WO2010131594A1 - 液晶表示素子 - Google Patents
液晶表示素子 Download PDFInfo
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- WO2010131594A1 WO2010131594A1 PCT/JP2010/057748 JP2010057748W WO2010131594A1 WO 2010131594 A1 WO2010131594 A1 WO 2010131594A1 JP 2010057748 W JP2010057748 W JP 2010057748W WO 2010131594 A1 WO2010131594 A1 WO 2010131594A1
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- liquid crystal
- crystal display
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- compound
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- 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
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- 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
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3009—Cy-Ph
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3019—Cy-Cy-Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
- C09K2019/3042—Cy-Cy-C2H4-Ph-Ph
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
- C09K2019/3075—Cy-COO-Ph
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- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
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- 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
- G02F1/0009—Materials therefor
- G02F1/0045—Liquid crystals characterised by their physical properties
Definitions
- the present invention mainly relates to a liquid crystal composition suitable for an AM (active matrix) device and the like, and an AM device containing the composition.
- a liquid crystal composition having a positive dielectric anisotropy, a TN (twistedistnematic) mode, an OCB (optically compensated bend) mode, an IPS (in-plane switching) mode, or a PSA (Polymer sustained) containing the composition. alignment) mode element.
- the classification based on the operation mode of the liquid crystal includes PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS ( in-plane switching), VA (vertical alignment), PSA (Polymer sustained alignment) mode, and the like.
- the classification based on the element drive system is PM (passive matrix) and AM (active matrix). PM is classified into static and multiplex, and AM is classified into TFT (thin film insulator), MIM (metal insulator metal), and the like. TFTs are classified into amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to the manufacturing process.
- the classification based on the light source includes a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both natural light and backlight.
- the elements contain a liquid crystal composition having appropriate characteristics.
- This liquid crystal composition has a nematic phase.
- the general characteristics of the composition are improved.
- the relationships in the two general characteristics are summarized in Table 1 below.
- the general characteristics of the composition will be further described based on a commercially available AM device.
- the temperature range of the nematic phase is related to the temperature range in which the device can be used.
- a preferred upper limit temperature of the nematic phase is about 70 ° C. or more, and a preferred lower limit temperature of the nematic phase is about ⁇ 10 ° C. or less.
- the viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. Therefore, a small viscosity in the composition is preferred. Small viscosities at low temperatures are more preferred.
- the optical anisotropy of the composition is related to the contrast ratio of the device.
- the product ( ⁇ n ⁇ d) of the optical anisotropy ( ⁇ n) of the composition and the cell gap (d) of the device is designed to maximize the contrast ratio.
- the appropriate product value depends on the type of operation mode. For a device with a mode such as TN, a suitable value is about 0.45 ⁇ m.
- a composition having a large optical anisotropy is preferable for a device having a small cell gap.
- a large dielectric anisotropy in the composition contributes to a low threshold voltage, a small power consumption and a large contrast ratio in the device. Therefore, a large dielectric anisotropy is preferable.
- a large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage is preferable.
- a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after being used for a long time is preferable.
- the stability of the composition against ultraviolet rays and heat relates to the lifetime of the liquid crystal display element. When their stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM device used in a liquid crystal projector, a liquid crystal television, and the like.
- a large elastic constant in the composition contributes to a short response time and a large contrast ratio in the device. Therefore, a large elastic constant is preferred.
- a composition having a positive dielectric anisotropy is used for an AM device having a TN mode.
- a composition having negative dielectric anisotropy is used for an AM device having a VA mode.
- a composition having a positive or negative dielectric anisotropy is used in an AM device having an IPS mode.
- a composition having a positive or negative dielectric anisotropy is used in an AM device having a PSA mode.
- Examples of liquid crystal compositions having positive dielectric anisotropy used for liquid crystal display elements are disclosed in the following patent documents.
- Desirable AM elements have such characteristics as a wide usable temperature range, a short response time, a large contrast ratio, a low threshold voltage, a large voltage holding ratio, and a long life. A shorter response time is desirable even at 1 millisecond. Therefore, desirable properties of the composition include a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a large optical anisotropy, a large dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light, a heat High stability against.
