阅读说明：本技术 胆甾醇型液晶组合物及其用途、液晶元件 (Cholesteric liquid crystal composition, use thereof, and liquid crystal element ) 是由 户畑仁志 冈部英二 于 2021-03-17 设计创作，主要内容包括：本发明涉及一种胆甾醇型液晶组合物及其用途、液晶元件。胆甾醇型液晶元件理想的是可使用的温度范围广、且具有高的显示品质、及低的驱动电压。因此,液晶组合物的特性要求胆甾醇相的上限温度高、胆甾醇相的下限温度低、比电阻大、光学各向异性比较大、介电各向异性大、粘度小、螺旋间距长度适当及所述间距长度的温度依存性小等。一种胆甾醇型液晶组合物、及含有所述组合物的液晶元件,所述胆甾醇型液晶组合物含有：作为添加物的选自式(1)所表示的化合物的群组中的至少一种光学活性化合物、作为第一成分的选自式(2)所表示的化合物的群组中的至少一种化合物、以及作为第二成分的选自式(3)所表示的化合物的群组中的至少一种化合物。(The invention relates to a cholesteric liquid crystal composition, application thereof and a liquid crystal element. Cholesteric liquid crystal elements desirably have a wide temperature range in which they can be used, high display quality, and low driving voltage. Therefore, the characteristics of the liquid crystal composition require a high upper limit temperature of the cholesteric phase, a low lower limit temperature of the cholesteric phase, a large specific resistance, a large optical anisotropy, a large dielectric anisotropy, a small viscosity, a proper spiral pitch length, and a small temperature dependence of the pitch length. A cholesteric liquid crystal composition comprising: at least one optically active compound selected from the group of compounds represented by formula (1) as an additive, at least one compound selected from the group of compounds represented by formula (2) as a first component, and at least one compound selected from the group of compounds represented by formula (3) as a second component.)

1. A cholesteric liquid crystal composition comprising: at least one optically active compound selected from the group of compounds represented by formula (1) as an additive, at least one compound selected from the group of compounds represented by formula (2) as a first component, and at least one compound selected from the group of compounds represented by formula (3) as a second component,

in the formula (1), R¹¹And R¹²Independently hydrogen, halogen, -C ≡ N, -N ═ C ═ O, -N ═ C ═ S, -SF₅Or an alkyl group having 1 to 10 carbon atoms, wherein at least one-CH group is present in the alkyl group₂-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of these groups may be substituted by fluorine or chlorine; ring A¹¹And ring A¹²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 1, 3-dioxane-2, 5-diyl, tetrahydropyran-3, 5-diyl, pyrimidine-2, 5-diyl, pyridine-2, 5-diyl, or 1, 4-bicyclo- (2,2,2) -octylene, in which rings at least one hydrogen may be substituted by fluorine or chlorine; z¹¹And Z¹²Independently a single bond or an alkylene group having 1 to 20 carbon atoms, wherein at least one-CH group is present in the alkylene group₂-may be substituted by-O-, -CO-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of which groups may be substituted by fluorine or chlorine; x¹¹And X¹²Independently a single bond, ethylene, methyleneoxy, carbonyloxy or difluoromethyleneoxy; n is¹¹And n¹²Independently 2, 3 or 4, there being a plurality of rings A¹¹Ring A¹²、Z¹¹Or Z¹²May be the same or different;

in the formulae (2) and (3), R²、R³¹And R³²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; ring A²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-Phenylene, 2, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, or tetrahydropyran-2, 5-diyl; ring A³Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, or 2, 6-difluoro-1, 4-phenylene; z²And Z³Independently a single bond, ethylene, ethenylene, methyleneoxy, carbonyloxy, difluoromethyleneoxy, ethynylene, or tetrafluoroethylene; x²is-C ≡ N or-N ═ C ═ S; y is²¹And Y²²Independently hydrogen or fluorine; n is²Is 1 or 2, in n²In the case of 2, there are a plurality of rings A²Or Z²May be the same or different; n is³Is 1, 2 or 3, in n³In the case of 2 or 3, a plurality of rings A are present³Or Z³The same or different.

2. The cholesteric liquid crystal composition according to claim 1, further comprising at least one compound selected from the group consisting of compounds represented by the formula (4) as a third component,

in the formula (4), R⁴Is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; ring A⁴¹And ring A⁴²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, or tetrahydropyran-2, 5-diyl; ring A⁴³Is 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, or 2, 6-difluoro-1, 4-phenylene; z⁴¹、Z⁴²And Z⁴³Independently a single bond, ethylene, vinylene, methyleneoxy, carbonyloxy, difluoromethyleneoxy, or tetrafluoroethylene; y is⁴¹And Y⁴²Independently of one another is hydrogenOr fluorine; x⁴Fluorine, chlorine, alkyl with 1-12 carbon atoms, at least one hydrogen substituted by halogen, alkoxy with 1-12 carbon atoms, at least one hydrogen substituted by halogen, or alkenyl with 2-12 carbon atoms, at least one hydrogen substituted by halogen; n is⁴Is 0, 1 or 2, at n⁴In the case of 2, there are a plurality of rings A⁴¹And Z⁴¹The same or different.

3. The cholesteric liquid crystal composition according to claim 1 or 2, comprising at least one optically active compound selected from the group of compounds represented by formulae (1-1) to (1-6) as an additive,

in the formulae (1-1) to (1-6), R¹¹And R¹²Independently hydrogen, halogen, -C ≡ N, -N ═ C ═ O, -N ═ C ═ S, -SF₅Or an alkyl group having 1 to 10 carbon atoms, wherein at least one-CH group is present in the alkyl group₂-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of these groups may be substituted by fluorine or chlorine.

4. The cholesteric liquid crystal composition according to claim 1 or 2, wherein the additive is in a proportion ranging from 0.1 to 10 parts by weight based on the weight of the liquid crystal composition.

5. The cholesteric liquid crystal composition according to claim 1 or 2, comprising at least one compound selected from the group of compounds represented by formulae (2-1) to (2-23) as a first component,

in the formulae (2-1) to (2-23), R²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; x²independently-C ≡ N or-N ═ C ═ S; y is²¹And Y²²Independently hydrogen or fluorine.

6. The cholesteric liquid crystal composition according to claim 1 or 2, wherein the proportion of the first component is in the range of 5 to 50% by weight based on the weight of the liquid crystal composition.

7. The cholesteric liquid crystal composition according to claim 1 or 2, comprising at least one compound selected from the group consisting of compounds represented by formulae (3-1) to (3-28) as a second component,

in the formulae (3-1) to (3-28), R³¹And R³²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms.

