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  • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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  • 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
  • C09K2019/181—Ph-C≡C-Ph
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  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
  • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
  • C09K2019/183—Ph-Ph-C≡C-Ph
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  • C09K19/3001—Cyclohexane rings
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  • C09K19/3001—Cyclohexane rings
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  • C09K19/3001—Cyclohexane rings
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  • C09K2019/301—Cy-Cy-Ph
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  • C09K2019/3016—Cy-Ph-Ph
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  • C09K19/3001—Cyclohexane rings
  • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
  • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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  • C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
  • C09K2019/3063—Cy-Ph-C≡C-Ph

Definitions

• the present invention relates to a compound, a liquid crystal composition containing the compound, and a device using the liquid crystal composition.
• a liquid crystal composition is used for mobile terminals such as smartphones and tablet devices, and display applications such as TVs and window displays.
• display applications such as TVs and window displays.
• an antenna for transmitting and receiving radio waves between a communication satellite and a mobile body such as a car is drawing attention.
• satellite communications use a parabolic antenna; however, when used in a mobile body, the parabolic antenna must be directed toward a satellite at any time, and is required to have a large movable portion.
• an antenna using a liquid crystal composition is capable of changing transmission-reception directions of radio waves by operating liquid crystal, and therefore, movement of the antenna itself is not necessary and the antenna is allowed to have a planar shape.
• a refractive index anisotropy ⁇ n of liquid crystal compositions required for these applications is, for example, about 0.4, which is much larger than ⁇ n required for display applications.
• a compound to be added to and used in a liquid crystal composition is required to have a large ⁇ n and a high compatibility with the liquid crystal composition.
• Non-Patent Literature 1 and Patent Literatures 1 and 2 a compound having a thienothiophene structure
• these compounds disadvantageously have low compatibility when added to a liquid crystal composition used for antennas and have precipitation caused by long-term storage
• Non-Patent Literature 1 and Patent Literatures 1 and 2 compounds having a thienothiophene structure and a thioisocyano group have been reported, but these compounds have a low dielectric constant anisotropy in a high frequency region and insufficient phase modulation characteristics.
• Patent Literatures 3 and 4 a compound having a large ⁇ n and a high compatibility with a liquid crystal composition, and exhibiting a large dielectric constant anisotropy in a high frequency region.
• Non-Patent Document 1 Chemistry of Materials, 2009, Vol. 21, No. 13, pp. 2727-2732
• Patent Literature 1 CN103472116A
• Patent Literature 4 WO2020/120586A1
• the problem to be solved by the present invention is to provide: a compound that has a large refractive index anisotropy ( ⁇ n) and a high compatibility with a liquid crystal composition, and exhibits a large dielectric constant anisotropy ( ⁇ ) in a high frequency region; a liquid crystal composition containing the compound; and a device using the liquid crystal composition.
• the present invention provides a compound represented by the following general formula (I) ,
• a 1 and A 2 each independently represent a hydrocarbon ring or a heterocycle having 3 to 16 carbon atoms which may be substituted; when multiple A 1 s are present, the A 1 s may be the same or different; and when multiple A 2 s are present, the A 2 s may be the same or different;
• Z 1 , Z 2 and Z 3 each independently represent a divalent linking group or a single bond; when multiple Z 1 s are present, the Z 1 s may be the same or different; and when multiple Z 2 s are present, the Z 2 s may be the same or different;
• n1 and m2 each independently represent an integer from 0 to 3;
• Y 1 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl group or alkoxy group having 1 to 8 carbon atoms in which an arbitrary hydrogen atom may be substituted with a fluorine atom, and when multiple Y 1 s are present, they may be the same or different;
• Y 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which an arbitrary hydrogen atom may be substituted with a fluorine atom and one -CH 2 - or two or more -CH 2 -’s in the alkyl group may be each independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O
• liquid crystal composition containing the compound and a device using the liquid crystal composition.
