WO2016186465A1 - Composé de cristaux liquides et composition de cristaux liquides le comprenant - Google Patents

Composé de cristaux liquides et composition de cristaux liquides le comprenant Download PDF

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WO2016186465A1
WO2016186465A1 PCT/KR2016/005326 KR2016005326W WO2016186465A1 WO 2016186465 A1 WO2016186465 A1 WO 2016186465A1 KR 2016005326 W KR2016005326 W KR 2016005326W WO 2016186465 A1 WO2016186465 A1 WO 2016186465A1
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liquid crystal
formula
independently
compound
crystal composition
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PCT/KR2016/005326
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Korean (ko)
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최진욱
송정인
강소희
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주식회사 동진쎄미켐
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Priority to CN201680022091.6A priority Critical patent/CN107532084A/zh
Publication of WO2016186465A1 publication Critical patent/WO2016186465A1/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
    • C09K19/10—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40

Definitions

  • Liquid crystal compound and liquid crystal composition comprising the same
  • the present invention relates to a liquid crystal compound having high dielectric anisotropy, high refractive index anisotropy and low viscosity, and a liquid crystal composition comprising the same.
  • Liquid crystal display devices are used in watches, electronic calculators, various electrical devices, measuring devices, automotive panels, word processors, electronic notebooks, printers, computers, televisions, and the like.
  • Typical liquid crystal displays include TN (Twist nematic), STN (Super, twisted nematic), In-lane switching (IPS) Fringe Field Switching (FFS), and Virtual Alignment (VA).
  • the liquid crystal material used in such a liquid crystal display device is capable of low voltage driving and high-speed ungdap, and is required to "be operable in a wide temperature range.
  • the liquid crystal material in order to drive stably in a wide temperature range, the liquid crystal material exhibits stable physical properties at about -20 ° C or lower (low temperature stability), and is required to have a transparent point of about 70 ° C or higher. Then, for low voltage driving and high speed response, the liquid crystal material is required to have a high absolute value of dielectric anisotropy, a low rotational viscosity, and an appropriate elastic modulus (K u , K 22) ⁇ 33 average value). It is impossible to satisfy the required physical properties of such liquid crystal materials by using one or two kinds of liquid crystal compounds, and usually seven to twenty kinds of liquid crystal compounds are compounded and stratified.
  • IPS or VA of the liquid crystal display method is characterized by using a liquid crystal material having a negative dielectric anisotropy, unlike the general-purpose TN or STN.
  • the negative liquid crystal material having negative dielectric anisotropy has a problem that a polar substituent exists on the side of the molecule, and the rotational viscosity is greatly increased even if the dielectric anisotropy is slightly changed compared to the positive liquid crystal material. Accordingly, In order to provide an IPS or VA type liquid crystal display device capable of high speed response, development of a liquid crystal compound having a negative dielectric anisotropy, a large absolute value, and a low viscosity is required.
  • the present invention is to provide a liquid crystal compound having high anisotropy, high refractive index anisotropy and low viscosity, and a method for producing the same.
  • the present invention is to provide a liquid crystal composition comprising at least one of the above liquid crystal compounds.
  • this invention is providing the liquid crystal display element containing the said liquid crystal composition.
  • the present invention provides a liquid crystal compound represented by the following formula (1):
  • Li, L 2 , L 3 and L 4 are each independently hydrogen or halogen
  • R represents hydrogen, d-) alkyl, C 2 - 10 alkenyl, or CHO, and alkoxy, and
  • nl and n2 are each independently an integer of 0 to 2, and the sum of nl and n2 is 0 or more and 2 or less.
  • the liquid crystal compound represented by Chemical Formula 1 is a liquid crystal compound having negative dielectric anisotropy, and may lower the viscosity of the liquid crystal by connecting the phenyl group with ethylene (-c3 ⁇ 4-c3 ⁇ 4-), thereby optimizing the liquid crystal phase. can do.
  • the sock end of Formula 1 has a 2,3-difluorophenyl group, at least one terminal does not have an alkyl group as a substituent, By having a negative dielectric constant anisotropy, it can exhibit a high dielectric constant value.
  • the liquid crystal compound of Chemical Formula 1 may be composed of only benzene rings, and may have a high refractive index anisotropy value by adjusting the number of benzene rings according to nl and n2, thereby realizing a quick response rate of the liquid crystal display device.
  • the, and L 4 are each independently hydrogen or fluoro eu
  • Ll and L 2 are the same.
  • L 3 and L 4 are the same.
  • L 2 may be both hydrogen or all fluoro.
  • R is hydrogen, methyl, ethyl, methoxy or ethoxy.
