WO2017038616A1 - ネマチック液晶組成物及びこれを用いた液晶表示素子 - Google Patents

ネマチック液晶組成物及びこれを用いた液晶表示素子 Download PDF

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WO2017038616A1
WO2017038616A1 PCT/JP2016/074799 JP2016074799W WO2017038616A1 WO 2017038616 A1 WO2017038616 A1 WO 2017038616A1 JP 2016074799 W JP2016074799 W JP 2016074799W WO 2017038616 A1 WO2017038616 A1 WO 2017038616A1
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mass
group
carbon atoms
liquid crystal
general formula
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PCT/JP2016/074799
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English (en)
French (fr)
Japanese (ja)
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須藤　豪
麻里奈 後藤
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Dic株式会社
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Priority to CN201680048230.2A priority Critical patent/CN107922844A/zh
Priority to JP2017537796A priority patent/JPWO2017038616A1/ja
Priority to KR1020187006131A priority patent/KR20180050306A/ko
Publication of WO2017038616A1 publication Critical patent/WO2017038616A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/60—Pleochroic dyes
    • C09K19/601—Azoic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/60—Pleochroic dyes
    • 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
    • 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
    • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering

Definitions

  • the present invention relates to a liquid crystal composition containing an azo dichroic dye and a liquid crystal display device or a light control device using the same.
  • Liquid crystal compositions containing dichroic dyes have been studied for a long time, and various liquid crystal display elements called GH (guest host) type using the same have been developed and proposed, and are characterized by viewing angle or brightness. Therefore, some have been put into practical use as liquid crystal display elements and light control elements for in-vehicle use.
  • GH guest host
  • the dichroic dye As characteristics required for the dichroic dye, not only the dichroic ratio and contrast when used as an element, but also solubility in a liquid crystal composition, light resistance, UV resistance, heat resistance and the like have been required. Specific examples of the dichroic dye include a blue dichroic dye (Patent Documents 1 and 2) and a yellow to red dichroic dye (Patent Document 3). In recent years, black has been favored, and black dichroic dyes obtained by mixing a plurality of dichroic dyes (Patent Documents 4, 5, and 6) have been proposed.
  • Patent Document 7 discloses a liquid crystal composition having a positive dielectric anisotropy. Has been.
  • liquid crystal display devices and light control devices that have useful device performance (large dichroic ratio, high contrast, high solubility, excellent light resistance, excellent UV resistance, and excellent heat resistance).
  • some liquid crystal compositions containing dichroic dyes are not suitable for use in liquid crystal display elements and light control elements, depending on the constituents.
  • dichroic ratio it is necessary to contain a large amount of dichroic dye in the liquid crystal composition, but there is a problem of composition solubility in which the dichroic dye and the liquid crystal compound are precipitated at room temperature. In some cases, it was fatal for practical use, such as a problem of dissolution stability at a low temperature that would precipitate after a day at a low temperature of ⁇ 20 ° C. or lower.
  • liquid crystal display elements and light control elements containing black dichroic dyes have been desired to have a clearer and more vivid appearance of blackness.
  • An object of the present invention is to provide a liquid crystal composition containing a dichroic dye, and to provide a liquid crystal display device or a light control device using the same.
  • a specific dichroic dye that is, a dichroic dye having a chromaticity of (0.287 ⁇ 0.05, 0.245 ⁇ 0.05) and exhibiting purple
  • the present inventors have found that the above problem can be solved by using a liquid crystal composition exhibiting black color together with other dichroic dyes, and have completed the present invention.
  • the present invention contains one or more dichroic dyes having a chromaticity of (0.287 ⁇ 0.05, 0.245 ⁇ 0.05) and exhibiting purple, and other dichroism.
  • a liquid crystal composition containing two or more dyes and exhibiting black color is provided, and a liquid crystal display device or a light control device using the same is provided.
  • liquid crystal composition containing a dichroic dye that achieves the required characteristics such as a large dichroic ratio, high solubility, good low-temperature stability, and a clear black color. Furthermore, by using this liquid crystal composition, it is possible to provide a liquid crystal display device or a light control device having high practicality as well as high display quality such as high contrast and good black appearance.
  • the liquid crystal composition of the present invention contains one or more dichroic dyes having a chromaticity of (0.287 ⁇ 0.05, 0.245 ⁇ 0.05) and exhibiting a purple color. It is a liquid crystal composition containing two or more chromatic dyes and exhibiting black.
  • the chromaticity of the liquid crystal composition is the same as that of the transmitted light transmitted through the horizontal alignment test panel (cell thickness 10 ⁇ m) in which the light of D65 standard light source is injected with the liquid crystal composition added with 1% of the dichroic dye. Chromaticity, expressed in the CIE 1931xy coordinate system.
  • the liquid crystal composition of the present invention contains a dichroic dye exhibiting a purple color. Further, the chromaticity of the dichroic dye exhibiting a purple color is (0.287 ⁇ 0.05, 0.245 ⁇ 0.05), but (0.287 ⁇ 0.04, 0.245 ⁇ 0.00). 04), preferably (0.287 ⁇ 0.03, 0.245 ⁇ 0.03), and (0.287 ⁇ 0.02, 0.245 ⁇ 0.02). It is preferable that it is (0.287 ⁇ 0.01, 0.245 ⁇ 0.01).
  • the maximum absorption wavelength ( ⁇ max) of the above violet dichroic dye is preferably in the range of 500 nm to 630 nm, preferably in the range of 530 nm to 600 nm, and preferably in the range of 540 nm to 590 nm. .
  • the liquid crystal composition of the present invention contains one or more dichroic dyes exhibiting the above purple color, and further contains two or more other dichroic dyes.
  • dichroic dyes exhibiting blue, dichroic dyes exhibiting red, and dichroic dyes exhibiting yellow are preferable.
  • liquid crystal composition of the present invention 0.01 to 3 parts by weight of a dichroic dye exhibiting a purple color and 0.01 to 3 parts by weight of a dichroic dye exhibiting a blue color with respect to 100 parts by weight of a host It is preferable that 0.01 part by weight to 3 parts by weight of the dichroic dye exhibiting red and 0.01 part by weight to 3 parts by weight of the dichroic dye exhibiting yellow are contained.
  • the content of the dichroic dye exhibiting purple is 0.01 to 3 parts by weight with respect to 100 parts by weight of the host, but the lower limit is preferably 0.02 parts by weight, and 0.03 parts by weight.
  • 0.04 parts by weight is preferred, 0.05 parts by weight is preferred, 0.06 parts by weight is preferred, 0.07 parts by weight is preferred, 0.08 parts by weight is preferred, 0.09 parts by weight is preferred, 0.1 part by weight is preferred, 0.12 part by weight is preferred, 0.14 part by weight is preferred, 0.06 part by weight is preferred, 0.18 part by weight is preferred, 0.2 part by weight is preferred, the upper limit thereof Is preferably 2.5 parts by weight, preferably 2.0 parts by weight, preferably 1.5 parts by weight, preferably 1.0 parts by weight, preferably 0.5 parts by weight, and preferably 0.4 parts by weight. .3 parts by weight is preferred and 0.2 parts by weight is preferred There.
  • the content of the dichroic dye exhibiting blue is 0.01 to 3 parts by weight with respect to 100 parts by weight of the host, but the lower limit is preferably 0.1 parts by weight, and 0.2 parts by weight.
  • the lower limit is preferably 0.1 parts by weight, and 0.2 parts by weight.
  • the content of the dichroic dye exhibiting red is 0.01 to 3 parts by weight with respect to 100 parts by weight of the host, but the lower limit is preferably 0.02 parts by weight, and 0.04 parts by weight.
  • 0.06 parts by weight is preferred
  • 0.08 parts by weight is preferred
  • 0.1 parts by weight is preferred
  • 0.15 parts by weight is preferred
  • 0.2 parts by weight is preferred
  • 0.25 parts by weight is preferred
  • 0.3 parts by weight is preferred
  • 0.35 parts by weight is preferred
  • 0.4 parts by weight is preferred
  • 0.45 parts by weight is preferred
  • 0.5 parts by weight is preferred
  • 0.6 parts by weight is preferred and the upper limit thereof Is preferably 2.5 parts by weight, preferably 2.0 parts by weight, preferably 1.5 parts by weight, preferably 1.0 parts by weight, preferably 0.9 parts by weight, preferably 0.8 parts by weight, 0.7 parts by weight is preferred, and 0.6 parts by weight is preferred.
  • the content of the dichroic dye exhibiting yellow is 0.01 to 3 parts by weight with respect to 100 parts by weight of the host, but the lower limit is preferably 0.02 parts by weight, and 0.04 parts by weight.
  • 0.06 parts by weight is preferred
  • 0.08 parts by weight is preferred
  • 0.1 parts by weight is preferred
  • 0.15 parts by weight is preferred
  • 0.2 parts by weight is preferred
  • 0.25 parts by weight is preferred
  • 0.3 parts by weight is preferred
  • 0.35 parts by weight is preferred
  • 0.4 parts by weight is preferred
  • 0.45 parts by weight is preferred
  • 0.5 parts by weight is preferred
  • 0.6 parts by weight is preferred and the upper limit thereof Is preferably 2.5 parts by weight, preferably 2.0 parts by weight, preferably 1.5 parts by weight, preferably 1.0 parts by weight, preferably 0.9 parts by weight, preferably 0.8 parts by weight, 0.7 parts by weight is preferred, and 0.6 parts by weight is preferred.