• the compound of the present invention has a large refractive index anisotropy ⁇ n and a high compatibility with a liquid crystal composition, and exhibits a large dielectric constant anisotropy in a high frequency region; and therefore, it is useful as a material for a device of a high-frequency phase shifter, a phased array antenna, an image recognition device, distance measuring equipment, a liquid crystal display device, a liquid crystal lens, a birefringent lens for stereoscopic image display, or the like.
• the present invention provides a compound represented by the general formula (I) , a liquid crystal composition containing the compound, and a device using the liquid crystal composition.
• a 1 and A 2 each independently represent a hydrocarbon ring or heterocycle having 3 to 16 carbon atoms that may be substituted wherein: when multiple A 1 s are present, they may be the same or different; and when multiple A 2 s are present, they may be the same or different.
• a 1 and A 2 may be each independently unsubstituted or substituted with one or more substituents L 1 and preferably represent a group selected from the group consisting of:
• a 1 s and A 2 s may be the same or different, and they may be each independently unsubstituted or substituted with one or more substituents L 1 ; and they more preferably represent a group selected from a 1, 4-phenylene group, a naphthalene-2, 6-diyl group, a naphthalene-1, 4-diyl group, a 5, 6, 7, 8 tetrahydronaphthalene-1, 4-diyl group, a phenanthrene-2, 7-diyl group, a benzothiophene-2, 5-diyl group, a benzothiophene-2, 6-diyl group, a benzothiazole-2, 5-diyl group, a benzothiazole-2, 6-diyl group, a dibenzothiophene-3, 7-diyl group, a dibenzothiophene-2, 6-diyl group or a thieno [3,
• the broken line represents a binding position, and when multiple L 1 s are present, they may be the same or different.
• a 1 s and A 2 s may be the same or different; and further more preferably, A 1 and A 2 each independently represent a group selected from the formulas (A-1) to (A-7) , (A-12) , (A-15) and (A-17) .
• a 1 and A 2 each independently represent a group selected from the formulas (A-1) , and (A-3) to (A-7) .
• L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms wherein one -CH 2 - or two or more -CH 2 -’s may be each independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-
• L 1 more preferably represents a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms wherein an arbitrary hydrogen atom in the group may be substituted with a fluorine atom and -CH 2 - in the group may be substituted with -O-.
• L 1 further preferably represents a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms.
• L 1 particularly preferably represents a fluorine atom or a linear alkyl group having 1 to 8 carbon atoms.
• Z 1 , Z 2 and Z 3 each independently represent a divalent linking group or a single bond, but when multiple Z 1 s are present, they may be the same or different; and when multiple Z 2 s are present, they may be the same or different.
• Z 1 s, Z 2 s and Z 3 s When multiple Z 1 s, Z 2 s and Z 3 s are present, they may be the same or different; and particularly preferably, they each independently represent -C ⁇ C- or a single bond.
• m1 and m2 each independently represent an integer from 0 to 3, and m1+m2 is preferably an integer from 0 to 4; in particular, when A x is a structure selected from the group consisting of the formulas (Ax-1) to (Ax-5) , m1+m2 is preferably an integer from 0 to 3, further preferably an integer from 0 to 2. In addition, when A x is not a structure selected from the group consisting of (Ax-1) to (Ax-5) , m1+m2 is preferably an integer from 1 to 4, more preferably an integer from 1 to 3.
• m1 and m2 each independently represent 0, 1, or 2 and m1+m2 represents an integer from 1 to 3; it is more preferred that m1 and m2 each independently represent 0, 1 or 2 and m1+m2 represents 1 or 2; it is further preferred that m1 and m2 each independently represent 0 or 1 and m1+m2 represents 1 or 2; and it is particularly preferred that m1 and m2 each independently represent 0 or 1 and m1+m2 represents 1.