  • the liquid crystal compound may contain 2, 3 or 4 benzene rings.
  • Can have Representative examples of the liquid crystal compound represented by Formula 1 are as follows:
  • the present invention provides a method for producing a liquid crystal compound represented by Chemical Formula 1, as shown in Scheme 1 below.
  • Step 1 is a compound represented by the formula (4) by reacting the compound represented by the formula (2) and the compound represented by the formula (3).
  • a step of preparing a compound a step of combining two compounds with an ethene (—CH ⁇ CH—) bond. It is preferable to use THF as a solvent. It is also preferred to react in the presence of Potassium tertiary-butoxide. The reaction temperature is preferably 0 ° C. or less.
  • Addition step 2 is to react the compound represented by the formula (4) with hydrogen
  • the compound is a step of preparing a compound represented by the formula (1). Hydrogenation catalysts can be used for this reaction, for example palladium / activated carbon.
  • the compound represented by Formula 2 as the starting material may be prepared by the same method as in Scheme 2 below.
  • the Reaction refers to bromo of the compound represented by Formula 5 by reacting the compound represented by Formula 5 with PPh 3 and adding P + Ph 3 Br. It is a reaction to substitute with —.
  • the present invention provides a liquid crystal composition comprising at least one liquid crystal compound represented by the formula (1).
  • the liquid crystal composition may include one or more liquid crystal compounds represented by Formula 1 in 3 wt% or more or 4 wt% or more based on the total weight of the liquid crystal composition. If the content of the liquid crystal compound represented by the formula (1) is less than the above range, the effect of improving the response rate can be insignificant.
  • the liquid crystal composition may include one or more liquid crystal compounds represented by Chemical Formula 1 in an amount of 60 wt% or less, 40 wt% or less, 30 wt% or 20 wt% or less, based on the total weight of the liquid crystal composition. If the content of the liquid crystal compound represented by the formula (1) exceeds the above range, the phase transition temperature of the liquid crystal composition is greatly increased may cause a problem that the liquid crystal phase cannot be secured in the low temperature region.
  • the liquid crystal composition may further include various liquid crystal compounds for overall performance of the liquid crystal display device in addition to the liquid crystal compound of Formula 1.
  • the liquid crystal composition may further include one or more liquid crystal compounds selected from the group consisting of the following Chemical Formulas 2 to 5 below.
  • the liquid crystal composition may further include a known low viscosity liquid crystal compound. As such a low viscosity liquid crystal compound, a liquid crystal compound represented by the following formula (2) may be used.
  • a 3 and A 4 are each independently cyclonuylene or phenylene. Transparent point, rotational viscosity, and the like of the liquid crystal composition while maintaining a high specific resistance using at least one liquid crystal compound selected from the group consisting of compounds represented by the following Formulas 2-1 and 2-2 as the liquid crystal compound represented by Formula 2
  • the refractive index anisotropy and the dielectric anisotropy can be easily adjusted.
  • R 11 and R 12 may be defined as R 11 and R 12 of formula (II).
  • the liquid crystal composition in a liquid crystal phase transition 0 the known compound It may further include a liquid crystal compound exhibiting a high temperature or high refractive index.
  • a liquid crystal compound represented by the following formula (3) may be used.
  • R 13 and R 14 are each independently a radical of any one of hydrogen, alkyl of 1 to 15 carbon atoms and alkoxy of 1 to 15 carbon atoms, or -c3 ⁇ 4- of at least one of the radicals is not directly linked to oxygen atoms ⁇ c-,
  • -CH CH-, -CF 2 0-, -0-, -COO- or — 0C0— or a radical substituted with one or more H of the radicals is replaced by halogen,
  • a 5 and A 7 are each independently cyclonuylene or phenylene
  • a 6 is cyclonuylene, phenylene or phenyl substituted with halogen and p is an integer of 1 or 2.
  • the liquid crystal compound represented by Chemical Formula 3 by using one or more liquid crystal compounds selected from the group consisting of Chemical Formulas 3-1 to 3-5, the transparent point, rotational viscosity, refractive index anisotropy and control of the liquid crystal composition may be maintained while maintaining high specific resistance. have.
  • R 13 and R 14 may be defined as in the general formula R 3 "and R 14.
  • the liquid crystal composition in addition to oil-in-water dielectric constant liquid crystal the known compound
  • a liquid crystal compound represented by the following Chemical Formula 4 may be used.
  • R 15 and R 16 are each independently a radical of any one of hydrogen, alkyl having 1 to 15 carbon atoms and alkoxy having 1 to 15 carbon atoms, or -c3 ⁇ 4- at least one of the radicals is not directly linked to oxygen atoms.