8. The cholesteric liquid crystal composition according to claim 1 or 2, wherein the proportion of the second component is in the range of 30 to 90% by weight based on the weight of the liquid crystal composition.

9. The cholesteric liquid crystal composition according to claim 2, further comprising at least one compound selected from the group consisting of compounds represented by formulae (4-1) to (4-19) as a third component,

in the formulae (4-1) to (4-19), R⁴Is alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms or alkenyl group having 2 to 12 carbon atoms, Y⁴¹And Y⁴²Independently hydrogen or fluorine; x⁴Fluorine, chlorine, alkyl with 1-12 carbon atoms, at least one hydrogen substituted by halogen, alkoxy with 1-12 carbon atoms, at least one hydrogen substituted by halogen, or alkenyl with 2-12 carbon atoms, at least one hydrogen substituted by halogen.

10. The cholesteric liquid crystal composition according to claim 2, wherein the proportion of the third component is in the range of 10 to 50% by weight, based on the weight of the liquid crystal composition.

11. The cholesteric liquid crystal composition according to claim 1 or 2, wherein an optical anisotropy at a wavelength of 589nm, measured at 25 ℃, is in a range of 0.10 to 0.40, and a dielectric anisotropy at a frequency of 1kHz, measured at 25 ℃, is in a range of 10 to 60.

12. A cholesteric liquid crystal composition according to claim 1 or 2, wherein the reflection wavelength is selected in the range of 350nm to 800 nm.

13. A liquid crystal cell comprising the cholesteric liquid crystal composition according to any one of claims 1 to 12.

14. Use of a cholesteric liquid crystal composition for a liquid crystal cell, the cholesteric liquid crystal composition being a cholesteric liquid crystal composition according to any one of claims 1 to 12.

Technical Field

The present invention relates to a cholesteric liquid crystal composition, a liquid crystal device including the composition, and the like, wherein the cholesteric liquid crystal composition: the liquid crystal composition contains an optically active compound having an octahydrobinaphthyl skeleton. In particular, it relates to a cholesteric liquid crystal composition exhibiting a large dielectric anisotropy, use thereof, and an element for driving the cholesteric liquid crystal composition.

Background

In the liquid crystal element, the operation mode of the liquid crystal molecules is classified into a Phase Change (PC), a Twisted Nematic (TN), a Super Twisted Nematic (STN), an Electrically Controlled Birefringence (ECB), an Optically Compensated Bend (OCB), an in-plane switching (IPS), a Vertical Alignment (VA), a Fringe Field Switching (FFS), a field-induced photo-reactive alignment (FPA), and the like. The driving methods of the elements are classified into Passive Matrix (PM) and Active Matrix (AM). The PM is classified into a static type (static) and a multiplexing type (multiplex), etc., and the AM is classified into a Thin Film Transistor (TFT), a Metal Insulator Metal (MIM), etc.

TFTs are classified into amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to the manufacturing process. The light source is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmission type using both natural light and backlight.

Liquid crystal compositions containing optically active compounds sometimes exhibit a "cholesteric phase". The cholesteric phase is a liquid crystal phase in which the orientation of the order of orientation of molecules rotates so as to describe a helix. The helical axis is perpendicular to the direction of the orientation order. In addition, the spiral period is referred to as "pitch".

Liquid crystal devices comprising a liquid crystal composition exhibiting a "cholesteric phase" are known. These liquid crystal compositions have a pitch length of the order of visible light. A liquid crystal composition exhibiting a cholesteric phase exhibits selective reflection of circularly polarized light, and the direction of rotation of the light vector corresponds to the left-right characteristic (handedness) of a cholesteric helix. The reflection wavelength λ can be calculated from formula (A) based on the pitch P of the cholesteric helix and the average birefringence n of the cholesteric liquid crystal.

λ＝n×P (A)

The most common Cholesteric liquid crystal devices are SSCT (Surface Stability Cholesteric Texture) and PSCT (Polymer Stability Cholesteric Texture) devices. SSCT and PSCT elements generally include a cholesteric liquid crystal composition, which exhibits a planar structure that reflects light of a specific wavelength in an initial stage, and is switched to a focal conic (focal conic) light scattering structure by application of an alternating current pulse, or vice versa, for example.

These liquid crystal elements are kept in their respective states after being bistable (bistable), that is, after the electric field is switched off, and are reversely transferred to their initial states only by applying the electric field again. When a higher voltage pulse is applied, the cholesteric liquid crystal composition shifts to a homeotropic (transparent) state, and relaxes to a planar state when the voltage is switched off rapidly from the state, and relaxes to a focal conic state when the voltage is switched off slowly.

Cholesteric liquid crystal elements generally do not require a backlight. In the planar state, the cholesteric liquid crystal composition in the pixel exhibits selective reflection of light of a specific wavelength according to said formula (a), as a result of which the pixel is visible in a corresponding reflection color, for example on a black background. If the transition is a scattering state or a vertical transparent state due to the focal conic structure, the reflected color disappears. For the above reasons, the power consumption of the cholesteric liquid crystal element is considerably small. Further, these are small in the scattering state even if, for example, there is viewing angle dependency. Thus, these displays can operate in simpler multiplexing or passive matrix modes without active matrix addressing. On the other hand, for the purpose of improving display quality, an element combined with an active matrix has been reported because of poor display quality (patent documents 1 and 2).

In order to be used in such a cholesteric liquid crystal device, the liquid crystal composition must have good chemical stability and thermal stability, and good stability against electric fields and electromagnetic radiation. Further, the liquid crystal material must have a high upper limit temperature of the cholesteric phase, a low lower limit temperature of the cholesteric phase, relatively large optical anisotropy, large dielectric anisotropy, and small viscosity. Furthermore, cholesteric liquid crystal materials must be able to display, in particular, different reflection wavelengths in the visible region by simple and controlled polarization. Regarding these, the temperature dependence of the reflection wavelength must be further reduced.

Liquid crystals are generally used as a mixture of a plurality of components, and it is important that the components can be easily mixed with each other. Further characteristics such as dielectric anisotropy and optical anisotropy must satisfy different requirements depending on the cell type. However, the preferred values for all of the parameters described cannot be achieved using the compositions available in the prior art. For example, patent document 3 describes a cholesteric liquid crystal composition containing a nematic liquid crystal containing two or more kinds of optically active compounds. However, the mixtures disclosed here are only of small optical anisotropy and a low upper temperature limit of the nematic phase. Further, these have a high ratio of the optically active compound of 26%.