• the compound represented by the general formula (I) includes a thieno [3, 2-b] thiophene-2, 5-diyl group having a sulfur atom bonded at the 2-position in the structure, it can effectively enhance ⁇ n due to the conjugated structure of a high electron density derived from 3 sulfur atoms and simultaneously shows an excellent effect of exhibiting a large dielectric constant anisotropy in a high frequency region. Further, since the general formula (I) has two or more ring structures in total in the molecule, it forms a rod-like molecular structure as the entire compound thereby to improve the liquid crystallinity and increase Tni, and therefore, addition thereof to a liquid crystal composition can effectively broaden the liquid crystal phase temperature range while maintaining a high compatibility.
• a x represents a structure selected from the group consisting of the following formulas (Ax-1) to (Ax-5) .
• Y 1 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl group or alkoxy group having 1 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom wherein: when multiple Y 1 s are present, the Y 1 s are may be the same or different;
• Y 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom and one -CH 2 - or two or more -CH 2 -’s in the alkyl group may be each independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-,
• a x preferably represents a structure selected from the group consisting of the following formulas (Ax-1-i) to (Ax-5-i) .
• Y 13 each independently represents a hydrogen atom, a fluorine atom or a chlorine atom) .
• the compound represented by the general formula (I) is preferably a compound represented by the following general formula (I-i) ,
• a 11 and A 21 each independently represent a 1, 4-phenylene group, a naphthalene-2, 6-diyl group, a naphthalene-1, 4-diyl group, a 5, 6, 7, 8-tetrahydronaphthalene-1, 4-diyl group, a phenanthrene-2, 7-diyl group, a benzothiophene-2, 5-diyl group, a benzothiophene-2, 6-diyl group, a benzothiazole-2, 5-diyl group, a benzothiazole-2, 6-diyl group, a dibenzothiophene-3, 7-diyl group, a dibenzothiophene-2, 6-diyl group or a thieno [3, 2-b] thiophene-2, 5-diyl group, wherein when multiple A 11 s are present, they may be the same or different;
• a 21 s when multiple A 21 s are present, they may be the same or different; and these groups may be unsubstituted or substituted with one or more substituents L 11 ;
• n11 and m21 each independently represent 0, 1 or 2;
• the compound represented by the general formula (I) is more preferably a compound represented by the following general formula (I-ii) ,
• a 12 and A 22 each independently represent a group selected from the following formulas (A-ii-1) to (A-ii-17) ,
• the broken line represents a binding position, and when multiple L 12 s are present, the L 12 s are optionally the same or different
• the A 12 s are optionally the same or different
• the A 22 s are optionally the same or different
• L 12 represents a fluorine atom, or a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms wherein an arbitrary hydrogen atom in the group is optionally substituted with a fluorine atom and -CH 2 -in the group is optionally substituted with -O-;
• n12 and m22 each independently represent 0, 1 or 2, and m12+m22 represents an integer from 0 to 2;
• a x2 represents a structure selected from the formulas (Ax-1-i) and (Ax-2-i) ) .
• the compound represented by the general formula (I) is further preferably a compound represented by the following general formula (I-iii) ,
• R 13 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 7 carbon atoms, or an alkynyl group having 2 to 8 carbon atoms;
• a 13 and A 23 each independently represent the following formulas (A-iii-1) to (A-iii-7) , (A-iii-12) , (A-iii-15) and (A-iii-17) ;
• the broken line represents a binding position, and when multiple L 13 s are present, the L 13 s are optionally the same or different) ;
• L 13 represents a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms;
• n13 and m23 each independently represent 0 or 1;
• Y 13 each independently represents a hydrogen atom, a fluorine atom or a chlorine atom) .
• the compound represented by the general formula (I) is particularly preferably a compound represented by the following general formula (I-iv-1) or (I-iv-2) ,
• R 14 represents an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkynyl group having 3 to 7 carbon atoms;
• a 24 represents a group selected from the following formulas (A-iv-1) , and (A-iv-3) to (A-iv-7) ;
• L 14 represents a fluorine atom or a linear alkyl group having 1 to 8 carbon atoms
• Z 24 and Z 34 independently represent -C ⁇ C-, -C ⁇ C-C ⁇ C-or a single bond
• Y 14 and Y 34 each independently represent a hydrogen atom or a fluorine atom) .