- One object of the present invention is to provide a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a large optical anisotropy, a large dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light, and a high resistance to heat. It is a liquid crystal composition satisfying at least one characteristic in characteristics such as high stability. Another object is a liquid crystal composition having an appropriate balance regarding at least two properties. Another object is a liquid crystal display device containing such a composition.
- Another object is a composition having a large optical anisotropy, a large dielectric anisotropy, a high stability to ultraviolet light, etc., and has a short response time, a large voltage holding ratio, a large contrast ratio, a long lifetime, etc. It is an AM element.
- a liquid crystal display device comprising an alignment layer, a polarizing plate and a transparent electrode, comprising at least one transparent substrate and having a liquid crystal composition sandwiched between the substrates, wherein the liquid crystal composition is a first liquid crystal composition.
- the liquid crystal display device is a liquid crystal composition containing at least one compound selected from the group of compounds represented by formula (1) as a component and having positive dielectric anisotropy.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which any hydrogen is replaced by fluorine.
- Ring A is independently tetrahydropyran-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4; -Phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, or 2,5-pyrimidine;
- Z 1 is independently a single bond, ethylene, or carbonyloxy Yes;
- X 1 and X 2 are independently hydrogen or fluorine;
- Y 1 is fluorine, chlorine, or trifluoromethoxy;
- m is 1, 2, or 3.
- Advantages of the present invention include a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a large optical anisotropy, a large dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light, and a high stability to heat. It is a liquid crystal composition that satisfies at least one characteristic such as property.
- One aspect of the present invention is a liquid crystal composition having an appropriate balance regarding at least two properties.
- Another aspect is a liquid crystal display device containing such a composition.
- the other aspect is a composition having a large optical anisotropy, a large dielectric anisotropy, a high stability to ultraviolet light, etc., and has a short response time, a large voltage holding ratio, a large contrast ratio, a long lifetime, etc. It is an AM element.
- liquid crystal composition of the present invention or the liquid crystal display device of the present invention may be abbreviated as “composition” or “device”, respectively.
- a liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module.
- Liquid crystal compound means a compound having a liquid crystal phase such as a nematic phase or a smectic phase, or a compound having no liquid crystal phase but useful as a component of a composition. This useful compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and has a rod-like molecular structure.
- An optically active compound or polymerizable compound may be added to the composition.
- Compound (1) means one compound or two or more compounds represented by formula (1). The same applies to compounds represented by other formulas. “Arbitrary” indicates that not only the position but also the number is arbitrary, but the case where the number is 0 is not included.
- the upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.
- the lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.
- “High specific resistance” means that the composition has a large specific resistance not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase, and after being used for a long time, not only at room temperature but also at the upper limit temperature of the nematic phase. It means having a large specific resistance even at a close temperature.
- “High voltage holding ratio” means that the device has a large voltage holding ratio not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase.
- the first component is one compound or two or more compounds.
- the “ratio of the first component” means the percentage by weight (% by weight) of the first component based on the total weight of the liquid crystal composition. The same applies to the ratio of the second component.
- the ratio of the additive mixed with the composition means a percentage by weight (% by weight) or a percentage by weight (ppm) based on the total weight of the liquid crystal composition.
- R 1 is used for a plurality of compounds.
- the meanings of any two R 1 may be the same or different.
- R 1 of compound (1-1) is ethyl
- R 1 of compound (1-1) is ethyl
- R 1 of compound (1-7) is propyl.
- R 2 , R 3 and the like represents chlorine.
- a liquid crystal display device comprising an alignment layer, a polarizing plate and a transparent electrode, comprising at least one transparent substrate and having a liquid crystal composition sandwiched between the substrates, wherein the liquid crystal composition is a first liquid crystal composition.
- a liquid crystal display device which is a liquid crystal composition containing at least one compound selected from the group of compounds represented by formula (1) as a component and having positive dielectric anisotropy.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which any hydrogen is replaced by fluorine.