  • the maximum absorption wavelength ( ⁇ max) of the dichroic dye exhibiting blue color is preferably in the range of 580 nm to 680 nm, and more preferably in the range of 580 nm to 650 nm.
  • the maximum absorption wavelength ( ⁇ max) of the dichroic dye exhibiting red color is preferably in the range of 480 nm to 580 nm, and more preferably in the range of 500 nm to 550 nm.
  • the maximum absorption wavelength ( ⁇ max) of the dichroic dye exhibiting yellow is preferably in the range of 380 nm to 450 nm, and more preferably in the range of 390 nm to 430 nm.
  • the dichroic dye contained in the liquid crystal composition of the present invention is preferably an azo dichroic dye, and more preferably a disazo dichroic dye or a trisazo dichroic dye.
  • one or two or more dichroic dyes exhibiting purple are added to the host liquid crystal composition, and the other dichroic dyes are blue dichroic dyes and red.
  • the other dichroic dyes are blue dichroic dyes and red.
  • the liquid crystal composition of the present invention has the general formula (II)
  • R 21 and R 22 are each independently an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 2 carbon atoms
  • To 10 alkenyloxy groups, and one or more hydrogen atoms present in the group may each independently be substituted with a fluorine atom or a chlorine atom, and n 21 is 0, 1 or It is preferable that 1 type or 2 types or more are contained.
  • R 21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R 22 is an alkyl group having 1 to 5 carbon atoms, a carbon atom.
  • An alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms More preferably.
  • At least one of R 21 and R 22 is preferably an alkenyl group having 2 to 5 carbon atoms, more preferably an alkenyl group having 2 to 3 carbon atoms, and R 21 and R 22.
  • R 21 and R 22 are preferably alkenyl groups having 2 to 5 carbon atoms, more preferably alkenyl groups having 2 to 3 carbon atoms.
  • R 21 and R 22 are preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, An alkyl group having 1 to 5 atoms is more preferred, and both R 21 and R 22 are preferably alkyl groups having 1 to 5 carbon atoms.
  • n 21 represents 0, 1 or 2, preferably 0 or 1, and particularly preferably a compound in which n 21 is 0.
  • n 21 is preferably 0 or 1, and more preferably 0.
  • n 21 is preferably 1 or 2.
  • the liquid crystal composition of the present invention preferably contains 1 to 80% by mass of the compound represented by the general formula (II), and the lower limit of the content is preferably 1% by mass, preferably 2% by mass, and 3% by mass. 4 mass% is preferable, 5 mass% is preferable, 10 mass% is preferable, 15 mass% is preferable, 20 mass% is preferable, 25 mass% is preferable, 30 mass% is preferable, and the upper limit of the content is 80 mass% is preferable, 75 mass% is preferable, 70 mass% is preferable, 65 mass% is preferable, 60 mass% is preferable, 55 mass% is preferable, and 50 mass% is preferable.
  • R V and R V1 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, but an alkyl group or carbon atom having 1 to 5 carbon atoms.
  • An alkenyl group having 2 to 5 carbon atoms is preferable, and an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is preferable.
  • the compounds represented by general formula (II-11) and / or general formula (II-12) are preferably, for example, general formulas (II-101) to (II-110).
  • the content of the compounds represented by the general formulas (II-11) and (II-12) is preferably 20 to 80% by mass. In the case where emphasis is placed on the suppression, the content is preferably 5 to 40% by mass. In the case where high voltage holding ratio (VHR) is important, it is preferable to contain 1 to 30% by mass of the compounds represented by general formula (II-11) and general formula (II-12). The content is preferably 20% by mass, and preferably 1 to 10% by mass.
  • R 21 is an alkyl group having 1 to 5 carbon atoms
  • R 22 Is preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and more preferably a compound having an alkyl group having 1 to 5 carbon atoms.
  • the liquid crystal composition of the present invention has a general formula (III-1) or a general formula (III-2) in order to make the dielectric anisotropy negative.
  • R 31 , R 32 , R 33 and R 34 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or represents an alkenyl group having 2 to 10 carbon atoms, one -CH 2 present in the radical - or nonadjacent two or more -CH 2 - are each independently, -O- or - may be substituted by S-, also at least one hydrogen atom present in groups each independently may but be substituted by a fluorine atom or a chlorine atom, R 31 and R 33 Are preferably independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, 1 to 5 atoms Alkyl or more preferably an alkenyl group
  • Ring A 32 , Ring B 31 and Ring B 32 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro- 1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.
  • Z 31 and Z 32 are each independently —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 — or a single bond represents a, -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond are preferred, -CH 2 O -, - CH 2 CH 2 - or a single bond Is more preferable, and —CH 2 O— or a single bond is particularly preferable.
  • the compound represented by the general formula (III-1) is preferably a compound represented by the following general formula (III-A1) to general formula (III-A4).
  • a compound represented by (III-A1) is preferred, a compound represented by general formula (III-A3) is preferred, and a compound represented by general formula (III-A4) is preferred.
  • it is more preferably a compound represented by the general formula (III-A1), more preferably a compound represented by the general formula (III-A3), represented by the general formula (III-A1).
  • Particularly preferred is a compound.
  • R 31 and R 32 represent the same meaning as described above.
  • the compound represented by the general formula (III-2) is preferably a compound represented by the following general formula (III-B1) to general formula (III-B6).
  • a compound represented by (III-B1) is preferred, a compound represented by general formula (III-B3) is preferred, and a compound represented by general formula (III-B4) is preferred.
  • a compound represented by general formula (III-B5) is preferable, a compound represented by general formula (III-B6) is preferable, and a compound represented by general formula (III-B1) is preferable.
  • compounds of the general formula (III-B3) are more preferred, compounds of the general formula (III-B5) are more preferred, and compounds of the general formula (III-B6) are more preferred.
  • Good Properly, particularly preferably a compound represented by formula (III-B1) it is particularly preferably a compound represented by formula (III-B5).
  • R 33 and R 34 have the same meaning as described above.
  • the liquid crystal composition of the present invention preferably comprises a combination of the general formula (III-A1) and the general formula (III-B1).
  • the general formula (III-A1), the general formula (III-B1) and the general formula ( III-B4) is more preferable, and a combination of general formula (III-A1), general formula (III-B1) and general formula (III-B5) is more preferable.
  • the liquid crystal composition of the present invention preferably comprises a combination of the general formula (III-A3) and the general formula (III-B5), and the general formula (III-A3), the general formula (III-B4) and the general formula ( More preferably, it consists of a combination of III-B5), more preferably a combination of general formula (III-A3), general formula (III-B5) and general formula (III-B1).
  • the liquid crystal composition of the present invention preferably comprises a combination of the general formula (III-A4) and the general formula (III-B1), and the general formula (III-A4), the general formula (III-A1) and the general formula ( III-B1) is more preferable, and a combination of general formula (III-A4) and general formula (III-B5) is preferable, and general formula (III-A4), general formula (III-B5) is preferable.
  • the general formula (III-B4) preferably the combination of the general formula (III-A4) and the general formula (III-B1), the general formula (III-A4), the general formula More preferably, it comprises a combination of (III-B1) and general formula (III-B5).
  • the liquid crystal composition of the present invention contains one or more compounds represented by general formula (III-1) or general formula (III-2), but preferably contains 2 to 10 compounds.
  • the total content is preferably 10 to 90% by mass, and the lower limit thereof is preferably 10% by mass, preferably 15% by mass, preferably 20% by mass, preferably 25% by mass, and preferably 30% by mass, 35% by mass is preferable, 40% by mass is preferable, and 45% by mass is preferable.
  • the upper limit is preferably 80% by mass, 75% by mass is preferable, 70% by mass is preferable, 65% by mass is preferable, and 60% by mass is preferable. 55 mass% is preferable, 50 mass% is preferable, and 45 mass% is preferable.
  • the liquid crystal composition of the present invention has the general formula (IV-A) to general formula (IV-H).
  • each of R 41 and R 42 independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or 2 carbon atoms.
  • 5 represents an alkenyloxy group, preferably an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.
  • X 41 represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom, preferably a methyl group, a fluorine atom or a hydrogen atom, More preferably, it is an atom.
  • the liquid crystal composition of the present invention preferably contains one or more compounds represented by formulas (IV-A) to (IV-H), and preferably contains 2 to 10 compounds.
  • the total content of these is 0 to 90% by mass, but the lower limit is preferably 1% by mass, preferably 5% by mass, preferably 10% by mass, preferably 15% by mass, and preferably 20% by mass. 25% by mass, preferably 30% by mass, preferably 35% by mass, preferably 40% by mass, and preferably 45% by mass, and the upper limit is preferably 90% by mass, preferably 80% by mass, and 75% by mass.
  • 70 mass% is preferable, 65 mass% is preferable, 60 mass% is preferable, 55 mass% is preferable, 50 mass% is preferable, and 45 mass% is preferable.
  • the liquid crystal composition of the present invention can contain one or more compounds represented by the general formula (V).
  • R 61 and R 62 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkyl group having 2 to 8 carbon atoms.
  • an alkenyloxyl group is represented, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable.
  • the upper limit of the content is preferably 10%, and preferably 5% 0% is particularly preferable.