  • ⁇ c-, -CH CH-, -CF 2 0-, -0-, -COO- or -0C0- or a radical substituted with one or more H of said radicals,
  • a 8 and A 9 are each independently cyclonuylene, ' tetrahydropyranylene, phenylene or phenyl substituted with halogen,
  • q is an integer between 0 and 2.
  • Transparent point, rotational viscosity, refractive index anisotropy and dielectric constant of the liquid crystal composition while maintaining a high resistivity using at least one liquid crystal compound selected from the group consisting of the following Chemical Formulas 4-1 to 4-4 as the liquid crystal compound represented by Chemical Formula 4 Anisotropy etc. can be adjusted easily.
  • R 15 and R 16 may be defined as R 15 and R 16 of formula (4).
  • the liquid crystal composition may further include a conventional high dielectric constant liquid crystal compound.
  • a liquid crystal compound represented by the following formula (5) may be used.
  • a 10 , A 11 and A 12 are each independently one of cyclonuclear styrene, tetrahydropyranylene, phenylene and phenylene substituted with halogen,
  • Z 4 and Z 5 are each independently -CH 2 CH 2- , -CH-CH-, —C ⁇ C ⁇ , — C3 ⁇ 40-,-0CH 2- , -CH 2 CF 2- , -CHFCHF-, -CF 2 CH 2- , -CH 2 CHF-, -CHFCH 2- , -C 2 F 4 _, -C00-,-0C0-, -CF 2 0-, -OCF2- or -0-,
  • r and v are 0 or 1 or 2
  • s and w are integers between 0 and 2.
  • Transparent point, rotational viscosity, refractive index anisotropy, and dielectric anisotropy of the liquid crystal composition while maintaining a high resistivity using at least one liquid crystal compound selected from the group consisting of the following Formulas 5—1 to 5-4 as the liquid crystal compound represented by Formula 5 Etc. can be easily adjusted.
  • R 17 and R 18 may be defined as R 17 and R 18 of formula (5).
  • the liquid crystal composition can 'be suitably comprises a liquid crystal compound and the intended use of at least one of liquid crystal compounds represented by considering the effect by the above formula (2) to formula (5) to the liquid crystal composition.
  • the liquid crystal composition may include a liquid crystal compound represented by Formula 2, Formula 3, and Formula 4 in order to balance various physical properties of the liquid crystal composition.
  • at least one liquid crystal compound may be used as the liquid crystal compound represented by Formulas 2 to 4, respectively.
  • the liquid crystal composition may further include various additives commonly used in the art to which the present invention belongs, in addition to the liquid crystal compound.
  • the liquid crystal composition may further include an antioxidant.
  • the liquid crystal composition may further include a reactive mesogen.
  • a reactive mesogen may be defined as a compound having a mesogenic group exhibiting liquid crystal phase behavior and an unsaturated functional group capable of photopolymerization, photocrosslinking or photocuring at least one end thereof, for example, a vinyl group, a (meth) acryl group, or an epoxy group.
  • any compound that satisfies this definition may be included as the semi-ungsogenic mesogen.
  • the semi-ungsogenic mesogen may include a diacrylate monomer having a liquid crystal skeleton or a dimethacrylate monomer having a liquid crystal skeleton.
  • the liquid crystal composition may further include a UV stabilizer.
  • the present invention provides a liquid crystal display device comprising the liquid crystal composition.
  • the liquid crystal composition according to the present invention exhibits high negative dielectric anisotropy and high refractive index anisotropy even under low rotational viscosity, and in particular, VA Virtical Alignment (MVA), Multidomain Virtical Alignment (MVA), Patterned Virtical Alignment (PVA), It is expected that high speed response can be achieved while maintaining excellent overall performance of liquid crystal display devices such as PS-VA (Polymer Stabilized Virtical Alignment) or IPS (In-Plane Switching) mode.
  • PS-VA Polymer Stabilized Virtical Alignment
  • IPS In-Plane Switching
  • the liquid crystal compound according to the present invention has high dielectric anisotropy, high refractive index anisotropy and low viscosity, and therefore various liquid crystal display devices, especially VA, MVA, PVA, PS-VA, PALC, FFS, PS-FFS, which require fast response time.
  • the liquid crystal composition optimized for the liquid crystal display element of the IPS or PS-IPS mode can be provided.
  • the bromine salt compound (Formula 1-1, 40 ⁇ 0 , 18.8 g) was dissolved in anhydrous THF, and potassium tertiary-butoxide (48.1 ⁇ ol, 5.4 g) was slowly added with stirring at -30 ° C for 30 minutes. Stirred.
