WO2014125924A1 - Nouveau composé ayant une structure cyclique présentant une anisotropie diélectrique négative, procédé pour la production dudit composé, composition à cristaux liquides et élément électro-optique à cristaux liquides - Google Patents

Nouveau composé ayant une structure cyclique présentant une anisotropie diélectrique négative, procédé pour la production dudit composé, composition à cristaux liquides et élément électro-optique à cristaux liquides Download PDF

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WO2014125924A1
WO2014125924A1 PCT/JP2014/052000 JP2014052000W WO2014125924A1 WO 2014125924 A1 WO2014125924 A1 WO 2014125924A1 JP 2014052000 W JP2014052000 W JP 2014052000W WO 2014125924 A1 WO2014125924 A1 WO 2014125924A1
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phe
tfce
tfcy
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compound
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今野　勉
孝 石原
智之 淺井
渭原　聡
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Ａｇｃセイミケミカル株式会社
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Priority to JP2015500176A priority Critical patent/JPWO2014125924A1/ja
Publication of WO2014125924A1 publication Critical patent/WO2014125924A1/fr

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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
    • C09K19/04—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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • 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
    • C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
    • 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
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3018—Ph-Cy-Ph

Definitions

  • the present invention relates to a novel compound having a novel ring structure that exhibits negative dielectric anisotropy ( ⁇ ) and a method for producing the same, and more specifically, 2,2,3,3-tetrafluorocyclohexane-1, Compound having 4-diyl group and compound having 5,5,6,6-tetrafluoro-2-cyclohexene-1,4-diyl group, respective production methods, liquid crystal composition containing these compounds, and liquid crystal
  • the present invention relates to a liquid crystal electro-optical element configured using a composition.
  • Liquid crystal electro-optical elements include mobile devices such as mobile phones and PDAs, display devices for OA devices such as copiers and personal computer monitors, display devices for home appliances such as liquid crystal televisions, clocks, calculators, measuring instruments, and automotive instruments. It is used for a wide range of applications such as cameras. There are TN (twisted nematic) method, STN (super twisted nematic) method, or TN-based active matrix (TFT: thin film transistor) method, etc., and these drive methods include ⁇ ( A liquid crystal composition having a positive dielectric anisotropy is used. However, one of the drawbacks of these display methods is a narrow viewing angle.
  • an IPS (in-plane switching) method or a VA (vertical alignment) method with improved viewing angle is often used as a driving method for large-sized liquid crystal electro-optic elements, among active matrix methods.
  • a liquid crystal composition having a positive or negative ⁇ is used for the IPS mode, and a liquid crystal composition having a negative ⁇ is used for the VA mode.
  • a liquid crystal composition in which several liquid crystalline compounds having one or two or more specific excellent properties are usually combined Is used as a material showing a liquid crystal phase used in a liquid crystal electro-optical element.
  • a liquid crystal compound having a negative ⁇ is indispensable, and a liquid crystal compound having a large absolute value of ⁇ is desired.
  • the function-expressing ring structure having a negative ⁇ used for general purposes is limited to a structure in which an electron-withdrawing group such as fluorine is introduced into a side orientation such as a phenyl ring or a naphthalene ring.
  • a compound represented by Formula (A) (see Patent Document 1) and a compound represented by Formula (B) (see Patent Document 2) having a 2,3-difluorophenylene group as a ⁇ negative function-expressing ring structure
  • a compound represented by the formula (C) in which a naphthalene ring has a ⁇ negative function-expressing ring structure (see Patent Document 3) is known.
  • JP-T-2-503441 Japanese Patent Laid-Open No. 10-176167 JP 2001-31597 A
  • the present invention is chemically stable, excellent in compatibility with other liquid crystal materials or non-liquid crystal materials, and has a high responsiveness, low viscosity, and a wide liquid crystal temperature range by designing a bonding group to the linking group.
  • Another object of the present invention is to provide a new ⁇ negative function-expressing ring structure-containing compound having a large ⁇ in order to develop a liquid crystalline compound that can also have characteristics such as a high clearing point.
  • the present invention also provides a novel ⁇ negative function-expressing ring structure, a method for producing a compound incorporating the same, a liquid crystal composition suitable for obtaining a highly reliable liquid crystal electro-optic element, and a liquid crystal composition thereof. It is an object of the present invention to provide a liquid crystal electro-optical element used.
  • a new ⁇ negative function-expressing ring structure includes 2,2,3,3-tetrafluorocyclohexane-1,4-diyl group and 5,5,6,6- We devised a tetrafluoro-2-cyclohexene-1,4-diyl group and succeeded in synthesizing a compound incorporating this new functional ring structure.
  • This new ⁇ negative function-expressing ring structure showed a negative ⁇ , which was found to be useful as a ⁇ -negative function-expressing ring structure.
  • the 2,2,3,3-tetrafluorocyclohexane-1,4-diyl group and the 5,5,6,6-tetrafluoro-2-cyclohexene-1,4-diyl group have completely new structures and have been synthesized so far. There is no example. Therefore, the compound containing this function-expressing ring structure is a novel compound, and its production method is also novel.
  • R 1 and R 2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 18 carbon atoms, wherein one or more hydrogen atoms may be substituted with a halogen atom Well, an etheric oxygen atom (—O—) or a thioetheric sulfur atom (—S—) may be inserted between carbon-carbon atoms (C—C) or at the bond terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH— or —C ⁇ C—.
  • a 1 , A 2 , A 3 , A 4 , A 5 and A 6 independently of each other, trans-1,4-cyclohexylene group, 1,4-cyclohexenylene group, 1,3-cyclobutylene Group, 1,2-cyclopropylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1, 4-phenylene group, and in each of these groups, one or more hydrogen atoms may be substituted with a halogen atom, and one or two ⁇ CH— may be substituted with a nitrogen atom.