Therefore, there is a great demand for a liquid crystal composition for a cholesteric liquid crystal element which has an appropriate helical pitch length, a wide operating temperature range, a short response time, a low driving voltage, and a low temperature dependence of the reflection wavelength, and which has no or at least greatly reduced drawbacks compared with the liquid crystal compositions of the prior art. The present invention has an object to provide a composition for a cholesteric liquid crystal element having the above-mentioned required characteristics, and having no or at least greatly reduced disadvantages of the prior art.

[ Prior art documents ]

[ patent document ]

[ patent document 1] Japanese patent laid-open No. Hei 7-140440

[ patent document 2] Japanese patent No. 5750818 publication

[ patent document 3] Japanese patent laid-open No. Hei 3-045906

[ patent document 4] Japanese patent application laid-open No. 2004-532345

Disclosure of Invention

[ problems to be solved by the invention ]

Cholesteric liquid crystal elements desirably have a wide temperature range in which they can be used, high display quality, and low driving voltage. Therefore, the characteristics of the liquid crystal composition require a high upper limit temperature of the cholesteric phase, a low lower limit temperature of the cholesteric phase, a large specific resistance, a large optical anisotropy, a large dielectric anisotropy, a small viscosity, a proper spiral pitch length, and a small temperature dependence of the pitch length.

The present invention aims to provide a liquid crystal composition having good required characteristics and an excellent balance of characteristics in a cholesteric liquid crystal cell.

[ means for solving problems ]

As a result of diligent research, the inventors have found that a liquid crystal composition containing an optically active compound having a specific structure solves the above problems, and have completed the present invention.

The present invention is as follows.

Item 1. a cholesteric liquid crystal composition, comprising: at least one optically active compound selected from the group of compounds represented by formula (1) as an additive, at least one compound selected from the group of compounds represented by formula (2) as a first component, and at least one compound selected from the group of compounds represented by formula (3) as a second component,

in the formula (1), R¹¹And R¹²Independently hydrogen, halogen, -C ≡ N, -N ═ C ═ O, -N ═ C ═ S, -SF₅Or an alkyl group having 1 to 10 carbon atoms, wherein at least one-CH group is present in the alkyl group₂-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of these groups may be substituted by fluorine or chlorine; ring A¹¹And ring A¹²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 1, 3-dioxane-2, 5-diyl, tetrahydropyran-3, 5-diyl, pyrimidine-2, 5-diyl, pyridine-2, 5-diyl, or 1, 4-bicyclo- (2,2,2) -octylene, in which rings at least one hydrogen may be substituted by fluorine or chlorine; z¹¹And Z¹²Independently a single bond or an alkylene group having 1 to 20 carbon atoms, wherein at least one-CH group is present in the alkylene group₂-may be substituted by-O-, -CO-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of which groups may be substituted by fluorine or chlorine; x¹¹And X¹²Independently a single bond, ethylene, methyleneoxy, carbonyloxy or difluoromethyleneoxy; n is¹¹And n¹²Independently 2, 3 or 4, there being a plurality of rings A¹¹Ring A¹²、Z¹¹Or Z¹²May be the same or different;

in the formulae (2) and (3), R²、R³¹And R³²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; ring A²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, or tetrahydropyran-2, 5-diyl; ring A³Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, or 2, 6-difluoro-1, 4-phenylene; z²And Z³Independently a single bond, ethylene, ethenylene, methyleneoxy, carbonyloxy, difluoromethyleneoxy, ethynylene, or tetrafluoroethylene; x²is-C ≡ N or-N ═ C ═ S; y is²¹And Y²²Independently hydrogen or fluorine; n is²Is 1 or 2, in n²In the case of 2, there are a plurality of rings A²Or Z²May be the same or different; n is³Is 1, 2 or 3, in n³In the case of 2 or 3, a plurality of rings A are present³Or Z³The same or different.

Item 2. the cholesteric liquid crystal composition according to item 1, further comprising at least one compound selected from the group of compounds represented by formula (4) as a third component,

in the formula (4), R⁴Is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; ring A⁴¹And ring A⁴²Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, or tetrahydropyran-2, 5-diyl; ring A⁴³Is 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, or 2, 6-difluoro-1, 4-phenylene; z⁴¹、Z⁴²And Z⁴³Independently a single bond, ethylene, vinylene, methyleneoxy, carbonyloxy, difluoromethyleneoxy, or tetrafluoroethylene; y is⁴¹And Y⁴²Independently hydrogen or fluorine; x⁴Fluorine, chlorine, alkyl with 1-12 carbon atoms, at least one hydrogen substituted by halogen, alkoxy with 1-12 carbon atoms, at least one hydrogen substituted by halogen, or alkenyl with 2-12 carbon atoms, at least one hydrogen substituted by halogen; n is⁴Is 0, 1 or 2, at n⁴In the case of 2, there are a plurality of rings A⁴¹And Z⁴¹The same or different.

Item 3. the cholesteric liquid crystal composition according to item 1 or 2, comprising, as an additive, at least one optically active compound selected from the group of compounds represented by formulae (1-1) to (1-6),

in the formulae (1-1) to (1-6), R¹¹And R¹²Independently hydrogen, halogen, -C ≡ N, -N ═ C ═ O, -N ═ C ═ S, -SF₅Or an alkyl group having 1 to 10 carbon atoms, wherein at least one-CH group is present in the alkyl group₂-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-, at least one of these groups may be substituted by fluorine or chlorine.

Item 4 the cholesteric liquid crystal composition according to any one of items 1 to 3, wherein a proportion of the additive ranges from 0.1 to 10 parts by weight based on the weight of the liquid crystal composition.

Item 5. the cholesteric liquid crystal composition according to any one of items 1 to 4, comprising at least one compound selected from the group of compounds represented by formulae (2-1) to (2-23) as a first component,

in the formulae (2-1) to (2-23), R²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; x²independently-C ≡ N or-N ═ C ═ S; y is²¹And Y²²Independently hydrogen or fluorine.

Item 6 the cholesteric liquid crystal composition according to any one of items 1 to 5, wherein the proportion of the first component is in the range of 5 to 50% by weight, based on the weight of the liquid crystal composition.

Item 7. the cholesteric liquid crystal composition according to any one of items 1 to 6, comprising, as a second component, at least one compound selected from the group of compounds represented by formulae (3-1) to (3-28),

in the formulae (3-1) to (3-28), R³¹And R³²Independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms.

Item 8 the cholesteric liquid crystal composition according to any one of items 1 to 7, wherein the proportion of the second component is in the range of 30 to 90% by weight, based on the weight of the liquid crystal composition.

