L.
  • the uniformity of vertical orientation in the liquid crystal cell produced above and the uneven orientation such as the presence or absence of dripping marks were observed using a polarizing microscope and evaluated in the following five stages. In this evaluation, the surface treatment time in the conventional production by our company was shortened, and the orientation test was emphasized.
  • A Vertical orientation is confirmed uniformly over the entire surface including the edges, etc.
  • B Level that is acceptable even if there are very few orientation defects
  • C Level that is unacceptable due to many orientation defects including the edges, etc.
  • D Orientation Bad is pretty bad
  • the pre-tilt angle of the liquid crystal molecule was measured using a pre-tilt angle measurement system (“OPTIPRO” manufactured by Shintec Co., Ltd.). This pre-tilt angle was used as the initial value.
  • the liquid crystal cell was continuously irradiated with light for 10 hours from the backlight while applying a rectangular voltage of 30 V at a frequency of 100 Hz. Then, the pre-tilt angle was measured again and used as the pre-tilt angle (value after the test).
  • the magnitude of the voltage of 30V is several times larger than the normal drive voltage, and it is an acceleration test.
  • Example 2 Add 34 g of pentaerythritol, 41 g of triethyl orthoacetate, 0.2 g of p-toluenesulfonic acid monohydrate, and 25 ml of toluene to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and heat at 80 ° C. It was. After removing all the generated ethanol, the temperature was raised and toluene was distilled off. Then, purification was carried out by a silica column to obtain 36 g of the compound represented by the formula (2-1).
  • Example 3 30 g of (5- (bromomethyl) 2-,2-dimethyl-1,3-dioxane-5-yl) methanol, 24 g of benzyl bromide, potassium carbonate in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 26 g, 150 ml of N, N-dimethylformamide was added, and the mixture was reacted at 50 ° C. for 6 hours. After completion of the reaction, the mixture was cooled, 300 ml of ethyl acid acid acid was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off.
  • Example 4 29 g of 2- (benzyloxy) etanol, 7 g of sodium hydride, and 50 ml of N, N-dimethylformamide were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and the mixture was reacted at room temperature for 1 hour. Then, 50 g of 2,2-bis (bromomethyl) propane-1,3-diyl was slowly added and reacted at 50 ° C. for 10 hours. After completion of the reaction, the mixture was cooled, 100 ml of ethyl acid acid was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was carried out by a silica column to obtain 25 g of the compound represented by the formula (4-1).
  • Example 5 30 g of 1-bromo-2-ethyl-4-methoxybenzene, 45 g of 3-fluoro-4- (4-pentyl (cyclohexyl)) phenylboric acid, 39 g of potassium carbonate in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. , Tetrakistriphenylphosphine palladium (8 g), THF (300 ml) and water (60 ml) were added, and the mixture was reacted at 50 ° C. for 9 hours.
  • Example 6 21 g of 2-chloroethanol, 40 g of triethyl methanetricarboxylic acid, 36 g of potassium carbonate, and 400 ml of THF were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and the mixture was reacted at 50 ° C. for 24 hours. After completion of the reaction, the mixture was cooled, 200 ml of water was added dropwise, 500 ml of ethyl acid acid was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, purification was performed with a silica gel column, and the formula (6-1) was used. 45 g of the compound to be used was obtained.
  • Example 7 30 g of (chloromethoxymethyl) benzene, 30 g of diethyl malonate, 7 g of sodium hydride, and 300 ml of THF were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and the mixture was reacted at 50 ° C. for 24 hours. After completion of the reaction, the mixture was cooled, 200 ml of water was added dropwise, 300 ml of ethyl acid acid was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, purification was performed using a silica gel column, and the formula (7-1) was used. 26 g of the compound to be used was obtained.
  • Example 9 Add 50 g of 2- (bromomethyl) -2- (hydroxymethyl) propane-1,3-diol, 89 g of triethylamine, and 500 ml of dichloromethane to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and keep the reaction vessel at 10 ° C. or lower. To cool down. Then, 75 g of acryloyl chloride was slowly added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 6 hours. After completion of the reaction, 500 ml of water was slowly added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was carried out by a silica column to obtain 82 g of the compound represented by the formula (9-1).
  • a list of the compounds of formula (i) obtained in Examples 1 to 12 is shown below.
