TW202035380A - Liquid crystal composition, display element and compound - Google Patents
Liquid crystal composition, display element and compound Download PDFInfo
- Publication number
- TW202035380A TW202035380A TW108143139A TW108143139A TW202035380A TW 202035380 A TW202035380 A TW 202035380A TW 108143139 A TW108143139 A TW 108143139A TW 108143139 A TW108143139 A TW 108143139A TW 202035380 A TW202035380 A TW 202035380A
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- group
- coo
- oco
- carbon atoms
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
-
- 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
- C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
-
- 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
- C09K19/28—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and sulfur atoms as chain links, e.g. thioesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
本發明係關於一種經改善波長色散性之液晶組成物及使用該液晶組成物之顯示元件、以及化合物。The present invention relates to a liquid crystal composition with improved wavelength dispersion, a display element using the liquid crystal composition, and a compound.
垂直配向型液晶顯示元件之特徵在於高對比度,而廣泛用於電視等製品中。然而,於自正面觀察該顯示元件之情形時及自斜側觀察該顯示元件之情形時,存在色調及色度等發生變化之問題。Vertical alignment type liquid crystal display elements are characterized by high contrast, and are widely used in products such as televisions. However, when the display element is viewed from the front and the display element is viewed from an oblique side, there is a problem that the hue and chromaticity change.
於以對於液晶組成物之入射光之波長λ為橫軸且以其折射率異向性(∆n)為縱軸而繪製之曲線圖中,當波長(λ)越短則折射率各向異性(∆n)越大之情形時,其液晶組成物可謂「正波長色散性」或「正色散性」,當波長(λ)越短則折射率各向異性(∆n)越小之情形時,其液晶組成物可謂「反波長色散性」或「反色散性」。液晶顯示元件中使用之驅動用液晶組成物為正色散性,因此,產生了上述問題。此前,報告有如下情況,即根據模擬結果,藉由使用具有反色散性之液晶材料,得以解決上述問題(專利文獻1)。然而,關於滿足對顯示器製品要求之各種物性且具有反色散性之液晶組成物,尚不存在報告例,要求開發此種液晶組成物。 先前技術文獻 專利文獻In a graph drawn with the wavelength λ of incident light to the liquid crystal composition as the horizontal axis and its refractive index anisotropy (∆n) as the vertical axis, the shorter the wavelength (λ), the refractive index anisotropy When the (∆n) is larger, the liquid crystal composition can be described as "positive wavelength dispersion" or "positive dispersion". When the wavelength (λ) is shorter, the refractive index anisotropy (∆n) is smaller The liquid crystal composition can be described as "inverse wavelength dispersion" or "inverse dispersion." The driving liquid crystal composition used in the liquid crystal display element is positively dispersive, and therefore, the above-mentioned problem occurs. Previously, it was reported that the above-mentioned problem was solved by using a liquid crystal material with anti-dispersion properties based on simulation results (Patent Document 1). However, there are no reported examples of liquid crystal compositions that satisfy various physical properties required for display products and have anti-dispersion properties, and the development of such liquid crystal compositions is required. Prior art literature Patent literature
專利文獻1:日本特開2018-105908號公報Patent Document 1: Japanese Patent Application Publication No. 2018-105908
[發明所欲解決之課題][The problem to be solved by the invention]
本發明所欲解決之課題在於提供一種波長色散性得到改善之主動驅動顯示元件用液晶組成物及使用該液晶組成物之顯示元件、以及化合物。 [解決課題之技術手段]The problem to be solved by the present invention is to provide a liquid crystal composition for an active display element with improved wavelength dispersion, a display element using the liquid crystal composition, and a compound. [Technical means to solve the problem]
本發明人等為了解決上述問題而進行了努力研究,結果完成了特定之液晶組成物之開發。即,本案發明提供一種主動驅動顯示元件用液晶組成物,其特徵在於:含有至少1種於垂直於分子長軸之方向上具有基(ZG)之化合物(Z),該基(ZG)具有大之波長色散性;本案發明並提供一種使用該液晶組成物之顯示元件、以及該化合物。 [發明之效果]The inventors of the present invention have made diligent studies to solve the above-mentioned problems, and as a result, completed the development of a specific liquid crystal composition. That is, the present invention provides a liquid crystal composition for actively driving display elements, which is characterized by containing at least one compound (Z) having a group (ZG) in a direction perpendicular to the long axis of the molecule, and the group (ZG) has a large The wavelength dispersion; the present invention also provides a display element using the liquid crystal composition and the compound. [Effects of Invention]
本案發明之液晶組成物於用於顯示元件之情形時,因電壓施加造成液晶配向變化時色調及色度等之變化較小,因此作為液晶顯示元件用之材料有用。When the liquid crystal composition of the present invention is used in a display device, the change in color tone and chromaticity when the alignment of the liquid crystal changes due to voltage application is small, so it is useful as a material for a liquid crystal display device.
本案發明之液晶組成物係主動驅動顯示元件用液晶組成物,其特徵在於:含有至少1種於垂直於分子長軸之方向上具有基(ZG)之化合物(Z),該基(ZG)具有大之波長色散性。就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,化合物(Z)較佳為由具有小之波長色散性之基(LA及LB)及具有大之波長色散性之基(ZG)(圖1)構成。將概念性地表示構成化合物(Z)之各基(LA、LB及ZG)之波長色散性之曲線圖示於圖2。The liquid crystal composition of the present invention is a liquid crystal composition for actively driving display elements, and is characterized in that it contains at least one compound (Z) having a group (ZG) in the direction perpendicular to the long axis of the molecule, and the group (ZG) has Large wavelength dispersion. From the viewpoints of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound (Z) is preferably composed of groups with small wavelength dispersion (LA and LB) and groups (ZG) with large wavelength dispersion (Figure 1). A graph conceptually showing the wavelength dispersion of each group (LA, LB, and ZG) constituting the compound (Z) is shown in FIG. 2.
於圖1中,基(LA及LB)分別意指表現小之波長色散性,基(ZG)意指表現大之波長色散性。化合物(Z)較佳為於分子長軸方向上具有基(LA及LB),於垂直於分子長軸之方向上具有基(ZG),上述基(LA及LB)具有小之波長色散性,上述基(ZG)具有大之波長色散性。將概念性地表示化合物(Z)之結構示於圖3。In Figure 1, base (LA and LB) respectively means small wavelength dispersion, and base (ZG) means large wavelength dispersion. The compound (Z) preferably has groups (LA and LB) in the direction of the long axis of the molecule, and groups (ZG) in the direction perpendicular to the long axis of the molecule. The above groups (LA and LB) have small wavelength dispersion. The above-mentioned base (ZG) has a large wavelength dispersion. The structure of the compound (Z) conceptually is shown in FIG. 3.
於圖3記載之結構中,各基(LA、LB及ZG)可藉由單鍵、雙鍵或三鍵而鍵結,亦可經由2價之連結基而鍵結,亦可形成相同之縮合環系。又,基(ZG)可於基(LA及LB)與基(ZG)之中央部鍵結,亦可於基(ZG)之端部鍵結。此處,所謂化合物(Z)中之「分子長軸」,係指於添加至由棒狀液晶化合物構成之液晶組成物之情形時,與棒狀液晶化合物之分子長軸一致之軸。所謂「於分子長軸方向上具有基(LA及LB),上述基(LA及LB)具有較小之波長色散性」,係指於將化合物(Z)添加至由棒狀液晶化合物構成之液晶組成物之情形時,包含基(LA及LB)之軸與棒狀液晶化合物之分子長軸一致。更具體而言,化合物(Z)較佳為下述通式(I)所表示之化合物,In the structure described in Figure 3, each group (LA, LB, and ZG) can be bonded by a single bond, a double bond, or a triple bond, or can be bonded via a divalent linking group, or form the same condensation Ring system. In addition, the base (ZG) can be bonded at the center of the base (LA and LB) and the base (ZG), or at the end of the base (ZG). Here, the “longer axis of the molecule” in the compound (Z) refers to the axis that coincides with the long axis of the molecule of the rod-shaped liquid crystal compound when it is added to a liquid crystal composition composed of a rod-shaped liquid crystal compound. The so-called "has groups (LA and LB) in the direction of the long axis of the molecule, and the aforementioned groups (LA and LB) have small wavelength dispersion"," refers to the addition of compound (Z) to a liquid crystal composed of a rod-shaped liquid crystal compound In the case of the composition, the axis containing the groups (LA and LB) coincides with the long axis of the molecule of the rod-shaped liquid crystal compound. More specifically, the compound (Z) is preferably a compound represented by the following general formula (I),
(式中,R11 及R12 各自獨立地表示碳原子數1至8之烷基、碳原子數1至7之烷氧基、碳原子數2至8之烯基或碳原子數2至7之烯氧基, A11 及A13 各自獨立地表示選自下述式(A1-1)至式(A1-11)之基。(In the formula, R 11 and R 12 each independently represent an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an alkenyl group with 2 to 8 carbon atoms or 2 to 7 carbon atoms For the alkenyloxy group, A 11 and A 13 each independently represent a group selected from the following formula (A1-1) to formula (A1-11).
(式中,虛線表示鍵結位置),於存在複數個A11 之情形時,其等可相同亦可不同,於存在複數個A13 之情形時,其等可相同亦可不同, A12 表示具有大之波長色散性之基(ZG),但基(ZG)朝向大致垂直於通式(I)所表示之化合物之分子長軸之方向, Z11 及Z12 各自獨立地表示-O-、-S-、-OCH2 -、-CH2 O-、-CH2 CH2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2 -、-CH2 S-、-CF2 O-、-OCF2 -、-CF2 S-、-SCF2 -、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2 CH2 -、-OCO-CH2 CH2 -、-CH2 CH2 -COO-、-CH2 CH2 -OCO-、-COO-CH2 -、-OCO-CH2 -、-CH2 -COO-、-CH2 -OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z11 之情形時,其等可相同亦可不同,於存在複數個Z12 之情形時,其等可相同亦可不同, m11及m12各自獨立地表示0至5之整數,但m11+m12表示0至5之整數)。(In the formula, the dotted line indicates the bonding position). When there are a plurality of A 11 , they can be the same or different. When there are a plurality of A 13s , they can be the same or different. A 12 means A group (ZG) with large wavelength dispersion, but the group (ZG) faces a direction roughly perpendicular to the molecular long axis of the compound represented by the general formula (I). Z 11 and Z 12 each independently represent -O-, -S-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO -O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH=CH-COO-, -CH=CH-OCO-, -COO- CH=CH-, -OCO-CH=CH-, -COO-CH 2 CH 2 -, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO-, -CH 2 CH 2 -OCO-,- COO-CH 2 -, -OCO-CH 2 -, -CH 2 -COO-, -CH 2 -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH- , -CH=NN=CH-, -CF=CF-, -C≡C- or single bond, but when there are plural Z 11 , they can be the same or different. When there are plural Z 12 In the case, they may be the same or different, m11 and m12 each independently represent an integer from 0 to 5, but m11+m12 represents an integer from 0 to 5).
於通式(I)中,A12 表示具有大之波長色散性之基(ZG),但基(ZG)朝向垂直於通式(I)所表示之化合物之分子長軸之方向。就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,A12 較佳為表示選自下述式(A12-1)至式(A12-4)之基。In the general formula (I), A 12 represents a group (ZG) with large wavelength dispersion, but the group (ZG) faces a direction perpendicular to the molecular long axis of the compound represented by the general formula (I). From the viewpoint of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, A 12 preferably represents a group selected from the following formula (A12-1) to formula (A12-4).
(式中,虛線表示鍵結位置,B1 表示亦可進而具有縮合環之5員環,B2 表示亦可進而具有縮合環之6員環,式(A12-1)至式(A12-4)所表示之基可經取代,任意之-CH=可各自獨立地被取代為-N=,-CH2 -可各自獨立地被取代為-O-、-S-、-NRT -(式中,RT 表示氫原子、碳原子數1至20之烷基、碳原子數6至20之芳香族基或碳原子數3至20之雜芳基)、-CS-或-CO-),A12 更佳為表示選自下述式(A12-1-1)至式(A12-4-9)之基。(In the formula, the dotted line represents the bonding position, B 1 represents a 5-membered ring that may further have a condensed ring, B 2 represents a 6-membered ring that may further have a condensed ring, formula (A12-1) to formula (A12-4 The group represented by) may be substituted, any -CH= may be independently substituted with -N=, -CH 2 -may be independently substituted with -O-, -S-, -NR T- (formula Where R T represents a hydrogen atom, an alkyl group with 1 to 20 carbon atoms, an aromatic group with 6 to 20 carbon atoms or a heteroaryl group with 3 to 20 carbon atoms), -CS- or -CO-), More preferably, A 12 represents a group selected from the following formula (A12-1-1) to formula (A12-4-9).
(式中,虛線表示鍵結位置,該等基可經取代,任意之-CH=可各自獨立地被取代為-N=,-CH2 -可各自獨立地被取代為-O-、-S-、-NRT1 -(式中,RT1 表示氫原子、碳原子數1至5之烷基、碳原子數6至10之芳香族基或碳原子數3至10之雜芳基)、-CS-或-CO-),A12 進而較佳為表示選自下述式(A122-1-1)至式(A122-3-3)之基。(In the formula, the dotted line indicates the bonding position, the groups can be substituted, any -CH= can be independently substituted with -N=, -CH 2 -can be independently substituted with -O-, -S -, -NR T1- (In the formula, R T1 represents a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, an aromatic group with 6 to 10 carbon atoms or a heteroaryl group with 3 to 10 carbon atoms),- CS- or -CO-), A 12 further preferably represents a group selected from the following formula (A122-1-1) to formula (A122-3-3).
(式中,虛線表示鍵結位置,該等基可經取代,任意之-CH=可各自獨立地被取代為-N=,-CH2 -可各自獨立地被取代為-O-、-S-、-NRT11 -(式中,RT11 表示碳原子數1至5之烷基、碳原子數6至9之芳香族基或碳原子數3至9之雜芳基)、-CS-或-CO-),A12 進而更佳為表示選自下述式(A123-1)至式(A123-8)之基。(In the formula, the dotted line indicates the bonding position, the groups can be substituted, any -CH= can be independently substituted with -N=, -CH 2 -can be independently substituted with -O-, -S -, -NR T11- (wherein, R T11 represents an alkyl group with 1 to 5 carbon atoms, an aromatic group with 6 to 9 carbon atoms or a heteroaryl group with 3 to 9 carbon atoms), -CS- or -CO-), A 12 more preferably represents a group selected from the following formula (A123-1) to formula (A123-8).