  • —CH 2 — may be substituted with —O— or —S—.
  • Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are each independently a single bond or an alkylene group having 1 to 4 carbon atoms, in which one or more hydrogen atoms are
  • One or more —CH 2 — may be substituted with —O— or —S—, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • —C ⁇ C— may be substituted, and one —CH 2 CH 2 — may be substituted with —COO— or —OCO—.
  • n, o, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + o + p + q + r ⁇ 4.
  • a broken line in the formula indicates that a bond may or may not be present.
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (1a).
  • the symbol in a formula shows the same meaning as the symbol in Formula (1) of Claim 1.
  • the compound represented by the formula (1a) is preferably a compound represented by the following formula (1a-1).
  • the symbols in the formula have the following meanings.
  • R 11 and R 21 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 18 carbon atoms, wherein one or more hydrogen atoms may be substituted with a halogen atom
  • an etheric oxygen atom or a thioetheric sulfur atom may be inserted between carbon-carbon atoms or at the bond terminal of the group, and one or more —CH 2 CH 2 — is substituted with —CH ⁇ CH—. It may be.
  • a 11 , A 21 , A 31 , A 41 , A 51 , and A 61 each independently a trans-1,4-cyclohexylene group or a 1,4-phenylene group,
  • One or more hydrogen atoms may be substituted with a halogen atom, one or two ⁇ CH— may be substituted with a nitrogen atom, and one or two —CH 2 — is an etheric oxygen It may be substituted with an atom or a thioetheric sulfur atom.
  • Z 11 , Z 21 , Z 31 , Z 41 , Z 51 and Z 61 are each independently a single bond or an alkylene group having 1 to 4 carbon atoms, and one or more hydrogen atoms in the alkylene group May be substituted with a fluorine atom, and one or more —CH 2 — may be substituted with an etheric oxygen atom or a thioetheric sulfur atom, and one or more —CH 2 CH 2 — may be —CH It may be substituted with ⁇ CH— or —C ⁇ C—.
  • m, n, o, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + o + p + q + r ⁇ 4.
  • the compound represented by the formula (1a) is more preferably a compound represented by the following formula (1a-2).
  • the symbols in the formula have the following meanings.
  • R 12 and R 22 are each independently an alkyl group having 1 to 10 carbon atoms, and one or more hydrogen atoms in the group may be substituted with a fluorine atom, and a carbon-carbon atom or An etheric oxygen atom may be inserted at the bond terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a 12 , A 22 , A 32 , A 42 , A 52 and A 62 independently of each other, a trans-1,4-cyclohexylene group, 1,4-phenylene group or one or two hydrogen atoms 1,4-phenylene group substituted by a fluorine atom.
  • Z 12 , Z 22 , Z 32 , Z 42 , Z 52 and Z 62 independently of each other, a single bond, —CH 2 CH 2 —, —CH ⁇ CH—, —C ⁇ C—, —CH 2 O —, —OCH 2 —, —CF 2 CF 2 —, —CF ⁇ CF—, —OCF 2 —, —CF 2 O—, —CH 2 CH 2 OCF 2 —, —CF 2 OCH 2 CH 2 —, — CF ⁇ CFCF 2 O— or —OCF 2 CF ⁇ CF—.
  • m, n, o, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + o + p + q + r ⁇ 4.
  • the compound represented by the formula (1) is also preferably a compound represented by the following formula (1b).
  • the symbols in each formula have the same meaning as the symbols in formula (1) of claim 1.
  • the compound represented by the formula (1b) is preferably a compound represented by the following formula (1b-1).
  • R 11 and R 21 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 18 carbon atoms, wherein one or more hydrogen atoms may be substituted with a halogen atom
  • an etheric oxygen atom or a thioetheric sulfur atom may be inserted between carbon-carbon atoms or at the bond terminal of the group, and one or more —CH 2 CH 2 — is substituted with —CH ⁇ CH—. It may be.
  • a 11 , A 21 , A 31 , A 41 , A 51 , and A 61 each independently a trans-1,4-cyclohexylene group or a 1,4-phenylene group,
  • One or more hydrogen atoms may be substituted with a halogen atom, one or two ⁇ CH— may be substituted with a nitrogen atom, and one or two —CH 2 — is an etheric oxygen It may be substituted with an atom or a thioetheric sulfur atom.
  • Z 11 , Z 21 , Z 31 , Z 41 , Z 51 and Z 61 are each independently a single bond or an alkylene group having 1 to 4 carbon atoms, and one or more hydrogen atoms in the alkylene group May be substituted with a fluorine atom, and one or more —CH 2 — may be substituted with an etheric oxygen atom or a thioetheric sulfur atom, and one or more —CH 2 CH 2 — may be —CH It may be substituted with ⁇ CH— or —C ⁇ C—.
  • m, n, o, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + o + p + q + r ⁇ 4.
  • the compound represented by the formula (1b) is more preferably a compound represented by the following formula (1b-2).
  • the symbols in the formula have the following meanings.
  • R 12 and R 22 are each independently an alkyl group having 1 to 10 carbon atoms, and one or more hydrogen atoms in the group may be substituted with a fluorine atom, and a carbon-carbon atom or An etheric oxygen atom may be inserted at the bond terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a 12 , A 22 , A 32 , A 42 , A 52 and A 62 independently of each other, a trans-1,4-cyclohexylene group, 1,4-phenylene group or one or two hydrogen atoms 1,4-phenylene group substituted by a fluorine atom.