Item 9. the cholesteric liquid crystal composition according to any one of items 2 to 8, further comprising at least one compound selected from the group of compounds represented by formulae (4-1) to (4-19) as a third component,

in the formulae (4-1) to (4-19), R⁴Is alkyl group having 1 to 12 carbon atoms, carbonAlkoxy group having 1 to 12 carbon atoms or alkenyl group having 2 to 12 carbon atoms, Y⁴¹And Y⁴²Independently hydrogen or fluorine; x⁴Fluorine, chlorine, alkyl with 1-12 carbon atoms, at least one hydrogen substituted by halogen, alkoxy with 1-12 carbon atoms, at least one hydrogen substituted by halogen, or alkenyl with 2-12 carbon atoms, at least one hydrogen substituted by halogen.

The cholesteric liquid crystal composition according to any one of claims 2 to 9, wherein the proportion of the third component is in a range of 10 to 50% by weight, based on the weight of the liquid crystal composition.

Item 11 the cholesteric liquid crystal composition according to any one of items 1 to 10, wherein an optical anisotropy at a wavelength of 589nm (measured at 25 ℃) is in a range of 0.10 to 0.40, and a dielectric anisotropy at a frequency of 1kHz (measured at 25 ℃) is in a range of 10 to 60.

Item 12 the cholesteric liquid crystal composition according to any one of items 1 to 11, wherein the reflection wavelength is selected in the range of 350nm to 800 nm.

A liquid crystal cell comprising the cholesteric liquid crystal composition according to any one of items 1 to 12.

Item 14 use of a cholesteric liquid crystal composition for a liquid crystal element, the cholesteric liquid crystal composition being the cholesteric liquid crystal composition according to any one of items 1 to 12.

[ Effect of the invention ]

The cholesteric liquid crystal composition of the invention satisfies at least one of the characteristics of a high upper limit temperature of a cholesteric phase, a low lower limit temperature of a cholesteric phase, a large specific resistance, a large optical anisotropy, a large dielectric anisotropy, a small viscosity, a proper helical pitch length, and a small temperature dependence of the pitch length. Furthermore, there is a proper balance between at least two properties. The liquid crystal element of the present invention has characteristics such as a wide range of use temperature, a large voltage holding ratio, a low driving voltage, a large contrast ratio, a short response time, easy control of reflection wavelength, and small deterioration of display quality due to a change in environmental temperature.

Detailed Description

The usage of the terms in the present specification is as follows. The terms "liquid crystal composition" and "liquid crystal element" may be simply referred to as "composition" and "element", respectively. The term "liquid crystal element" is a generic name of a liquid crystal display panel, a liquid crystal display module, a liquid crystal device, and the like, each using a liquid crystal composition. The "liquid crystalline compound" is a general term for compounds having a liquid crystal phase such as a nematic phase, a cholesteric phase, or a smectic phase, and compounds which do not have a liquid crystal phase but are mixed in the composition for the purpose of adjusting characteristics such as a temperature range, viscosity, and dielectric anisotropy of the liquid crystal phase. The compounds have a six-membered ring, for example 1, 4-cyclohexylene or 1, 4-phenylene, whose molecular structure is rod-like. At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as "compound (1)". The "compound (1)" means one compound, a mixture of two compounds, or a mixture of three or more compounds represented by the formula (1). The same applies to compounds represented by other formulae.

The liquid crystal composition is prepared by mixing a plurality of liquid crystalline compounds. The proportion (content) of the liquid crystalline compound is represented by a weight percentage (wt%) based on the weight of the liquid crystal composition. Additives such as optically active compounds, antioxidants, ultraviolet absorbers, pigments, antifoaming agents, polymerizable compounds, polymerization initiators, and polymerization inhibitors are optionally added to the liquid crystal composition. The additive may be referred to as a "host liquid crystal composition" or a "host nematic liquid crystal composition" together with the type of liquid crystal phase. In addition, each liquid crystalline compound in the "host liquid crystal composition" may be referred to as a "component compound".

The proportion (addition amount) of the additive is represented by the blending amount (part by weight) when the weight of the host liquid crystal composition is taken as 100. Further, parts per million (ppm) by weight may be used depending on additives. The proportions of the polymerization initiator and the polymerization inhibitor are exceptionally expressed based on the weight of the polymerizable compound.

In the present invention, a liquid crystal composition in which an optically active compound is added to a bulk liquid crystal composition exhibiting a nematic phase to exhibit a "cholesteric phase" is referred to as "cholesteric liquid crystal" or "cholesteric liquid crystal composition".

The "upper limit temperature of the nematic phase or cholesteric phase" may be simply referred to as "upper limit temperature". The "lower limit temperature of the nematic phase or cholesteric phase" may be simply referred to as "lower limit temperature". The "large specific resistance" means that the composition has a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase in the initial stage, and also has a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase after long-term use. The phrase "high voltage holding ratio" means that the device has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase in the initial stage, and also has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase after long-term use.

The expression "at least one 'a'" means that the number of 'a's is arbitrary. The expression "at least one 'a' may be substituted with 'B' means that when the number of 'a' is one, the position of 'a' is arbitrary, and when the number of 'a' is two or more, the positions may be selected without limitation. The rules also apply to the expression "at least one 'a' is substituted with 'B'.

In the chemical formula of the component compound, the terminal group R¹¹Etc. for a variety of compounds. In these compounds, any two R¹¹The two radicals indicated may be identical or else different. For example, there is R of the compound (1)¹¹Is ethyl, and R of the compound (1-1)¹¹In the case of ethyl. Also R of the compound (1)¹¹Is ethyl, and R of the compound (1-1)¹¹In the case of propyl. The rules also apply to the notation of other end groups and the like. In the formula (1), n is¹¹When 2, there are two rings A¹¹. In the compounds, two rings A¹¹The two rings shown may be the same or may be different. The rule also applies to n¹¹Any 2 rings A greater than 2¹¹. The rule also applies to Z¹¹Ring A¹²、Z¹²Ring A²、Z²Ring A³、Z³Ring A⁴¹、Z⁴¹And the like.

The alkyl group of the liquid crystalline compound is linear or branched and does not contain a cyclic alkyl group. Straight chain alkyls are preferred to branched alkyls. The same applies to terminal groups such as alkoxy groups and alkenyl groups. For the configuration (configuration) related to 1, 4-cyclohexylene, the trans configuration is preferred over the cis configuration in order to increase the upper limit temperature. Since 2-fluoro-1, 4-phenylene is asymmetric in the left-right direction, it is present in the left (L) and right (R) directions. The same applies to divalent radicals such as tetrahydropyran-2, 5-diyl. The same applies to a bonding group (-COO-or-OCO-) such as a carbonyloxy group.