(式中,虛線表示鍵結位置,該等基可未經取代或經1個以上之取代基LG 取代,T1 表示選自下述式(T1-1)至式(T1-6)之基。(In the formula, the dotted line indicates the bonding position. The groups may be unsubstituted or substituted by one or more substituents L G. T 1 represents a group selected from the following formula (T1-1) to formula (T1-6) base.
(式中,於任意位置具有1個鍵結鍵,任意之-CH=可各自獨立地被取代為-N=,-CH2 -可各自獨立地被取代為-O-或-S-。此處,所謂於任意位置具有1個鍵結鍵,例如,於式(T1-1)與式(A123-1)至式(A123-8)之T1 鍵結之情形時,意圖於式(T1-1)之任意位置具有1個鍵結鍵(以下,於本發明中,於任意位置具有鍵結鍵表示相同之含義)。又,該等基可未經取代或經1個以上之取代基LG 取代), LG 表示鹵素原子、氰基、硝基、五氟甲硫烷基(pentafluorosulfanyl)、可經取代之胺基、可經取代之矽基、任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之烷基),A12 進而更佳為表示選自下述式(A124-1)至式(A124-4)之基。(In the formula, there is 1 bonding bond at any position, any -CH= can be independently substituted with -N=, and -CH 2 -can be independently substituted with -O- or -S-. This at an arbitrary position in the so-called bonded having a bond, for example, when the knot in the case of formula (T1 - 1) and formula (A123-1) T to formula (A123-8) of a key, intended to formula (T1 -1) has one bonding bond at any position (hereinafter, in the present invention, a bonding bond at any position means the same meaning). In addition, these groups may be unsubstituted or substituted with more than one substituent L G substitution), L G represents a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group (pentafluorosulfanyl), a substituted amino group, a substituted silyl group, any hydrogen atom may be substituted with fluorine Atoms and 1 -CH 2 -or 2 or more non-adjacent -CH 2 -can be independently substituted into -O-, -S-, -CO-, -COO-, -OCO-, -CO -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH =CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- alkyl group with 1 to 20 carbon atoms), A 12 is more preferably selected from The following formula (A124-1) to the base of formula (A124-4).
(式中,虛線表示鍵結位置,該等基可未經取代或經1個以上之取代基LG1 取代,T11 表示選自下述式(T11-1)至式(T11-3)之基。(In the formula, the dashed line indicates the bonding position, the groups may be unsubstituted or substituted by one or more substituents L G1 , and T 11 is selected from the following formula (T11-1) to formula (T11-3) base.
(式中,於任意位置具有1個鍵結鍵,該等基可未經取代或經1個以上之取代基LG1 取代),LG1 表示氟原子、氯原子、五氟甲硫烷基、任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-COO-、-OCO-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至10之烷基),A12 尤佳為表示選自下述式(A125-1)至式(A125-4)之基。(In the formula, there is one bonding bond at any position, and these groups may be unsubstituted or substituted by one or more substituents L G1 ), L G1 represents a fluorine atom, a chlorine atom, a pentafluoromethylsulfanyl group, Any hydrogen atom can be substituted with a fluorine atom and one -CH 2 -or two or more non-adjacent -CH 2 -s can be independently substituted with -O-, -S-, -COO-,- OCO-, -CH=CH-, -CF=CF- or -C≡C- alkyl group with 1 to 10 carbon atoms), A 12 is particularly preferably selected from the following formula (A125-1) to formula (A125-4) basis.
(式中,虛線表示鍵結位置,T12 表示選自下述式(T12-1)及式(T12-2)之基。(In the formula, the dotted line represents the bonding position, and T 12 represents a group selected from the following formulas (T12-1) and (T12-2).
(式中,於任意位置具有1個鍵結鍵,該等基可未經取代或經1個以上之取代基LG2 取代),但LG2 表示氟原子、五氟甲硫烷基、任意之氫原子可被取代為氟原子且1個-CH2 -可被取代為-O-或-CH=CH-之碳原子數1至5之烷基)。(In the formula, there is one bond at any position, and these groups may be unsubstituted or substituted by one or more substituents L G2 ), but L G2 represents a fluorine atom, a pentafluoromethylsulfanyl group, any The hydrogen atom may be substituted with a fluorine atom and one -CH 2 -may be substituted with -O- or -CH=CH- (alkyl group with 1 to 5 carbon atoms).
通式(I)所表示之化合物就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,較佳為下述通式(I-i)所表示之化合物。The compound represented by the general formula (I) changes the color tone and chromaticity when the liquid crystal alignment changes due to voltage application, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric anisotropy, rotational viscosity and From the viewpoint of the modulus of elasticity, the compound represented by the following general formula (Ii) is preferred.
(式中,R111 及R121 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基、碳原子數2至5之烯基或碳原子數2至4之烯氧基, A111 及A131 各自獨立地表示選自下述式(A11-1)至式(A11-9)之基。(In the formula, R 111 and R 121 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 5 carbon atoms or 2 to 4 carbon atoms For the alkenyloxy group, A 111 and A 131 each independently represent a group selected from the following formula (A11-1) to formula (A11-9).
(式中,虛線表示鍵結位置),但於存在複數個A111 之情形時,其等可相同亦可不同,於存在複數個A131 之情形時,其等可相同亦可不同, A121 表示選自上述式(A12-1-1)至式(A12-4-9)之基, Z111 及Z12 1 各自獨立地表示-OCH2 -、-CH2 O-、-CH2 CH2 -、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH=CH-COO-、-OCO-CH=CH-、-CH=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z111 之情形時,其等可相同亦可不同,於存在複數個Z12 1 之情形時,其等可相同亦可不同, m111及m121各自獨立地表示1至4之整數,但m111+m121表示1至4之整數)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 111 , they can be the same or different; when there are a plurality of A 131 , they can be the same or different, A 121 Represents a group selected from the above formula (A12-1-1) to formula (A12-4-9), Z 111 and Z 12 1 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH- , -CF=CF-, -C≡C- or single bond, but when there are plural Z 111 , they can be the same or different, when there are plural Z 12 1 , they can be the same It may be different, m111 and m121 each independently represent an integer from 1 to 4, but m111+m121 represents an integer from 1 to 4).
通式(I)所表示之化合物更佳為下述通式(I-ii)所表示之化合物。The compound represented by the general formula (I) is more preferably a compound represented by the following general formula (I-ii).
(式中,R112 及R122 各自獨立地表示碳原子數1至4之烷基、碳原子數1至3之烷氧基、碳原子數2至4之烯基或碳原子數2至3之烯氧基, A112 及A132 各自獨立地表示選自下述式(A112-1)至式(A112-7)之基。(In the formula, R 112 and R 122 each independently represent an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 3 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, or 2 to 3 carbon atoms. For the alkenyloxy group, A 112 and A 132 each independently represent a group selected from the following formula (A112-1) to formula (A112-7).
(式中,虛線表示鍵結位置),但於存在複數個A112 之情形時,其等可相同亦可不同,於存在複數個A132 之情形時,其等可相同亦可不同, A122 表示選自上述式(A122-1-1)至式(A122-3-3)之基, Z112 及Z12 2 各自獨立地表示-OCH2 -、-CH2 O-、-CH2 CH2 -、-COO-、-OCO-、-CF2 O-、-OCF2 -或單鍵,但於存在複數個Z112 之情形時,其等可相同亦可不同,於存在複數個Z12 2 之情形時,其等可相同亦可不同,m112及m122各自獨立地表示1、2或3,但m112+m122表示1至4之整數)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 112 , they can be the same or different; when there are a plurality of A 132 , they can be the same or different, A 122 Represents a group selected from the above formula (A122-1-1) to formula (A122-3-3), Z 112 and Z 12 2 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 -or a single bond, but when there are plural Z 112 , they may be the same or different. When there are plural Z 12 2 In this case, they may be the same or different, m112 and m122 each independently represent 1, 2 or 3, but m112+m122 represents an integer from 1 to 4).
通式(I)所表示之化合物進而較佳為下述通式(I-iii)所表示之化合物。The compound represented by general formula (I) is more preferably a compound represented by the following general formula (I-iii).
(式中,R113 及R123 各自獨立地表示碳原子數1至3之烷基、碳原子數1或2之烷氧基或碳原子數2至3之烯基, A113 及A133 各自獨立地表示選自下述式(A113-1)至式(A113-5)之基。(In the formula, R 113 and R 123 each independently represent an alkyl group with 1 to 3 carbon atoms, an alkoxy group with 1 or 2 carbon atoms, or an alkenyl group with 2 to 3 carbon atoms. A 113 and A 133 each independently It independently represents a group selected from the following formula (A113-1) to formula (A113-5).
(式中,虛線表示鍵結位置),但於存在複數個A113 之情形時,其等可相同亦可不同,於存在複數個A133 之情形時,其等可相同亦可不同, A123 表示選自上述式(A123-1)至式(A123-8)之基, Z113 及Z12 3 各自獨立地表示-OCH2 -、-CH2 O-、-CF2 O-、-OCF2 -或單鍵,但於存在複數個Z113 之情形時,其等可相同亦可不同,於存在複數個Z12 3 之情形時,其等可相同亦可不同, m113及m123各自獨立地表示1或2,但m113+m123表示2、3或4)。(In the formula, the dotted line indicates the bonding position), but when there are multiple A 113s , they can be the same or different. When there are multiple A 133s , they can be the same or different. A 123 Represents a group selected from the above formula (A123-1) to formula (A123-8), Z 113 and Z 12 3 each independently represent -OCH 2 -, -CH 2 O-, -CF 2 O-, -OCF 2 -Or single bond, but when there are multiple Z 113 , they can be the same or different, when there are multiple Z 12 3 , they can be the same or different, m113 and m123 each independently represents 1 or 2, but m113+m123 represents 2, 3 or 4).
通式(I)所表示之化合物進而更佳為選自由下述通式(I-iv-1)至通式(I-iv-4)所表示之化合物所組成之群中之化合物。The compound represented by general formula (I) is more preferably a compound selected from the group consisting of compounds represented by the following general formula (I-iv-1) to general formula (I-iv-4).
(式中,R114 及R124 各自獨立地表示碳原子數1至3之烷基、碳原子數1或2之烷氧基或碳原子數2或3之烯基, A114 及A134 各自獨立地表示選自下述式(A114-1)至式(A114-5)之基。(In the formula, R 114 and R 124 each independently represent an alkyl group with 1 to 3 carbon atoms, an alkoxy group with 1 or 2 carbon atoms, or an alkenyl group with 2 or 3 carbon atoms. A 114 and A 134 each independently It independently represents a group selected from the following formula (A114-1) to formula (A114-5).
(式中,虛線表示鍵結位置),但於存在複數個A114 之情形時,其等可相同亦可不同,於存在複數個A134 之情形時,其等可相同亦可不同, A124 表示選自上述式(A124-1)至式(A124-4)之基, Z1141 、Z1142 、Z12 41 及Z12 42 各自獨立地表示-OCH2 -、-CH2 O-、-CF2 O-、-OCF2 -或單鍵)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 114 , they can be the same or different; when there are a plurality of A 134 , they can be the same or different, A 124 Represents a group selected from the above formula (A124-1) to formula (A124-4), Z 1141 , Z 1142 , Z 12 41 and Z 12 42 each independently represent -OCH 2 -, -CH 2 O-, -CF 2 O-, -OCF 2 -or single bond).
通式(I)所表示之化合物尤佳為選自由下述通式(I-v-1)及通式(I-v-2)所表示之化合物所組成之群中之化合物。The compound represented by the general formula (I) is particularly preferably a compound selected from the group consisting of compounds represented by the following general formula (I-v-1) and general formula (I-v-2).
(式中,R115 及R125 各自獨立地表示碳原子數1至3之烷基、碳原子數1或2之烷氧基或碳原子數2或3之烯基, A125 表示選自上述式(A125-1)至式(A125-4)之基, Z115 及Z12 5 各自獨立地表示-OCH2 -、-CH2 O-或單鍵)。(In the formula, R 115 and R 125 each independently represent an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or an alkenyl group having 2 or 3 carbon atoms, and A 125 represents selected from the above In the base of formula (A125-1) to formula (A125-4), Z 115 and Z 12 5 each independently represent -OCH 2 -, -CH 2 O- or a single bond).
作為通式(I)所表示之化合物,具體而言,可列舉下述式(I-1)至式(I-30)。As the compound represented by general formula (I), specifically, the following formula (I-1) to formula (I-30) can be cited.
所表示之化合物。The compound represented.
於本案發明之液晶組成物含有通式(I)所表示之化合物之情形時,可含有通式(I)所表示之1種化合物,亦可含有通式(I)所表示之複數種化合物。於本案發明之液晶組成物含有通式(I)所表示之化合物之情形時,液晶組成物中之通式(I)所表示之化合物之含量之合計較佳為5質量%以上且95質量%以下,更佳為6質量%以上且40質量%以下,進而較佳為8質量%以上且37質量%以下,進而更佳為12質量%以上且33質量%以下,尤佳為20質量%以上且25質量%以下。此處,所謂「通式(I)所表示之化合物之含量之合計」,於液晶組成物含有通式(I)所表示之1種化合物之情形時,係指通式(I)所表示之化合物之含量,於液晶組成物含有通式(I)所表示之複數種化合物之情形時,係指通式(I)所表示之複數種化合物之含量之合計。When the liquid crystal composition of the present invention contains a compound represented by the general formula (I), it may contain one compound represented by the general formula (I), or may contain a plurality of compounds represented by the general formula (I). When the liquid crystal composition of the present invention contains the compound represented by the general formula (I), the total content of the compound represented by the general formula (I) in the liquid crystal composition is preferably 5% by mass or more and 95% by mass Below, more preferably 6 mass% or more and 40 mass% or less, still more preferably 8 mass% or more and 37 mass% or less, still more preferably 12 mass% or more and 33 mass% or less, particularly preferably 20 mass% or more And 25% by mass or less. Here, the "total of the contents of the compounds represented by the general formula (I)" refers to those represented by the general formula (I) when the liquid crystal composition contains one compound represented by the general formula (I) The content of the compound, when the liquid crystal composition contains multiple compounds represented by the general formula (I), refers to the total content of the multiple compounds represented by the general formula (I).
本案發明之液晶組成物較佳為含有下述通式(III)所表示之化合物。The liquid crystal composition of the present invention preferably contains a compound represented by the following general formula (III).