  • Z 12 , Z 22 , Z 32 , Z 42 , Z 52 and Z 62 independently of each other, a single bond, —CH 2 CH 2 —, —CH ⁇ CH—, —C ⁇ C—, —CH 2 O —, —OCH 2 —, —CF 2 CF 2 —, —CF ⁇ CF—, —OCF 2 —, —CF 2 O—, —CH 2 CH 2 OCF 2 —, —CF 2 OCH 2 CH 2 —, — CF ⁇ CFCF 2 O— or —OCF 2 CF ⁇ CF—.
  • m, n, o, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + o + p + q + r ⁇ 4.
  • the present invention can provide the following method as an example of a method for producing the above compound.
  • the symbol in each formula has the same meaning as the symbol in formula (1) according to claim 1.
  • a broken line in the formula indicates that a bond may or may not be present.
  • the compound represented by the formula (2) is a compound represented by the following formula (2a), and the compound represented by the formula (1) is a compound represented by the following formula (1a). Certain manufacturing methods are preferred.
  • the symbols in each formula have the same meaning as the symbols in the formula (1).
  • the present invention also provides a method for producing a compound represented by the following formula (1a) by hydrogenating a compound represented by the following formula (1b).
  • the symbols in each formula have the same meaning as the symbols in the formula (1).
  • the present invention also provides a liquid crystal composition comprising the compound represented by the formula (1).
  • the present invention also provides a liquid crystal electro-optical element formed by sealing the liquid crystal composition between two substrates provided with electrodes.
  • the compound of the present invention has a novel ⁇ negative function-expressing ring structure, ⁇ is negatively large, and is useful for an operation mode utilizing vertical alignment.
  • the ring structure is a structure in which ⁇ is negatively large
  • the compound of the present invention has a feature that ⁇ is negatively large, but the ring group, substituent, and linking group constituting the compound are also included.
  • a compound having a 2-cyclohexene-1,4-diyl group has high versatility and can be easily and efficiently produced easily and efficiently industrially.
  • a compound represented by the formula (1) is referred to as a compound (1), and compounds represented by other formulas are also described in the same manner.
  • the one closer to R 1 in the formula (1) is always the first place, and the one closer to R 2 is always the fourth place.
  • —O— and / or —S— are not linked.
  • “ ⁇ is negatively large” means that ⁇ is negative and the absolute value thereof is large. That is, if the value of ⁇ is ⁇ 1 and ⁇ 2, -2 is “ ⁇ is negatively larger”.
  • the bond described by the solid line in each formula includes all stereoisomers.
  • the liquid crystal electro-optical element is not limited to a display element, but various functional elements that use the electrical or optical characteristics of liquid crystal, such as a liquid crystal display element, a light control window, and an optical shutter. And elements used for applications such as a polarization conversion element and a variable focus lens.
  • the group in which one or more hydrogen atoms in the alkyl group are substituted with halogen atoms includes a fluoroalkyl group, chloro An alkyl group etc. are mentioned.
  • a fluorine atom is preferable.
  • Examples of the group in which —O— or —S— is inserted between C—C in the alkyl group include an alkoxyalkyl group or an alkylthioalkyl group, and —O— or —S— is inserted at the bond terminal of the group.
  • Examples of the group include an alkoxy group and an alkylthio group.
  • Examples of the group in which —CH 2 CH 2 — in the alkyl group is substituted with —CH ⁇ CH— or —C ⁇ C— include an alkenyl group and an alkynyl group.
  • substitution with — or —C ⁇ C— may be performed simultaneously on the same alkyl group.
  • Examples of the group in which substitution of a fluorine atom and insertion of —O— are simultaneously performed include a fluoroalkoxy group and a fluoroalkoxyalkyl group.
  • Examples of the group in which —CH ⁇ CH— or —C ⁇ C— substitution and fluorine atom substitution are simultaneously performed include a fluoroalkenyl group and a fluoroalkynyl group.
  • Examples of the group in which substitution of —CH ⁇ CH— or —C ⁇ C— and insertion of —O— or —S— between C—C are performed simultaneously include alkenyloxyalkyl group, alkynyloxyalkyl group, alkenyl A thioalkyl group and an alkynylthioalkyl group can be mentioned.
  • Examples of the group in which —CH ⁇ CH— or —C ⁇ C— is substituted and —O— or —S— is inserted at the bonding end of the group include an alkenyloxy group, an alkynyloxy group, an alkenylthio group, and an alkynylthio group.
  • Groups. Further, groups in which fluorine atom substitution, —CH ⁇ CH— or —C ⁇ C— substitution, and —O— or —S— insertion are performed simultaneously include fluoroalkenyloxy group, fluoroalkynyloxy group And a fluoroalkenylthio group. These groups may be either linear or branched, but are preferably linear.
  • R 1 and R 2 are preferably fluorine atoms and groups having 1 to 18 carbon atoms because reactivity and side reactions are less likely to occur.
  • R 1 and R 2 are alkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkenyloxy groups, alkenyloxyalkyl groups, fluoroalkyl groups, fluoroalkoxy groups, fluoroalkoxyalkyls having 1 to 10 carbon atoms.
  • Group, a fluoroalkenyl group is more preferable, and an alkyl group, an alkoxy group, and an alkenyl group having 1 to 10 carbon atoms are particularly preferable.
  • substitution of a hydrogen atom with a halogen atom, ⁇ CH—to a nitrogen atom substituted, and, -CH 2 - substituted Roh -O- or -S- to may be carried out simultaneously for the same group.
  • a halogen atom a chlorine atom or a fluorine atom is preferable.