  • the liquid crystal composition of the present invention may contain one or more compounds represented by the general formula (N-001).
  • R N1 and R N2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or 2 to 8 carbon atoms.
  • An alkenyloxyl group is represented, but an alkyl group having 1 to 5 carbon atoms is preferred.
  • L 1 and L 2 each independently represent a hydrogen atom, a fluorine atom, CH 3 or CF 3 , but at least one of L 1 and L 2 is preferably a fluorine atom, and both are fluorine atoms. It is also preferable that there is.
  • the liquid crystal composition of the present invention has the general formula (III-B7)
  • R 33 and R 34 represent the same meaning as described above, and is preferably contained.
  • the liquid crystal composition of the present invention has a general formula (M) in order to make the dielectric anisotropy positive.
  • R M1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO— may be substituted
  • n M1 represents 0, 1, 2, 3 or 4
  • a M1 and A M2 are each Independently, (A) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O- or -S- And (b) a 1,4-phenylene group (one —CH ⁇ present in this group or two or more non-adjacent —CH ⁇ may be replaced by —N ⁇ ).
  • a hydrogen atom on the group (a) and the group (b) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • Z M1 and Z M2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, Represents —COO—, —OCO— or —C ⁇ C—
  • n M1 is 2, 3 or 4 and a plurality of A M2 are present, they may be the same or different, and n M1 is 2, 3 or 4 and a plurality of Z M1 is present
  • X M1 and X M3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom
  • X M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a
  • R M1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy having 2 to 8 carbon atoms.
  • An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.
  • R M1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.
  • the ring structure to which it is bonded is an aromatic ring, it is a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and 4 carbon atoms.
  • An alkenyl group of 5 is preferable, and when the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a linear carbon atom An alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferable.
  • the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • a M1 and A M2 are each preferably an aromatic ring when it is required to increase ⁇ n independently, and an aliphatic ring is preferable for improving the response speed.
  • a M1 and A M2 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, Represents a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group Preferably, it represents
  • Z M1 and Z M2 each independently -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CF 2 O-, —CH 2 CH 2 — or a single bond is more preferable, and —CF 2 O— or a single bond is particularly preferable.
  • the compound represented by the general formula (M) is used, for example, as one embodiment of the present invention, or used in two types, or used in three types. Furthermore, in another embodiment of the present invention, four types are used, five types are used, six types are used, or seven or more types are used.
  • the content of the compound represented by the general formula (M) is determined by determining the nematic phase-isotropic liquid phase transition temperature (T ni ), birefringence, dielectric anisotropy, etc. Adjust appropriately according to the performance to be achieved.
  • the lower limit of the preferable content of the compound represented by the general formula (M) with respect to the total amount of the liquid crystal composition of the present invention is 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 80% by mass. It is.
  • the upper limit of the preferable content is, for example, 95% by mass, 85% by mass, 75% by mass, and 65% by mass in one embodiment of the present invention with respect to the total amount of the composition of the present invention. , 55% by mass, 45% by mass, 35% by mass, and 25% by mass.
  • a liquid crystal composition of the present invention When a liquid crystal composition of the present invention has a low viscosity and a composition having a high response speed is required, it is preferable to lower the lower limit and lower the upper limit. Furthermore, when the liquid crystal composition of the present invention maintains a nematic phase-isotropic liquid phase transition temperature (T ni ) and a liquid crystal composition having good temperature stability is required, the above lower and upper limits are lowered. It is preferable to do. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the lower limit value and the upper limit value.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • R M1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.
  • the compound represented by the general formula (M) is preferably, for example, a compound represented by the general formula (M-1).
  • R M11 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M11 to X M15 each independently represents hydrogen. represents an atom or a fluorine atom
  • Y M11 represents a fluorine atom or OCF 3.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • birefringence dielectric constant anisotropy, etc.
  • the type of the compound used is, for example, one type as one embodiment of the present invention, two types, and three or more types.
  • the lower limit of the preferable content of the compound represented by the general formula (M-1) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, and 5% by mass. 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, 20% by mass, 22% by mass, 25% by mass, 30% by mass, % By mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-1) is specifically preferably a compound represented by the formula (M-1.1) to the formula (M-1.4).
  • a compound represented by M-1.1) or formula (M-1.2) is preferred, and a compound represented by formula (M-1.2) is more preferred. It is also preferred to use the compounds represented by formula (M-1.1) or formula (M-1.2) at the same time.
  • the lower limit of the preferable content of the compound represented by the formula (M-1.1) is 1% by mass, 2% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 6% by mass.
  • the upper limit of preferable content is 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the lower limit of the preferable content of the compound represented by the formula (M-1.2) is 1% by mass, 2% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 6% by mass.
  • the upper limit of the preferable content is 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, and 13% by mass, 10% by mass and 8% by mass.
  • the lower limit of the preferable total content of the compounds represented by formula (M-1.1) and formula (M-1.2) is 1% by mass with respect to the total amount of the liquid crystal composition of the present invention. 2% by mass, 5% by mass, and 6% by mass.
  • the upper limit of the preferable content is 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, and 13% by mass, 10% by mass and 8% by mass.
  • the compound represented by the general formula (M) is preferably, for example, a compound represented by the general formula (M-2).
  • R M21 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M21 and X M22 each independently represent hydrogen
  • the lower limit of the preferable content of the compound represented by the formula (M-2) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, and 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, 20% by mass, 22% by mass, 25% by mass, 30% by mass %.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-2) is preferably a compound represented by the formula (M-2.1) to the formula (M-2.5). 3) or a compound represented by the formula (M-2.5) is preferable.
  • the lower limit of the preferable content of the compound represented by the formula (M-2.2) is 1% by mass, 2% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 6% by mass.
  • the upper limit of preferable content is 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the lower limit of the preferable content of the compound represented by the formula (M-2.3) is 1% by mass, 2% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 6% by mass.
  • the upper limit of the preferable content is 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, and 13% by mass, 10% by mass and 8% by mass.
  • the lower limit of the preferable content of the compound represented by the formula (M-2.5) is 1% by mass, 2% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 6% by mass.
  • the upper limit of the preferable content is 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, and 13% by mass, 10% by mass and 8% by mass.
  • the lower limit of the preferable total content of the compounds represented by formulas (M-2.2), (M-2.3) and formula (M-2.5) with respect to the total amount of the liquid crystal composition of the present invention The values are 1% by weight, 2% by weight, 5% by weight and 6% by weight.
  • the upper limit of the preferable content is 30% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, and 13% by mass, 10% by mass and 8% by mass.
  • the compound represented by the general formula (M) used in the liquid crystal composition of the present invention is preferably a compound represented by the general formula (M-3).
  • R M31 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M31 to X M36 are each independently hydrogen. represents an atom or a fluorine atom
  • Y M31 represents a fluorine atom, a chlorine atom or OCF 3.
  • the content of the compound represented by the general formula (M-3) has an upper limit value and a lower limit value for each embodiment in consideration of characteristics such as a transition temperature and a birefringence.
  • the lower limit of the preferable content of the compound represented by the formula (M-3) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 4% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of preferable content is 20% by mass, 18% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-3) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-3.1) to the formula (M-3.4).
  • the lower limit of the preferable content of the compound represented by the formula (M-3.1) is 1% by mass, 2% by mass, and 4% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of preferable content is 20% by mass, 18% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the lower limit of the preferable content of the compound represented by the formula (M-3.2) is 1% by mass, 2% by mass, and 4% by mass with respect to the total amount of the liquid crystal composition of the present invention. Yes, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18%, and 20%.
  • the upper limit of preferable content is 20% by mass, 18% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the lower limit of the preferable total content of the compounds represented by formula (M-3.1) and formula (M-3.2) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass. 2% by weight, 4% by weight, 5% by weight, 8% by weight, 10% by weight, 13% by weight, 15% by weight, 18% by weight, % By mass.
  • the upper limit of preferable content is 20%, 18% by mass, 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-4).
  • R M41 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M41 to X M48 are each independently fluorine.
  • Y M41 represents a fluorine atom, a chlorine atom or OCF 3.
  • the content of the compound represented by the general formula (M-4) has an upper limit and a lower limit for each embodiment in consideration of characteristics such as a transition temperature and a birefringence.
  • the lower limit of the preferable content of the compound represented by the formula (M-4) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 4% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the liquid crystal composition of the present invention When used for a liquid crystal display device having a small cell gap, it is suitable to increase the content of the compound represented by the general formula (M-4). When used for a liquid crystal display element having a low driving voltage, it is suitable to increase the content of the compound represented by the general formula (M-4). Further, when used for a liquid crystal display element used in a low temperature environment, it is suitable to reduce the content of the compound represented by the general formula (M-4). In the case of a composition used for a liquid crystal display device having a high response speed, it is suitable to reduce the content of the compound represented by the general formula (M-4).
  • the compound represented by the general formula (M-4) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-4.1) to the formula (M-4.4).
  • the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-5).
  • R M51 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M51 and X M52 are each independently hydrogen. represents an atom or a fluorine atom
  • Y M51 represents a fluorine atom, a chlorine atom or OCF 3.
  • the lower limit of the preferable content of the compound represented by the formula (M-5) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, 20% by mass, 22% by mass, 25% by mass, 30% by mass %.