(式中,R31 及R32 各自獨立地表示碳原子數1至8之烷基、碳原子數1至7之烷氧基、碳原子數2至8之烯基或碳原子數2至7之烯氧基, A31 及A32 各自獨立地表示選自下述式(A3-1)至式(A3-8)之基。(In the formula, R 31 and R 32 each independently represent an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an alkenyl group with 2 to 8 carbon atoms or 2 to 7 carbon atoms For the alkenyloxy group, A 31 and A 32 each independently represent a group selected from the following formula (A3-1) to formula (A3-8).
(式中,虛線表示鍵結位置),但於存在複數個A32 之情形時,其等可相同亦可不同, m31表示1至4之整數)。就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,通式(III)所表示之化合物較佳為下述通式(III-i)所表示之化合物。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 32 , they may be the same or different, and m31 indicates an integer from 1 to 4). From the viewpoints of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, The compound represented by formula (III) is preferably a compound represented by the following general formula (III-i).
(式中,R311 及R321 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基、碳原子數2至5之烯基或碳原子數2至4之烯氧基, A311 及A321 各自獨立地表示選自下述式(A31-1)至式(A31-6)之基。(In the formula, R 311 and R 321 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 5 carbon atoms, or 2 to 4 carbon atoms. For the alkenyloxy group, A 311 and A 321 each independently represent a group selected from the following formula (A31-1) to formula (A31-6).
(式中,虛線表示鍵結位置),但於存在複數個A321 之情形時,其等可相同亦可不同, m311表示1至3之整數),通式(III)所表示之化合物更佳為下述通式(III-ii)所表示之化合物。When (wherein the broken line represents a bonding position), but in the case of the presence of a plurality of A 321, and the like which may be identical or different, M311 represents an integer of 1-3), a compound of formula (III) more preferably represented by the It is a compound represented by the following general formula (III-ii).
(式中,R312 及R322 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基、碳原子數2至5之烯基或碳原子數2至4之烯氧基, A312 及A322 各自獨立地表示選自下述式(A32-1)至式(A32-4)之基。(In the formula, R 312 and R 322 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 5 carbon atoms, or 2 to 4 carbon atoms. For the alkenyloxy group, A 312 and A 322 each independently represent a group selected from the following formula (A32-1) to formula (A32-4).
(式中,虛線表示鍵結位置),但於存在複數個A322 之情形時,其等可相同亦可不同, m312表示1或2),通式(III)所表示之化合物進而較佳為下述通式(III-iii)所表示之化合物。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 322 , they can be the same or different, m312 represents 1 or 2), the compound represented by general formula (III) is more preferably A compound represented by the following general formula (III-iii).
(式中,R313 及R323 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基或碳原子數2至5之烯基, A313 及A323 各自獨立地表示選自下述式(A33-1)及式(A33-2)之基。(In the formula, R 313 and R 323 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 2 to 5 carbon atoms. A 313 and A 323 each independently It independently represents a group selected from the following formula (A33-1) and formula (A33-2).
(式中,虛線表示鍵結位置),但於存在複數個A323 之情形時,其等可相同亦可不同, m313表示1或2),通式(III)所表示之化合物尤佳為選自由下述通式(III-iv-1)至通式(III-iv-10)所表示之化合物所組成之群中之化合物。When (wherein the broken line represents a bonding position), but in the case of the presence of a plurality of A 323, and the like which may be identical or different, M313 represents 1 or 2), a compound of formula (III) is particularly preferably selected from the group represented by the Compounds from the group consisting of compounds represented by the following general formula (III-iv-1) to general formula (III-iv-10).
(式中,R314 及R324 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基或碳原子數2至5之烯基)。(In the formula, R 314 and R 324 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms).
於本案發明之液晶組成物含有通式(III)所表示之化合物之情形時,可含有通式(III)所表示之1種化合物,亦可含有通式(III)所表示之複數種化合物。於本案發明之液晶組成物含有通式(III)所表示之化合物之情形時,液晶組成物中之通式(III)所表示之化合物之含量之合計較佳為5質量%以上且95質量%以下,更佳為8質量%以上且55質量%以下,進而較佳為10質量%以上且50質量%以下,進而更佳為15質量%以上且45質量%以下,尤佳為20質量%以上且40質量%以下。此處,所謂「通式(III)所表示之化合物之含量之合計」,於液晶組成物含有通式(III)所表示之1種化合物之情形時,係指通式(III)所表示之化合物之含量,於液晶組成物含有通式(III)所表示之複數種化合物之情形時,係指通式(III)所表示之複數種化合物之含量之合計。When the liquid crystal composition of the present invention contains a compound represented by the general formula (III), it may contain one compound represented by the general formula (III), or may contain a plurality of compounds represented by the general formula (III). When the liquid crystal composition of the present invention contains the compound represented by the general formula (III), the total content of the compound represented by the general formula (III) in the liquid crystal composition is preferably 5% by mass or more and 95% by mass Below, more preferably 8% by mass or more and 55% by mass or less, still more preferably 10% by mass or more and 50% by mass or less, still more preferably 15% by mass or more and 45% by mass or less, particularly preferably 20% by mass or more And 40% by mass or less. Here, the "total of the contents of the compounds represented by the general formula (III)" refers to those represented by the general formula (III) when the liquid crystal composition contains one compound represented by the general formula (III) The content of the compound, when the liquid crystal composition contains multiple compounds represented by the general formula (III), refers to the total content of the multiple compounds represented by the general formula (III).
本案發明之液晶組成物較佳為介電各向異性(∆ε)為-5.0以上且-1.0以下。就液晶組成物之液晶相溫度範圍、驅動電壓、旋轉黏度及彈性模數之觀點而言,介電各向異性(∆ε)較佳為-4.9以上且-1.5以下,更佳為-4.8以上且-2.0以下,進而較佳為-4.7以上且-2.5以下,進而更佳為-4.6以上且-2.7以下,尤佳為-4.5以上且-3.0以下。The liquid crystal composition of the present invention preferably has a dielectric anisotropy (∆ε) of -5.0 or more and -1.0 or less. From the viewpoints of the liquid crystal phase temperature range, driving voltage, rotational viscosity, and elastic modulus of the liquid crystal composition, the dielectric anisotropy (∆ε) is preferably -4.9 or more and -1.5 or less, more preferably -4.8 or more And -2.0 or less, more preferably -4.7 or more and -2.5 or less, still more preferably -4.6 or more and -2.7 or less, particularly preferably -4.5 or more and -3.0 or less.
本案發明之液晶組成物亦可含有下述通式(II)所表示之化合物。The liquid crystal composition of the present invention may also contain a compound represented by the following general formula (II).
(式中,R21 及R22 各自獨立地表示碳原子數1至8之烷基、碳原子數1至7之烷氧基、碳原子數2至8之烯基或碳原子數2至7之烯氧基, A21 及A22 各自獨立地表示選自下述式(A2-1)至式(A2-11)之基。(In the formula, R 21 and R 22 each independently represent an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an alkenyl group with 2 to 8 carbon atoms or 2 to 7 carbon atoms For the alkenyloxy group, A 21 and A 22 each independently represent a group selected from the following formula (A2-1) to formula (A2-11).
(式中,虛線表示鍵結位置),但於存在複數個A21 之情形時,其等可相同亦可不同,於存在複數個A22 之情形時,其等可相同亦可不同, Z21 及Z22 各自獨立地表示-O-、-S-、-OCH2 -、-CH2 O-、-CH2 CH2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2 -、-CH2 S-、-CF2 O-、-OCF2 -、-CF2 S-、-SCF2 -、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2 CH2 -、-OCO-CH2 CH2 -、-CH2 CH2 -COO-、-CH2 CH2 -OCO-、-COO-CH2 -、-OCO-CH2 -、-CH2 -COO-、-CH2 -OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z21 之情形時,其等可相同亦可不同,於存在複數個Z22 之情形時,其等可相同亦可不同, m21及m22各自獨立地表示0至3之整數,但m21+m22表示1至3之整數)。就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,通式(II)所表示之化合物較佳為下述通式(II-i)所表示之化合物。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 21 , they can be the same or different, when there are a plurality of A 22 , they can be the same or different, Z 21 And Z 22 each independently represent -O-, -S-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH- O-, -O-NH-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH 2 CH 2 -, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO- , -CH 2 CH 2 -OCO-, -COO-CH 2 -, -OCO-CH 2 -, -CH 2 -COO-, -CH 2 -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond, but when there are plural Z 21 , they can be the same It may be different. When there are a plurality of Z 22 , they may be the same or different. m21 and m22 each independently represent an integer from 0 to 3, but m21+m22 represents an integer from 1 to 3). From the viewpoints of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, The compound represented by formula (II) is preferably a compound represented by the following general formula (II-i).
(式中,R211 及R221 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基、碳原子數2至5之烯基或碳原子數2至4之烯氧基, A211 及A221 各自獨立地表示選自下述式(A21-1)至式(A21-9)之基。(In the formula, R 211 and R 221 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 5 carbon atoms, or 2 to 4 carbon atoms. For the alkenyloxy group, A 211 and A 221 each independently represent a group selected from the following formula (A21-1) to formula (A21-9).
(式中,虛線表示鍵結位置),但於存在複數個A211 之情形時,其等可相同亦可不同,於存在複數個A221 之情形時,其等可相同亦可不同, Z211 及Z221 各自獨立地表示-OCH2 -、-CH2 O-、-CH2 CH2 -、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH=CH-COO-、-OCO-CH=CH-、-CH=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z211 之情形時,其等可相同亦可不同,於存在複數個Z221 之情形時,其等可相同亦可不同, m211及m221各自獨立地表示0至3之整數,但m211+m221表示1至3之整數)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 211 , they can be the same or different; when there are a plurality of A 221 , they can be the same or different, Z 211 And Z 221 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH=CH-COO -, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond, but when there are plural Z 211 , the like which may be the same or different, when Z in the presence of a plurality of case 221, and the like which may be identical or different, M211 and M221 each independently represent an integer of 0 to 3, but m211 + m221 represents an integer of 1 to 3).
通式(II)所表示之化合物較佳為下述通式(II-ii)所表示之化合物。The compound represented by the general formula (II) is preferably a compound represented by the following general formula (II-ii).
(式中,R212 及R222 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基、碳原子數2至5之烯基或碳原子數2至4之烯氧基, A212 及A222 各自獨立地表示選自下述式(A22-1)至式(A22-7)之基。(In the formula, R 212 and R 222 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 5 carbon atoms or 2 to 4 carbon atoms. For the alkenyloxy group, A 212 and A 222 each independently represent a group selected from the following formula (A22-1) to formula (A22-7).
(式中,虛線表示鍵結位置),但於存在複數個A212 之情形時,其等可相同亦可不同,於存在複數個A222 之情形時,其等可相同亦可不同, Z212 及Z222 各自獨立地表示-OCH2 -、-CH2 O-、-CH2 CH2 -、-COO-、-OCO-、-CF2 O-、-OCF2 -或單鍵,但於存在複數個Z212 之情形時,其等可相同亦可不同,於存在複數個Z222 之情形時,其等可相同亦可不同, m212及m222各自獨立地表示0、1或2,但m212+m222表示1或2)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 212 , they can be the same or different, when there are a plurality of A 222 , they can be the same or different, Z 212 And Z 222 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 -or a single bond, but when there is In the case of a plurality of Z 212 , they may be the same or different. In the case of a plurality of Z 222 , they may be the same or different. m212 and m222 each independently represent 0, 1 or 2, but m212 + m222 represents 1 or 2).
通式(II)所表示之化合物更佳為下述通式(II-iii)所表示之化合物。The compound represented by the general formula (II) is more preferably a compound represented by the following general formula (II-iii).
(式中,R212 及R222 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基或碳原子數2至5之烯基, A213 及A223 各自獨立地表示選自下述式(A23-1)至式(A23-5)之基。(In the formula, R 212 and R 222 each independently represent an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 2 to 5 carbon atoms. A 213 and A 223 each independently It independently represents a group selected from the following formula (A23-1) to formula (A23-5).
(式中,虛線表示鍵結位置),但於存在複數個A213 之情形時,其等可相同亦可不同,於存在複數個A223 之情形時,其等可相同亦可不同, Z213 及Z223 各自獨立地表示-OCH2 -、-CH2 O-、-CH2 CH2 -或單鍵,但於存在複數個Z213 之情形時,其等可相同亦可不同,於存在複數個Z223 之情形時,其等可相同亦可不同, m213及m223各自獨立地表示0、1或2,但m213+m223表示1或2)。(In the formula, the dotted line indicates the bonding position), but when there are multiple A 213s , they can be the same or different, and when there are multiple A 223s , they can be the same or different, Z 213 And Z 223 each independently represent -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -or a single bond, but when there are plural Z 213 , they may be the same or different. In the case of a Z 223 , they can be the same or different, m213 and m223 each independently represent 0, 1, or 2, but m213+m223 represents 1 or 2).
通式(II)所表示之化合物尤佳為選自由下述通式(II-iv-1)至通式(II-iv-8)所表示之化合物所組成之群中之化合物。The compound represented by the general formula (II) is particularly preferably a compound selected from the group consisting of compounds represented by the following general formula (II-iv-1) to general formula (II-iv-8).
(式中,R214 及R224 各自獨立地表示碳原子數1至5之烷基、碳原子數1至4之烷氧基或碳原子數2至5之烯基)。(In the formula, R 214 and R 224 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms).
於將本案發明之液晶組成物用於PSA、PS-VA、PS-IPS、PI-Less型液晶顯示元件之情形時,較佳為含有下述通式(IV)所表示之化合物。When the liquid crystal composition of the present invention is used in PSA, PS-VA, PS-IPS, and PI-Less type liquid crystal display elements, it preferably contains a compound represented by the following general formula (IV).
(式中,P41 及P42 各自獨立地表示藉由自由基聚合、陽離子聚合或陰離子聚合進行聚合之基, Sp41 及Sp42 各自獨立地表示間隔基或單鍵, A41 及A42 各自獨立地表示選自下述式(A4-1)至式(A4-9)之基。(In the formula, P 41 and P 42 each independently represent a group polymerized by radical polymerization, cationic polymerization or anionic polymerization, Sp 41 and Sp 42 each independently represent a spacer or a single bond, and A 41 and A 42 each independently It independently represents a group selected from the following formula (A4-1) to formula (A4-9).