  • the aldehyde compound (Formula 1-2, 43.7 mmol, 8.13 g) was added dropwise in THF at -30 ° C. After the temperature was lowered to -10 ° C and stirred for 1 hour, water and toluene 1: 1 solvent were added to the reaction vessel to terminate the reaction.
  • ethene compound (Formula 1-3, 60%, 7.1 g).
  • the obtained ethene compound (Formula 1-3, 24 ⁇ 0 1, 7.1 g) and palladium / activated carbon (10 ⁇ vt., 1.5 g) were dissolved in THF and methanol 1: 1 solvent and reacted for 3 hours in a hydrogen reactor. Filtered. After the filtrate was concentrated, the target compound (Formula 1, 94%, 6.7 g) was obtained through column chromatography.
  • bromine salt compound (Formula 2-1 , 40 ⁇ ol, 18.8 g) was dissolved in anhydrous THF
  • the bromine salt compound (Formula 3-2, 27.3 ⁇ ol, 14 g) was dissolved in anhydrous THF, and potassium tertiary-butoxide (32.7 ⁇ ol, 3.7 g) was slowly added with stirring at ⁇ 30 ° C. and stirred for 30 minutes. It was.
  • the aldehyde compound (Formula 3-1, 29.7 ⁇ ol, 6.49 g) was added dropwise in THF at -30 ° C. After raising the temperature to -KC and stirred for 1 hour, the reaction was terminated by adding water and toluene 1: 1 solvent in the reaction vessel.
  • the organic solvent layer was extracted, and the solid obtained by distillation under reduced pressure was separated by column chromatography to obtain an ethene compound (Formula 3-3, 65%, 6.6 g).
  • the obtained ethene compound (Formula 3-3, 17.7 ⁇ ol, 6.6 g) and palladium / activated carbon (10 wt.%, 1.65 g) were dissolved in THF and methanol 1: 1 solvent and reacted for 3 hours in a hydrogen reactor, followed by filtration. It was.
  • the filtrate was concentrated and then subjected to column chromatography to give the target compound (Formula 3, 94%, 6.24 g).
  • the bromine salt compound (Formula 4-1, 21.3 ⁇ ol, 10 g) was dissolved in anhydrous THF and potassium tertiary-butoxide (25.6 mmol, 2.9 g) was added slowly with stirring at -30 ° C and stirred for 30 minutes. .
  • the aldehyde compound (Formula 4-2, 23.2 ⁇ ol, 7.86 g) was added dropwise in THF at -30 ° C. After raising the temperature with -KTC and stirring for 1 hour, the reaction vessel was terminated by adding water and toluene 1: 1 solvent.
  • the organic solvent was extracted and the solid produced by distillation under reduced pressure was separated by column chromatography to obtain an ethene compound (Formula 4-3, 59, 5.64 g).
  • the obtained ethene compound (Formula 4-3, 12.6 ⁇ 0 1, 5.64 g) and palladium / activated carbon (10 wt.%, 1.4 g) were dissolved in THF and methane in a 1: 1 solvent and reacted for 3 hours in a hydrogen reactor. And filtered. The filtrate was concentrated and then subjected to column chromatography to give the target compound (Formula 4, 97%, 3.9 g).
  • the bromine salt compound (Formula 5-2, 20.2 ⁇ ol, 12.5. G) was dissolved in anhydrous THF, and then potassium tertiary-subside (25.4 ⁇ ol, 2.86 g) was added slowly with stirring at -30 ° C for 30 minutes. Stirred.
  • the aldehyde compound (Formula 5-1, 23.1 ⁇ ol, 5.04 g) was added dropwise in THF at -30 ° C. After the temperature was raised to -10 ° C and stirred for 1 hour, water and toluene 1: 1 solvent were added to the reaction vessel to terminate the reaction.
  • the organic solvent layer was extracted, and the solid obtained by distillation under reduced pressure was separated by column chromatography to obtain an ethene compound (Formula 5-3, 74%, 7 g).
  • the obtained ethene compound (Formula 5-3, 15.6 ⁇ ol, 7 g) and palladium / activated carbon (10 wt.%, 1.75 g) were dissolved in THF and methanol 1: 1 solvent and reacted for 3 hours in a hydrogen reactor, followed by filtration. It was.
  • the filtrate was concentrated and then subjected to column chromatography to give the target compound (Formula 5, 81%, 5.69 g).
  • the brine compound (Formula 6-2, 15.6 ⁇ ol, 8 g) was dissolved in anhydrous THF, and then potassium tertiary-buside (18.7 ⁇ ol, 2.1 g) was added slowly with stirring at -30 ° C and stirred for 30 minutes. It was.