- Ring A is independently tetrahydropyran-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4; -Phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, or 2,5-pyrimidine;
- Z 1 is independently a single bond, ethylene, or carbonyloxy Yes;
- X 1 and X 2 are independently hydrogen or fluorine;
- Y 1 is fluorine, chlorine, or trifluoromethoxy;
- m is 1, 2, or 3.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which any hydrogen is replaced by fluorine. .
- the first component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formula (1-1), and at least selected from the group of compounds represented by formula (1-7) Item 3.
- the first component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formula (1-12), and at least selected from the group of compounds represented by formula (1-24) Item 3.
- Item 13 The liquid crystal display device according to any one of items 1 to 12, wherein the liquid crystal composition has a ratio of the first component in the range of 10% by weight to 70% by weight based on the total weight of the liquid crystal composition.
- Item 14 The liquid crystal display element according to any one of items 1 to 13, wherein the liquid crystal composition further contains at least one compound selected from the group of compounds represented by formula (2) as the second component.
- R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine.
- Ring B and ring C are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene. Or 2,5-difluoro-1,4-phenylene;
- Z 2 is independently a single bond, ethylene, or carbonyloxy;
- p is 1, 2, or 3.
- Item 15 The liquid crystal display device according to item 14, wherein the second component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formulas (2-1) to (2-11).
- R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon 2 having any hydrogen substituted with fluorine. To 12 alkenyl.
- the second component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formula (2-1), and at least selected from the group of compounds represented by formula (2-5) Item 16.
- the second component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formula (2-1), and at least selected from the group of compounds represented by formula (2-7) Item 16.
- the second component of the liquid crystal composition is at least one compound selected from the group of compounds represented by formula (2-1), and at least one compound selected from the group of compounds represented by formula (2-5) Item 16.
- Item 20 The liquid crystal display device according to any one of items 14 to 19, wherein the liquid crystal composition has a ratio of the second component in the range of 30% by weight to 90% by weight based on the total weight of the liquid crystal composition.
- Item 21 The liquid crystal display device according to any one of items 1 to 20, wherein an operation mode of the liquid crystal display device is a TN mode, an OCB mode, an IPS mode, or a PSA mode, and a driving method of the liquid crystal display device is an active matrix method. .
- Item 22 A liquid crystal composition contained in the liquid crystal display element according to any one of items 1 to 21.
- Item 23 The liquid crystal composition according to item 22, wherein the elastic constant (K) is 13 pN or more, and the ratio of the elastic constant (K) to the viscosity ( ⁇ ) is 0.8 nN / Pa ⁇ s (nm 2 / s) or more.
- Item 24 The liquid crystal composition according to any one of items 22 or 23, wherein the frequency dependence of dielectric anisotropy at ⁇ 20 ° C. ( ⁇ (5 kHz) / ⁇ (50 Hz)) is 0.50 or more.
- Item 27 Use of the liquid crystal composition according to any one of items 22 to 26 for a liquid crystal display element.
- the present invention includes the following items. 1) The above composition further containing an optically active compound, 2) the above composition further containing additives such as an antioxidant, an ultraviolet absorber, an antifoaming agent, a polymerizable compound and a polymerization initiator. 3) AM device containing the above composition 4) Device containing the above composition and having a TN, ECB, OCB, IPS, or PSA mode 5) Transmission type containing the above composition 6) Use of the above composition as a composition having a nematic phase, 7) Use of the above composition as an optically active composition by adding an optically active compound to the above composition.
- additives such as an antioxidant, an ultraviolet absorber, an antifoaming agent, a polymerizable compound and a polymerization initiator.
- AM device containing the above composition 4) Device containing the above composition and having a TN, ECB, OCB, IPS, or PSA mode 5) Transmission type containing the above composition 6) Use of the above composition as a composition
- composition of the present invention will be described in the following order. First, the constitution of component compounds in the composition will be described. Second, the main characteristics of the component compounds and the main effects of the compounds on the composition will be explained. Third, the combination of components in the composition, the preferred ratio of the component compounds, and the basis thereof will be described. Fourth, a preferred form of the component compound will be described. Fifth, specific examples of component compounds are shown. Sixth, additives that may be mixed into the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Finally, the use of the composition will be described.
- the composition of the component compounds in the composition will be described.