  • the upper limit of the preferable content is 50% by mass, 45% by mass, 40% by mass, 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, 13% by mass, 10% by mass, 8% by mass, 5% by mass %.
  • the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.1) to the formula (M-5.4), and the formula (M-5.
  • a compound represented by formula (M-5.4) is preferable.
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 5% by mass, 8% by mass, and 10% by mass with respect to the total amount of the liquid crystal composition of the present invention. It is 13% by mass and 15% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.11) to the formula (M-5.17), and the formula (M-5. 11), a compound represented by formula (M-5.13) and formula (M-5.17) is preferable.
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 5% by mass, 8% by mass, and 10% by mass. It is 13% by mass and 15% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.21) to the formula (M-5.28), and the formula (M-5. 21), a compound represented by formula (M-5.22), formula (M-5.23) and formula (M-5.25).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 5% by mass, 8% by mass, and 10% by mass. 13% by mass, 15% by mass, 18% by mass, 20% by mass, 22% by mass, 25% by mass, and 30% by mass.
  • the upper limit of the preferable content is 40% by mass, 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, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-6).
  • R M61 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms
  • X M61 to X M64 are each independently fluorine.
  • Y M61 represents a fluorine atom, a chlorine atom or OCF 3
  • the lower limit of the preferable content of the compound represented by the formula (M-6) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 4% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13%, 10% by mass, 8% by mass, and 5% by mass.
  • the liquid crystal composition of the present invention When used for a liquid crystal display device having a low driving voltage, it is suitable to increase the content of the compound represented by the general formula (M-6). In the case of a composition used for a liquid crystal display device having a high response speed, it is suitable to reduce the content of the compound represented by the general formula (M-6).
  • the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.1) to the formula (M-6.4). It is preferable to contain a compound represented by M-6.2) and formula (M-6.4).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.11) to the formula (M-6.14). It is preferable to contain a compound represented by M-6.12) and formula (M-6.14).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.21) to the formula (M-6.24). It is preferable to contain a compound represented by formula (M-6.21), formula (M-6.22) and formula (M-6.24).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.31) to the formula (M-6.34). Among them, it is preferable to contain a compound represented by the formula (M-6.31) and the formula (M-6.32).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20%.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.41) to the formula (M-6.44). It is preferable to contain a compound represented by M-6.42).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-7).
  • X M71 to X M76 each independently represent a fluorine atom or a hydrogen atom, and R M71 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or 1 carbon atom
  • 4 represents an alkoxy group
  • Y M71 represents a fluorine atom or OCF 3.
  • the content of the compound represented by the general formula (M-7) has an upper limit and a lower limit for each embodiment in consideration of characteristics such as a transition temperature and a birefringence.
  • the lower limit of the preferable content of the compound represented by the formula (M-7) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 2% by mass, 4% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the liquid crystal composition of the present invention When used for a liquid crystal display device having a small cell gap, it is suitable to increase the content of the compound represented by the general formula (M-7). When used for a liquid crystal display element with a low driving voltage, it is suitable to increase the content of the compound represented by the general formula (M-7). In addition, when used for a liquid crystal display element used in a low temperature environment, it is suitable to reduce the content of the compound represented by the general formula (M-7). In the case of a composition used for a liquid crystal display device having a high response speed, it is suitable to reduce the content of the compound represented by the general formula (M-7).
  • the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.1) to the formula (M-7.4), and the formula (M-7. It is preferable that it is a compound represented by 2).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.11) to the formula (M-7.14), and the formula (M-7. 11) and a compound represented by the formula (M-7.12) are preferable.
  • the lower limit of preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.21) to the formula (M-7.24). 21) and a compound represented by the formula (M-7.22) are preferable.
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-8).
  • X M81 to X M84 each independently represent a fluorine atom or a hydrogen atom
  • Y M81 represents a fluorine atom, a chlorine atom or OCF 3
  • R M81 represents an alkyl group having 1 to 5 carbon atoms
  • a M81 and A M82 each independently represents a 1,4-cyclohexylene group, a 1,4-phenylene group
  • the hydrogen atom on the 1,4-phenylene group may be substituted with a fluorine atom.
  • the lower limit of the preferable content of the compound represented by the general formula (M-8) is 1% by mass, 2% by mass, and 4% by mass with respect to the total amount of the liquid crystal composition of the present invention. 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28%, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, 13% % By mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.1) to the formula (M-8.4).
  • it is a compound, and among them, it is preferable to contain a compound represented by formula (M-8.1) or formula (M-8.2).
  • the lower limit of preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-8.11) to the formula (M-8.14).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18%, 15% by mass, and 13% by mass. % By mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-8.21) to the formula (M-8.24). It is preferable to contain a compound represented by the formula (M-8.22).
  • the lower limit of preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18%, and 20%.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-8.31) to the formula (M-8.34). Among them, it is preferable to contain a compound represented by the formula (M-8.32).
  • the lower limit of the preferable content of these compounds is 1%, 2%, 4%, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-8.41) to the formula (M-8.44). It is preferable to contain a compound represented by the formula (M-8.42).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the compound represented by the general formula (M-8) used in the liquid crystal composition of the present invention is specifically represented by the formula (M-8.51) to the formula (M-8.54). It is preferable to contain a compound represented by the formula (M-8.52).
  • the lower limit of the preferable content of these compounds is 1% by mass, 2% by mass, 4% by mass, 5% by mass, and 8% by mass with respect to the total amount of the liquid crystal composition of the present invention. 10% by mass, 13% by mass, 15% by mass, 18% by mass, and 20% by mass.
  • the upper limit of the preferable content is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, and 15% by mass, 13% by mass, 10% by mass, 8% by mass, and 5% by mass.
  • the liquid crystal composition of the present invention may contain one or more compounds represented by general formula (VIII-a), general formula (VIII-c) or general formula (VIII-d).
  • each of R 51 and R 52 independently represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms
  • X 51 and X 52 each independently represents a fluorine atom or a hydrogen atom, and at least one of X 51 and X 52 represents a fluorine atom.
  • the lower limit of the preferable content of these compounds is 0% by mass, 1% by mass, 2% by mass, 4% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention.
  • the liquid crystal composition of the present invention may contain one or more compounds represented by formulas (V-9.1) to (V-9.3).
  • the lower limit of the preferable content of these compounds is 0% by mass, 1% by mass, 2% by mass, 4% by mass, and 5% by mass with respect to the total amount of the liquid crystal composition of the present invention. 8% by mass, 10% by mass, 13% by mass, 15% by mass, 18% by mass, 20% by mass, and the upper limit of the preferred content is 30% by mass 28% 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 mass% and 5 mass%.
  • the liquid crystal composition of the present invention preferably contains three or four or more dichroic dyes including the violet dichroic dye, and a compound represented by the general formula (II) at the same time, 3 or 4 or more kinds of dichroic dyes including a dichroic dye exhibiting a purple color, a compound represented by the formula (II), and a compound represented by the general formula (III-1)
  • three or four or more dichroic dyes including the violet dichroic dye, a compound represented by the formula (II), and a compound represented by the general formula (III-2) are simultaneously contained.
  • dichroic dyes including the purple dichroic dye, a compound represented by the formula (II), a compound represented by the general formula (III-1), and It is preferable to contain the compound represented by the general formula (III-2) at the same time. Arbitrariness.
  • a compound represented by general formula (IV-A) and / or a compound represented by general formula (IV-F) and / or a compound represented by general formula (IV-G) is contained. It is also preferable.
  • the liquid crystal composition of the present invention comprises three or four or more dichroic dyes containing the purple dichroic dye, a compound represented by the formula (II), and a general formula (IV-F). It is preferable that the compound is simultaneously contained, and three or four or more dichroic dyes including the violet dichroic dye, a compound represented by the formula (II), a general formula (IV-F) It is preferable to simultaneously contain the compound represented by formula (III-G) and the compound represented by formula (IV-A) in addition to these.
  • the liquid crystal composition of the present invention preferably contains three or four or more dichroic dyes including the purple dichroic dye and the compound represented by the general formula (M-1) at the same time.
  • 3 or 4 or more types of dichroic dyes including the purple dichroic dye, a compound represented by the formula (II), and a compound represented by the general formula (M-2) are simultaneously contained
  • three or four or more dichroic dyes containing the purple dichroic dye, a compound represented by the formula (II), and a compound represented by the general formula (M-3) It is preferably contained at the same time, and is represented by three or four or more dichroic dyes including the purple dichroic dye, a compound represented by the formula (II), and a general formula (M-4).
  • the dichroic dye exhibiting the purple color preferably contains at least one species or four or more dichroic dyes, a compound represented by the formula (II), and a compound represented by the general formula (M-6).
  • 3 or 4 or more types of dichroic dyes, a compound represented by the formula (II), and a compound represented by the general formula (M-7) are preferably contained at the same time.
  • dichroic dyes including a chromatic dye, a compound represented by the formula (II), and a compound represented by the general formula (M-8).
  • the dichroic dyes are preferably azo dichroic dyes. Since all of the dichroic dyes are azo dichroic dyes, the dichroic ratio, the solubility of the liquid crystal composition, and the low-temperature stability are further improved.
  • the liquid crystal composition of the present invention contains, in addition to the above-mentioned compounds, ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, chiral agents, polymerizable compounds, antioxidants, ultraviolet absorbers, light stabilizers or infrared absorbers. You may do it.