  • a 1 , A 2 , A 3 , A 4 , A 5 and A 6 are 1,4-phenylene groups and further have a halogen atom as a substituent
  • a halogen atom to be substituted with one 1,4-phenylene group The number of is from 1 to 4, with 1 or 2 being preferred.
  • the number of halogen atoms is preferably 1 to 4.
  • the halogen atom may be bonded to the 1st or 4th carbon atom of the cyclohexylene group.
  • Examples of the group in which one or two ⁇ CH— in the 1,4-phenylene group are substituted with a nitrogen atom include a 2,5-pyrimidinylene group and a 2,5-pyridinylene group.
  • Examples of the group in which one or two —CH 2 — in the trans-1,4-cyclohexylene group is substituted with —O— or —S— include a 1,3-dioxane-2,5-diyl group, A 1,3-dithian-2,5-diyl group may be mentioned.
  • a 1,4-phenylene group substituted with at least one of a halogen atom and a nitrogen atom is referred to as a “substituted 1,4-phenylene group” and substituted with at least one of a halogen atom, —O— and —S—.
  • the 1,4-cyclohexylene group thus prepared is referred to as “substituted trans-1,4-cyclohexylene group”.
  • a 1 , A 2 , A 3 , A 4 , A 5 and A 6 are trans-1,4-cyclohexylene group, 1,4-phenylene because of reactivity and availability of raw materials.
  • a group, a substituted trans-1,4-cyclohexylene group, or a substituted 1,4-phenylene group is preferred.
  • a trans-1,4-cyclohexylene group, a 1,4-phenylene group, or a 1,4-phenylene group in which one or two hydrogen atoms in the group are substituted with fluorine atoms is more preferable.
  • a 1,4-cyclohexylene group or a 1,4-phenylene group is particularly preferred.
  • a 1 , A 2 , A 3 , A 4 , A 5 and A 6 of the compound (1) is a 2,3-difluoro-1,4-phenylene group or the following ring group
  • ⁇ of the compound is considered to be larger due to being negative.
  • the one closer to R 1 in the formula (1) is the first place, and the one closer to R 2 is the fourth place.
  • Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 have the same meaning as described above.
  • substitution of a hydrogen atom with a fluorine atom substitution of —CH 2 — with —O— or —S—, —CH ⁇ CH— of —CH 2 CH 2 —, —C ⁇ C—, —COO— , —OCO— may be substituted simultaneously for the same group.
  • alkylene group in which one or more hydrogen atoms in the group are substituted with fluorine atoms examples include —CF 2 CF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CHFCH 2 —, —CH 2 CHF—, —CF 2 CHF—, —CHFCF 2 — and the like can be mentioned.
  • alkylene group in which one or more —CH 2 — in the group is substituted by —O— or —S— include —CH 2 O—, —OCH 2 —, —CH 2 S—, —SCH 2 — and the like. Is mentioned.
  • groups in which the substitution of a hydrogen atom in a group with a fluorine atom and the substitution of —CH 2 — in the group with —O— are performed simultaneously include —CF 2 O—, —OCF 2 — Etc.
  • the alkylene group in which one or more —CH 2 CH 2 — in the group is substituted with —CH ⁇ CH— or —C ⁇ C— includes an alkenylene group or an alkynylene group.
  • the alkenylene group or alkynylene group includes —CH ⁇ CH—, —CH ⁇ CH—CH 2 —, —CH ⁇ CH—CH 2 —CH 2 —, —CH ⁇ CH—CH ⁇ CH—, —CH 2 —CH.
  • ⁇ CH—CH 2 —, —C ⁇ C—, —C ⁇ C—CH 2 —, —C ⁇ C—CH 2 —CH 2 —, —C ⁇ C—C ⁇ C—, —CH 2 —C ⁇ C—CH 2 — and the like can be mentioned. Further, double bonds and triple bonds may be mixed as in —CH ⁇ CH—C ⁇ C—. These groups may be reversed. Examples of groups in which —CH ⁇ CH— or —C ⁇ C— and fluorine atoms are simultaneously substituted include —CF ⁇ CF—, —CF ⁇ CF—C ⁇ C— and the like.
  • Examples of the group in which one —CH 2 CH 2 — is substituted with —COO— or —OCO— include —COO—, —OCO—, —CH 2 CH 2 —COO—, —CH 2 CH 2 -OCO- and the like.
  • Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are preferably a single bond or an alkylene group having 1 to 4 carbon atoms from the viewpoint of ease of synthesis.
  • One or more hydrogen atoms in the group may be substituted with a fluorine atom, and one or more —CH 2 — in the group may be substituted with —O— or —S—.
  • Two or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH— or —C ⁇ C—.
  • a single bond, —CH 2 CH 2 —, —C ⁇ C—, —CH 2 O—, —OCH 2 —, —OCF 2 —, and —CF 2 O— are preferable.
  • m, n, o, p, q and r have the same meaning as described above.
  • m, n, o, p, q, and r can be suitably selected according to the characteristics required for the compound. For example, when importance is attached to the low viscosity of the compound (1) or the excellent compatibility of the compound with other liquid crystal materials or non-liquid crystal materials, it is preferable that 0 ⁇ m + n + o + p + q + r ⁇ 1. On the other hand, when emphasizing the high liquid crystal temperature range of the compound, it is preferable that 1 ⁇ m + n + o + p + q + r ⁇ 3.
  • the compound (1a) is preferable.
  • the symbols in the formula are as described above.
  • the compound (1a) As the compound (1a), the compound (1a-1) is preferable.
  • the symbols in the formula are as described above.
  • the compound (1a) is more preferable.
  • the symbols in the formula are as described above.
  • the compound (1b) is also preferable.
  • the symbols in the formula are as described above.