(式中,虛線表示鍵結位置,L4 表示鹵素原子、氰基、硝基、五氟甲硫烷基、可經取代之胺基、可經取代之矽基、任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之烷基、或者PL -SPL -所表示之基(式中,PL 表示藉由自由基聚合、陽離子聚合或陰離子聚合進行聚合之基,SpL 表示間隔基或單鍵),但於存在複數個L4 之情形時,其等可相同亦可不同),但於存在複數個A42 之情形時,其等可相同亦可不同, Z41 表示-O-、-S-、-OCH2 -、-CH2 O-、-CH2 CH2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2 -、-CH2 S-、-CF2 O-、-OCF2 -、-CF2 S-、-SCF2 -、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2 CH2 -、-OCO-CH2 CH2 -、-CH2 CH2 -COO-、-CH2 CH2 -OCO-、-COO-CH2 -、-OCO-CH2 -、-CH2 -COO-、-CH2 -OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z41 之情形時,其等可相同亦可不同, m41表示1至4之整數)。就電壓保持率、傾斜角穩定性、與液晶組成物之相容性之觀點而言,通式(IV)所表示之化合物較佳為含有下述通式(IV-i)所表示之化合物。(In the formula, the dotted line represents the bonding position, L 4 represents a halogen atom, a cyano group, a nitro group, a pentafluoromethylsulfanyl group, a substituted amino group, a substituted silyl group, and any hydrogen atom may be substituted It is a fluorine atom and one -CH 2 -or two or more non-adjacent -CH 2 -s can be independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO -CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- alkyl group with 1 to 20 carbon atoms, or PL -SP L- (In the formula, PL represents a group polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp L represents a spacer or a single bond), but when there are more than one L 4 , they can be The same or different), but when there are a plurality of A 42 , they can be the same or different. Z 41 represents -O-, -S-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO -NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH 2 CH 2 -, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO-, -CH 2 CH 2 -OCO-, -COO-CH 2 -, -OCO-CH 2 -, -CH 2 -COO -, -CH 2 -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡ C- or a single bond, but when there are plural Z 41 , they can be the same or different, m41 represents an integer from 1 to 4). From the viewpoint of voltage retention, tilt angle stability, and compatibility with the liquid crystal composition, the compound represented by the general formula (IV) preferably contains a compound represented by the following general formula (IV-i).
(式中,P411 及P421 各自獨立地表示選自下述式(P-1)至式(P-20)之基。(In the formula, P 411 and P 421 each independently represent a group selected from the following formula (P-1) to formula (P-20).
(式中,虛線表示鍵結位置), Sp411 及Sp421 各自獨立地表示基中之任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之直鏈狀或支鏈狀伸烷基或單鍵, A411 及A421 各自獨立地表示選自下述式(A41-1)至式(A41-9)之基。(In the formula, the dotted line indicates the bonding position), Sp 411 and Sp 421 each independently indicate that any hydrogen atom in the group can be substituted with a fluorine atom and 1 -CH 2 -or 2 or more non-adjacent- CH 2 -can be independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- linear or branched chain alkylene or single bond with 1 to 20 carbon atoms , A 411 and A 421 each independently represent a group selected from the following formula (A41-1) to formula (A41-9).
(式中,虛線表示鍵結位置,L41 表示氟原子、氯原子、任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-COO-、-OCO-、-CH=CH-COO-、-OCO-CH=CH-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至10之烷基、或者PL -SpL -所表示之基(式中,PL 表示上述式(P-1)至式(P-20),SpL 表示基中之任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之直鏈狀或支鏈狀伸烷基或單鍵),但於存在複數個L41 之情形時,其等可相同亦可不同),但於存在複數個A421 之情形時,其等可相同亦可不同, Z411 表示-OCH2 -、-CH2 O-、-CH2 CH2 -、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH=CH-COO-、-OCO-CH=CH-、-CH=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z411 之情形時,其等可相同亦可不同, m411表示1、2或3),通式(IV)所表示之化合物更佳為含有下述通式(IV-ii)所表示之化合物。(In the formula, the dotted line represents the bonding position, L 41 represents a fluorine atom, a chlorine atom, any hydrogen atom can be substituted with a fluorine atom and one -CH 2 -or two or more non-adjacent -CH 2- Each is independently substituted with -O-, -COO-, -OCO-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C -An alkyl group having 1 to 10 carbon atoms, or a group represented by PL -Sp L- (wherein, PL represents the above formula (P-1) to (P-20)), and Sp L represents the group Any hydrogen atom can be substituted with fluorine atom and 1 -CH 2 -or 2 or more non-adjacent -CH 2 -can be independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF -Or -C≡C- linear or branched alkylene or single bond with 1 to 20 carbon atoms), but when there are more than one L 41 , they may be the same or different), However, when there are multiple A 421s , they can be the same or different. Z 411 represents -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- Or a single bond, but when there are plural Z 411 , they may be the same or different, m411 represents 1, 2 or 3), and the compound represented by general formula (IV) more preferably contains the following general formula ( IV-ii) The compound represented.
(式中,P412 及P422 各自獨立地表示選自式(P-1)、式(P-2)、式(P-3)、式(P-4)、式(P-5)、式(P-7)、式(P-11)、式(P-13)、式(P-15)及式(P-18)之基, Sp412 及Sp422 各自獨立地表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-COO-、-OCO-或-O-CO-O-之碳原子數2至12之直鏈狀或支鏈狀伸烷基或單鍵, A412 及A422 各自獨立地表示選自下述式(A42-1)至式(A42-7)之基。(In the formula, P 412 and P 422 are each independently selected from formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), The base of formula (P-7), formula (P-11), formula (P-13), formula (P-15) and formula (P-18), Sp 412 and Sp 422 each independently represent 1 -CH 2 -or 2 or more non-adjacent -CH 2 -s can be independently substituted with -O-, -COO-, -OCO- or -O-CO-O- with carbon atoms ranging from 2 to 12 A chain or branched alkylene group or a single bond, A 412 and A 422 each independently represent a group selected from the following formula (A42-1) to formula (A42-7).
(式中,虛線表示鍵結位置,L42 表示氟原子、任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-之碳原子數1至5之烷基,但於存在複數個L42 之情形時,其等可相同亦可不同),但於存在複數個A422 之情形時,其等可相同亦可不同, Z412 表示-CH=CH-COO-、-OCO-CH=CH-、-CH=CH-、-CF=CF-或單鍵,但於存在複數個Z412 之情形時,其等可相同亦可不同, m412表示1或2),通式(IV)所表示之化合物進而較佳為含有下述通式(IV-iii)所表示之化合物。(In the formula, the dotted line represents the bonding position, L 42 represents a fluorine atom, any hydrogen atom can be substituted with a fluorine atom, and one -CH 2 -or two or more non-adjacent -CH 2 -s can be each independently Alkyl groups with 1 to 5 carbon atoms substituted with -O-, but when there are a plurality of L 42 , the same or different), but when there are a plurality of A 422 , the same Can be the same or different, Z 412 means -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or single bond, but when there are multiple Z 412 , They may be the same or different, m412 represents 1 or 2), and the compound represented by general formula (IV) further preferably contains a compound represented by the following general formula (IV-iii).
(式中,P413 及P423 各自獨立地表示選自式(P-1)、式(P-2)、式(P-3)及式(P-18)之基, Sp413 及Sp423 各自獨立地表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-之碳原子數2至8之直鏈狀伸烷基或單鍵, A413 及A423 各自獨立地表示選自下述式(A43-1)至式(A43-7)之基。(In the formula, P 413 and P 423 each independently represent a base selected from formula (P-1), formula (P-2), formula (P-3) and formula (P-18), Sp 413 and Sp 423 Each independently represents 1 -CH 2 -or 2 or more non-adjacent -CH 2 -which can be each independently substituted with a linear alkylene group having 2 to 8 carbon atoms or a single bond , A 413 and A 423 each independently represent a group selected from the following formula (A43-1) to formula (A43-7).
(式中,虛線表示鍵結位置,L43 表示氟原子、碳原子數1至5之烷基、碳原子數1至4之烷氧基、氫原子被取代為氟原子之碳原子數1至5之烷基或氫原子被取代為氟原子之碳原子數1至4之烷氧基,但於存在複數個L43 之情形時,其等可相同亦可不同),但於存在複數個A423 之情形時,其等可相同亦可不同, Z413 表示-CH=CH-COO-、-OCO-CH=CH-或單鍵,但於存在複數個Z413 之情形時,其等可相同亦可不同, m413表示1或2),通式(IV)所表示之化合物尤佳為含有選自由下述通式(IV-iv-1)至通式(IV-iv-5)所表示之化合物所組成之群中之化合物。(In the formula, the dotted line represents the bonding position, L 43 represents a fluorine atom, an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, and a hydrogen atom is substituted with a fluorine atom. Alkyl group or hydrogen atom of 5 is replaced with alkoxy group of fluorine atom with 1 to 4 carbon atoms, but when there are multiple L 43 , they may be the same or different), but when there are multiple A In the case of 423 , they can be the same or different. Z 413 means -CH=CH-COO-, -OCO-CH=CH- or a single bond, but when there are more than one Z 413 , they can be the same It may be different, m413 represents 1 or 2), and the compound represented by general formula (IV) preferably contains one selected from the following general formula (IV-iv-1) to general formula (IV-iv-5) A compound in the group of compounds.
(式中,P414 及P424 各自獨立地表示選自式(P-1)及式(P-2)之基, Sp414 及Sp424 各自獨立地表示碳原子數2至5之直鏈狀伸烷基或單鍵, A414 、A424 及A434 各自獨立地表示選自下述式(A44-1)至式(A44-7)之基。(In the formula, P 414 and P 424 each independently represent a group selected from formula (P-1) and formula (P-2), and Sp 414 and Sp 424 each independently represent a linear chain with 2 to 5 carbon atoms An alkylene group or a single bond, A 414 , A 424 and A 434 each independently represent a group selected from the following formula (A44-1) to formula (A44-7).
(式中,虛線表示鍵結位置,L44 表示氟原子、碳原子數1至5之烷基或碳原子數1至4之烷氧基,但於存在複數個L44 之情形時,其等可相同亦可不同))。作為通式(IV)所表示之化合物,具體而言,可列舉下述通式(IV-v-1)至通式(IV-v-15)所表示之化合物。(In the formula, the dotted line represents the bonding position, L 44 represents a fluorine atom, an alkyl group with 1 to 5 carbon atoms, or an alkoxy group with 1 to 4 carbon atoms, but when there are more than one L 44 , etc. Can be the same or different)). As the compound represented by the general formula (IV), specifically, compounds represented by the following general formula (IV-v-1) to (IV-v-15) can be cited.
(式中,P415 及P425 各自獨立地表示選自式(P-1)及式(P-2)之基, Sp425 表示碳原子數2至5之直鏈狀伸烷基)。(In the formula, P 415 and P 425 each independently represent a group selected from formula (P-1) and formula (P-2), and Sp 425 represents a linear alkylene group having 2 to 5 carbon atoms).
於本發明之液晶組成物中,亦可添加穩定劑,以提昇其保存穩定性。作為可使用之穩定劑,例如可列舉對苯二酚類、對苯二酚單烷基醚類、第三丁基兒茶酚類、鄰苯三酚(pyrogallol)類、苯硫酚類、硝基化合物類、β-萘胺類、β-萘酚類、亞硝基化合物等。使用穩定劑之情形時之添加量相對於組成物較佳為0.005質量%至1質量%之範圍,更佳為0.02質量%至0.8質量%,進而較佳為0.03質量%至0.5質量%。又,可使用1種穩定劑,亦可併用使用2種以上之穩定劑。作為穩定劑,可列舉下述通式(X1)所表示之化合物。In the liquid crystal composition of the present invention, a stabilizer can also be added to improve its storage stability. Examples of stabilizers that can be used include hydroquinones, hydroquinone monoalkyl ethers, tertiary butylcatechols, pyrogallols, thiophenols, and nitrosamine. Based compounds, β-naphthylamines, β-naphthols, nitroso compounds, etc. In the case of using a stabilizer, the addition amount relative to the composition is preferably in the range of 0.005% to 1% by mass, more preferably 0.02% to 0.8% by mass, and still more preferably 0.03% to 0.5% by mass. In addition, one type of stabilizer may be used, or two or more types of stabilizers may be used in combination. As a stabilizer, the compound represented by the following general formula (X1) is mentioned.
(式中,Spx 1 表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之伸烷基或單鍵,Ax1 表示選自下述式(Ax1-1)至式(Ax1-8)之基。(In the formula, Sp x 1 represents one -CH 2 -or two or more non-adjacent -CH 2 -s that can be independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO -, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- alkylene or single bond with 1 to 20 carbon atoms, A x1 represents a group selected from the following formula (Ax1-1) to formula (Ax1-8).
(式中,虛線表示鍵結位置),但於存在複數個Ax1 之情形時,其等可相同亦可不同, Zx1 表示-O-、-S-、-OCH2 -、-CH2 O-、-CH2 CH2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2 -、-CH2 S-、-CF2 O-、-OCF2 -、-CF2 S-、-SCF2 -、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2 CH2 -、-OCO-CH2 CH2 -、-CH2 CH2 -COO-、-CH2 CH2 -OCO-、-COO-CH2 -、-OCO-CH2 -、-CH2 -COO-、-CH2 -OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Zx1 之情形時,其等可相同亦可不同,mx1表示0或1, mx2表示0至4之整數)。就電壓保持率、與液晶組成物之相容性之觀點而言,通式(X1)所表示之化合物較佳為下述通式(X1-i)所表示之化合物。(In the formula, the dotted line indicates the bonding position), but when there are multiple A x1 , they can be the same or different. Z x1 represents -O-, -S-, -OCH 2 -, -CH 2 O -, -CH 2 CH 2 -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH- CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH 2 -, -CH 2 S-, -CF 2 O -, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH 2 CH 2 -, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO-, -CH 2 CH 2 -OCO-, -COO-CH 2 -, -OCO-CH 2 -, -CH 2 -COO-, -CH 2 -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF -, -C≡C- or a single bond, but when there are plural Z x1 , they can be the same or different, mx1 represents 0 or 1, mx2 represents an integer from 0 to 4). From the viewpoint of voltage retention and compatibility with the liquid crystal composition, the compound represented by the general formula (X1) is preferably the compound represented by the following general formula (X1-i).
(式中,Spx 11 表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-COO-或-OCO-之碳原子數1至20之伸烷基或單鍵,Ax11 表示選自下述式(Ax11-1)及式(Ax11-2)之基,(In the formula, Sp x 11 represents 1 -CH 2 -or 2 or more non-adjacent -CH 2 -which can be independently substituted with the number of carbon atoms of -O-, -COO- or -OCO- 1 The alkylene group or single bond to 20, A x11 represents a group selected from the following formula (Ax11-1) and formula (Ax11-2),
(式中,虛線表示鍵結位置),但於存在複數個Ax11 之情形時,其等可相同亦可不同, Zx11 表示-COO-、-OCO-、-OCO-CH2 CH2 -、-CH2 CH2 -COO-或單鍵,但於存在複數個Zx11 之情形時,其等可相同亦可不同, mx11表示0或1, mx21表示0或1),通式(X1)所表示之化合物尤佳為下述通式(X1-ii-1)至通式(X1-ii-4)所表示之化合物。(In the formula, the dotted line indicates the bonding position), but when there are multiple A x11 , they can be the same or different. Z x11 represents -COO-, -OCO-, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO- or a single bond, but when there are plural Z x11 , they can be the same or different, mx11 represents 0 or 1, mx21 represents 0 or 1), the general formula (X1) The compound represented is particularly preferably a compound represented by the following general formula (X1-ii-1) to (X1-ii-4).