  • the chiral agent for inducing pitch may be any compound having an asymmetric carbon atom, but a 1,4-phenylene group (one hydrogen atom in this group or Two may be substituted with fluorine, methyl group, or methoxy group.
  • the molecular structure preferably has one or more.
  • the liquid crystal composition of the present invention is a nematic liquid crystal composition having a positive or negative dielectric anisotropy ( ⁇ ), but is preferably a chiral nematic liquid crystal composition having a negative ⁇ .
  • a plurality of chiral agents may be mixed and used.
  • a compound having an asymmetric atom, an axially asymmetric compound, or a mixture of these may be used.
  • the compound having an asymmetric atom is preferably a compound represented by the general formula (Ch-I).
  • R 100 and R 101 are each independently a hydrogen atom, —CN, —NO 2 , a halogen atom, —OCN, —SCN, —SF 5 , a chiral or achiral alkyl having 1 to 30 carbon atoms.
  • R 100 or R 101 in the general formula (Ch-I) is a chiral or achiral alkyl group having 1 to 30 carbon atoms, one or more non-adjacent methylenes in the alkyl group
  • the group (—CH 2 —) represents —O—, —S—, —NH—, —N (CH 3 ) —, —CO—, —COO—, in which oxygen atoms or sulfur atoms are not directly bonded to each other.
  • C ⁇ C— may be substituted, and one or more hydrogen atoms in the alkyl group may be substituted with a halogen atom or a cyano group.
  • the alkyl group may be a linear group, a branched chain group, or a group containing a ring structure.
  • R 100 or R 101 is any of these groups, they are bonded to A 100 (or D or Z 101 ) or A 101 (or D or Z 100 ) at the left end, respectively.
  • R 103 and R 104 each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms or a hydrogen atom.
  • R 103 was subjected to a carbon atom to R 103 are bonded (* R 103 is a linear or branched alkyl group having 1 to 10 carbon atoms so that the (position) is an asymmetric atom.
  • One or more methylene groups of the alkyl group are —O—, —S—, —NH—, —N (CH 3 ) —, —CO, in which oxygen atoms or sulfur atoms are not directly bonded to each other.
  • the alkyl group may have a polymerizable group.
  • the polymerizable group include a vinyl group, an allyl group, and a (meth) acryloyl group.
  • R 103 in the general formulas (Ra) to (Rj) is a linear or branched group having 1 to 12 carbon atoms in which a methylene group or a hydrogen atom is not substituted with another group (ie, unsubstituted). It is preferably a branched alkyl group, more preferably an unsubstituted straight chain or branched alkyl group having 1 to 8 carbon atoms, and an unsubstituted straight chain having 1 to 6 carbon atoms. More preferably, the alkyl group is in the form of a ring.
  • R 104 in the general formula (Rd) or (Ri) is preferably a hydrogen atom or an unsubstituted linear or branched alkyl group having 1 to 5 carbon atoms, and an unsubstituted carbon atom. It is more preferably a linear alkyl group of 1 to 3, more preferably a hydrogen atom or a methyl group.
  • n 12 is an integer from 0 to 20, preferably an integer from 0 to 10, and any integer from 0 to 5 Is more preferred, and 0 is even more preferred.
  • n 13 is 0 or 1.
  • n 14 is any integer from 0 to 5.
  • X 101 and X 102 each independently represent a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, or a phenyl group (1 of the phenyl group). Or two or more arbitrary hydrogen atoms may be substituted with a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group (—CF 3 ), a trifluoromethoxy group (—OCF 3 ), or a carbon.
  • halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom
  • a cyano group or a phenyl group (1 of the phenyl group.
  • two or more arbitrary hydrogen atoms may be substituted with a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group (—CF 3
  • the carbon atom (position marked with *) to which X 101 is bonded is an asymmetric atom.
  • X 101 and R 103 are groups different from each other.
  • X 101 and X 102 are groups different from each other so that the carbon atom to which X 101 is bonded (position marked with *) is an asymmetric atom.
  • X 101 and X 102 in the general formulas (Ra), (Rb), (Rc), (Rf), (Rg), (Rh), and (Rk) are each independently a halogen atom, a phenyl group ( One or more arbitrary hydrogen atoms of the phenyl group may be substituted with a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or a trifluoromethoxy group), a methyl group, a methoxy group, A trifluoromethyl group or a trifluoromethoxy group is preferred.
  • X 101 and X 102 in the general formulas (Ra), (Rb), (Rc), (Rf), (Rg), and (Rh) are each independently a phenyl group (1 of the phenyl group).
  • the hydrogen atom or two or more arbitrary hydrogen atoms may be substituted with a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or a trifluoromethoxy group, and more preferably an unsubstituted phenyl group. .
  • X 101 in the general formula (Rk) is more preferably a halogen atom, a cyano group, an alkyl group, an alkoxy group, a trifluoromethyl group, or a trifluoromethoxy group, and a halogen atom, a methyl group, or a trifluoromethyl group. Or a trifluoromethoxy group is more preferable.
  • Q is a divalent hydrocarbon group.
  • the divalent hydrocarbon group may be linear, branched, or a group having a cyclic structure.
  • the number of carbon atoms of the divalent hydrocarbon group is preferably 1 to 16, more preferably 1 to 10, and further preferably 1 to 6.
  • the divalent hydrocarbon group is preferably a group that single-bonds with two oxygen atoms in the general formulas (Re) and (Rj) at one carbon atom.
  • two carbon atoms marked with an asterisk, two oxygen atoms bonded to them, and one carbon atom in Q are each a 5-membered ring. Is forming.
  • Specific examples include an unsubstituted methylene group, a cyclopropylidene group, a cyclobutylidene group, a cyclopentylidene group, a cyclohexylidene group, or the like, in which one or two hydrogen atoms are substituted by a hydrocarbon group. More preferred are a methylene group, an isopropylidene group, and a cyclohexylidene group.
  • n 12 is any integer from 0 to 5
  • X 101 is one or more phenyl group (said phenyl group In which R 103 is an unsubstituted carbon atom having 1 to 6 carbon atoms, which may be substituted with a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or a trifluoromethoxy group.
  • a group that is a linear or branched alkyl group is preferred, n 12 is an integer of 0 to 5, X 101 is an unsubstituted phenyl group, and R 103 is the number of unsubstituted carbon atoms. More preferred are groups that are 1 to 6 linear or branched alkyl groups.
  • the group represented by the general formula (Rf), the general formula (Rf), is any integer from n 12 is 0 5, n 13 is 0 or 1, X 103 is a halogen atom, methyl Or a trifluoromethyl group, and R 103 is preferably an unsubstituted linear alkyl group having 2 to 12 carbon atoms.
  • R 100 or R 101 of the compound represented by the general formula (Ch-I) in particular, the following formulas (Ra-1) to (Ra-3) or the general formulas (Rf-1) to (Rf-3) The group represented by these is preferable.
  • R 100 or R 101 is these groups, the left end is bonded to A 100 (or D or Z 101 ) or A 101 (or D or Z 100 ), respectively.
  • An asterisk represents a chiral carbon atom.
  • n 13 represents 0 or 1.
  • n represents an integer of 2 to 12.
  • n is preferably an integer of 3 to 8, and is preferably 4, 5, or 6. More preferred.
  • R 100 or R 101 in the general formula (Ch-I) is a polymerizable group
  • the polymerizable group is represented by any of the following formulas (R-1) to (R-16): Groups having a structure are preferred.
  • the groups represented by formulas (R-1) to (R-14) and (R-16) are at the right end, and the group represented by formula (R-15) is at the left end with A 100 (or D or Z 101 ) or A 101 (or D or Z 100 ), respectively.
  • These polymerizable groups are cured by radical polymerization, radical addition polymerization, cationic polymerization, or anionic polymerization.
  • the formula (R-1), formula (R-2), formula (R-4), formula (R-5), formula (R-7), formula (R ⁇ 11), the formula (R-13), the formula (R-15) or the group represented by the formula (R-16) are preferable, and the formula (R-1), the formula (R-2), the formula (R— 7), a group represented by formula (R-11), formula (R-13) or formula (R-16) is more preferred, and formula (R-1), formula (R-2) or formula (R— The group represented by 16) is more preferable.
  • R 100 or R 101 in the general formula (Ch-I) is a chiral group including a ring structure
  • the ring structure included in the group may be aromatic or aliphatic.
  • the ring structure that the alkyl group can take include a monocyclic structure, a condensed ring structure, and a spirocyclic structure, and can contain one or more heteroatoms.
  • Z 100 and Z 101 are each independently —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—N.
  • R 105 represents a linear or branched alkyl group having 1 to 12 carbon atoms, preferably a linear or branched alkyl group having 1 to 6 carbon atoms, 1 to 3 linear alkyl groups are more preferred.
  • m 11 is an integer of 2 or more and a plurality of Z 100 are present in one molecule, they may be the same or different.
  • m 12 is an integer of 2 or more and a plurality of Z 101 are present in one molecule, they may be the same or different.
  • a 100 and A 101 are each independently the following (a ′) group, (b ′) group, or (c ′) group.
  • m 11 is an integer of 2 or more and a plurality of A 100 are present in one molecule, they may be the same or different.
  • m 12 is an integer of 2 or more and a plurality of A 101 are present in one molecule, they may be the same or different.