- the composition of the present invention is classified into Composition A and Composition B.
- the composition A may further contain other liquid crystal compounds, additives, impurities and the like.
- the “other liquid crystal compound” is a liquid crystal compound different from the compound (1) and the compound (2). Such compounds are mixed into the composition for the purpose of further adjusting the properties.
- a smaller amount of cyano compound is preferable from the viewpoint of stability to heat or ultraviolet light.
- a more desirable ratio of the cyano compound is 0% by weight.
- Additives include optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, and the like. Impurities are compounds mixed in a process such as synthesis of component compounds. Even if this compound is a liquid crystal compound, it is classified as an impurity here.
- Composition B consists essentially of a compound selected from compound (1) and compound (2). “Substantially” means that the composition may contain additives and impurities, but does not contain a liquid crystal compound different from these compounds. Composition B has fewer components than composition A. From the viewpoint of reducing the cost, the composition B is preferable to the composition A. The composition A is preferable to the composition B from the viewpoint that the physical properties can be further adjusted by mixing other liquid crystal compounds.
- the main characteristics of the component compounds and the main effects of the compounds on the characteristics of the composition will be explained.
- the main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention.
- L means large or high
- M means moderate
- S means small or low.
- L, M, and S are classifications based on a qualitative comparison among the component compounds, and 0 (zero) means that the value is close to zero.
- Compound (1) decreases the minimum temperature and increases the dielectric anisotropy.
- Compound (2) increases the maximum temperature or decreases the viscosity.
- the combination of the components in the composition is a first component and a first component + second component.
- the combination of the components in a preferred composition is a first component + second component.
- a desirable ratio of the first component is approximately 10% by weight or more for decreasing the minimum temperature and increasing the dielectric anisotropy, and approximately 70% by weight or less for decreasing the viscosity.
- a more desirable ratio is in the range of approximately 10% by weight to approximately 65% by weight.
- a particularly preferred ratio is in the range of approximately 15% by weight to approximately 60% by weight.
- a desirable ratio of the second component is approximately 30% by weight or more for increasing the maximum temperature or decreasing the viscosity, and approximately 90% by weight or less for increasing the dielectric anisotropy.
- a more desirable ratio is in the range of approximately 35% by weight to approximately 85% by weight.
- a particularly desirable ratio is in the range of approximately 40% by weight to approximately 80% by weight.
- R 1 , R 2 , and R 3 are each independently an alkyl having 1 to 12 carbons, an alkoxy having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, or a carbon in which any hydrogen is replaced with fluorine 2 to 12 alkenyl.
- Desirable R 1 is alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat.
- Desirable R 2 or R 3 is alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat.
- Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. More desirable alkyl is ethyl, propyl, butyl, pentyl, or heptyl for decreasing the viscosity.
- Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.
- Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl for decreasing the viscosity.
- the preferred configuration of —CH ⁇ CH— in these alkenyls depends on the position of the double bond.
- Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity.
- Cis is preferable in alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.
- linear alkenyl is preferable to branching.
- alkenyl in which any hydrogen is replaced by fluorine include 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4- Pentenyl and 6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinyl and 4,4-difluoro-3-butenyl for decreasing the viscosity.
- Ring A is tetrahydropyran-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3 Any two rings A when -fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, or 2,5-pyrimidine and m is 2 or 3 are the same; May be different. Desirable ring A is 1,4-phenylene for increasing the optical anisotropy.
- Tetrahydropyran-2,5-diyl is Ring B and Ring C are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro- Any two rings B when 1,4-phenylene and p is 2 or 3 may be the same or different.
- Desirable ring B or ring C is 1,4-cyclohexylene for decreasing the viscosity, and 1,4-phenylene for increasing the optical anisotropy.
- Z 1 and Z 2 are independently a single bond, ethylene, or carbonyloxy, and any two Z 1 when m is 2 or 3 may be the same or different, and p is Any two Z 2 when 2 or 3 may be the same or different. Desirable Z 1 or Z 2 is a single bond for decreasing the viscosity.
- X 1 and X 2 are independently hydrogen or fluorine. Desirable X 1 or X 2 is fluorine for increasing the dielectric anisotropy.