(式中,Spx 12 表示碳原子數1至20之伸烷基或單鍵)。(In the formula, Sp x 12 represents an alkylene group or single bond with 1 to 20 carbon atoms).
又,可列舉下述通式(X2)所表示之化合物。Moreover, the compound represented by the following general formula (X2) is mentioned.
(式中,Rx21 、Rx22 、Rx23 及Rx24 各自獨立地表示氫原子、氧原子、羥基、碳原子數1至20之烷基或碳原子數1至20之烷氧基, Spx21 、Spx22 、Spx23 及Spx24 各自獨立地表示間隔基或單鍵, mx21表示0或1, mx22表示0或1, mx23表示0或1)。就電壓保持率、與液晶組成物之相容性之觀點而言,通式(X2)所表示之化合物較佳為下述通式(X2-i)所表示之化合物。 (Wherein, R x21, R x22, R x23 and R x24 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, or an alkyl group having a carbon number of 1 to 20 carbon atoms, an alkoxy group of 1 to 20, Sp x21 , Sp x22 , Sp x23, and Sp x24 each independently represent a spacer or a single bond, mx21 represents 0 or 1, mx22 represents 0 or 1, mx23 represents 0 or 1). From the viewpoint of voltage retention and compatibility with the liquid crystal composition, the compound represented by the general formula (X2) is preferably a compound represented by the following general formula (X2-i).
(式中,Rx211 、Rx221 、Rx231 及Rx241 各自獨立地表示氫原子、氧原子、羥基、碳原子數1至10之烷基或碳原子數1至10之烷氧基, Spx 211 、Spx 221 、Spx 231 及Spx 241 各自獨立地表示基中之任意之氫原子可被取代為氟原子且1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-之碳原子數1至20之直鏈狀或支鏈狀伸烷基或單鍵, mx211表示0或1, mx221表示0或1, mx231表示0或1),通式(X2)所表示之化合物更佳為下述通式(X2-ii)所表示之化合物。(In the formula, R x211 , R x221 , R x231 and R x241 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, Sp x 211 , Sp x 221 , Sp x 231 and Sp x 241 each independently represent that any hydrogen atom in the group can be substituted with a fluorine atom and 1 -CH 2 -or 2 or more non-adjacent -CH 2- Can be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO- NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- linear or branched alkylene or single bond with 1 to 20 carbon atoms, mx211 represents 0 or 1, mx221 represents 0 or 1, mx231 represents 0 or 1), and the compound represented by general formula (X2) is more preferably a compound represented by the following general formula (X2-ii).
(式中,Rx212 及Rx222 各自獨立地表示氫原子、碳原子數1至10之烷基或碳原子數1至10之烷氧基, Spx 212 及Spx 222 各自獨立地表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-O-、-COO-或-OCO-之碳原子數1至10之直鏈狀伸烷基或單鍵, mx212表示0或1),通式(X2)所表示之化合物尤佳為下述通式(X2-iii)所表示之化合物。(In the formula, R x212 and R x222 each independently represent a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, or an alkoxy group with 1 to 10 carbon atoms, and Sp x 212 and Sp x 222 each independently represent one -CH 2 -or 2 or more non-adjacent -CH 2 -can be each independently substituted with -O-, -COO- or -OCO- linear alkylene having 1 to 10 carbon atoms or A single bond, mx212 represents 0 or 1), and the compound represented by the general formula (X2) is particularly preferably a compound represented by the following general formula (X2-iii).
(式中,Rx213 及Rx223 各自獨立地表示氫原子、碳原子數1至10之烷基或碳原子數1至10之烷氧基, Spx 213 表示1個-CH2 -或不相鄰之2個以上之-CH2 -可各自獨立地被取代為-COO-或-OCO-之碳原子數1至10之直鏈狀伸烷基)。(In the formula, R x213 and R x223 each independently represent a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, or an alkoxy group with 1 to 10 carbon atoms, and Sp x 213 represents 1 -CH 2 -or different Two or more adjacent -CH 2 -s may be independently substituted with -COO- or -OCO- (a linear alkylene group having 1 to 10 carbon atoms).
本案發明之液晶組成物較佳為將波長450 nm之折射率各向異性(∆n(450))除以波長550 nm之折射率各向異性(∆n(550))所得之值(∆n(450)/∆n(550))滿足下述式(式1): ∆n(450)/∆n(550)<1.10 (式1)。 就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,∆n(450)/∆n(550)較佳為大於0.72且小於1.06,更佳為大於0.74且小於1.02,進而較佳為大於0.76且小於0.98,進而更佳為大於0.78且小於0.94,尤佳為大於0.80且小於0.90。The liquid crystal composition of the present invention is preferably a value (∆n) obtained by dividing the refractive index anisotropy (∆n(450)) at a wavelength of 450 nm by the refractive index anisotropy (∆n(550)) at a wavelength of 550 nm (450)/∆n(550)) satisfies the following formula (Equation 1): ∆n(450)/∆n(550)<1.10 (Equation 1). From the viewpoint of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus, ∆ n(450)/∆n(550) is preferably greater than 0.72 and less than 1.06, more preferably greater than 0.74 and less than 1.02, still more preferably greater than 0.76 and less than 0.98, still more preferably greater than 0.78 and less than 0.94, especially It is greater than 0.80 and less than 0.90.
本案發明之液晶組成物較佳為將波長650 nm之折射率各向異性(∆n(650))除以波長550 nm下之折射率各向異性(∆n(550))所得之值(∆n(650)/∆n(550))滿足下述式(式2): 0.90<∆n(650)/∆n(550)<1.50 (式2)。 就因電壓施加造成液晶配向變化時色調及色度等之變化、液晶組成物之液晶相溫度範圍、折射率各向異性、介電各向異性、旋轉黏度及彈性模數之觀點而言,∆n(650)/∆n(550)較佳為大於0.95且小於1.45,更佳為大於1.00且小於1.40,進而較佳為大於1.05且小於1.35,進而更佳為大於1.10且小於1.30,尤佳為大於1.16且小於1.20。The liquid crystal composition of the present invention is preferably a value obtained by dividing the refractive index anisotropy (Δn(650)) at a wavelength of 650 nm by the refractive index anisotropy (Δn(550)) at a wavelength of 550 nm (Δ n(650)/∆n(550)) satisfies the following formula (Equation 2): 0.90<∆n(650)/∆n(550)<1.50 (Equation 2). From the viewpoint of changes in hue and chromaticity when the alignment of the liquid crystal changes due to voltage application, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus, ∆ n(650)/∆n(550) is preferably greater than 0.95 and less than 1.45, more preferably greater than 1.00 and less than 1.40, still more preferably greater than 1.05 and less than 1.35, still more preferably greater than 1.10 and less than 1.30, especially It is greater than 1.16 and less than 1.20.
本案發明之液晶組成物較佳為用於顯示元件。於夾於具有2片透明電極之基板之液晶單元中,於利用液晶之雙折射率變化使透光率變化之ECB(Electronic Controlled Birefringenence)模式下,於正交偏光之偏光板配置下,穿透率按照下述式發生變化。 液晶方位角:相對於偏光板之穿透軸(OR吸收軸)之角度,根據下述式設為45度效率最良好。The liquid crystal composition of the present invention is preferably used in display devices. In a liquid crystal cell sandwiched between a substrate with two transparent electrodes, in the ECB (Electronic Controlled Birefringenence) mode that uses the birefringence of the liquid crystal to change the light transmittance, in the cross-polarized polarizing plate configuration, it penetrates The rate changes according to the following formula. Liquid crystal azimuth angle: The angle with respect to the transmission axis (OR absorption axis) of the polarizing plate, the best efficiency is 45 degrees according to the following formula.
T:穿透率 Ψ:液晶方位角 λ:波長 d:單元厚 於本式中,作為向液晶層施加電壓時發生變化之參數,有液晶組成物之∆n。只要該∆n除以光源波長λ即∆n/λ於任一波長均能夠保持一定,則光於各波長(每種顏色)以相同比率穿透,不會發生液晶顯示元件之色度偏移,而較為理想。於本案發明中,1,4-伸環己基、十氫化萘-2,6-二基及1,3-二烷-2,5-二基所含之環結構可為各個反式體及順式體之任一者,但就液晶性之觀點而言,較佳為各個反式體之含有率多於順式體之含有率,更佳為環結構中之反式體之含有率為80%以上,進而較佳為環結構中之反式體之含有率為90%以上,進而更佳為環結構中之反式體之含有率為95%以上,尤佳為環結構中之反式體之含有率為98%以上。又,於本案發明中,下述表記(CY-1)係指1,4-伸環己基之反式體及/或順式體。T: Transmittance Ψ: Liquid crystal azimuth angle λ: Wavelength d: Cell thickness is greater than in this formula, as a parameter that changes when voltage is applied to the liquid crystal layer, there is Δn of the liquid crystal composition. As long as the ∆n divided by the light source wavelength λ, that is, ∆n/λ can be kept constant at any wavelength, the light will penetrate at the same ratio at each wavelength (each color), and the chromaticity shift of the liquid crystal display element will not occur. , And more ideal. In the present invention, 1,4-cyclohexylene, decalin-2,6-diyl and 1,3-diyl The ring structure contained in the alkane-2,5-diyl group may be any of each of the trans form and the cis form, but from the viewpoint of liquid crystallinity, it is preferable that the content of each trans form is more than that of the cis form. The content rate of the formula body is more preferably the content rate of the trans body in the ring structure is 80% or more, further preferably the content rate of the trans body in the ring structure is 90% or more, and even more preferably the content rate in the ring structure The content of the trans form is more than 95%, and the content of the trans form in the ring structure is more than 98%. In addition, in the present invention, the following notation (CY-1) refers to the trans isomer and/or cis isomer of 1,4-cyclohexylene.
(式中,虛線表示鍵結位置),下述表記(CY-1-t)及表記(CY-2-t)係指1,4-伸環己基之反式體。(In the formula, the dotted line indicates the bonding position), the following expressions (CY-1-t) and (CY-2-t) refer to the trans form of 1,4-cyclohexylene.
(式中,虛線表示鍵結位置)。(In the formula, the dotted line indicates the bonding position).
於本案發明中,所謂於任意位置具有鍵結鍵,係指於任意位置具有所需數量之鍵結鍵。例如,於為1價基之情形時,意圖於任意位置具有1個鍵結鍵。具體而言,例如於下述式(ex-sub)In the present invention, the so-called having bonding bonds at any position means having a required number of bonding bonds at any position. For example, in the case of a monovalent group, it is intended to have one bonding bond at any position. Specifically, for example in the following formula (ex-sub)
所表示之基為1價基且於任意位置具有鍵結鍵之情形時,係指表示選自下述式(ex-sub-1)至式(ex-sub-3)之基。When the represented group is a monovalent group and has a bonding bond at any position, it means a group selected from the following formulas (ex-sub-1) to (ex-sub-3).
(式中,虛線表示鍵結位置)。(In the formula, the dotted line indicates the bonding position).
又,於本案發明中,各元素亦可被取代為相同元素之同位體。In addition, in the present invention, each element may be substituted with the homotope of the same element.
本案發明之化合物係下述通式(I)所表示之化合物。The compound of the present invention is a compound represented by the following general formula (I).
(式中,R11 及R12 各自獨立地表示碳原子數1至8之烷基、碳原子數1至7之烷氧基、碳原子數2至8之烯基或碳原子數2至7之烯氧基, A11 及A13 各自獨立地表示選自下述式(A1-1)至式(A1-11)之基。(In the formula, R 11 and R 12 each independently represent an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an alkenyl group with 2 to 8 carbon atoms or 2 to 7 carbon atoms For the alkenyloxy group, A 11 and A 13 each independently represent a group selected from the following formula (A1-1) to formula (A1-11).
(式中,虛線表示鍵結位置),但於存在複數個A11 之情形時,其等可相同亦可不同,於存在複數個A13 之情形時,其等可相同亦可不同, A12 表示包含具有大之波長色散性之基(ZG)之基,但上述具有大之波長色散性之基(ZG)朝向大致垂直於通式(I)所表示之化合物之分子長軸之方向, Z11 及Z12 各自獨立地表示-O-、-S-、-OCH2 -、-CH2 O-、-CH2 CH2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2 -、-CH2 S-、-CF2 O-、-OCF2 -、-CF2 S-、-SCF2 -、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2 CH2 -、-OCO-CH2 CH2 -、-CH2 CH2 -COO-、-CH2 CH2 -OCO-、-COO-CH2 -、-OCO-CH2 -、-CH2 -COO-、-CH2 -OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-或單鍵,但於存在複數個Z11 之情形時,其等可相同亦可不同,於存在複數個Z12 之情形時,其等可相同亦可不同,m11及m12各自獨立地表示0至5之整數,但m11+m12表示0至5之整數)。(In the formula, the dotted line indicates the bonding position), but when there are a plurality of A 11 , they can be the same or different, when there are a plurality of A 13 , they can be the same or different, A 12 It means a group containing a group with large wavelength dispersion (ZG), but the group with large wavelength dispersion (ZG) is oriented in a direction substantially perpendicular to the molecular long axis of the compound represented by the general formula (I), Z 11 and Z 12 each independently represent -O-, -S-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 -, -CO-, -COO-, -OCO-, -CO-S -, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH -O-, -O-NH-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH=CH-COO- , -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH 2 CH 2 -, -OCO-CH 2 CH 2 -, -CH 2 CH 2 -COO -, -CH 2 CH 2 -OCO-, -COO-CH 2 -, -OCO-CH 2 -, -CH 2 -COO-, -CH 2 -OCO-, -CH=CH-, -N=N- , -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond, but when there are plural Z 11 , they can be The same or different, when there are a plurality of Z 12 , they may be the same or different, m11 and m12 each independently represent an integer from 0 to 5, but m11+m12 represents an integer from 0 to 5).