  • the compound (1b) As the compound (1b), the compound (1b-1) is preferable.
  • the symbols in the formula are as described above.
  • the compound (1a) is more preferable.
  • the symbols in the formula are as described above.
  • Preferable examples of compound (1) include the following compounds.
  • R 1 , R 2 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 have the same meaning as described above, and other symbols have the following meanings.
  • -Cy- trans-1,4-cyclohexylene group.
  • -Phe- 1,4-phenylene group optionally substituted by one or two fluorine atoms.
  • -TFFCy- trans-2,2,3,3-tetrafluorocyclohexane-1,4-diyl group
  • TFCe- 5,5,6,6-tetrafluoro-2-cyclohexene-1,4-diyl group
  • a series of reactions for obtaining the compound (1) by the above production method can be expressed as follows. For example, a method in which the compound (3) is cyclized to give the compound (2b), then further hydrogenated to give the compound (2a), and then further dehydroxylated to give the compound (1a).
  • R 3 in each formula is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and other symbols in each formula have the same meaning as the symbols in formula (1).
  • R 3 in each formula is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and other symbols in each formula have the same meaning as the symbols in formula (1).
  • R 3 in each formula is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and other symbols in each formula have the same meaning as the symbols in formula (1).
  • the compound (3) can be synthesized, for example, as follows.
  • M in the formula is a metal atom or a group containing a metal atom.
  • Other symbols have the same meaning as described above.
  • the compound (5) is lithiated with methyllithium and reacted with the aldehyde of the compound (6) to obtain the compound (7).
  • the double bond of compound (7) is ozonolyzed and converted to hemiacetal (8).
  • the diketone (11) is obtained by reacting the compound (8) with the organometallic reagent (9) to convert it to the diol (10) and then oxidizing it.
  • Compound (3) is synthesized by reacting diketone (11) with alkenyl magnesium chloride (12).
  • MgI, MgBr, MgCl and Li are preferable, and MgBr is particularly preferable.
  • Compound (2b) is obtained by subjecting compound (3) to a ring-closing metathesis reaction.
  • Ring closure metathesis reactions are described in the literature (Schwab, P .; France, MB; Ziller, JW; Grubbs, RH Angew. Chem. Int. Ed. 1995, 34, 2039., Nguyen, ST; Johnson, LK; Grubbs, RH; Ziller , JWJ Am. Chem. Soc. 1992, 114, 3974.).
  • Solvents include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; tetrahydrofuran, diethyl ether, diisopropyl ether, dibutyl ether, and t-butylmethyl.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene
  • aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane
  • tetrahydrofuran diethyl ether
  • diisopropyl ether dibutyl ether
  • t-butylmethyl t-butylmethyl
  • Ether-based solvents such as ether and dimethoxyethane; petroleum ethers, halogen-based solvents such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and parkrene, or a suitable mixed solvent of the above solvents can be used.
  • halogen solvents such as methylene chloride and 1,2-dichloroethane
  • aromatic hydrocarbon solvents such as benzene and toluene are preferable.
  • the transition metal catalyst is preferably a Grubbs catalyst, and the amount used is preferably 0.00001 equivalent to 10 equivalents, more preferably 0.001 equivalent to 1 equivalent, relative to 1 mol of the compound (2).
  • the reaction temperature is preferably 0 to 150 ° C, more preferably 10 to 100 ° C.
  • the reaction time is preferably 0.1 to 120 hours, more preferably 0.1 to 72 hours, and even more preferably 1 to 48 hours.
  • Compound (2a) is obtained by hydrogenating compound (2b).
  • the hydrogenation reaction is preferably carried out in a solvent using a heterogeneous catalyst.
  • Solvents that can be used include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene; aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; such as ethyl acetate, methyl acetate, and propyl acetate.
  • Ester solvents alcohol solvents such as methanol and ethanol; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as tetrahydrofuran, diethyl ether, dibutyl ether, t-butyl methyl ether, and dimethoxyethane; petroleum ethers or the aforementioned solvents
  • a suitable mixed solvent or the like can be used.
  • alcohol solvents such as methanol, ester solvents such as ethyl acetate, and mixed solvents of these solvents are preferable.
  • heterogeneous catalyst examples include transition metal catalysts such as palladium carbon, rhodium carbon, ruthenium carbon, Raney nickel, and platinum oxide.
  • the amount of the catalyst used is preferably 0.01 to 1.0 times, more preferably 0.1 to 0.5 times the mass of the compound (2b).
  • the reaction temperature is preferably ⁇ 50 to 100 ° C., more preferably 0 to 40 ° C.
  • the reaction time is preferably 0.1 to 72 hours, more preferably 0.1 to 48 hours.
  • Compound (1) can be obtained by dehydroxylation of compound (2).
  • Dehydroxylation can be carried out as follows. This applies not only when the compound (1a) is obtained from the compound (2a) but also when the compound (1b) is obtained from the compound (2b) or when the compound (4) is obtained from the compound (3). It is believed that there is.
  • Organic solvents include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene; aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; tetrahydrofuran, diethyl ether, diisopropyl ether, dibutyl ether, t-butyl Ether-based solvents such as methyl ether and dimethoxyethane; petroleum ethers and the like, or a suitable mixed solvent of the above solvents can be used.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene
  • aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane
  • tetrahydrofuran diethyl ether, diisopropyl ether, dibutyl
  • An inorganic base or an organic base can be used as the base.
  • inorganic bases include alkali metals such as sodium metal and metal potassium and carbonates thereof, hydroxides, hydrides and metal cesium, alkaline earth metals such as metal aluminum and carbonates, hydroxides and hydrogen thereof.
  • the monster is raised.