- Y 1 is fluorine, chlorine, or trifluoromethoxy. Desirable Y 1 is fluorine for decreasing the minimum temperature.
- n and p are independently 1, 2, or 3. Desirable m is 2 for decreasing the minimum temperature. Preferred p is 1 for decreasing the viscosity.
- R 4 is straight chain alkyl having 1 to 12 carbons.
- R 5 is straight-chain alkyl having 1 to 12 carbons or straight-chain alkoxy having 1 to 12 carbons.
- R 6 and R 7 are independently straight-chain alkyl having 1 to 12 carbons or straight-chain alkenyl having 2 to 12 carbons.
- trans is preferable to cis for the configuration of 1,4-cyclohexylene for increasing the maximum temperature.
- Desirable compounds (1) are from the compound (1-1-1) to the compound (1-41-1). More desirable compounds (1) are the compound (1-1-1), the compound (1-7-1), the compound (1-8-1), the compound (1-11-1), the compound (1-12-1). 1), Compound (1-22-1), Compound (1-23-1), Compound (1-24-1), Compound (1-25-1), Compound (1-34-1), and Compound (1-39-1). Particularly preferred compounds (1) are the compound (1-1-1), the compound (1-7-1), the compound (1-11-1), the compound (1-12-1), and the compound (1-2-2). 1), the compound (1-23-1), the compound (1-24-1), and the compound (1-34-1). Desirable compounds (2) are from the compound (2-1-1) to the compound (2-11-1).
- More desirable compounds (2) are the compound (2-1-1), the compound (2-3-1), the compound (2-5-1), the compound (2-7-1), and the compound (2-8- 1) and compound (2-11-1). Particularly preferred compounds (2) are the compound (2-1-1), the compound (2-5-1), the compound (2-7-1), and the compound (2-11-1).
- additives that may be mixed with the composition will be described.
- Such additives are optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, and the like.
- An optically active compound is mixed with the composition for the purpose of inducing a helical structure of liquid crystal to give a twist angle. Examples of such compounds are compound (3-1) to compound (3-4).
- a desirable ratio of the optically active compound is approximately 5% by weight or less. A more desirable ratio is in the range of approximately 0.01% by weight to approximately 2% by weight.
- oxidation prevention An agent is mixed into the composition.
- Preferred examples of the antioxidant include a compound (4) where n is an integer of 1 to 9.
- n is 1, 3, 5, 7, or 9. Further preferred n is 1 or 7. Since the compound (4) in which n is 1 has high volatility, it is effective in preventing a decrease in specific resistance due to heating in the atmosphere. Since the compound (4) in which n is 7 has low volatility, it is effective for maintaining a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after using the device for a long time.
- a desirable ratio of the antioxidant is approximately 50 ppm or more for achieving its effect, and is approximately 600 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 300 ppm.
- the ultraviolet absorber examples include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Also preferred are light stabilizers such as sterically hindered amines.
- a desirable ratio in these absorbents and stabilizers is approximately 50 ppm or more for obtaining the effect thereof, and approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.
- a dichroic dye such as an azo dye or an anthraquinone dye is mixed with the composition so as to be adapted to a device having a guest host (GH) mode.
- a preferred ratio of the dye is in the range of approximately 0.01% by weight to approximately 10% by weight.
- an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is mixed with the composition.
- a desirable ratio of the antifoaming agent is approximately 1 ppm or more for obtaining the effect thereof, and approximately 1000 ppm or less for preventing a poor display.
- a more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.
- a polymerizable compound is mixed with the composition in order to adapt to a device having a polymer sustained alignment (PSA) mode.
- Preferred examples of the polymerizable compound are compounds having a polymerizable group such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), vinyl ketone and the like. Particularly preferred examples are acrylate or methacrylate derivatives.
- a desirable ratio of the polymerizable compound is approximately 0.05% by weight or more for obtaining the effect thereof, and approximately 10% by weight or less for preventing a display defect. A more desirable ratio is in the range of approximately 0.1% by weight to approximately 2% by weight.