通式(I)所表示之化合物係於垂直於分子長軸之方向上具有基(ZG)之化合物(Z),上述基(ZG)具有大之波長色散性。通式(I)所表示之化合物能夠改善液晶組成物之波長色散性。The compound represented by the general formula (I) is a compound (Z) having a group (ZG) in the direction perpendicular to the long axis of the molecule, and the group (ZG) has a large wavelength dispersion. The compound represented by the general formula (I) can improve the wavelength dispersion of the liquid crystal composition.
通式(I)所表示之化合物之詳情係如上述液晶組成物之項中之說明。 實施例The details of the compound represented by the general formula (I) are as described in the item of the above-mentioned liquid crystal composition. Example
以下,列舉實施例對本發明進行進一步說明,但本發明並不限定於該等實施例。又,以下之實施例及比較例之組成物中之「%」係指「質量%」。於在各步驟中處理對於氧及/或水分不穩定之物質時,較佳為於氮氣、氬氣等非活性氣體中進行作業。各化合物之純度係由UPLC(Waters ACQUITY UPLC、BEH C18 (100×2.1 mm×1.7 μm)、乙腈/水或含有0.1%甲酸之乙腈/水、PDA、管柱溫度40℃)、GPC(島津製作所 HPLC Prominence、Shodex KF-801(300 mm×8 mm×6 μm)+KF-802(300 mm×8 mm×6 μm)、四氫呋喃、RI、UV(254 nm)、管柱溫度40℃)、GC(Agilent 6890A、J&W DB-1、30 m×0.25 mm×0.25 μm、載氣He、FID、100℃(1分鐘)→升溫10℃/分鐘→300℃(12分鐘))或1 H NMR(JEOL、400 MHz)來確定。 (實施例1)式(I-1)所表示之化合物之製造Hereinafter, the present invention will be further described with examples, but the present invention is not limited to these examples. In addition, the "%" in the composition of the following examples and comparative examples means "mass %". When processing substances unstable to oxygen and/or moisture in each step, it is preferable to operate in an inert gas such as nitrogen and argon. The purity of each compound is determined by UPLC (Waters ACQUITY UPLC, BEH C 18 (100×2.1 mm×1.7 μm), acetonitrile/water or acetonitrile/water containing 0.1% formic acid, PDA, column temperature 40℃), GPC (Shimadzu HPLC Prominence, Shodex KF-801 (300 mm×8 mm×6 μm) + KF-802 (300 mm×8 mm×6 μm), tetrahydrofuran, RI, UV (254 nm), column temperature 40°C), GC (Agilent 6890A, J&W DB-1, 30 m×0.25 mm×0.25 μm, carrier gas He, FID, 100°C (1 minute) → heating up 10°C/min → 300°C (12 minutes)) or 1 H NMR (JEOL) , 400 MHz) to determine. (Example 1) Production of compound represented by formula (I-1)
(實施例1-1)(Example 1-1)
使式(I-1-1)所表示之化合物2.5 g溶解於二氯甲烷35 mL,於室溫向其中緩慢添加三溴化硼2.3 g。於室溫攪拌2小時後,添加水30 mL,攪拌一段時間。藉由分液提取有機層,將其利用飽和食鹽水洗淨後,添加無水硫酸鈉並使其乾燥。將溶劑於減壓蒸餾去除,而獲得式(I-1-2)所表示之化合物2.1 g。 MS(EI):m/z=271 (實施例1-2)Dissolve 2.5 g of the compound represented by formula (I-1-1) in 35 mL of dichloromethane, and slowly add 2.3 g of boron tribromide to it at room temperature. After stirring for 2 hours at room temperature, add 30 mL of water and stir for a while. The organic layer was extracted by liquid separation, washed with saturated brine, and anhydrous sodium sulfate was added and dried. The solvent was distilled off under reduced pressure to obtain 2.1 g of the compound represented by formula (I-1-2). MS(EI): m/z=271 (Example 1-2)
使式(I-1-3)所表示之化合物50 g及二氮雜雙環[2.2.2]辛烷(DABCO)23 g溶解於二氯甲烷300 mL,將其於氮氣下冰浴冷卻。向其中緩慢滴加使甲磺酸氯化物23.6 g溶解於二氯甲烷50 mL所得之溶液。滴加結束後,於室溫攪拌3小時後,添加水100 mL而進行分液。將有機層利用稀鹽酸洗淨數次,進而利用飽和碳酸氫鈉水溶液洗淨,接著利用飽和食鹽水洗淨。於有機層添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除,而獲得式(I-1-4)所表示之化合物63 g。 MS(EI):m/z=316 (實施例1-3)Dissolve 50 g of the compound represented by formula (I-1-3) and 23 g of diazabicyclo[2.2.2]octane (DABCO) in 300 mL of dichloromethane, and cool it in an ice bath under nitrogen. A solution obtained by dissolving 23.6 g of methanesulfonic acid chloride in 50 mL of dichloromethane was slowly added dropwise. After the dripping was completed, after stirring at room temperature for 3 hours, 100 mL of water was added for liquid separation. The organic layer was washed several times with dilute hydrochloric acid, and then washed with a saturated aqueous sodium hydrogen carbonate solution, and then washed with saturated brine. After adding anhydrous sodium sulfate to the organic layer and drying it, the solvent was distilled off under reduced pressure to obtain 63 g of a compound represented by formula (I-1-4). MS (EI): m/z=316 (Example 1-3)
一面使先前合成之式(I-1-2)所表示之化合物2.1 g、式(I-1-4)所表示之化合物5.5 g及碳酸銫5.6 g懸濁於丙酮35 mL,一面進行攪拌,使溫度升至發生回流為止。使反應進行5小時左右,確認反應完成後使溫度下降至室溫。向其中添加甲苯50 mL及水100 mL而使固形物溶解後,進行分液。於水層中添加甲苯30 mL而進行溶析,將其與先前之有機層一起利用稀鹽酸洗淨數次後,利用飽和碳酸氫鈉水溶液及飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得目標之式(I-1)所表示之化合物3.4 g。 MS(EI):m/z=683 (實施例2)式(I-2)所表示之化合物之製造While suspending 2.1 g of the compound represented by formula (I-1-2), 5.5 g of the compound represented by formula (I-1-4), and 5.6 g of cesium carbonate synthesized previously in 35 mL of acetone, they were stirred, The temperature is increased until reflux occurs. The reaction was allowed to proceed for about 5 hours, and after the completion of the reaction, the temperature was lowered to room temperature. After adding 50 mL of toluene and 100 mL of water to dissolve the solid matter, liquid separation was performed. 30 mL of toluene was added to the water layer for elution, and the organic layer was washed with dilute hydrochloric acid several times together with the previous organic layer, and then washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying, the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized, thereby obtaining 3.4 g of the target compound represented by formula (I-1). MS (EI): m/z=683 (Example 2) Production of compound represented by formula (I-2)
(實施例2-1)(Example 2-1)
一面使先前合成之式(I-2-2)所表示之化合物3.0 g、式(I-1-4)所表示之化合物7.6 g及碳酸銫7.8 g懸濁於丙酮47 mL,一面進行攪拌,使溫度升至發生回流為止。使反應進行5小時左右,確認反應完成後使溫度下降至室溫。向其中添加甲苯60 mL及水100 mL而使固形物溶解後進行分液。於水層添加甲苯40 mL而進行溶析,將其與先前之有機層一起利用稀鹽酸洗淨數次後,利用飽和碳酸氫鈉水溶液及飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得目標之式(I-2)所表示之化合物4.5 g。 MS(EI):m/z=689 (實施例3)式(I-3)所表示之化合物之製造While suspending 3.0 g of the compound represented by formula (I-2-2), 7.6 g of compound represented by formula (I-1-4) and 7.8 g of cesium carbonate synthesized previously in 47 mL of acetone, they were stirred, The temperature is increased until reflux occurs. The reaction was allowed to proceed for about 5 hours, and after the completion of the reaction, the temperature was lowered to room temperature. To this, 60 mL of toluene and 100 mL of water were added to dissolve the solid matter, and then the liquid was separated. 40 mL of toluene was added to the water layer for elution, and the organic layer was washed with dilute hydrochloric acid several times together with the previous organic layer, and then washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying, the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized, thereby obtaining 4.5 g of the compound represented by the target formula (I-2). MS (EI): m/z=689 (Example 3) Production of compound represented by formula (I-3)
(實施例3-1)(Example 3-1)
使式(I-3-1)所表示之化合物30 g溶解於THF150 mL,並於氮氣下冷卻至-78度。向其中緩慢滴加1.9 mol/L之第三丁基鋰溶液86 mL,攪拌30分鐘。向其中緩慢滴加使4'-丙基-[1,1'-雙(環己烷)]-4-酮36 g溶解於THF72 mL之溶液。攪拌30分鐘後,添加水100 mL,使溫度恢復至室溫,進行分液。將有機層利用飽和食鹽水洗淨,添加飽和硫酸鈉而使其乾燥。將溶劑於減壓蒸餾去除,而獲得固形物51 g。 MS(EI):m/z=655 (實施例3-2)Dissolve 30 g of the compound represented by formula (I-3-1) in 150 mL of THF, and cool to -78 degrees under nitrogen. Slowly add 86 mL of 1.9 mol/L tertiary butyl lithium solution to it, and stir for 30 minutes. A solution in which 36 g of 4'-propyl-[1,1'-bis(cyclohexane)]-4-one was dissolved in 72 mL of THF was slowly added dropwise. After stirring for 30 minutes, 100 mL of water was added, the temperature was returned to room temperature, and liquid separation was performed. The organic layer was washed with saturated brine, and saturated sodium sulfate was added and dried. The solvent was distilled off under reduced pressure to obtain 51 g of solids. MS (EI): m/z=655 (Example 3-2)
使先前所獲得之式(I-3-2)所表示之化合物51 g及對甲苯磺酸1.3 g溶解於甲苯100 mL並進行加熱攪拌。將溶劑適當蒸餾去除,將水去除。進行反應直至蒸餾去除之水消失為止。冷卻至室溫後,添加水50 mL而進行分液,進而利用飽和碳酸氫鈉水溶液洗淨,接著利用飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥,將溶劑於減壓蒸餾去除而獲得固形物。使其溶解於包含己烷之甲苯,使其通過矽膠管柱而獲得溶析物。將所獲得之固形物使用己烷與乙醇之混合溶劑進行再結晶,而獲得式(I-3-3)所表示之化合物43 g。 MS(EI):m/z=619 (實施例3-3)51 g of the compound represented by the formula (I-3-2) and 1.3 g of p-toluenesulfonic acid obtained previously were dissolved in 100 mL of toluene and heated and stirred. The solvent is appropriately distilled off and the water is removed. The reaction proceeds until the water removed by distillation disappears. After cooling to room temperature, 50 mL of water was added for liquid separation, and then washed with saturated sodium bicarbonate aqueous solution, and then washed with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was distilled off under reduced pressure to obtain a solid. It was dissolved in toluene containing hexane and passed through a silica gel column to obtain an eluate. The obtained solid was recrystallized using a mixed solvent of hexane and ethanol to obtain 43 g of a compound represented by formula (I-3-3). MS (EI): m/z=619 (Example 3-3)
使所獲得之式(I-3-3)所表示之化合物43 g溶解於THF與乙醇之混合溶劑,向其中添加5%之鈀碳(palladium carbon)1 g,施加氫氣壓力1 Mpa。確認反應完成,並利用氮氣置換系統後,進行過濾而將鈀去除。於將溶劑於減壓蒸餾去除所獲得之固形物中添加包含己烷之甲苯而使其溶解,使其通過矽膠管柱而獲得溶析物。將其利用包含乙醇之己烷的混合溶劑進行再結晶,進而利用包含甲苯之己烷溶液進行多次再結晶,藉此獲得式(I-3)所表示之化合物5.2 g。 MS(EI):m/z=623 (實施例4)式(I-4)所表示之化合物之製造Dissolve 43 g of the obtained compound represented by the formula (I-3-3) in a mixed solvent of THF and ethanol, add 1 g of 5% palladium carbon, and apply a hydrogen pressure of 1 Mpa. After confirming the completion of the reaction and replacing the system with nitrogen, filtration was performed to remove palladium. Toluene containing hexane is added to the solid substance obtained by distilling off the solvent under reduced pressure to dissolve it, and it is passed through a silica gel column to obtain an eluate. This was recrystallized using a mixed solvent containing ethanol and hexane, and then recrystallized multiple times using a hexane solution containing toluene, thereby obtaining 5.2 g of a compound represented by formula (I-3). MS (EI): m/z=623 (Example 4) Production of compound represented by formula (I-4)
(實施例4-1)(Example 4-1)
一面使式(I-4-1)所表示之化合物3.0 g、式(I-1-4)所表示之化合物7.8 g及碳酸銫8.1 g懸濁於丙酮60 mL,一面進行攪拌,使溫度升至發生回流為止。使反應進行5小時左右,確認反應完成後使溫度下降至室溫。向其中添加甲苯60 mL及水100 mL而使固形物溶解後進行分液。於水層添加甲苯40 mL而進行溶析,將其與先前之有機層一起利用稀鹽酸洗淨數次後,利用飽和碳酸氫鈉水溶液及飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得目標之式(I-4)所表示之化合物4.3 g。 MS(EI):m/z=682 (實施例5)式(I-5)所表示之化合物之製造While suspending 3.0 g of the compound represented by the formula (I-4-1), 7.8 g of the compound represented by the formula (I-1-4), and 8.1 g of cesium carbonate in 60 mL of acetone, stir to increase the temperature Until reflux occurs. The reaction was allowed to proceed for about 5 hours, and after the completion of the reaction, the temperature was lowered to room temperature. To this, 60 mL of toluene and 100 mL of water were added to dissolve the solid matter, and then the liquid was separated. 40 mL of toluene was added to the water layer for elution, and the organic layer was washed with dilute hydrochloric acid several times together with the previous organic layer, and then washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying, the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized, thereby obtaining 4.3 g of the target compound represented by formula (I-4). MS (EI): m/z=682 (Example 5) Production of compound represented by formula (I-5)
(實施例5-1)(Example 5-1)
於氮氣下,使式(I-5-1)所表示之化合物15 g、2-噻吩硼酸7.1 g、四(三苯基膦)鈀(0)1.9 g溶解於THF120 mL,向其中添加1 mol/L之碳酸鉀水溶液55 mL,使溫度升高至60度並攪拌4小時。使溫度下降至室溫,添加甲苯及水而進行分液,將有機層利用稀鹽酸洗淨後,利用飽和碳酸氫鈉水溶液洗淨,接著利用飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥,將溶劑於減壓蒸餾去除而獲得固形物。使其溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使用乙醇與甲苯之混合溶劑進行再結晶,而獲得式(I-5-2)所表示之化合物11.2 g。 MS(EI):m/z=276 (實施例5-2)Under nitrogen, 15 g of the compound represented by formula (I-5-1), 7.1 g of 2-thiopheneboronic acid, and 1.9 g of tetrakis(triphenylphosphine)palladium(0) were dissolved in 120 mL of THF, and 1 mol was added to it /L of potassium carbonate aqueous solution 55 mL, raise the temperature to 60 degrees and stir for 4 hours. The temperature was lowered to room temperature, toluene and water were added for liquid separation, the organic layer was washed with dilute hydrochloric acid, then washed with a saturated aqueous sodium hydrogen carbonate solution, and then washed with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was distilled off under reduced pressure to obtain a solid. It was dissolved in toluene and passed through a silica gel column to obtain an eluate. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 11.2 g of the compound represented by formula (I-5-2). MS (EI): m/z=276 (Example 5-2)
使式(I-5-2)所表示之化合物11.2 g溶解於二氯甲烷50 mL,於室溫向其中緩慢添加三溴化硼10 g。於室溫進行2小時攪拌後,添加水30 mL,攪拌一段時間。藉由分液提取有機層,將其利用飽和食鹽水洗淨後,添加無水硫酸鈉並使其乾燥。將溶劑於減壓蒸餾去除,而獲得式(I-5-3)所表示之化合物9.5 g。 MS(EI):m/z=248 (實施例5-3)11.2 g of the compound represented by formula (I-5-2) was dissolved in 50 mL of dichloromethane, and 10 g of boron tribromide was slowly added thereto at room temperature. After stirring for 2 hours at room temperature, add 30 mL of water and stir for a while. The organic layer was extracted by liquid separation, washed with saturated brine, and anhydrous sodium sulfate was added and dried. The solvent was distilled off under reduced pressure to obtain 9.5 g of a compound represented by formula (I-5-3). MS (EI): m/z=248 (Example 5-3)