  • organic base include chain organic amines such as triethylamine and diisopropylamine, cyclic organic amines such as pyridine, morpholine, pyridine, quinoline and imidazole, and organic amines having a substituent in the ring.
  • the amount of base, carbon disulfide and methyl iodide used is preferably 1.0 to 20 equivalents relative to the number of moles of compound (2).
  • the reaction temperature is preferably 0 to 200 ° C, more preferably 20 to 150 ° C.
  • the reaction time is preferably 0.5 to 72 hours, more preferably 1 to 24 hours.
  • Radical reduction can be performed using a radical reducing agent such as trialkyltin.
  • a radical initiator may be added.
  • trialkyltin tributyltin, which is easily available, is preferable.
  • the radical initiator azo compounds, borane compounds, and inorganic salts can be used. For example, 2,2′-azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2-methylpropionamidine) dihydrochloride, 4,4′-azobis (4-cyanopentanoic acid), triethylborane and sodium dithionite are preferred.
  • compound (1a) can be obtained by hydrogenating compound (1b).
  • the hydrogenation reaction is preferably carried out in a solvent using a heterogeneous catalyst.
  • Solvents that can be used include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene; aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; such as ethyl acetate, methyl acetate, and propyl acetate.
  • Ester solvents alcohol solvents such as methanol and ethanol; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as tetrahydrofuran, diethyl ether, dibutyl ether, t-butyl methyl ether, and dimethoxyethane; petroleum ethers or the aforementioned solvents
  • a suitable mixed solvent or the like can be used.
  • alcohol solvents such as methanol, ester solvents such as ethyl acetate, and mixed solvents of these solvents are preferable.
  • heterogeneous catalyst examples include transition metal catalysts such as palladium carbon, rhodium carbon, ruthenium carbon, Raney nickel, and platinum oxide.
  • the amount of the catalyst used is preferably 0.01 to 1.0 times, more preferably 0.1 to 0.6 times the mass of the compound (1b).
  • the reaction temperature is preferably ⁇ 50 to 100 ° C., more preferably 0 to 40 ° C.
  • the reaction time is preferably 0.1 to 72 hours, more preferably 0.1 to 48 hours.
  • Compound (2) is useful as an intermediate for synthesizing compound (1) and also as a liquid crystal compound.
  • the compound (1) of the present invention is useful as a liquid crystal compound.
  • the liquid crystal compound means a compound that exhibits a liquid crystal phase and a compound that does not exhibit a liquid crystal phase but is useful as a constituent of a liquid crystal composition.
  • the present invention provides a liquid crystal composition comprising the compound (1) of the present invention.
  • This liquid crystal composition is constituted by mixing the compound (1) of the present invention with other liquid crystal compounds or non-liquid crystal compounds (collectively referred to as “other compounds”).
  • the content of the compound (1) in the liquid crystal composition of the present invention can be appropriately changed depending on the purpose of use, the purpose of use, the type of other compounds, and the like. 5 to 80% by mass is preferable, and 2 to 50% by mass is particularly preferable. Moreover, you may contain 2 or more types of compounds (1) in a liquid-crystal composition by a use, a use purpose, etc. In that case, the total amount of the compound (1) is preferably 0.5 to 80% by mass, particularly preferably 2 to 50% by mass, based on the total amount of the liquid crystal composition.
  • Other compounds used in combination with the compound (1) include components for adjusting the refractive index anisotropy value, components for reducing the viscosity, components exhibiting liquid crystallinity at low temperatures, components for improving the dielectric anisotropy, and cholesteric A component for imparting properties, a component exhibiting dichroism, a component for imparting conductivity, and various other additives. These are appropriately selected depending on the application, required performance and the like, but usually those composed of a liquid crystal compound, a main component having a similar structure to the liquid crystal compound, and an additive component added if necessary.
  • the other compound is preferably a compound represented by the following formula (D) in which ⁇ is negative.
  • D formula (D) in which ⁇ is negative.
  • the symbols in the formula have the following meanings.
  • R d1 and R d2 are each independently an alkyl group having 1 to 10 carbon atoms, and in the alkyl group, one or more hydrogen atoms may be substituted with a fluorine atom, —O— may be inserted at the bond terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a d1 , A d2 , A d3 and A d4 each independently a trans-1,4-cyclohexylene group or a 1,4-phenylene group, wherein one or more hydrogen atoms in the group are It may be substituted with a fluorine atom.
  • Z d1 , Z d2 and Z d3 independently of each other, a single bond, —COO—, —C ⁇ C—, —OCO—, —OCH 2 —, —CH 2 O— or —C 2 H 4 —.
  • m d and n d 0 or 1 independently of each other.
  • one or more of A d1 , A d2 , A d3 and A d4 is a 2,3-difluoro-1,4-phenylene group.
  • the compound (D) for compound m d and n d are both 0 are compounds of the 2 rings, low viscosity, it is useful when requiring fast response of the device. It can also be used to adjust the threshold voltage and refractive index anisotropy.
  • a compound in which one of m d and n d is 1 and the other is 0 is a tricyclic compound. Therefore, the clearing point is higher than that of the bicyclic compound, and the nematic phase This is useful for expanding the liquid crystal temperature range. It can also be used to adjust the refractive index anisotropy.
  • a compound in which both m d and n d are 1 is a tetracyclic compound, and therefore has a particularly high clearing point, and thus is particularly useful for expanding the liquid crystal temperature range.
  • Preferable compounds (D) include the following compounds.
  • -Ph- represents a 1,4-phenylene group
  • -Cy- has the same meaning as described above. Indicates.