The liquid crystal element of the present invention contains a cholesteric liquid crystal composition which is a liquid crystal composition having a cholesteric phase. The composition has suitable properties. By improving the characteristics of the composition, a liquid crystal element having good characteristics can be obtained. The associations between the two properties are summarized in table 1 below. The characteristics of the composition will be further described based on a commercially available liquid crystal cell. The temperature range of the cholesteric phase is associated with the usable temperature range of the component. The preferred upper temperature limit for the cholesteric phase is about 70 ℃ or higher and the preferred lower temperature limit for the cholesteric phase is about-10 ℃ or lower. The large specific resistance of the composition contributes to a large voltage holding ratio of the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase is preferable. A composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the cholesteric phase after a long-term use is preferable. The specific resistance of the liquid crystal composition at room temperature is preferably 1X 10¹⁰Omega cm or more, more preferably 1X 10¹²Omega cm or more, and further excellentIs selected to be 1 × 10¹⁴Omega cm or more.

TABLE 1 characteristics of liquid crystal compositions and liquid crystal elements

The optical anisotropy of the composition correlates with a bright display. In order to realize a bright display, a liquid crystal composition having a relatively large optical anisotropy is required. The optical anisotropy (measured at 25 ℃) at a wavelength of 589nm is preferably in the range of 0.10 to 0.40, more preferably in the range of 0.12 to 0.35, and still more preferably in the range of 0.15 to 0.30. Since a large dielectric anisotropy of the composition contributes to a low driving voltage of the device, the dielectric anisotropy is preferably large. The dielectric anisotropy (measured at 25 ℃) at a frequency of 1kHz is preferably within a range of 10 to 60, more preferably within a range of 15 to 55, and still more preferably within a range of 20 to 50. The viscosity of the composition correlates to the response time of the element. In order to display a moving image using the device, the response time is preferably short. Ideally shorter than 1 millisecond of response time. Therefore, it is preferable that the viscosity of the composition is small. The viscosity at 20 ℃ is preferably 120 mPas or less, more preferably 80 mPas or less. More preferably, the viscosity at low temperature is low. The helical pitch length of the composition is preferably adjusted to the visible region by using an optically active compound in an amount as small as possible so as not to impair the properties of the bulk nematic liquid crystal composition. In addition, in order not to deteriorate the display quality due to a temperature change in the environment, it is preferable that the temperature dependency of the spiral pitch length is hardly present or small.

The present invention also includes the following items. (a) The composition further contains at least one additive selected from the group consisting of antioxidants, ultraviolet absorbers, pigments, defoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds. (b) A liquid crystal cell comprising the composition. (c) A transmissive and reflective element comprising the composition.

The cholesteric liquid crystal composition of the invention is explained in the following order. First, the composition is explained. Second, the main characteristics of the additive and the component compounds in the host liquid crystal composition, and the main effects of the compounds on the composition will be described. Third, preferred proportions of additives and combinations of component compounds in the composition and their basis will be described. Fourth, preferred additives and component compounds are shown. Fifth, additives that can be added to the composition will be described.

First, the composition is explained. The compositions of the present invention are classified as composition a and composition B. The composition a is a composition containing the compound (1) as an additive and a liquid crystalline compound selected from the group consisting of the compound (2), the compound (3) and the compound (4) as a component compound, and may further contain other liquid crystalline compounds, other additives, and the like. The "other liquid crystalline compound" is a liquid crystalline compound different from the compound (2), the compound (3) and the compound (4). The "other additives" are additives different from the compound (1) and are mixed in the composition for the purpose of further adjusting the characteristics. Other additives include antioxidants, ultraviolet absorbers, pigments, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds, and the like.

The composition B substantially contains only the additive which is the compound (1) and the liquid crystalline compound (component compound) selected from the compounds (2), (3) and (4). "substantially" means that the composition may contain other additives but does not contain other liquid crystalline compounds. From the viewpoint of reducing the cost by reducing the number of components of the liquid crystalline compound, composition B is superior to composition a. From the viewpoint that the characteristics can be further adjusted by mixing other liquid crystalline compounds, the composition a is superior to the composition B.

Second, the main characteristics of the additive and the component compound in the host liquid crystal composition, and the main effects of the compound on the composition or the device will be described. The optically active compound (1) as an additive is added to the host nematic liquid crystal composition, and a cholesteric phase is developed. Thus, the structure of formula (1) is not a racemate. The optically active compound of formula (1) can be produced by the method described in international publication No. 2014/097952. The main properties of the component compounds are summarized in table 2 on the basis of the effect of the present invention. In the notation of table 2, L means large or high, M means medium, and S means small or low. The notation L, M, S is a classification based on qualitative comparisons between component compounds, with 0 (zero) meaning infinitesimal.

TABLE 2 characterization of the Compounds

Compound (I)	Compound (2)	Compound (3)	Compound (4)
				Upper limit temperature	S～L	S～L	S～L
Viscosity of the oil	M～L	S～M	M～L
				Optical anisotropy	S～M	S～L	M～L
Dielectric anisotropy	M～L	0	M～L
				Specific resistance	L	L	L

The main effects of the component compounds on the properties of the composition are as follows. The compound (2) as the first component improves the dielectric anisotropy. The compound (3) as the second component increases the optical anisotropy and also increases the upper limit temperature or decreases the lower limit temperature. The compound (4) as the third component improves the dielectric anisotropy.

Third, preferred proportions of additives and combinations of component compounds in the composition and their basis will be described. Preferred combinations in the composition are compound (1) + compound (2) + compound (3), or compound (1) + compound (2) + compound (3) + compound (4). Further preferred combinations are compound (1) + compound (2) + compound (3) + compound (4).

The compound (1) is preferably added in an amount of 0.1 part by weight or more based on the weight of the bulk nematic liquid crystal composition in order to obtain a stable twisted state of the cholesteric liquid crystal composition, and the compound (1) is preferably added in an amount of 10 parts by weight or less in order not to impair the characteristics of the bulk nematic liquid crystal composition. Further, the preferable addition ratio is in the range of 0.5 to 7 parts by weight. Particularly preferred addition ratio is in the range of 1 to 5 parts by weight.

The preferable proportion of the compound (2) as the first component is 5% by weight or more in order to increase the dielectric anisotropy based on the weight of the host nematic liquid crystal composition, and the preferable proportion of the compound (2) as the first component is 50% by weight or less in order not to increase the viscosity. A more preferable ratio is in the range of 10 to 45% by weight. A particularly preferred ratio is in the range of 15 to 40% by weight.

The preferred proportion of the compound (3) as the second component is 30% by weight or more in order to adjust the optical anisotropy based on the weight of the host nematic liquid crystal composition, and the preferred proportion of the compound (3) as the second component is 90% by weight or less in order not to decrease the dielectric anisotropy. A more preferable ratio is in the range of 40 to 85 wt%. A particularly preferred ratio is in the range of 45 to 80% by weight.