  • a ′ trans-1,4-cyclohexylene group (one methylene group present in the group or two or more methylene groups not adjacent to each other may be substituted with an oxygen atom or a sulfur atom) Good.
  • B ′ 1,4-phenylene group (one —CH ⁇ present in this group or two or more non-adjacent —CH ⁇ may be substituted with a nitrogen atom).
  • the (a ′) group, (b ′) group, and (c ′) group may be all unsubstituted, and one or two or more hydrogen atoms in the group are halogen atoms, cyano A group, a nitro group, an alkyl group having 1 to 7 carbon atoms (one or more hydrogen atoms in the alkyl group may be substituted by a fluorine atom or a chlorine atom), 1 carbon atom
  • an alkoxy group one or two or more hydrogen atoms in the alkoxy group may be substituted by a fluorine atom or a chlorine atom
  • an alkylcarbonyl group having 1 to 7 carbon atoms (the alkyl 1 or 2 or more hydrogen atoms in the carbonyl group may be substituted by a fluorine atom or a chlorine atom)
  • an alkoxycarbonyl group having 1 to 7 carbon atoms one in the alkoxycarbonyl group
  • 2 Hydrogen atoms of the above may be substitute
  • the (a ′) group or the (b ′) group is preferable, and an unsubstituted trans-1,4-cyclohexylene group
  • An unsubstituted 1,4-phenylene group, one or more hydrogen atoms are fluorine atoms, chlorine atoms, cyano groups, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, A trans-1,4-cyclohexylene group substituted by an alkylcarbonyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or one or more hydrogen atoms; Fluorine atom, chlorine atom, cyano group, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, alkylcarbonyl group having 1 to 4 carbon atoms, or 1 to carbon atoms 1,4-phenylene group substitute
  • n 11 represents 0 or 1, but when n 11 is 0, m 12 is 0 and m 11 is 0, 1, 2, 3, 4 or 5. . When n 11 and m 12 are 0, m 11 is preferably 1, 2, 3, or 4, and more preferably 1, 2, or 3.
  • n 11 is 1, m 11 and m 12 are each independently 0, 1, 2, 3, 4 or 5, preferably 1, 2, 3, or 4, more preferably 1, 2 or 3. .
  • n 11 is 1, m 11 and m 12 may be different from each other, but are preferably the same.
  • D is a divalent group represented by the above formulas (D1) to (D4).
  • any one or two or more arbitrary hydrogen atoms of the benzene ring are each independently a halogen atom (F, Cl, Br, I), carbon It may be substituted with an alkyl group having 1 to 20 atoms or an alkoxy group having 1 to 20 carbon atoms.
  • one or more hydrogen atoms in the group may be substituted with a fluorine atom
  • One or more methylene groups in the group are —O—, —S—, —COO—, —OCO—, —CF 2 —, —CF ⁇ CH—, —CH ⁇ CF—, —CF
  • An oxygen atom or a sulfur atom may be substituted by ⁇ CF— or —C ⁇ C— so that they are not directly bonded to each other.
  • the remaining partial structure excluding R 100 and R 101 at both ends of the compound has the following general formula (b1)
  • a structure represented by (b13) is preferred.
  • either one of both ends is bonded to R 100 and the other is bonded to R 101 .
  • at least one of R 100 and R 101 is a chiral alkyl group.
  • Z 102 is the same as Z 100 and Z 101 in the general formula (Ch-I).
  • a 102 represents a 1,4-phenylene group (one —CH ⁇ present in the group or two or more —CH ⁇ not adjacent to each other)
  • a nitrogen atom may be substituted, and one or more arbitrary hydrogen atoms present in the group are substituted by a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or a trifluoromethoxy group It may be done.
  • —CH ⁇ or a hydrogen atom in the 1,4-phenylene group it is possible to control the decrease in crystallinity and the direction and magnitude of dielectric anisotropy of a liquid crystal composition containing the compound.
  • a compound in which the ring structure in A 102 is a heterocyclic ring such as a pyridine ring or a pyrimidine ring (that is, one —CH ⁇ present in a 1,4-phenylene group or not adjacent 2
  • a compound that is a benzene ring rather than a compound in which more than one —CH ⁇ is a group substituted with a nitrogen atom that is, —CH ⁇ present in a 1,4-phenylene group is not substituted with a nitrogen atom
  • the compound which is a group is preferred.
  • a compound in which the ring structure in A 102 is a heterocyclic ring such as a pyridine ring or a pyrimidine ring is preferable to a compound in which the ring structure in A 102 is a benzene ring.
  • a compound having a hydrocarbon ring such as a benzene ring or a cyclohexane ring has a relatively small polarizability, but a compound having a heterocyclic ring such as a pyridine ring or a pyrimidine ring has a relatively polarizability of the compound. It is large and preferable for decreasing the crystallinity and stabilizing the liquid crystallinity.
  • the compounds having n 11 and m 12 of 0 are preferably the following general formulas (Ch-I-1) to (Ch-I-30).
  • R 100, R 101 and Z 100 represents the same meaning as R 100, R 101 and Z 100 in the general formula (Ch-I)
  • R 100 and R 101 each represents a chiral alkyl group
  • L 100 to L 105 each independently represents a hydrogen atom or a fluorine atom
  • L 100 to L 105 each independently represents a hydrogen atom or a fluorine atom. Represents an atom.
  • R 100 and R 101 are represented by any one of the general formulas (Ra) to (Rk). And one or both of R 100 and R 101 are represented by the formulas (Ra-1) to (Ra-3) or the general formulas (Rf-1) to (Rf-3).
  • the compound which is group is more preferable.
  • the remaining one of R 100 and R 101 has 1 to 1 carbon atoms.
  • achiral alkyl groups (one or more non-adjacent methylene groups in the alkyl group are -O-, -S-, -NH-, -N (CH 3 )-, -CO —, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH ⁇ CH—, —CF 2 —, —CF ⁇ CH—, —CH ⁇ CF—. , —CF ⁇ CF— or C ⁇ C—, and one or more hydrogen atoms in the alkyl group may be substituted by a halogen atom or a cyano group.
  • Certain compounds are preferred, an alkyl group having 1 to 16 carbon atoms, and 1 to 6 alkoxy group, more preferred compounds are alkenyl groups or alkenyloxy group having 2 to 16 carbon atoms of 2 to 16 carbon atoms.
  • the liquid crystal composition of the present invention preferably contains at least one compound represented by any one of the general formulas (Ch-I-1) to (Ch-I-30). More preferably, it contains a compound represented by -I-30). Specific examples of the compound represented by the general formula (Ch-I-30) include the following general formulas (Ch-I-30-1) to (Ch-I-30-6):
  • R 102 represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, or 2 carbon atoms. Represents an alkenyl group having 16 to 16 carbon atoms or an alkenyloxy group having 2 to 16 carbon atoms).
  • R 102 represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or the number of carbon atoms.
  • An alkenyl group having 2 to 6 carbon atoms or an alkenyloxy group having 2 to 6 carbon atoms is preferable.
  • the compound represented by the general formula (Ch-I) has a structure having an asymmetric carbon in the ring structure portion.
  • the compound represented by the general formula (Ch-I) As, the compound whose D is the said formula (D2) or (D4) is preferable, and the compound whose D is a formula (D4) is more preferable.
  • D As the compound in which D is the formula (D2), compounds represented by the following general formulas (K2-1) to (K2-8) are preferable.
  • the compound in which D is the formula (D4) the following general formula ( Compounds represented by K3-1) to (K3-6) are preferred.
  • R K is independently the same as R 100 and R 101 in formula (Ch-I). Represents meaning.
  • R K is Each independently a chiral or achiral alkyl group having 1 to 30 carbon atoms (one or more non-adjacent methylene groups in the alkyl group are -O-, -S-, -NH —, —N (CH 3 ) —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH ⁇ CH—, —CF 2 —.
  • a compound which is optionally substituted by a cyano group) is preferred, More preferred are compounds having 16 alkyl groups, alkoxy groups having 1 to 16 carbon atoms, alkenyl groups having 2 to 16 carbon atoms, or alkenyloxy groups having 2 to 16 carbon atoms, and alkyl having 3 to 10 carbon atoms. Further preferred is a compound which is a group, an alkoxy group having 3 to 9 carbon atoms, an alkenyl group having 3 to 10 carbon atoms, or an alkenyloxy group having 3 to 9 carbon atoms.
  • an axially asymmetric compound can be used, and specifically, a compound represented by the general formula (IV-1) or (IV-2) is preferable.
  • R 71 and R 72 are each independently a hydrogen atom, a halogen atom, a cyano group, an isocyanate group, iso thiocyanate group, or 1 carbon atoms To 20 alkyl groups. Any one or more methylene groups in the alkyl group are defined as those in which an oxygen atom and a sulfur atom are not directly bonded to each other, and —O—, —S—, —COO—, —OCO—, —CH ⁇ CH—, —CF ⁇ CF—, or —C ⁇ C— may be substituted. Furthermore, any one or two or more hydrogen atoms in the alkyl group may be substituted with a halogen atom.
  • R 71 and R 72 are each independently an unsubstituted or optionally substituted carbon atom number.
  • the alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted alkyl group having 1 to 20 carbon atoms, and further preferably an unsubstituted alkyl group having 1 to 6 carbon atoms.