  • the content of the compound (D) is 5 to 60 mass with respect to the total amount of the liquid crystal composition. % Is preferable, and 5 to 50% by mass is more preferable. When two or more types of compounds (D) are included, the total amount is preferably in the above range.
  • a compound represented by the following formula (E) having a small absolute value of ⁇ and close to neutrality is also preferable.
  • R e1 and R e2 each independently an alkyl group having 1 to 10 carbon atoms, in which one or more hydrogen atoms may be substituted with a fluorine atom, —O— may be inserted at the bond terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a e1 , A e2 , A e3 and A e4 independently of each other, a trans-1,4-cyclohexylene group, a pyrimidine-2,5-diyl group, or a 1,4-phenylene group, One or more hydrogen atoms therein may be substituted with fluorine atoms.
  • Z e1 , Z e2 , Z e3 and Z e4 independently of each other, a single bond, —COO—, —C ⁇ C—, —OCO—, —CH ⁇ CH— or —C 2 H 4 —.
  • m e and n e 0 or 1 independently of each other.
  • a compound in which m e and n e are both 0 is a bicyclic compound, which is useful when the viscosity is low and high-speed response of the device is required. It can also be used to adjust the refractive index anisotropy.
  • a one is 1 m e and n e, compounds other is 0, because it is a compound of three rings, a high clearing point compared to the compound of the 2 rings, a nematic phase This is useful for expanding the liquid crystal temperature range. It can also be used to adjust the refractive index anisotropy.
  • for compound m e and n e are both 1 is the compound of 4 ring, because the clearing point is particularly high, is particularly useful for the expansion of the liquid crystal temperature range.
  • Preferable compounds (E) include the following compounds.
  • -Pm- represents a pyrimidine-2,5-diyl group
  • -Cy- and -Ph- Indicates the same meaning.
  • the content of the compound (E) is 10 to 50% by mass with respect to the total amount of the liquid crystal composition. Is preferable, and 20 to 40% by mass is more preferable.
  • the total amount is preferably in the above range.
  • an optically active compound may be added in order to achieve uniform twist alignment.
  • an optically active compound for example, the compound marketed by names, such as CN, S-811, CB-15, is mentioned.
  • the pitch length is preferably in the range of 40 to 200 ⁇ m for TFT and TN, 6 to 20 ⁇ m for STN, and 1.5 to 4 ⁇ m for bistable TN.
  • liquid crystal composition of the present invention examples include the following.
  • the symbols in the formulas of Table 1 and Table 2 have the same meaning as described above.
  • the hydrogen atom of each group may be substituted with a deuterium atom.
  • the present invention provides a liquid crystal electro-optical element that uses the liquid crystal composition as a constituent material of a liquid crystal layer.
  • a liquid crystal electro-optical element having an electro-optical element portion formed by sandwiching a liquid crystal layer formed by, for example, injecting the liquid crystal composition of the present invention into a liquid crystal cell between two substrates having electrodes.
  • the liquid crystal composition of the present invention can be suitably used in liquid crystal electro-optical elements such as VA mode, IPS mode, and OCB mode regardless of passive driving or active driving.
  • the liquid crystal composition of the present invention is particularly useful in a mode in which liquid crystal molecules such as OCB mode and VA mode are aligned perpendicular to the electrode.
  • a VA (vertical alignment) mode liquid crystal element As a typical liquid crystal element in which liquid crystal molecules are aligned perpendicularly to an electrode, a VA (vertical alignment) mode liquid crystal element can be given.
  • an undercoat layer such as SiO 2 or Al 2 O 3 or a color filter layer is first formed on a substrate such as plastic or glass as necessary, and In 2 O 3 —SnO. 2
  • a film made of (ITO), SnO 2 or the like is formed, and an electrode having a required pattern is formed by photolithography or the like.
  • an overcoat layer of polyimide, polyamide, SiO 2 , Al 2 O 3 or the like is formed and oriented.
  • a sealing material is printed on this, and it arrange
  • composition of the present invention is injected into an empty cell, and the injection port is sealed with a sealant to form a liquid crystal cell.
  • this liquid crystal cell is laminated with a polarizing plate, a color polarizing plate, a light source, a color filter, a transflective plate, a reflecting plate, a light guide plate, an ultraviolet cut filter, etc., printing characters, figures, etc., non-glare processing, etc.
  • a liquid crystal electro-optical element can be obtained.
  • ODF liquid crystal dropping method
  • a substrate using a two-layer electrode a substrate using a two-layer electrode
  • a two-layer liquid crystal cell formed with a two-layer liquid crystal layer a substrate using a reflective electrode
  • an active element such as a TFT, MIM, etc.
  • Various configurations such as an active matrix element using an active matrix substrate on which are formed can be employed.
  • the composition of the present invention is also suitable for active matrix devices such as TFT and MIM.
  • composition of the present invention uses an in-plane switching (IPS) type liquid crystal element that drives liquid crystal molecules in parallel to the substrate in a mode other than the VA type, that is, a horizontal electric field, and a polychromatic dye. It can be used in various ways such as a guest-host (GH) type liquid crystal element and a ferroelectric liquid crystal element. Furthermore, the composition of the present invention can be used not only for an electric writing method but also for a writing method using heat.
  • IPS in-plane switching
  • GH guest-host
  • phase transition point of the compound of the present invention was measured as follows.
  • phase transition point A sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope, heated at 1 ° C./min, and the phase change was observed. In addition, using a differential scanning calorimeter (DSC 6220, manufactured by SII Nanotechnology Co., Ltd.), the temperature was raised at 1 ° C./min to confirm the phase change. C represents a crystalline phase, N represents a nematic phase, and I represents an isotropic phase.