The preferable proportion of the compound (4) as the third component is 10% by weight or more based on the weight of the host nematic liquid crystal composition in order to increase the dielectric anisotropy, and the preferable proportion of the compound (4) as the third component is 50% by weight or less in order not to increase the viscosity and not to increase the lower limit temperature.

Fourth, preferred additives and component compounds are shown. Preferred optically active compounds as additives are the compounds (1-1) to (1-6) described in the above item 3. Among these optically active compounds, at least one is preferably the compound (1-2), the compound (1-3), or the compound (1-4). The most preferred optically active compound is (1-4).

Preferred compounds as the first component are the compounds (2-1) to (2-23) described in the above item 5. Of these compounds, at least one is preferably compound (2-1), compound (2-2), compound (2-7), or compound (2-9). Further preferred is compound (2-7).

Preferred compounds as the second component are the compounds (3-1) to (3-27) described in the above item 7. Of these compounds, at least one is preferably compound (3-1), compound (3-6), compound (3-7), compound (3-9), compound (3-17), compound (3-18), compound (3-20), compound (3-23), compound (3-24), compound (3-27), or compound (3-28).

Preferred compounds as the third component are the compounds (4-1) to (4-18) described in the above 9. Of these compounds, it is preferable that at least one is compound (4-2), compound (4-3), compound (4-4), compound (4-5), compound (4-9), compound (4-10), compound (4-14), compound (4-15), compound (4-16), compound (4-18), or compound (4-19). Further preferred is compound (4-2), compound (4-5), compound (4-9), compound (4-15) or compound (4-19).

Fifth, additives that can be added to the composition will be described. Such additives include optically active compounds other than those represented by the formula (1), antioxidants, ultraviolet absorbers, pigments, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds, and the like.

Examples of the optically active compound other than the compound of formula (1) include compounds (5-1) to (5-5). The preferable proportion of the optically active compound other than the compound represented by formula (1) is about 5% by weight or less. A more preferable ratio is in the range of about 0.01 to about 2% by weight.

In order to prevent a decrease in specific resistance due to heating in the atmosphere or to maintain a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after the device is used for a long time, an antioxidant such as the compounds (6-1) to (6-3) may be further added to the composition.

Since the compound (6-2) has low volatility, it is effective for maintaining a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after the device is used for a long time. In order to obtain the above-mentioned effects, the preferable ratio of the antioxidant is about 50ppm or more, and the preferable ratio of the antioxidant is about 600ppm or less so that the upper limit temperature is not lowered or the lower limit temperature is not raised. A more preferable range is about 100ppm to about 300 ppm.

Preferable examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Further, light stabilizers such as sterically hindered amines are also preferred. Preferable examples of the light stabilizer are compound (7-1) to compound (7-16) and the like. The preferable proportion of these absorbents or stabilizers is about 50ppm or more in order to obtain the above effects, and about 10000ppm or less in order not to lower the upper limit temperature or to raise the lower limit temperature. A more preferable range is about 100ppm to about 10000 ppm.

The matting agent is a compound that receives light energy absorbed by the liquid crystalline compound and converts the light energy into thermal energy to prevent decomposition of the liquid crystalline compound. Preferable examples of the matting agent are a compound (8-1) to a compound (8-7), and the like. The preferable proportion of these matting agents is about 50ppm or more in order to obtain the above effects, and about 20000ppm or less in order not to raise the lower limit temperature. A more preferable range is about 100ppm to about 10000 ppm.

Finally, the use of the composition is illustrated. The composition of the present invention has a lower limit temperature of about-10 ℃ or lower, an upper limit temperature of about 70 ℃ or higher, and an optical anisotropy in the range of about 0.10 to about 0.40. The device containing the composition has a large voltage holding ratio. The composition is suitable for liquid crystal elements. The composition is particularly suitable for reflective liquid crystal elements. By controlling the ratio of the component compounds or by mixing other liquid crystalline compounds, a composition having an optical anisotropy in the range of about 0.10 to about 0.20 can be prepared, and a composition having an optical anisotropy in the range of about 0.20 to about 0.30 can also be prepared. The composition can be used as a cholesteric liquid crystal composition by adding an optically active compound.

[ examples ]

The present invention will be further described in detail by way of examples. The present invention is not limited by these examples. The invention also includes mixtures of at least two of the compositions of the examples. The properties of the composition and the device were measured by the following methods.

The determination method comprises the following steps: the characteristics were measured by the following methods. These methods are mostly described in JEITA standard (JEITA. ED-2521B) examined and established by the Japan electronic Information Technology Industries Association (JEITA), or modified. In the tn (twisted nematic) device used for the measurement, a Thin Film Transistor (TFT) was not mounted.

(1) Upper limit temperature of nematic phase (NI;) or cholesteric phase (N;): the sample was placed on a hot plate of a melting point measuring apparatus including a polarizing microscope, and heated at a rate of 1 ℃ per minute. The temperature at which a part of the sample changes from a nematic phase or a cholesteric phase to an isotropic liquid is measured. The upper limit temperature of the nematic phase or the cholesteric phase is sometimes simply referred to as "upper limit temperature".

(2) Lower limit temperature (T) of nematic phase_C(ii) a C.) or the lower temperature (T) of the cholesteric phase_C(ii) a C): a sample having a nematic phase or a cholesteric phase was placed in a glass bottle, and the liquid crystal phase was observed after 10 days in a freezer at 0 ℃, -10 ℃, -20 ℃, -30 ℃ and-40 ℃. For example, when a sample maintains a nematic phase at-20 ℃ and changes to a crystalline or smectic phase at-30 ℃, it is described as T_C< -20 ℃. The lower limit temperature of the nematic phase or cholesteric phase may be simply referred to as "lower limit temperature".

(3) Viscosity (. eta.; measured at 20 ℃ C.; mPas): for the measurement, an E-type rotational viscometer manufactured by tokyo counter gmbh was used.

(4) Optical anisotropy (refractive index anisotropy; Δ n; measured at 25 ℃): the bulk nematic liquid crystal composition was measured using an Abbe refractometer having a polarizer attached to an eyepiece using light having a wavelength of 589 nm. After rubbing the surface of the main prism in one direction, the sample was dropped onto the main prism. The refractive index n/, is measured when the direction of polarization is parallel to the direction of rubbing. And measuring the refractive index n ″) when the direction of the polarized light is vertical to the direction of the friction. The value of the optical anisotropy is calculated from the formula Δ n ═ n/n ″.