  • a 71 and A 72 are each independently an aromatic or non-aromatic 3, 6 to 8 membered ring, or 9 carbon atoms
  • the above condensed ring is represented. Any one or more hydrogen atoms in these ring structures may be substituted with a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms. Further, any one or two or more methylene groups not adjacent to each other in the ring structure may be substituted with —O—, —S—, or —NH—. Any one or two or more —CH ⁇ that are not adjacent to each other may be substituted with —N ⁇ .
  • n 71 is 2 or more and a plurality of A 71 are present in one molecule, they may be the same as or different from each other.
  • m 72 is 2 or more and a plurality of A 72 are present in one molecule, they may be the same as or different from each other.
  • a 71 and A 72 are each independently 1,4-phenylene group, trans-1,4-cyclohexylene group, Pyridine-2,5-diyl group, pyrimidine-2,5-diyl group and naphthalene-2,6-diyl group are preferred.
  • a group in which one or two or more hydrogen atoms in these groups are substituted with a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms is also preferable.
  • 1,4-phenylene group in which one or two or more hydrogen atoms may be substituted with fluorine atoms, or trans-1,4-cyclohexylene group is more preferable, and unsubstituted 1,4-phenylene.
  • a group or an unsubstituted trans-1,4-cyclohexylene group is more preferable.
  • any one or two or more hydrogen atoms in the alkylene group may be substituted with a halogen atom.
  • m 71 is 2 or more and a plurality of Z 71 are present in one molecule, they may be the same as or different from each other.
  • m 72 is 2 or more and a plurality of Z 72 are present in one molecule, they may be the same as or different from each other.
  • Z 71 and Z 72 are each independently a single bond, an unsubstituted alkylene group having 1 to 4 carbon atoms, —COO —, —OCO—, —CH ⁇ CH—, or —C ⁇ C— are preferred, and a single bond, —CH 2 —, —CH 2 CH 2 —, —COO—, —OCO—, —CH ⁇ CH—, Alternatively, —C ⁇ C— is more preferable, and a single bond, —COO—, or —OCO— is more preferable.
  • X 71 and X 72 are each independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, — CF 2 O—, —OCF 2 —, or —CH 2 CH 2 — is represented.
  • X 71 and X 72 are each independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 — or —CH 2 CH 2 — is preferable, and a single bond, —COO—, or —OCO— is more preferable.
  • R 73 represents a hydrogen atom, a halogen atom, or —X 71 — (A 71 —Z 71 ) m 71 —R 71 .
  • m 71 and m 72 each independently represents an integer of 1 to 4.
  • R 73 is —X 71 — (A 71 —Z 71 ) m 71 —R 71
  • m 71 and m 72 are each independently preferably 2 or 3, and more preferably 2.
  • the chiral agent may be right-handed or left-handed, and may be properly used depending on the configuration of the liquid crystal display element.
  • liquid crystal composition of the present invention a chiral agent used in the TN mode or STN mode may be diverted as a chiral agent that induces pitch.
  • the liquid crystal composition of the present invention is represented by the formulas (ch-r001) to (ch-r006) as chiral agents that induce pitch.
  • the liquid crystal composition of the present invention has the formula (RM-001) to (RM-007) used in the PS mode, PSA mode or PSVA mode.
  • a polymerizable compound represented by the formula (1) may be appropriately contained in the range of 0% by mass to 5% by mass.
  • a hydrogen atom or a fluorine atom in the 1,4-phenyl group constituting the molecular structure of the polymerizable compound may be optionally substituted with a fluorine atom, a methyl group or a methoxy group.
  • the polymerizable compound used in the present invention may contain an alkylene group generally called a spacer between the ring and the polymerizable group, such as RM-005, and the alkylene group has 1 to 10 carbon atoms. Is preferred.
  • the spacer is preferably an alkylene group having 1 to 6 carbon atoms, and a plurality of types of polymerizable compounds Is more preferable from the viewpoint of improving the solubility.
  • the liquid crystal composition of the present invention contains 0.1% by mass to 1% by mass of a polymerizable compound, one type of polymerizable compound represented by the formulas (RM-001) to (RM-007) or It is preferable to contain 2 or more types.
  • the liquid crystal composition of the present invention may contain a hindered phenol compound represented by general formula (H-1) to general formula (H-4) as an antioxidant.
  • R H1 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or It represents an alkenyloxy group having 2 to 10 carbon atoms, one -CH 2 present in the radical - or non-adjacent two or more -CH 2 - are each independently -O- or -S- In addition, one or two or more hydrogen atoms present in the group may be independently substituted with a fluorine atom or a chlorine atom.
  • alkyl group having 2 to 7 carbon atoms an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms.
  • An alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms is more preferable.
  • M H4 is -CH 2 1, two or more of the alkylene group (the alkylene group having from 1 to 15 carbon atoms - as the oxygen atoms are not directly adjacent, - O—, —CO—, —COO—, —OCO— may be substituted.), —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, — OCF 2 —, —CF 2 CF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, — C ⁇ C—, a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted with a fluorine atom) or a trans-1,4-cyclohexylene group.
  • an alkylene group having 1 to 14 carbon atoms In consideration of the viscosity, a large number of carbon atoms is preferable, but in consideration of the viscosity, the number of carbon atoms is preferably not too large. Therefore, the number of carbon atoms is more preferably 2 to 12, more preferably 3 to 10. 4 to 10 carbon atoms are more preferred, 5 to 10 carbon atoms are more preferred, and 6 to 10 carbon atoms are more preferred.
  • one or more non-adjacent —CH ⁇ in the 1,4-phenylene group may be substituted by —N ⁇ .
  • each hydrogen atom in the 1,4-phenylene group may be independently substituted with a fluorine atom or a chlorine atom.
  • each hydrogen atom in the 1,4-cyclohexylene group may be independently substituted with a fluorine atom or a chlorine atom.
  • the lower limit of the content is preferably 10 mass ppm, preferably 20 mass ppm, more preferably 50 mass ppm, and the upper limit is preferably 10,000 mass ppm, 1000 mass. ppm is preferable, 500 ppm by mass is preferable, and 100 ppm by mass is preferable.
  • the liquid crystal composition of the present invention may contain a polymerizable compound used for PS type, PSA type, PSVA type, etc., for example, polymerizable having two or three 1,4-phenylene groups. Compounds are preferred, and the polymerizing group is preferably acrylate or methacrylate.
  • the dielectric anisotropy ( ⁇ ) at 25 ° C. is from ⁇ 2.0 to ⁇ 8.0, but from ⁇ 2.0 to ⁇ 6.0 is preferable, ⁇ 2.0 to ⁇ 5.0 is more preferable, and ⁇ 2.5 to ⁇ 5.0 is particularly preferable.
  • the dielectric anisotropy ( ⁇ ) at 25 ° C. is 2.0 to 20.0, but 2.0 to 15.0 is Preferably, 2.0 to 10.0 is more preferable, and 2.0 to 9.0 is particularly preferable.
  • the liquid crystal composition of the present invention has a refractive index anisotropy ( ⁇ n) at 25 ° C. of 0.08 to 0.14, more preferably 0.09 to 0.13, and 0.09 to 0.12. Particularly preferred. More specifically, it is preferably 0.10 to 0.13 when dealing with a thin cell gap, and preferably 0.08 to 0.10 when dealing with a thick cell gap.
  • the liquid crystal composition of the present invention has a viscosity ( ⁇ ) at 20 ° C. of 10 to 100 mPa ⁇ s, preferably 10 to 90 mPa ⁇ s, preferably 10 to 80 mPa ⁇ s, and 10 to 70 mPa ⁇ s.
  • S preferably 10 to 60 mPa ⁇ s, more preferably 10 to 50 mPa ⁇ s, more preferably 10 to 40 mPa ⁇ s, and preferably 10 to 30 mPa ⁇ s. Is particularly preferred.
  • the liquid crystal composition of the present invention has a rotational viscosity ( ⁇ 1 ) at 25 ° C. of 20 to 250 mPa ⁇ s, preferably 25 to 200 mPa ⁇ s, preferably 30 to 160 mPa ⁇ s, 30 To 140 mPa ⁇ s, preferably 40 to 140 mPa ⁇ s, preferably 40 to 130 mPa ⁇ s, preferably 40 to 125 mPa ⁇ s, and 40 to 120 mPa ⁇ s. More preferably, the pressure is 40 to 115 mPa ⁇ s, still more preferably 40 to 110 mPa ⁇ s, and particularly preferably 40 to 100 mPa ⁇ s.
  • the liquid crystal composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T ni ) of 60 ° C to 130 ° C, more preferably 70 ° C to 120 ° C, further preferably 75 ° C to 110 ° C, 80 ° C. to 95 ° C. is particularly preferred.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • the liquid crystal composition of the present invention has a black color, and since dichroic dyes and unprecedented high solubility are obtained, precipitation at a low temperature of 25 ° C. or ⁇ 20 ° C. or lower is suppressed or suppressed. It can be used in a wide temperature range. Therefore, it can be easily applied to in-vehicle display devices that are highly adaptable to harsh environments, mobile terminals such as smartphones and tablets, and light control devices such as window glasses. Moreover, it is excellent in light resistance or UV resistance or heat resistance, and has no change in color or is suppressed.