  • the total number of P i2 , Pi3 T k1 and T k 2 is shown in Table 3 below.
  • Example C1 Preparation of polymerizable liquid crystal composition
  • the liquid crystal composition HLC-1 composed of the compounds shown in Table 4 below and the mixing ratio is 100 parts by mass
  • 0.3 parts by mass of the following polymerizable compound (R-1-0) is added.
  • the base composition melted by heating was designated as LC-1.
  • Examples C2 to C24 To 100 parts by mass of LC-1, the compounds of formula (i) synthesized in Examples 1 to 12 were added in the addition amounts shown in Table 5 below, and heated and dissolved to obtain the polymerizable liquid crystals of Examples C2 to C24. Each composition was prepared. Each of the obtained polymerizable liquid crystal compositions was subjected to the above-mentioned evaluation tests. The results are shown in Table 6.
  • Liquid crystal compositions HLC-2 to HLC-8 composed of the compounds and mixing ratios as shown in Table 7 below were prepared.
  • the compounds of formula (i) synthesized in Examples 1 to 12 described above with respect to 100 parts by mass of the base composition were prepared in Tables 8 and 10 below, respectively.
  • the polymerizable liquid crystal compositions of Examples C25 to C84 were prepared by adding in the amount shown in (1) and dissolving by heating. Each of the obtained polymerizable liquid crystal compositions was subjected to the above-mentioned evaluation tests. The results are shown in Tables 9 and 11.
  • the compound of formula (i) synthesized in Examples 1 to 12 described above was added to the base compositions LC-2 to LC-16 with respect to 100 parts by mass of the base composition.
  • a polymerizable liquid crystal composition was prepared by heating and dissolving the mixture at an appropriate concentration different from the amount added in the table.
  • Example RC1 A polymerizable liquid crystal composition (that is, base composition LC-1) was prepared in the same manner as in Example C1 except that the compound of formula (i-571) was not added.
  • any of the following compounds Ref-1 to Ref-6 was added to 100 parts by mass of the base composition.
  • a polymerizable liquid crystal composition was prepared in the same manner as in Example C1 except that the amounts were added as shown in Table 13 below.
  • the number of the compound Ref-1 in the Ref-6, P i1, P i2 and the number of P i3 (polymerizable group), T k1 and T k2 (polar group), and P i1, P i2, P i3 The total number of T k1 and T k2 is shown in Table 12 below.
  • the polymerizable liquid crystal composition of the example containing the compound represented by the general formula (i) is particularly dropwise as compared with the composition of the comparative example containing no compound represented by the general formula (i). It was confirmed that excellent vertical orientation without traces and uneven orientation and excellent pre-tilt angle stability were exhibited, and it was shown that it was excellent in a display element having no alignment film on at least one surface. In particular, when the number of T k1 and T k2 (polar groups at predetermined positions) in the general formula (i) is large, the orientation is excellent, while the Pi 1 , Pi 2 and P in the general formula (i) are excellent.
  • the pretilt angle stability was excellent. Further, since the polymerizable liquid crystal composition of the example had a small amount of residual monomers, the compound represented by the general formula (i) has good low-temperature storage stability and good compatibility with the liquid crystal composition. It was confirmed that.

Abstract

La présente invention aborde le problème de fournir : une composition de cristaux liquides polymérisables qui peut subir un alignement vertical uniforme sans fourniture d'une couche PI, peut empêcher l'apparition de marques de coulure ou d'irrégularité d'alignement, présente une capacité élevée à subir un alignement vertical et une stabilité élevée d'angle de pré-inclinaison, et possède une excellente compatibilité ; et un élément d'affichage à cristaux liquides utilisant cette composition de cristaux liquides. De plus, la présente invention aborde un autre problème : celui de fournir un composé pour la production de la composition de cristaux liquides précitée. La présente invention fournit : une composition de cristaux liquides polymérisables, contenant au moins un composé représenté par la formule générale (i) ; un élément d'affichage à cristaux liquides utilisant cette composition de cristaux liquides polymérisables ; ainsi qu'un composé représenté par la formule générale (i).
PCT/JP2020/015723 2019-05-15 2020-04-07 Composition de cristaux liquides polymérisables et élément d'affichage à cristaux liquides, ainsi que composé WO2020230480A1 (fr)

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