(5) Dielectric anisotropy (. DELTA.. di-elect cons.; measured at 25 ℃): the measurement was carried out using a bulk nematic liquid crystal composition. A sample was placed in a TN cell having a cell gap of 9 μm and a twist angle of 80 degrees between two glass substrates. A sine wave (10V, 1kHz) was applied to the cell, and the dielectric constant (. epsilon. /) in the long axis direction of the liquid crystal molecules was measured after 2 seconds. Sine wave (0.5V, 1kHz) was applied to the element, and the dielectric constant (∈ ∈ in the short axis direction of the liquid crystal molecules was measured after 2 seconds. The value of the dielectric anisotropy is calculated according to the formula Δ ∈/∈ j.

(6) Specific resistance (. rho.; measured at 25 ℃ C.;. omega. cm): a1.0 mL sample was placed in the container including the electrodes. A DC voltage (10V) was applied to the vessel, and a DC current after 10 seconds was measured. The specific resistance is calculated according to the following equation. (specific resistance) { (voltage) × (capacitance of container) }/{ (direct current) × (dielectric constant of vacuum) }

(7) Selecting the reflection wavelength (. lamda.; measured at 25 ℃ C.; nm): the selective reflection wavelength λ is measured by a selective reflection method, which is referred to as a pitch length measuring method of 196 pages in the "liquid crystal review" (published in 2000, bod). The apparatus used in the measurement was V650DS (manufactured by JASCO). First, the cells are subjected to a parallel alignment process so that the screw axis is perpendicular to the cells. Linearly polarized light (wavelength: 300nm to 800nm) was incident on the cell at an incident angle of 5 °, the detector was set to-5 °, and the reflected light was measured. In the reflected light, the wavelength of one of the left and right polarization components is specifically reflected. The peak top of the measurement result was defined as 100%, and 2 points of the wavelength at 50% were recorded, and the value obtained by adding the wavelength at 2 points and halving this time was referred to as the selective reflection wavelength.

Examples of compositions are shown below. The liquid crystalline compound is represented by a symbol based on the definition in table 3 below. In Table 3, the configuration of the 1, 4-cyclohexylene group-related stereo-configuration is trans configuration. The numbers in parentheses following the marked compounds indicate the chemical formula to which the compound belongs. The symbol (-) indicates other liquid crystalline compounds. The proportion (percentage) of the liquid crystalline compound is a weight percentage (wt%) based on the weight of the host nematic liquid crystal composition containing no additive. Finally, the values of the properties of the compositions are summarized.

TABLE 3 formulation of Compounds Using symbols

R-(A₁)-Z₁-·····-Z_n-(A_n)-R′

[ example 1]

Bulk nematic liquid Crystal composition A

The physical property value of the main nematic liquid crystal composition A is that NI is 89.1 ℃; specific resistance ρ of 1.0 × 10¹²Ω·cm；Δn＝0.237；Δε＝25.8。

The cholesteric liquid crystal composition a-1, which was obtained by adding 2.616 parts by weight of the compound (1-4-a) shown below to the bulk nematic liquid crystal composition a, had a physical property value of N × I ═ 86.3 ℃; the reflection wavelength was chosen to be 627 nm.

The cholesteric liquid crystal composition a-2, which was prepared by adding 3.030 parts by weight of the compound (1-4-b) shown below to the bulk nematic liquid crystal composition a, had a physical property value of N × I ═ 85.9 ℃; the reflection wavelength was chosen to be 547 nm.

Further, a cholesteric liquid crystal composition a-3, which was obtained by adding 3.710 parts by weight of the compound (1-4-a) shown below to the bulk nematic liquid crystal composition a, had a physical property value of N × I ═ 85.5 ℃; the reflection wavelength was chosen to be 456 nm.

The cholesteric liquid crystal composition a-4, which was obtained by adding 1.78 parts by weight of the compound (1-4-a) shown above to the bulk nematic liquid crystal composition a, had a physical property value of N × I of 86.9 ℃, and the temperature dependence of the selective reflection wavelength was as follows, and the fluctuation of the selective reflection wavelength due to the temperature change was small (0.6nm/° c).

	10℃	20℃	30℃	40℃	50℃	60℃	70℃
								Selective reflection wavelength (nm)	760	755	750	730	725	724	722

Comparative example 1

As for the bulk nematic liquid crystal composition A, cholesteric liquid crystal compositions A-X each containing 30 parts by weight of the optically active compound X were prepared so as to have a selective reflection wavelength equivalent to that of the cholesteric liquid crystal composition A-4. The cholesteric liquid crystal compositions a to X had a physical property value N × I of 58.3 ℃, and a large change in the selective reflection wavelength (4.4nm/° c) due to a change in temperature, as described below, due to the temperature dependence of the selective reflection wavelength.

	20℃	30℃	40℃	50℃	55℃
						SelectingReflection wavelength (nm)	735	650	605	590	580

According to the above-mentioned circumstances, when the compound (1) is used as an optically active compound, the selective reflection wavelength can be adjusted to 350nm to 800nm by adding a small amount, and therefore, not only the physical properties of the nematic liquid crystal composition are not affected, but also the temperature dependency of the selective reflection wavelength is small, and therefore, a cholesteric liquid crystal composition in which the deterioration of the display quality due to the temperature change is suppressed can be produced.

[ example 2]

Bulk nematic liquid crystal composition B

The physical property value of the host nematic liquid crystal composition B is that NI is 88.2 ℃; Δ n ═ 0.233; Δ ∈ 28.6.

The physical properties of the host nematic liquid crystal composition B to which the compound (1-4-a) or the compound (1-4-B) was added were as follows in the same manner as in example 1.

[ example 3]

Host nematic liquid crystal composition C

The physical property value of the host nematic liquid crystal composition C is that NI is 79.8 ℃; Δ n is 0.231; Δ ∈ 20.8.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition C, a cholesteric liquid crystal composition C-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 4]

Host nematic liquid crystal composition D

The physical property value of the host nematic liquid crystal composition D is that NI is 82.0 ℃; Δ n ═ 0.238; Δ ∈ 16.6.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition D, a cholesteric liquid crystal composition D-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 5]

Bulk nematic liquid crystal composition E

The physical property value of the host nematic liquid crystal composition E is that NI is 84.3 ℃; Δ n ═ 0.230; Δ ∈ 26.9.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition E, a cholesteric liquid crystal composition E-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be prepared.