  • the aldehyde compound (Formula 6-1, 16.99 ⁇ ol, 5 g) was added dropwise in THF at -30 ° C. After raising the temperature to -10 ° C and stirred for 1 hour, the reaction vessel was terminated by adding water and toluene 1: 1 solvent.
  • the organic solvent layer was extracted, and the solid obtained by distillation under reduced pressure was separated by column chromatography to obtain an ethene compound (Formula 6-3, 90%, 6.29 g).
  • the obtained ethene compound (Formula 6-3, 14 ⁇ ol, 6.29 g) and palladium / activated carbon (10 wt.%, 1.6 g) were dissolved in a 1: 1 solvent of THF and methane, and then hydrogen The reaction was reacted for 3 hours in the reactor and filtered. The filtrate was concentrated and then subjected to column chromatography to give the target compound (Formula 6, 79%, 5 g).
  • the physical properties of the liquid crystal compounds prepared in Preparation Examples and Comparative Preparation Examples were evaluated. Specifically, the physical properties of the liquid crystal compound were defined as an extrapolation value obtained by substituting the measured value of the sample prepared by mixing 10 wt% of the liquid crystal compound to be measured with 90 wt% of the mother liquid crystal. In this case, as the mother liquid crystal, a transparent point Tni of 78 ° C. and an refractive index anisotropy [ ⁇ ] of 0.10 were used.
  • TA-series differential scanning calorimetry of ⁇ was used to observe the phase transition temperature by heating and concentrating 1 cycle of the liquid crystal compound to Tni + 50 ° C at room temperature at a rate of rc / min under nitrogen.
  • Cry, Sm, N, ISO means crystalline phase, Smetic phase, nematic phase, isotropic phase, respectively,
  • the temperature between means the corresponding phase transition temperature.
  • the Tni of the liquid crystal compound is measured by observing the temperature when a liquid crystal compound is placed on a hot plate of a melting point measuring device equipped with a polarization microscope and heated at a rate of 3 ° C./min to change a part of the liquid crystal compound into an isotropic liquid on the liquid crystal phase. It was.
  • SCHOTT CT52 equipment was used for the viscosity measurement, and 2 mL of the liquid crystal composition to be measured after mounting a capillary viscometer capable of measuring the viscosity for a volume of 2 mL. Thereafter, the liquid crystal composition was stabilized at 20 ° C. for 30 minutes, and then the liquid crystal composition was pulled down to the measurement site using a sporad louver. Subsequently, the rate at which the liquid crystal composition fell was measured through a timer, and the viscosity (mm 2 / s) was obtained through the timer. The results are shown in Table 2 below.
  • each value means weight%.
  • the liquid crystal compound was placed on a hot plate of a melting point measuring device equipped with a silver polarization microscope of the liquid crystal compound, and heated at a rate of 3 ° C./min to observe the temperature when a part of the liquid crystal compound changed to an isotropic liquid on the liquid crystal phase. It was.

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  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

La présente invention concerne le composé de cristaux liquides représenté par la formule chimique 1 selon la présente invention présentant une anisotropie diélectrique élevée, une anisotropie d'indice de réfraction élevée et une faible viscosité, et ainsi peut fournir une composition de cristaux liquides optimisée pour divers dispositifs d'affichage à cristaux liquides, particulièrement, les dispositifs d'affichage à cristaux liquides en mode VA, MVA, PVA, PS-VA, PALC, FFS, PS-FFS, IPS ou PS-IPS qui nécessitent des temps de réponse rapide (où L1, L2, L3 et L4 sont chacun indépendamment un atome d'hydrogène ou un groupe halogéno, R est un atome d'hydrogène, un groupe alkyle en C1 à C10, alcényle en C2 à C10 ou alcoxy en C1 à C10, et n1 et n2 sont chacun indépendamment un nombre entier d'une valeur s'étendant de 0 à 2, et la somme de n1 et n2 présente la valeur de 0 à 2).
PCT/KR2016/005326 2015-05-19 2016-05-19 Composé de cristaux liquides et composition de cristaux liquides le comprenant WO2016186465A1 (fr)

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JP2022119164A (ja) * 2021-02-03 2022-08-16 株式会社Ｊａｃｔａコラボレーション 化合物、化合物を含有する液晶組成物、及び、液晶組成物を使用した液晶表示素子
JP7297269B2 (ja) 2021-02-03 2023-06-26 株式会社Ｊａｃｔａコラボレーション 化合物、化合物を含有する液晶組成物、及び、液晶組成物を使用した液晶表示素子

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