  • the above physical property values were prepared by mixing 90% by mass of the liquid crystal composition “MLC-6608” manufactured by Merck & Co., Ltd. at a ratio of 10% by mass of the compound of the present invention, and using this liquid crystal composition. The measurement was performed by the following method.
  • Example 1 Synthesis of Compound (1a-A)
  • Compound (2a-A) (0.34 g, 0.82 mmol) obtained in the same manner as above was dissolved in THF (10 mL). Thereafter, NaH (0.33 g, 13.8 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 10 minutes. Thereafter, 0.86 mL of iodomethane was added dropwise, and the mixture was stirred at room temperature for 2 hours, carbon disulfide (0.86 mL) was added, and the mixture was further stirred at room temperature for 2 hours. The reaction was quenched with distilled water and extracted three times with diethyl ether.
  • Example 2 Synthesis of compound (1a-B)
  • the compound (1a-B) was synthesized in the same manner as in Example 1 using the compound (2a-B) obtained in the same manner as described above as a raw material to obtain a diastereomeric mixture. (Yield 51%). By recrystallizing this diastereomeric mixture from a methanol / diethyl ether mixed solvent, only the trans isomer of compound (1a-B) was selectively obtained. (Yield 20%) [trans form] 19 F NMR (CDCl 3 , CFCl 3 ) d -128.9 to -128.1 (m. 1F), -127.9 to -127.1 (m, 1F), -125.7 to -125.6 (m, 2F). Phase transition temperature C117.2 °C I Tc of this compound was 89.7 ° C., and ⁇ was ⁇ 7.9.
  • the compound having a 2,2,3,3-tetrafluorocyclohexane-1,4-diyl group (1a-C) and 5,5,6,6-tetrafluoro- which are ⁇ negative function-expressing ring structures of the present invention The ⁇ of the compound (1b-C) having a 2-cyclohexene-1,4-diyl group and 2,3-difluorophenyl-1,4-, which is the most commonly used negative function expression ring structure of ⁇ at present.
  • ⁇ of the compound (C1) having a diyl group was compared (Table 3).
  • the compound (1a-C) and the compound (1b-C) showed negatively larger ⁇ . From this result, the 2,2,3,3-tetrafluorocyclohexane-1,4-diyl group and the 5,5,6,6-tetrafluoro-2-cyclohexene- which are ⁇ negative function-expressing ring structures of the present invention are shown. It was confirmed that the 1,4-diyl group is a strong ⁇ negative function-expressing ring structure.
  • C 2 H 5 -Ph-Ph-TFCy-OC 2 H 5 C 3 H 7 -Ph-Ph-TFCy-C 2 H 5 compound (1a-B) C 4 H 9 -Ph-Ph-CH 2 O-TFCy-OC 2 H 5 C 5 H 11 -Ph-C ⁇ C-Ph-TFCy-OC 2 H 5 C 5 H 11 -Ph-Ph (2F, 3F) -TFCy-OC 2 H 5 C 3 H 7 -Cy-Ph-TFCy-OC 2 H 5 C 3 H 7 -Cy-Ph-TFCy-C 2 H 5 compound (1a-A) C 3 H 7 -Cy-Ph-CF 2 O-TFCy-C 3 H 7 C 4 H 9 -Cy-CH 2 CH 2 -Ph-TFCy-C 2 H 5 CH 2 CHC 2
  • Examples of the pentacyclic compound include the following.
  • the compound of the present invention has a novel ⁇ negative function-expressing ring structure, and it has been found that ⁇ is negatively larger than that of a widely used compound having a 2,3-difluorophenyl group. Further, by appropriately selecting the ring group, substituent and linking group constituting the compound, the compound of the present invention can prepare a liquid crystal composition satisfying various performances required for a liquid crystal element such as a wide operating temperature range. it is conceivable that. Moreover, it turned out that the compound of this invention can be easily manufactured with the manufacturing method of this invention.

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Abstract

La présente invention a pour objet : un nouveau composé qui contient une structure cyclique pouvant développer une fonction et qui a une valeur de Δε négative, qui a une grande valeur de Δε dans le négatif et qui peut être utilisé pour le développement d'un composé à cristaux liquides qui est chimiquement stable, qui a une excellente compatibilité avec d'autres matières à cristaux liquides ou matières ne formant pas de cristaux liquides et qui peut avoir des propriétés telles qu'une réponse à grande vitesse, une faible viscosité, une large plage de température de formation de cristaux liquides et un point de transparence élevé selon les manières de concevoir un groupe de liaison à un lieur ; un procédé pour la production du composé ; une composition à cristaux liquides contenant le composé ; et un élément électro-optique à cristaux liquides. A cet effet, la présente invention porte sur un composé représenté par la formule (1).
PCT/JP2014/052000 2013-02-12 2014-01-29 Nouveau composé ayant une structure cyclique présentant une anisotropie diélectrique négative, procédé pour la production dudit composé, composition à cristaux liquides et élément électro-optique à cristaux liquides WO2014125924A1 (fr)

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WO2015041006A1 (fr) * 2013-09-19 2015-03-26 Jnc株式会社 Composé de cristaux liquides ayant un squelette tétrafluorocyclohexadiène et présentant une anisotropie diélectrique négative, composition de cristaux liquides, et élément d'affichage à cristaux liquides
US10221114B2 (en) 2013-09-19 2019-03-05 Jnc Corporation Liquid crystal compound having tetrafluoro cyclohexadiene structure showing negative anisotropy, liquid crystal composition, and liquid crystal display device
JP2017165710A (ja) * 2016-03-10 2017-09-21 Jnc株式会社 ターシクロヘキシルを有する液晶性化合物、液晶組成物および液晶表示素子

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