• Specific examples of the compound represented by the general formula (I) include compounds represented by the following formulas (I-1) to (I-69) .
• the compound of the present invention can be produced by the following production method.
• R 1s , A 1s , A 2s , Z 1s , Z 2s , Z 3s , m1s, m2s and A xs have the same meanings as R 1 , A 1 , A 2 , Z 1 , Z 2 , Z 3 , m1, m2 and A x in the above general formula (I) . )
• the compound represented by the formula (s-3) is reacted with trimethylsilylacetylene and then, reacted with tetrafluoroammonium fluoride (TBAF) , and thereby, a compound represented by the general formula (s-4) is obtained.
• TBAF tetrafluoroammonium fluoride
• Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base.
• the palladium catalyst include tetrakis (triphenylphosphine) palladium (0) .
• Specific examples of the copper catalyst include copper (I) iodide.
• Specific examples of the base include triethylamine.
• Reaction of the compound represented by the formula (s-4) with a compound represented by the formula (s-16) provides a compound represented by the general formula (s-5) .
• the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base.
• Specific examples of the palladium catalyst include those described above.
• Specific examples of the copper catalyst include copper iodide (I) .
• Specific examples of the base include triethylamine.
• R 1s , A 1s , Z 1s , m1s and Y 1s have the same meanings as R 1 , A 1 , Z 1 , m1 and Y 1 in the above general formula (I) . )
• Reaction of a compound represented by the formula (s-3) with a compound represented by the general formula (s-6) provides a compound represented by the general formula (s-7) .
• the reaction method include a method of cross-coupling in the presence of a metal catalyst and a base.
• Specific examples of the metal catalyst include
• 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl may be added.
• Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.
• the above-mentioned Production Method 1 shows the production method of the compound wherein A x in the above general formula (I) is represented by the above formula (Ax-1) , but the compound wherein A x in the above general formula (I) is represented by the above formula (Ax-2) can be synthesized by the same method as the compound represented by the general formula (s-10) .
• (Production method 3) Production of a compound represented by the following formula (s-14)
• the compound represented by the formula (s-12) is reacted with trimethylsilylacetylene and then reacted with tetrafluoroammonium fluoride (TBAF) , and thereby, a compound represented by the general formula (s-13) can be obtained.
• the reaction method includes a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base.
• the palladium catalyst include tetrakis (triphenylphosphine) palladium (0) .
• Specific examples of the copper catalyst include copper (I) iodide.
• Specific examples of the base include triethylamine.
• reaction conditions other than those described in each step include those described in literature such as Experimental Chemistry Course (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd. ) , Organic Syntheses (A John Wiley & Sons, Inc., Publication) , Beilstein Handbook of Organic Chemistry (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co. K) , Fiesers' Reagents for Organic Synthesis (John Wiley & Sons, Inc. ) or the like, or those listed in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society) , Reaxys (Elsevier Ltd. ) or the like.
• a functional group can be protected as needed.
• a protective group include protective groups described in GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS ( (Fourth Edition) , co-authored by PETER G.M. WUTS, and THEODORA W. GREENE, A John Wiley & Sons, Inc., Publication) or the like.
• purification can be performed as needed in each step. Examples of the purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation treatment. Specific examples of the purifying agent include silica gel, alumina, and activated carbon.
• the compound represented by the general formula (I) is preferably used by addition to a liquid crystal composition.
• a liquid crystal composition contains a compound represented by the general formula (I)
• it may contain one compound represented by the general formula (I) , or it may contain a plurality of compounds represented by the general formula (I) .
• the liquid crystal composition of the present invention contains a compound represented by the general formula (I)
• the total content of the compounds represented by the general formula (I) in the liquid crystal composition is preferably 5%by mass or more, more preferably 10%by mass or more and 95%by mass or less, further preferably 15%by mass or more and 90%by mass or less, and particularly preferably 20%by mass or more and 85%by mass or less.
• the total content of the compounds represented by the general formula (I) used herein means a content of the compound represented by the general formula (I) ; and when the liquid crystal composition contains a plurality of compounds represented by the general formula (I) , it means a total of contents of the plurality of compounds represented by the general formula (I) .