[ example 6]

Bulk nematic liquid crystal composition F

The physical property value of the host nematic liquid crystal composition F is that NI is 84.3 ℃; Δ n is 0.234; Δ ∈ 27.4.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition F, a cholesteric liquid crystal composition F-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 7]

Host nematic liquid crystal composition G

The physical property value of the host nematic liquid crystal composition G is that NI is 85.6 ℃; Δ n is 0.239; Δ ∈ 22.2.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition G, a cholesteric liquid crystal composition G-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 8]

Host nematic liquid crystal composition H

The physical property value of the host nematic liquid crystal composition H is 88.7 ℃; Δ n ═ 0.237; Δ ∈ 24.6.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition H, a cholesteric liquid crystal composition H-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 9]

Bulk nematic liquid-crystal composition I

The physical property value of the host nematic liquid crystal composition I is that NI is 86.1 ℃; Δ n ═ 0.230; Δ ∈ 26.0.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition I, a cholesteric liquid crystal composition I-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be prepared.

[ example 10]

Bulk nematic liquid crystal composition J

The physical property value of the host nematic liquid crystal composition J is that NI is 89.7 ℃; Δ n is 0.232; Δ ∈ 27.3.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition J, a cholesteric liquid crystal composition J-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 11]

Host nematic liquid crystal composition K

The physical property value of the host nematic liquid crystal composition K is 87.1 ℃; Δ n ═ 0.230; Δ ∈ 30.3.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition K, a cholesteric liquid crystal composition K-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 12]

Bulk nematic liquid crystal composition L

The physical property value of the host nematic liquid crystal composition L is that NI is 90.9 ℃; Δ n is 0.239; Δ ∈ 30.2.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition L, a cholesteric liquid crystal composition L-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 13]

Host nematic liquid crystal composition M

The physical property value of the master nematic liquid crystal composition M is that NI is 93.2 ℃; Δ n is 0.240; Δ ∈ 28.4.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition M, a cholesteric liquid crystal composition M-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 14]

Host nematic liquid crystal composition N

The physical property value of the main nematic liquid crystal composition N is 91.9 ℃; Δ n is 0.209; Δ ∈ 30.3.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition N, a cholesteric liquid crystal composition N-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 15]

Bulk nematic liquid crystal composition O

The physical property value of the host nematic liquid crystal composition O is that NI is 90.1 ℃; Δ n is 0.178; Δ ∈ 33.0.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition O, a cholesteric liquid crystal composition O-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 16]

Host nematic liquid crystal composition P

The physical property value of the host nematic liquid crystal composition P is 83.5 ℃; Δ n is 0.170; Δ ∈ 32.1.

The physical property values when the compound (1-4-a) was added to the bulk nematic liquid crystal composition P in the same manner as in example 1 were as follows.

[ example 17]

Bulk nematic liquid crystal composition Q

The physical property value of the host nematic liquid crystal composition Q is that NI is 86.0 ℃; Δ n is 0.148; Δ ∈ 30.0.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition Q, a cholesteric liquid crystal composition Q-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 18]

Host nematic liquid crystal composition R

The physical property value of the host nematic liquid crystal composition R is that NI is 82.8 ℃; Δ n ═ 0.154; Δ ∈ 30.3.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition R, a cholesteric liquid crystal composition R-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 19]

Bulk nematic liquid crystal composition S

The physical property value of the host nematic liquid crystal composition S is that NI is 84.1 ℃; Δ n is 0.151; Δ ∈ 30.0.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition S, a cholesteric liquid crystal composition S-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 20]

Host nematic liquid crystal composition T

The physical property value of the host nematic liquid crystal composition T is 83.5 ℃; Δ n ═ 0.132; Δ ∈ 18.3.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition T, a cholesteric liquid crystal composition T-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 21]

Host nematic liquid crystal composition U

The physical property value of the host nematic liquid crystal composition U is that NI is 83.0 ℃; Δ n is 0.131; Δ ∈ 20.2.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition U, a cholesteric liquid crystal composition U-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 22]

Bulk nematic liquid crystal composition V

The physical property value of the host nematic liquid crystal composition V is that NI is 83.9 ℃; Δ n ═ 0.132; Δ ∈ 20.6.

The physical property values when the compound (1-4-a) was added to the bulk nematic liquid crystal composition V in the same manner as in example 1 were as follows.

[ example 23]

Bulk nematic liquid crystal composition W

The physical property value of the host nematic liquid crystal composition W is that NI is 85.1 ℃; Δ n ═ 0.228; Δ ∈ 26.5.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition W, a cholesteric liquid crystal composition W-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be prepared.

[ example 24]

Host nematic liquid crystal composition X

The physical property value of the host nematic liquid crystal composition X is that NI is 86.8 ℃; Δ n is 0.223; Δ ∈ 29.4.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition X, a cholesteric liquid crystal composition X-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 25]

Bulk nematic liquid crystal composition Y

The physical property value of the host nematic liquid crystal composition Y is 87.5 ℃; Δ n is 0.221; Δ ∈ 28.7.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition Y, a cholesteric liquid crystal composition Y-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

[ example 26]

Bulk nematic liquid crystal composition Z

The physical property value of the host nematic liquid crystal composition Z is 91.0 ℃; Δ n ═ 0.233; Δ ∈ 30.2.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition Z, a cholesteric liquid crystal composition Z-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be prepared.

[ example 27]

Bulk nematic liquid crystal composition AA

The physical property value of the main nematic liquid crystal composition AA is that NI is 89.6 ℃; Δ n is 0.211; Δ ∈ 30.6.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition AA, a cholesteric liquid crystal composition AA-1 whose selective reflection wavelength is adjusted to 350 to 800nm, or the like can be prepared.

[ example 28]

Bulk nematic liquid crystal composition BB

The physical property value of the bulk nematic liquid crystal composition BB is NI 82.6 ℃; Δ n is 0.200; Δ ∈ 24.6.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the bulk nematic liquid crystal composition BB, a cholesteric liquid crystal composition BB-1 whose selective reflection wavelength is adjusted to 350 to 800nm, or the like can be produced.

[ example 29]

Bulk nematic liquid crystal composition CC

The physical property value of the host nematic liquid crystal composition CC is that NI is 83.5 ℃; Δ n ═ 0.219; Δ ∈ 24.8.

By adding 2.5 to 4.0 parts by weight of the compound (1-4-a) or the compound (1-4-b) described above to the nematic host liquid crystal composition CC, a cholesteric liquid crystal composition CC-1 having a selective reflection wavelength adjusted to 350 to 800nm, or the like can be produced.

Compared with the comparative example, the optically active compound showed selective reflection with a small amount of addition, and the temperature dependence of the selective reflection wavelength was suppressed to be low, so that N × I could be maintained at a high temperature, and cholesteric liquid crystals having large Δ N and Δ ∈couldbe obtained.