一面使式(I-5-3)所表示之化合物4.5 g、式(I-1-4)所表示之化合物11.5 g及碳酸銫11.8 g懸濁於丙酮100 mL,一面進行攪拌,使溫度升至發生回流為止。使反應進行5小時左右,確認反應完成後使溫度下降至室溫。向其中添加甲苯80 mL及水100 mL而使固形物溶解後進行分液。於水層添加甲苯40 mL而進行溶析,將其與先前之有機層一起利用稀鹽酸洗淨數次後,利用飽和碳酸氫鈉水溶液及飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得目標之式(I-5)所表示之化合物4.9 g。 MS(EI):m/z=688 (實施例6)式(I-6)所表示之化合物之製造While 4.5 g of compound represented by formula (I-5-3), 11.5 g of compound represented by formula (I-1-4) and 11.8 g of cesium carbonate were suspended in 100 mL of acetone, the temperature was increased while stirring Until reflux occurs. The reaction was allowed to proceed for about 5 hours, and after the completion of the reaction, the temperature was lowered to room temperature. To this, 80 mL of toluene and 100 mL of water were added to dissolve the solid matter, and then the liquid was separated. 40 mL of toluene was added to the water layer for elution, and the organic layer was washed with dilute hydrochloric acid several times together with the previous organic layer, and then washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying, the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized, thereby obtaining 4.9 g of the compound represented by the target formula (I-5). MS (EI): m/z=688 (Example 6) Production of compound represented by formula (I-6)
(實施例6-1) (Example 6-1)
一面使式(I-6-1)所表示之化合物4.5 g、式(I-1-4)所表示之化合物11.6 g及碳酸銫17.9 g懸濁於丙酮100 mL,一面進行攪拌,使溫度升至發生回流為止。使反應進行5小時左右,確認反應完成後使溫度下降至室溫。向其中添加甲苯80 mL及水100 mL而使固形物溶解後進行分液。於水層添加甲苯40 mL而進行溶析,將其與先前之有機層一起利用稀鹽酸洗淨數次後,利用飽和碳酸氫鈉水溶液及飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥後,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得式(I-6-2)所表示之化合物8.8 g。 MS(EI):m/z=684 (實施例6-2)While 4.5 g of compound represented by formula (I-6-1), 11.6 g of compound represented by formula (I-1-4), and 17.9 g of cesium carbonate were suspended in 100 mL of acetone, the temperature was increased while stirring Until reflux occurs. The reaction was allowed to proceed for about 5 hours, and after the completion of the reaction, the temperature was lowered to room temperature. To this, 80 mL of toluene and 100 mL of water were added to dissolve the solid matter, and then the liquid was separated. 40 mL of toluene was added to the water layer for elution, and the organic layer was washed with dilute hydrochloric acid several times together with the previous organic layer, and then washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying, the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized to obtain 8.8 g of the compound represented by formula (I-6-2). MS (EI): m/z=684 (Example 6-2)
於氮氣下,使式(I-6-2)所表示之化合物8.8 g、式(I-6-3)所表示之化合物4.2 g、四(三苯基膦)鈀(0)1.5 g溶解於THF500 mL,向其中添加1 mol/L之碳酸鉀水溶液58 mL,使溫度升高至60度並攪拌8小時。使溫度下降至室溫,添加甲苯及水而進行分液,將有機層利用稀鹽酸洗淨後,利用飽和碳酸氫鈉水溶液洗淨,接著利用飽和食鹽水洗淨。添加無水硫酸鈉並使其乾燥,將溶劑於減壓蒸餾去除而獲得固形物。使其溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使用乙醇與甲苯之混合溶劑進行再結晶,而獲得式(I-6)所表示之化合物5.2 g。 MS(EI):m/z=808 (實施例7)式(I-7)所表示之化合物之製造Under nitrogen, 8.8 g of the compound represented by formula (I-6-2), 4.2 g of the compound represented by formula (I-6-3), and 1.5 g of tetrakis(triphenylphosphine)palladium(0) were dissolved in THF500 mL, add 58 mL of 1 mol/L potassium carbonate aqueous solution to it, raise the temperature to 60 degrees and stir for 8 hours. The temperature was lowered to room temperature, toluene and water were added for liquid separation, the organic layer was washed with dilute hydrochloric acid, then washed with a saturated aqueous sodium hydrogen carbonate solution, and then washed with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was distilled off under reduced pressure to obtain a solid. It was dissolved in toluene and passed through a silica gel column to obtain an eluate. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 5.2 g of the compound represented by formula (I-6). MS (EI): m/z=808 (Example 7) Production of compound represented by formula (I-7)
(實施例7-1)(Example 7-1)
藉由與實施例3相同之方法,製造式(I-7-1)所表示之化合物至式(I-7)所表示之化合物。 MS(EI):m/z=594 (實施例8)式(I-8)所表示之化合物之製造By the same method as in Example 3, the compound represented by formula (I-7-1) to the compound represented by formula (I-7) were produced. MS (EI): m/z=594 (Example 8) Production of compound represented by formula (I-8)
(實施例8-1)(Example 8-1)
藉由與實施例3相同之方法,製造式(I-8-1)所表示之化合物至式(I-8)所表示之化合物。 MS(EI):m/z=614 (實施例9)式(I-9)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-8-1) to the compound represented by the formula (I-8) were produced. MS (EI): m/z=614 (Example 9) Production of compound represented by formula (I-9)
(實施例9-1)(Example 9-1)
藉由與實施例3相同之方法,製造式(I-9-1)所表示之化合物至式(I-9)所表示之化合物。 MS(EI):m/z=629 (實施例10)式(I-10)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-9-1) to the compound represented by the formula (I-9) were produced. MS (EI): m/z=629 (Example 10) Production of compound represented by formula (I-10)
(實施例10-1)(Example 10-1)
藉由與實施例3相同之方法,製造式(I-10-1)所表示之化合物至式(I-10)所表示之化合物。 MS(EI):m/z=445 (實施例11)式(I-11)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-10-1) to the compound represented by the formula (I-10) were produced. MS (EI): m/z=445 (Example 11) Production of compound represented by formula (I-11)
(實施例11-1)(Example 11-1)
藉由與實施例3相同之方法,製造式(I-11-1)所表示之化合物至式(I-11)所表示之化合物。 MS(EI):m/z=395 (實施例12)式(I-12)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-11-1) to the compound represented by the formula (I-11) were produced. MS (EI): m/z=395 (Example 12) Production of compound represented by formula (I-12)
(實施例12-1)(Example 12-1)
藉由與實施例3相同之方法,製造式(I-12-1)所表示之化合物至式(I-12)所表示之化合物。 MS(EI):m/z=446 (實施例13)式(I-13)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-12-1) to the compound represented by the formula (I-12) were produced. MS (EI): m/z=446 (Example 13) Production of compound represented by formula (I-13)
(實施例13-1)(Example 13-1)
藉由與實施例3相同之方法,製造式(I-13-1)所表示之化合物至式(I-13)所表示之化合物。 MS(EI):m/z=355 (實施例14)式(I-22)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-13-1) to the compound represented by the formula (I-13) were produced. MS (EI): m/z=355 (Example 14) Production of compound represented by formula (I-22)
(實施例14-1)(Example 14-1)
藉由與實施例3相同之方法,製造式(I-22-1)所表示之化合物至式(I-22)所表示之化合物。 MS(EI):m/z=597 (實施例15)式(I-24)所表示之化合物之製造By the same method as in Example 3, the compound represented by formula (I-22-1) to the compound represented by formula (I-22) were produced. MS (EI): m/z=597 (Example 15) Production of compound represented by formula (I-24)
(實施例15-1)(Example 15-1)
藉由與實施例3相同之方法,製造式(I-24-1)所表示之化合物至式(I-24)所表示之化合物。 MS(EI):m/z=622 (實施例16)式(I-25)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-24-1) to the compound represented by the formula (I-24) were produced. MS (EI): m/z=622 (Example 16) Production of compound represented by formula (I-25)
(實施例16-1)(Example 16-1)
藉由與實施例3相同之方法,製造式(I-25-1)所表示之化合物至式(I-25)所表示之化合物。 MS(EI):m/z=586 (實施例17)式(I-26)所表示之化合物之製造By the same method as in Example 3, the compound represented by formula (I-25-1) to the compound represented by formula (I-25) were produced. MS (EI): m/z=586 (Example 17) Production of compound represented by formula (I-26)
(實施例17-1)(Example 17-1)
藉由與實施例3相同之方法,製造式(I-26-1)所表示之化合物至式(I-26)所表示之化合物。 MS(EI):m/z=648 (實施例18)式(I-28)所表示之化合物之製造By the same method as in Example 3, the compound represented by formula (I-26-1) to the compound represented by formula (I-26) were produced. MS (EI): m/z=648 (Example 18) Production of compound represented by formula (I-28)
(實施例18-1)(Example 18-1)
藉由與實施例3相同之方法,製造式(I-28-1)所表示之化合物至式(I-28)所表示之化合物。 MS(EI):m/z=630 (實施例19)式(I-14)所表示之化合物之製造By the same method as in Example 3, the compound represented by the formula (I-28-1) to the compound represented by the formula (I-28) were produced. MS (EI): m/z=630 (Example 19) Production of compound represented by formula (I-14)
(實施例19-1)(Example 19-1)
藉由與實施例1相同之方法,製造式(I-14-1)所表示之化合物、式(I-14-2)所表示之化合物、及式(I-14-3)所表示之化合物至式(I-14)所表示之化合物。 MS(EI):m/z=648 (實施例20)式(I-15)所表示之化合物之製造By the same method as Example 1, the compound represented by formula (I-14-1), the compound represented by formula (I-14-2), and the compound represented by formula (I-14-3) were produced To the compound represented by formula (I-14). MS (EI): m/z=648 (Example 20) Production of compound represented by formula (I-15)
(實施例20-1)(Example 20-1)
藉由與實施例1相同之方法,製造式(I-15-1)所表示之化合物、式(I-15-2)所表示之化合物、及式(I-15-3)所表示之化合物至式(I-15)所表示之化合物。 MS(EI):m/z=746 (實施例21)式(I-16)所表示之化合物之製造By the same method as in Example 1, the compound represented by formula (I-15-1), the compound represented by formula (I-15-2), and the compound represented by formula (I-15-3) were produced To the compound represented by formula (I-15). MS (EI): m/z=746 (Example 21) Production of compound represented by formula (I-16)
(實施例21-1)(Example 21-1)
藉由與實施例1相同之方法,製造式(I-16-1)所表示之化合物及式(I-16-2)所表示之化合物至式(I-16)所表示之化合物。 MS(EI):m/z=686 (實施例22)式(I-17)所表示之化合物之製造By the same method as in Example 1, the compound represented by the formula (I-16-1) and the compound represented by the formula (I-16-2) to the compound represented by the formula (I-16) were produced. MS (EI): m/z=686 (Example 22) Production of compound represented by formula (I-17)
(實施例22-1)(Example 22-1)
藉由與實施例1相同之方法,製造式(I-17-1)所表示之化合物、式(I-17-2)所表示之化合物、及式(I-17-3)所表示之化合物至式(I-17)所表示之化合物。 MS(EI):m/z=608 (實施例23)式(I-18)所表示之化合物之製造By the same method as in Example 1, the compound represented by the formula (I-17-1), the compound represented by the formula (I-17-2), and the compound represented by the formula (I-17-3) were produced To the compound represented by formula (I-17). MS (EI): m/z=608 (Example 23) Production of compound represented by formula (I-18)
(實施例23-1)(Example 23-1)
藉由與實施例1相同之方法,製造式(I-18-1)所表示之化合物、式(I-18-2)所表示之化合物、及式(I-18-3)所表示之化合物至式(I-18)所表示之化合物。 MS(EI):m/z=670 (實施例24)式(I-21)所表示之化合物之製造By the same method as in Example 1, the compound represented by formula (I-18-1), the compound represented by formula (I-18-2), and the compound represented by formula (I-18-3) were produced To the compound represented by formula (I-18). MS (EI): m/z=670 (Example 24) Production of compound represented by formula (I-21)
(實施例24-1)(Example 24-1)
藉由與實施例1相同之方法,製造式(I-21-1)所表示之化合物及式(I-21-2)所表示之化合物至式(I-21)所表示之化合物。 MS(EI):m/z=693 (實施例25)式(I-27)所表示之化合物之製造By the same method as in Example 1, the compound represented by the formula (I-21-1) and the compound represented by the formula (I-21-2) to the compound represented by the formula (I-21) were produced. MS (EI): m/z=693 (Example 25) Production of compound represented by formula (I-27)
(實施例25-1)(Example 25-1)
藉由與實施例1相同之方法,製造式(I-27-1)所表示之化合物及式(I-27-2)所表示之化合物至式(I-27)所表示之化合物。 MS(EI):m/z=786 (實施例26)式(I-29)所表示之化合物之製造By the same method as in Example 1, the compound represented by the formula (I-27-1) and the compound represented by the formula (I-27-2) to the compound represented by the formula (I-27) were produced. MS (EI): m/z=786 (Example 26) Production of compound represented by formula (I-29)
(實施例26-1)(Example 26-1)
藉由與實施例1相同之方法,製造式(I-29-1)所表示之化合物及式(I-29-2)所表示之化合物至式(I-29)所表示之化合物。 MS(EI):m/z=736 (實施例27)式(I-30)所表示之化合物之製造By the same method as in Example 1, the compound represented by the formula (I-29-1) and the compound represented by the formula (I-29-2) to the compound represented by the formula (I-29) were produced. MS (EI): m/z=736 (Example 27) Production of compound represented by formula (I-30)
(實施例27-1)(Example 27-1)
藉由與實施例1相同之方法,製造式(I-30-1)所表示之化合物及式(I-30-2)所表示之化合物至式(I-30)所表示之化合物。 MS(EI):m/z=724 (實施例28)式(I-20)所表示之化合物之製造By the same method as in Example 1, the compound represented by formula (I-30-1) and the compound represented by formula (I-30-2) to the compound represented by formula (I-30) were produced. MS (EI): m/z=724 (Example 28) Production of compound represented by formula (I-20)
(實施例28-1)(Example 28-1)
於氮氣環境下,於反應容器中添加式(I-20-1)所表示之化合物5.0 g、式(I-20-2)所表示之化合物9.0 g、4-二甲胺基吡啶0.2 g、二氯甲烷100 mL。一面進行冰浴冷卻,一面滴加二異丙基碳二醯亞胺5.6 g,並於室溫攪拌8小時。將析出之固體藉由過濾去除,將濾液依序利用5%鹽酸、水及食鹽水洗淨,將溶劑於減壓蒸餾去除。使所獲得之固形物溶解於甲苯,使其通過矽膠管柱而獲得溶析物。使所獲得之固形物加熱溶解於甲苯與乙醇之混合溶劑而進行再結晶,從而獲得目標之式(I-20)所表示之化合物8.0 g。 MS(EI):m/z=660 (實施例29)式(I-23)所表示之化合物之製造In a nitrogen atmosphere, add 5.0 g of the compound represented by formula (I-20-1), 9.0 g of the compound represented by formula (I-20-2), 0.2 g of 4-dimethylaminopyridine, and Dichloromethane 100 mL. While cooling in an ice bath, 5.6 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 8 hours. The precipitated solid was removed by filtration, the filtrate was washed with 5% hydrochloric acid, water and brine in order, and the solvent was distilled off under reduced pressure. The obtained solid is dissolved in toluene, and passed through a silica gel column to obtain an eluate. The obtained solid substance was heated and dissolved in a mixed solvent of toluene and ethanol to be recrystallized to obtain 8.0 g of the compound represented by the target formula (I-20). MS (EI): m/z=660 (Example 29) Production of compound represented by formula (I-23)
(實施例29-1)(Example 29-1)
藉由與實施例28相同之方法,製造式(I-23-1)所表示之化合物及式(I-23-2)所表示之化合物至式(I-23)所表示之化合物。 MS(EI):m/z=683 (實施例30至實施例41、比較例1至比較例4) 於實施例中,針對液晶化合物之記載,使用以下簡稱。 (環結構)By the same method as in Example 28, the compound represented by formula (I-23-1) and the compound represented by formula (I-23-2) to the compound represented by formula (I-23) were produced. MS (EI): m/z=683 (Example 30 to Example 41, Comparative Example 1 to Comparative Example 4) In the examples, the following abbreviations are used for the description of the liquid crystal compound. (Ring structure)
(側鏈結構及連結結構)(Side chain structure and connection structure)
[表1]
實施例中,測定之特性如下所述。再者,只要未特別記載,則測定係依據JEITA ED-2521B中規定之方法。In the examples, the measured characteristics are as follows. Furthermore, unless otherwise stated, the measurement is based on the method specified in JEITA ED-2521B.