• the liquid crystal composition containing the compound represented by the general formula (I) preferably has a refractive index anisotropy ( ⁇ n, wavelength for measurement: 589 nm) of 0.15 or more and 1.00 or less.
• the refractive index anisotropy ( ⁇ n) is preferably 0.20 or more and 0.95 or less, more preferably 0.25 or more and 0.90 or less, further preferably 0.30 or more and 0.85 or less, and particularly preferably 0.35 or more and 0.80 or less.
• the liquid crystal composition containing a compound represented by the general formula (I) When used for a high-frequency phase shifter, a phased array antenna, an image recognition device, distance measuring equipment, a liquid crystal display device, a liquid crystal lens, or a birefringent lens for displaying a stereoscopic image, the liquid crystal composition containing the compound represented by the general formula (I) preferably has a dielectric constant anisotropy at 1 kHz ( ⁇ (1 kHz) ) of 2 or more and 60 or less.
• the dielectric constant anisotropy at 1 kHz ( ⁇ (1 kHz) ) is preferably 2.5 or more and 50 or less, more preferably 3 or more and 40 or less, and particularly preferably 3.5 or more and 30 or less.
• the liquid crystal composition containing the compound represented by the general formula (I) is preferably used for a high frequency device.
• the frequency range is preferably 1 MHz or more and 1 THz or less, more preferably 1 GHz or more and 500 GHz or less, further preferably 2 GHz or more and 300 GHz or less, and particularly preferably 5 GHz or more and 150 GHz or less.
• the liquid crystal composition containing the compound represented by the general formula (I) preferably contains a compound represented by the following general formula (VI) .
• R 2 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms;
• a 3 represents a group selected from the following formulas (A6-1) to (A6-8) ;
• n3 represents an integer from 1 to 4.
• a y represents a group selected from the following formulas (Ay-1) and (Ay-2)
• Y 7 , Y 9 , Y 10 and Y 12 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom
• Y 8 and Y 11 each independently represent a fluorine atom, a chlorine atom, a cyano group, a thioisocyano group, a nitro group, a pentafluorosulfanyl group, an alkyl group having 1 to 8 carbon atoms wherein an arbitrary hydrogen atom is substituted with a fluorine atom, an alkoxy group having 1 to 7 carbon atoms wherein an arbitrary hydrogen atom is substituted with a fluorine atom, an alkenyl group having 2 to 8 carbon atoms wherein an arbitrary hydrogen atom is substituted with a fluorine atom, or an alkenyloxy group having 2 to 7 carbon atoms wherein an arbitrary hydrogen atom is substituted with a fluorine atom wherein one
• the compound represented by the general formula (VI) is preferably a compound represented by the following general formula (VI-i) ,
• R 21 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms;
• a 31 represents a group selected from the formulas (A6-1) to (A6-6) , wherein when multiple A 31 s are present, they are optionally the same or different;
• n31 represents an integer from 1 to 3;
• a y1 represents a group selected from the following formulas (Ay-1-i) and (Ay-2-i) ,
• Y 71 , Y 91 , Y 101 and Y 121 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom
• Y 81 and Y 111 each independently represent a fluorine atom, a chlorine atom, a cyano group, a thioisocyano group, a nitro group, a pentafluorosulfanyl group, an alkyl group having 1 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom, an alkoxy group having 1 to 7 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom, an alkenyl group having 2 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom or an alkenyloxy group having 2 to 7 carbon atoms wherein an arbitrary hydrogen atom may be substituted with an arbitrary hydrogen atom may be substituted with a fluor
• R 22 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms;
• a 32 represents a group selected from the above formulas (A6-1) to (A6-5) wherein when multiple A 32 s are present, they may be the same or different;
• n32 represents 1, 2 or 3;
• Y 72 and Y 92 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom
• Y 82 represents a fluorine atom, a chlorine atom, a cyano group, a thioisocyano group, a nitro group, a pentafluorosulfanyl group, an alkyl group having 1 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom, an alkoxy group having 1 to 7 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom, an alkenyl group having 2 to 8 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom or an alkenyloxy group having 2 to 7 carbon atoms wherein an arbitrary hydrogen atom may be substituted with a fluorine atom) .