  • the device using the liquid crystal composition of the present invention has a large absorption near 550 nm, the black color is excellent, and the metallic black with a clear and transparent appearance is not a conventional dull black. And a high contrast can be obtained. Moreover, there is no conventional problem that it becomes impossible to use at low temperature, or it is suppressed. Moreover, it is excellent in light resistance or UV resistance or heat resistance, and has no change in color or is suppressed.
  • the liquid crystal composition of the present invention is a liquid crystal composition having a negative dielectric anisotropy
  • it is preferably a liquid crystal display element having APL (anti-parallel) and VA (vertical alignment), but has high contrast.
  • APL anti-parallel
  • VA vertical alignment
  • it is more preferable to twist the orientation axis by 90 °, more preferably by 240 °, and if it is desired to obtain a higher contrast, it is technically more difficult, but a twist of 250 ° or 260 ° A 270 ° twist is preferable, and a 360 ° twist is also preferable.
  • the liquid crystal composition of the present invention is preferably a so-called TN liquid crystal display element.
  • the alignment axis is 180 °. Twist is more preferable, and 240 ° twist, 250 ° twist, 260 ° twist, or 270 ° twist is more preferable.
  • the liquid crystal composition of the present invention can be used for a liquid crystal display device or a light control device.
  • the liquid crystal display element using the liquid crystal composition of the present invention is useful for a liquid crystal display element for active matrix driving, and includes a PSA mode, a PSVA mode, a VA mode, a PS-IPS mode, a TN mode, an STN mode, and an IPS mode.
  • a PS-FFS mode liquid crystal display element can be used for a PS-FFS mode liquid crystal display element.
  • the two substrates of the liquid crystal cell used in the liquid crystal display element can be made of a transparent material having flexibility such as glass or plastic, and one of them can be an opaque material such as silicon.
  • a transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method.
  • a method for producing a color filter by a pigment dispersion method will be described as an example.
  • a curable coloring composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this process for each of the three colors red, green, and blue, a pixel portion for a color filter can be created.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element can be provided on the substrate.
  • the substrate is opposed so that the transparent electrode layer is on the inside.
  • the thickness of the obtained light control layer is 1 to 100 ⁇ m. More preferably, the thickness is 1.5 to 10 ⁇ m.
  • the polarizing plate it is preferable to adjust the product of the refractive index anisotropy ⁇ n of the liquid crystal and the cell thickness d so that the contrast is maximized.
  • the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good.
  • a retardation film for widening the viewing angle can also be used.
  • the spacer examples include glass particles, plastic particles, alumina particles, and a photoresist material.
  • a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.
  • a normal vacuum injection method or an ODF method can be used as a method of sandwiching the liquid crystal composition between the two substrates.
  • the measured characteristics are as follows.
  • T ni Nematic phase-isotropic liquid phase transition temperature (° C.)
  • T cn Solid phase-nematic phase transition temperature (° C)
  • ⁇ n refractive index anisotropy at 25 ° C.
  • ⁇ 1 rotational viscosity at 25 ° C. (mPa ⁇ s) [Delta] [epsilon]: 25 ° C. in a dielectric anisotropy
  • K 33 elastic constant K 33 at 25 ° C.
  • Solubility About 1 g of the liquid crystal composition was placed in a vial, and after 240 hours, the presence or absence of precipitation was visually observed. The result was “1” when there was no precipitation, and “2” when precipitation was confirmed.
  • the storage temperature was 25 ° C. or ⁇ 20 ° C.
  • Tint Visually observing the quality of the black color of the test panel into which the liquid crystal composition was injected. When the black color is transparent, it is “1". When it is close to dark gray, it is “3”. In the case of degree, it was set to “2”.
  • T (0 V) The transmittance T (%) when the applied voltage is 0 (V) when the electro-optical characteristics are evaluated at 25 ° C. with a DMS-501 manufactured by autonic Co. It is.
  • Heat resistance test The color of the test panel injected with the liquid crystal composition was visually observed after heating at 70 ° C. for 240 hours. When the color did not change, “1”, the color changed slightly. In the case of “2”, the color was clearly changed to "3".
  • the cell thickness of the test panel was 3.5 ⁇ m
  • the alignment film for vertical alignment was JALS2096
  • the alignment film for horizontal alignment was AL1051.
  • Liquid crystal compositions of LC-A (Comparative Example 1), LC-B (Comparative Example 2), LC-11 (Example 1) and LC-12 (Example 2) in combination with the present dichroic dye SI-426 Products were prepared and their physical properties and properties were measured. Table 1 shows the composition of the combined liquid crystal compositions, their physical properties, characteristics and test results.
  • the chromaticity of the dichroic dye G-241 exhibiting a purple color was (0.287, 0.245).
  • the maximum absorption wavelength of the dichroic dye G-241 is 564 nm
  • the maximum absorption wavelength of the dichroic dye G-472 is 636 nm
  • the maximum absorption wavelength of the dichroic dye M-137 is 640 nm.
  • the maximum absorption wavelength of the dichroic dye SI-486 was 402 nm
  • the maximum absorption wavelength of the dichroic dye SI-426 was 522 nm.
  • the maximum absorption wavelength of the dichroic dye was determined by injecting a liquid crystal composition containing 0.5% of the dichroic dye into a vertically aligned test panel (cell thickness 10 ⁇ m) coated with the alignment film JALS2096. It calculated
  • LC-11 was prepared by adding dichroic dyes SI-426, SI-486, G-241 and G-472 to the liquid crystal composition of Host-1.
  • Example 1 LC-12 was further prepared by adding a chiral agent c01 to LC-11.
  • Example 2 On the other hand, a liquid crystal composition excluding the dichroic dye G-241 having a purple color among the dichroic dyes contained in LC-11 was prepared as LC-A.
  • Comparative Example 1 A liquid crystal composition to which M-137 (non-azo dichroic dye) was added instead of the purple dichroic dye G-241 was prepared as LC-B.
  • LC-11 and LC-12 are clear, clear black and satisfactory in appearance, whereas the colors of LC-A and LC-B are close to gray Because it was dark gray without transparency, it was not satisfactory in appearance.
  • liquid crystal compositions LC-11 and LC-12 of the present invention are superior to LC-A and LC-B.
  • LC-11 to which an antioxidant (H-11), (H-12) or (H-14) is appropriately added in the range of 5 ppm to 200 ppm, is also soluble, tint, T (0 V), T In (8V), the light resistance test and the heat resistance test, it was confirmed that the results were the same as those of LC-11.
  • LC-21 Example 3
  • LC-22 Example 4
  • liquid crystal compositions were prepared, and their physical properties and characteristics were measured. The composition of the liquid crystal composition and the results of the physical properties and characteristics are shown in Table 2.
  • LC-21 was prepared by adding dichroic dyes SI-426, SI-486, G-241 and G-472 to the liquid crystal composition of Host-2.
  • LC-22 with addition of c02 was prepared.
  • LC-31 was prepared by adding dichroic dyes SI-426, SI-486, G-241 and G-472 to the liquid crystal composition of Host-3.
  • LC-32 to which c-01 was added was prepared.
  • a liquid crystal composition LC-C in which M-137 (non-azo dichroic dye) was added instead of G-472 was prepared.
  • LC-C was confirmed to be deposited immediately after preparation, and could not be injected into a test panel for performing various tests. Precipitation was confirmed after 240 hours of storage at 25 ° C. Actually, it was precipitated after 24 hours and was not satisfactory for practical use. From this, it was confirmed that the use of a non-azo dichroic dye such as M-137 is not preferable from the viewpoint of solubility.
  • LC-31 and LC-32 have a large T (0V) value and a small T (8V) value, so it was confirmed that the dichroic ratio was large and the contrast was high.
  • Example 7, Example 8, Example 9 and Example 10 LC-41 (Example 7), LC-42 (Example 8), LC-43 (Example 9), and LC-44 (Example 10) were prepared as liquid crystal compositions having a positive dielectric anisotropy. Tables 4, 5, 6, and 7 show the structures of the liquid crystal compositions and their physical properties.
  • Example 7 was a liquid crystal composition LC-41 of the present invention in which dichroic dyes SI-426, SI-486, G-241 and G-472 were added to Host-4.
  • Example 8 was a liquid crystal composition LC-42 of the present invention in which dichroic dyes SI-426, SI-486, G-241 and G-472 were added to Host-5.
  • Example 9 was a liquid crystal composition LC-43 of the present invention in which dichroic dyes SI-426, SI-486, G-241 and G-472 were added to Host-6.
  • Example 10 was a liquid crystal composition LC-44 of the present invention, in which dichroic dyes SI-426, SI-486, G-241 and G-472 were added to Host-7. About Example 7, Example 8, Example 9, and Example 10, when evaluation similar to Example 1 was performed, it was confirmed that the subject of this invention is solved. Further, it was confirmed that T (8V) was a smaller value when a chiral agent was further added.
  • the test panel was a TN type, the cell thickness was 6 ⁇ m, and the alignment film was AL1051 manufactured by JSR. From the above, it was confirmed that the liquid crystal composition of the present invention solved the problems of the present invention regardless of whether the dielectric constant was negative or positive.
  • the liquid crystal composition of the present invention has high solubility, excellent color as black, high dichroic ratio and high contrast, and a liquid crystal display device or a light control device using this is practically required. It satisfies the characteristics.

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