∆n:於25℃之折射率各向異性 @589 nm ∆ε:於25℃之介電各向異性 於測試單元中,使用添加有本發明之化合物之液晶組成物進行以下評價。 (液晶評價單元之製成方法) 首先,將本實施例中記載之液晶組成物藉由真空注入法注入包含附ITO之基板之液晶單元中,上述附ITO之基板係塗佈「單元間隙3.5 μm間誘發垂直配向之聚醯亞胺配向膜」後對上述聚醯亞胺配向膜進行摩擦處理所得者。作為垂直配向膜形成材料,使用JSR公司製造之JALS2096。 於注入完成後,於單元之正面及背面,以與液晶配向方位(=摩擦方位)相差45度之方式且成為正交偏光下之方式貼附偏光板。 (色度變化之測定) 於液晶單元之上下電極間,依序自0 V至10 V施加AC電壓,自單元正面測定各電壓下之穿透波長光譜,計算光源D65條件下之單元色度。 此時,根據下述式算出0 V之色度及10 V之色度(x,y)之變化量∆delta,於處於各範圍內之情形時,各自定義為◎〇∆×。 0 V之顏色座標(x0,y0) 10 V之顏色座標(x10,y10)∆n: Refractive index anisotropy at 25℃ @589 nm ∆ε: Dielectric anisotropy at 25℃ In the test unit, the following evaluation was performed using the liquid crystal composition added with the compound of the present invention. (Method of manufacturing liquid crystal evaluation unit) First, the liquid crystal composition described in this embodiment is injected into a liquid crystal cell including a substrate with ITO by a vacuum injection method. The substrate with ITO is coated with a polyimide that induces vertical alignment between a cell gap of 3.5 μm. Alignment film" is obtained by rubbing the above-mentioned polyimide alignment film. As the vertical alignment film forming material, JALS2096 manufactured by JSR Corporation was used. After the injection is completed, a polarizing plate is attached to the front and back of the cell in a way that is 45 degrees different from the orientation of the liquid crystal (= rubbing orientation) and becomes under orthogonal polarization. (Measurement of chromaticity change) Between the upper and lower electrodes of the liquid crystal cell, an AC voltage is applied sequentially from 0 V to 10 V, and the transmission wavelength spectrum at each voltage is measured from the front of the cell, and the cell chromaticity under the condition of light source D65 is calculated. At this time, the chromaticity of 0 V and the chromaticity of 10 V (x, y) change Δdelta are calculated according to the following formula, and when they are in each range, each is defined as ◎〇Δ×. Color coordinates of 0 V (x0,y0) 10 V color coordinates (x10, y10)
[表2]
將測定結果示於下表。The measurement results are shown in the table below.
[表3]
[表4]
[表5]
[表6]
藉此,於添加有本發明之化合物之液晶組成物中,抑制了因電壓施加造成之色度變化。根據以上之結果,本案發明之液晶組成物於用於顯示元件之情形時,由於因電壓施加造成液晶配向變化時色調及色度等之變化較小,故作為液晶顯示元件用之材料有用。Thereby, in the liquid crystal composition added with the compound of the present invention, the chromaticity change caused by voltage application is suppressed. Based on the above results, when the liquid crystal composition of the present invention is used in a display device, since the change in color tone and chromaticity when the liquid crystal alignment changes due to voltage application is small, it is useful as a material for liquid crystal display devices.
無no
[圖1]係化合物(Z)之概念圖。 [圖2]係概念性地表示構成化合物(Z)之各基(LA、LB及ZG)之波長色散性之曲線圖。 [圖3]係概念性地表示化合物(Z)之結構。[Figure 1] A conceptual diagram of compound (Z). [Figure 2] A graph conceptually showing the wavelength dispersion of each group (LA, LB, and ZG) constituting the compound (Z). [Figure 3] Conceptually shows the structure of compound (Z).
Claims (20)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JPJP2018-231624 | 2018-12-11 | ||
JP2018231624 | 2018-12-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
TW202035380A true TW202035380A (en) | 2020-10-01 |
Family
ID=71075323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW108143139A TW202035380A (en) | 2018-12-11 | 2019-11-27 | Liquid crystal composition, display element and compound |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP6836733B2 (en) |
CN (1) | CN112739799A (en) |
TW (1) | TW202035380A (en) |
WO (1) | WO2020121823A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112851562A (en) * | 2021-01-22 | 2021-05-28 | 烟台显华化工科技有限公司 | Aromatic ring liquid crystal compound, liquid crystal composition and application thereof |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD265155A1 (en) * | 1987-09-24 | 1989-02-22 | Univ Halle Wittenberg | NEMATIC LIQUID CRYSTALS WITH GLASS PHASES |
JP5084293B2 (en) * | 2006-02-07 | 2012-11-28 | 富士フイルム株式会社 | Optical film, retardation plate, and liquid crystal compound |
JP2008174717A (en) * | 2006-12-18 | 2008-07-31 | Fujifilm Corp | Liquid crystal composition and liquid crystal element |
JP2010163482A (en) * | 2009-01-13 | 2010-07-29 | Fujifilm Corp | Cellulose composition, optical film, retardation plate, and liquid crystal display |
US8747695B2 (en) * | 2009-10-24 | 2014-06-10 | Merck Patent Gmbh | Compounds for a liquid-crystalline medium, and use for high-frequency components |
JP2011207965A (en) * | 2010-03-29 | 2011-10-20 | Fujifilm Corp | Cellulosic film, polarizing plate, liquid crystal display device, and compound |
WO2013145574A1 (en) * | 2012-03-30 | 2013-10-03 | コニカミノルタ株式会社 | Method and apparatus for producing elongate drawn film |
CN104870352B (en) * | 2012-12-13 | 2017-03-22 | 柯尼卡美能达株式会社 | Optical film roll, method for producing same, polarizing plate, and display device |
US20160200851A1 (en) * | 2013-08-19 | 2016-07-14 | Lg Chem, Ltd. | Optical Film Having Reverse Wavelength Dispersion and Display Device Including the Same (As Amended) |
JP6343902B2 (en) * | 2013-10-16 | 2018-06-20 | Jnc株式会社 | Polymerizable compound, polymerizable composition, and liquid crystal display device |
US9809668B2 (en) * | 2013-11-29 | 2017-11-07 | Dic Corporation | Polymerizable compound, composition, polymer, optically anisotropic body, liquid crystal display device, and organic EL device |
JP6648438B2 (en) * | 2014-08-27 | 2020-02-14 | Jnc株式会社 | Liquid crystal compound, liquid crystal composition and polymer thereof |
JP6597244B2 (en) * | 2014-12-02 | 2019-10-30 | Jnc株式会社 | Liquid crystal compound, liquid crystal composition and polymer thereof |
KR20160106513A (en) * | 2015-03-02 | 2016-09-12 | 제이엔씨 주식회사 | Polymerizable liquid crystal composition and optically anisotropic film |
JPWO2017038267A1 (en) * | 2015-09-03 | 2017-11-09 | Dic株式会社 | Compound having mesogenic group, composition containing the same, polymer obtained by polymerizing polymerizable composition, optical anisotropic body, and retardation film |
JP6624696B2 (en) * | 2015-12-08 | 2019-12-25 | Dic株式会社 | Polymerizable compound and optically anisotropic substance |
JP6265312B1 (en) * | 2016-04-27 | 2018-01-24 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display device using the same |
WO2018101196A1 (en) * | 2016-11-29 | 2018-06-07 | 富士フイルム株式会社 | Polymerizable liquid crystal composition, optically anisotropic membrane, optical film, polarizing plate, image display device, and organic electroluminescent display device |
JP6418476B1 (en) * | 2017-01-06 | 2018-11-07 | Dic株式会社 | Polymerizable compound and optical anisotropic body |
-
2019
- 2019-11-27 TW TW108143139A patent/TW202035380A/en unknown
- 2019-11-28 CN CN201980061409.5A patent/CN112739799A/en active Pending
- 2019-11-28 WO PCT/JP2019/046539 patent/WO2020121823A1/en active Application Filing
- 2019-11-28 JP JP2020528062A patent/JP6836733B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP6836733B2 (en) | 2021-03-03 |
JPWO2020121823A1 (en) | 2021-02-15 |
CN112739799A (en) | 2021-04-30 |
WO2020121823A1 (en) | 2020-06-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7331033B2 (en) | Liquid-crystalline media with homeotropic alignment | |
CN106536679B (en) | Liquid-crystalline medium with homeotropic alignment | |
JP6513624B2 (en) | Liquid crystal display and liquid crystal medium having homeotropic alignment | |
CN104870612B (en) | Liquid crystal display and the liquid crystal media with vertical plane orientation | |
CN103834414B (en) | Liquid crystal medium, stabilizing method thereof and liquid crystal display | |
TWI527884B (en) | Polymerisable compounds and the use thereof in liquid-crystal displays | |
JP5519659B2 (en) | Emissive liquid crystal compound, optical film including the same, and liquid crystal display device | |
TW200918648A (en) | Calamitic mesogenic compounds | |
TW201620892A (en) | 4,6-difluorodibenzothiophene derivatives | |
TW201139365A (en) | Polymerisable compounds and the use thereof in liquid-crystal media and liquid-crystal displays | |
JP2019112628A (en) | Liquid crystal medium showing homeotropic alignment | |
TW201012904A (en) | Mesogenic compounds comprising discotic and calamitic groups | |
CN112029512A (en) | Liquid crystal composition and liquid crystal display element | |
JP2013087109A (en) | Polymerizable chiral compound | |
WO2019098040A1 (en) | Polymerizable compound, and liquid crystal composition and liquid crystal display element using same | |
CN111770909A (en) | Polymerizable compound, and liquid crystal composition and liquid crystal display element using same | |
TW202035380A (en) | Liquid crystal composition, display element and compound | |
TWI717463B (en) | Liquid crystal composition and single-layer coating type horizontal alignment film | |
JP4602645B2 (en) | Fluorinated naphthalene, liquid crystal mixture containing them, and liquid crystal display | |
KR20160001773A (en) | Thienothiophenes liquid crystal compounds, liquid crystal compositions containing TT, and electro-optical device | |
CN113493694A (en) | Compound, liquid crystal composition and liquid crystal display element | |
TW202021958A (en) | Compound, liquid crystal composition, liquid crystal display element, and liquid crystal display | |
TWI691483B (en) | Chiral dopants having a nortricyclan unit | |
JP5686434B2 (en) | Liquid crystalline polymer with diacetylene structure | |
JP7395940B2 (en) | Liquid crystal composition and liquid crystal display element |