• the compound represented by the general formula (VI) is further preferably a compound represented by the following general
• R 23 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 2 to 5 carbon atoms,
• a 33 represents a group selected from the above formulas (A6-1) to (A6-5) , wherein when multiple A 33 s are present, they may be the same or different;
• n33 represents 1, 2 or 3;
• Y 73 and Y 93 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom, and Y 83 represents a fluorine atom, a chlorine atom, a cyano group or a thioisocyano group) .
• the compound represented by the general formula (VI) is particularly preferably a compound represented by the following general formulas (VI-iv-1) to (VI-iv-21) ,
• R 614 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
• the liquid crystal composition containing the compound represented by the general formula (I) may contain a compound represented by the following general formula (III) ,
• R 31 and R 32 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms; and A 31 and A 32 each independently represent a group selected from the following formulas (A3-1) to (A3-8) ,
• n31 represents an integer from 1 to 4) .
• the compound represented by the general formula (III) is preferably a compound represented by the following general formula (III-i) ,
• R 311 and R 321 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms; and A 311 and A 321 each independently represent a group selected from the following formulas (A31-1) to (A31-6) ,
• m311 represents an integer from 1 to 3) .
• the compound represented by the general formula (III) is more preferably a compound represented by the following general formula (III-ii) ,
• R 312 and R 322 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms;
• a 312 and A 322 each independently represent a group selected from the following formulas (A32-1) to (A32-4) ,
• m312 represents 1 or 2) .
• the compound represented by the general formula (III) is further preferably a compound represented by the following general formula (III-iii) ,
• R 313 and R 323 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;
• a 313 and A 323 each independently represent a group selected from the following formulas (A33-1) and (A33-2) ,
• m313 represents 1 or 2) ) .
• the compound represented by the general formula (III) is particularly preferably a compound represented by the following general formulas (III-iv-1) to (III-iv-10) ,
• R 314 and R 324 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms) .
• the compound represented by the general formula (I) may be added to and used for a liquid crystal composition having a neutral or negative dielectric constant anisotropy ( ⁇ ) .
• the liquid crystal composition containing the compound represented by the general formula (I) preferably has a dielectric constant anisotropy ( ⁇ ) of -20 or more and 2 or less.
• the dielectric constant anisotropy ( ⁇ ) is preferably -15 or more and 1.5 or less, more preferably -10 or more and 1 or less, and particularly preferably -5 or more and 0.5 or less.
• the liquid crystal composition may contain a compound represented by the following general formula (IV) ,
• R 41 and R 42 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms;
• a 41 and A 42 each independently represent a group selected from the following formulas (A4-1) to (A4-11) ,
• the broken line represents a binding position wherein: when multiple A 41 s are present, they may be the same or different; and when multiple A 42 s are present, they may be the same or different;
• n41 and m42 each independently represent an integer from 0 to 3, and m41+m42 represents an integer from 1 to 3) .
• the compound represented by the general formula (IV) is preferably a compound represented by the following general formula (IV-i) ,
• R 411 and R 421 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms;
• a 411 and A 421 each independently represent a group selected from the formulas (A4-1) to (A4-9) , wherein: when multiple A 411 s are present, they may be the same or different; and when multiple A 421 s are present, they may be the same or different;
• n411 and m421 each independently represent an integer from 0 to 3 and m411+m421 represents an integer from 1 to 3) .
• the compound represented by the general formula (IV) is more preferably a compound represented by the following general formula (IV-ii) ,
• R 412 and R 422 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms;
• a 412 and A 422 each independently represent a group selected from the formulas (A4-1) to (A4-7) , wherein: when multiple A 412 s are present, they may be the same or different; and when multiple A 422 s are present, they may be the same or different;
• Z 412 and Z 422 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 - or a single bond, wherein: when multiple Z 412 s are present, they may be the same or different; and when multiple Z 422 s are present, they may be the same or different;
• n 1 or 2
• m412+m422 1 or 2)
• the compound represented by the general formula (IV) is further preferably a compound represented by the following general formula (IV-iii) ,
• R 413 and R 423 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;
• a 413 and A 423 each independently represent a group selected from the formulas (A4-1) to (A4-5) , wherein when multiple A 413 s are present, they may be the same or different; and when multiple A 423 s are present, they may be the same or different;
• Z 413 and Z 423 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond, wherein: when multiple Z 413 s are present, they may be the same or different; and when multiple Z 423 s are present, they may be the same or different; and
• the compound represented by the general formula (IV) is particularly preferably a compound represented by the following general formulas (IV-iv-1) to (IV-iv-8) ,
• R 414 and R 424 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms) .
• a stabilizer may be added to the liquid crystal composition containing the compound represented by the general formula (I) in order to improve its storage stability.
• stabilizers usable therefor include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols and nitroso compounds.
• the amount to be added relative to the composition is in the range of preferably 0.005%by mass to 1%by mass, more preferably 0.02%by mass to 0.8%by mass, and further preferably 0.03%by mass to 0.5%by mass.
• one kind of stabilizer may be used, or two or more kinds of stabilizers may be used in combination.
• the stabilizer include a compound represented by the following general formula (X1) ,
• a x1 represents a group selected from the following formulas (Ax1-1) to (Ax1-8) ,
• mx1 represents 0 or 1
• mx2 represents an integer from 0 to 4) .
• the compound represented by the general formula (X1) is preferably a compound represented by the following general formula (X1-i) ,
• Sp x11 represents an alkylene group having 1 to 20 carbon atoms in which one -CH 2 -or two or more nonadjacent -CH 2 -’s may be each independently substituted with -O-, -COO- or -OCO-, or a single bond;
• a x11 represents a group selected from the following formulas (Ax11-1) and (Ax11-2) ,
• Z x11 represents -COO-, -OCO-, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO- or a single bond, wherein when multiple Z x11 s are present, they may be the same or different;
• mx11 represents 0 or 1
• mx21 represents 0 or 1) .
• the compound represented by the general formula (X1) is particularly preferably a compound represented by the following general formulas (X1-ii-1) to (X1-ii-4) ,
• Sp x12 represents an alkylene group having 1 to 20 carbon atoms or a single bond
• liquid crystal composition containing the compound represented by the general formula (I) examples include a compound represented by the following general formula (X2) ,
• R x21 , R x22 , R x23 and R x24 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms;
• Sp x21 , Sp x22 , Sp x23 and Sp x24 each independently represent a spacer group or a single bond
• mx21 represents 0 or 1
• mx22 represents 0 or 1
• mx23 represents 0 or 1) .
• the compound represented by the general formula (X2) is preferably a compound represented by the following general formula (X2-i) ,
• R x211 , R x221 , R x231 and R x241 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms;
• mx211 represents 0 or 1
• mx221 represents 0 or 1
• mx231 represents 0 or 1) .
• the compound represented by the general formula (X2) is more preferably a compound represented by the following general formula (X2-ii) ,
• R x212 and R x222 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms;
• Sp x212 and Sp x222 each independently represent a linear alkylene group having 1 to 10 carbon atoms in which one -CH 2 -or two or more nonadjacent -CH 2 -’s may be each independently substituted with -O-, -COO-or -OCO-, or a single bond; and
• mx212 represents 0 or 1) .
• the compound represented by the general formula (X2) is particularly preferably a compound represented by the following general formula (X2-iii) ,
• R x 213 and R x 223 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms;
• Sp x213 represents a linear alkylene group having 1 to 10 carbon atoms in which one -CH 2 -or two or more nonadjacent -CH 2 -’s may be each independently substituted with -COO-or -OCO-) .
• ring structures contained in a 1, 4-cyclohexylene group, a decahydronaphthalene-2, 6-diyl group and a 1, 3-dioxane-2, 5-diyl group each may be either of a trans form and a cis form.
• the content of trans form is preferably higher than that of the cis form for each of the above groups, the content of the trans form in the ring structure is more preferably 80%or more; the content of the trans form in the ring structure is further preferably 90%or more; the content of the trans form in the ring structure is further more preferably 95%or more; and the content of the trans form in the ring structure is particularly preferably 98%or more.
• the following notation (CY-1) signifies trans form and/or cis form of a 1, 4-cyclohexylene group.
• each element may be substituted with an isotope of the same element.
• % used for the compositions of Examples and Comparative Examples described below means “mass %. " When a substance unstable to oxygen and/or water is handled in each process, it is preferred to carry out operations in an inert gas such as nitrogen gas or argon gas.
• a compound represented by the formula (I-3) was produced by the same method as in Example 2 except that the compound represented by the formula (I-2-2) in Example 2 was replaced with a compound represented by the formula (I-3-4) .
• a compound represented by the formula (I-5-2) was produced by the method described in WO2010/115279A1. Under a nitrogen atmosphere, 10 g of a compound represented by the formula (I-5-1) , 9.5 g of the compound represented by formula (I-5-2) , 13.5 g of potassium carbonate, 0.1 g of dichlorobis [di-t-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , 80 mL of toluene, 30 mL of ethanol, and 20 mL of water were charged into a reaction vessel, and the mixture was heated and refluxed for 6 hours. The reaction solution was poured into water and extraction was carried out with toluene.
• reaction vessel 5 g of a compound represented by the formula (I-6-1) , 0.05 g of copper (I) iodide, 0.25 g of tetrakistriphenylphosphine palladium, 25 mL of triethylamine, and 25 mL of N, N-dimethylformamide (DMF) were charged. The mixture was heated and stirred at 80°C for 4 hours. The reaction solution was poured into water and extraction was carried out with toluene.
• a compound represented by the formula (I-6-1) 5 g, 0.05 g of copper (I) iodide, 0.25 g of tetrakistriphenylphosphine palladium, 25 mL of triethylamine, and 25 mL of N, N-dimethylformamide (DMF) were charged. The mixture was heated and stirred at 80°C for 4 hours. The reaction solution was poured into water and extraction was carried out with toluene.
• a host liquid crystal N composed of the following compounds was prepared.
• Each compound for evaluation was evaluated in terms of the storage stability.
• For storage stability 2 mL of each prepared liquid crystal composition was sealed in a glass vial under an argon atmosphere and stored at 10°C for 4 weeks, and then, the state thereof was visually evaluated. Evaluation results are shown in tables below.
• the compounds of the present invention are less likely to cause precipitation when added to the liquid crystal composition, and have a high compatibility with the liquid crystal composition.
• each compound to be evaluated in a high frequency region was evaluated.
• a transmission delay-mode cut back type strip-line method and a relative permittivity/dielectric loss tangent measuring device manufactured by KEYCOM Corporation
• the dielectric constant anisotropy of each of the prepared liquid crystal compositions at 13.17 GHz and 20°C was measured, and the dielectric constant anisotropy ⁇ (13.17 GHz) of each compound for evaluation was calculated by extrapolation.
• liquid crystal compositions (M-1) to (M-6) containing the compound of the present invention all exhibited a material characteristic ( ⁇ ) of 20 or more.
• Material characteristic ( ⁇ ) is defined as follows.
• tan ⁇ (3 ⁇ averagetan ⁇ average- ⁇ tan ⁇ ) /2 ⁇
• the compounds of the present invention have a large refractive index anisotropy ⁇ n and a high compatibility with a liquid crystal composition, and exhibit a large dielectric constant anisotropy in a high frequency region; and therefore, they are useful as a material for devices of a high-frequency phase shifter, a phased array antenna, an image recognition device, distance measuring equipment, a liquid crystal display device, a liquid crystal lens, a birefringent lens for displaying a stereoscopic image or the like.

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