- the polymerizable compound is preferably polymerized by UV irradiation or the like in the presence of a suitable initiator such as a photopolymerization initiator.
- a suitable initiator such as a photopolymerization initiator.
- Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature.
- Irgacure 651 registered trademark
- Irgacure 184 registered trademark
- Darocure 1173 registered trademark
- the polymerizable compound preferably comprises a photopolymerization initiator in the range of about 0.1% to about 5% by weight.
- the photopolymerization initiator is contained in the range of about 1 wt% to about 3 wt%.
- the composition of the present invention mainly has a minimum temperature of about ⁇ 10 ° C. or lower, a maximum temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20.
- a device containing this composition has a large voltage holding ratio.
- This composition is suitable for an AM device.
- This composition is particularly suitable for a transmissive AM device.
- a composition having an optical anisotropy in the range of about 0.08 to about 0.25 by controlling the proportion of the component compounds or by mixing other liquid crystal compounds, and further from about 0.10 Compositions having optical anisotropy in the range of about 0.30 may be prepared.
- This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.
- This composition can be used for an AM device. Further, it can be used for PM elements.
- This composition can be used for an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, VA, and PSA.
- Use for an AM device having a TN, OCB or IPS mode is particularly preferable.
- These elements may be reflective, transmissive, or transflective. Use in a transmissive element is preferred. It can also be used for an amorphous silicon-TFT device or a polycrystalline silicon-TFT device.
- NCAP non-curvilinear-aligned-phase
- PD polymer-dispersed
- the liquid crystal display element is a liquid crystal display element including an alignment layer, a polarizing plate, and a transparent electrode, which includes a liquid crystal composition sandwiched between a pair of substrates at least one of which is transparent.
- the glass substrate includes two glass substrates called an array substrate and a color filter substrate, and a thin film transistor (TFT), a pixel, a colored layer, and the like are formed on each glass substrate.
- TFT thin film transistor
- a liquid crystal composition is injected between the two glass substrates to form a liquid crystal display element.
- aluminosilicate glass or aluminoborosilicate glass is used for the glass substrate.
- the alignment agent used for the alignment layer is not particularly limited as long as it is a compound that provides alignment to the liquid crystal molecules by having an alignment property by rubbing treatment.
- Typical examples include polyimide, polyamide, polyamideimide, polyvinyl alcohol, polyester, polycarbonate, and Examples thereof include polyamic acid, which is a precursor of polyimide, and those added with a substance that maintains or enhances orientation characteristics.
- polyimide, polyamic acid or polyvinyl alcohol is preferred.
- the polarizing plate can be obtained, for example, by adsorbing and orienting iodine molecules in the same direction as the stretching direction on a uniaxially stretched polyvinyl alcohol (Poly Vinyl Alcohol; PVA) film.
- PVA Poly Vinyl Alcohol
- indium-tin oxide Indium-Tin Oxide
- indium-zinc oxide Indium-Zinc Oxide
- the composition and this compound are used as measurement objects.
- the object to be measured was a composition
- the measurement object was a compound
- a sample for measurement was prepared by mixing this compound (15% by weight) with mother liquid crystals (85% by weight).
- the ratio of the compound and the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight in this order. changed.
- the maximum temperature, optical anisotropy, viscosity and dielectric anisotropy values for the compound were determined.
- the components of the mother liquid crystals are as follows. The ratio of each component is% by weight.
- Measured characteristic values according to the following method. Many of them are the methods described in the Standard of Electronics Industry Association of Japan EIAJ ED-2521A, or a modified method thereof.
- NI Maximum temperature of nematic phase
- a sample was placed on a hot plate of a melting point measuring device equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature was measured when a part of the sample changed from a nematic phase to an isotropic liquid.
- the upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.
- T C Minimum temperature of nematic phase
- Viscosity (bulk viscosity; ⁇ ; measured at 20 ° C .; mPa ⁇ s): An E-type rotational viscometer was used for measurement.
- Viscosity (rotational viscosity; ⁇ 1; measured at 25 ° C .; mPa ⁇ s): Measurement was performed according to the method described in M. ⁇ Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was put in a TN device having a twist angle of 0 ° and a distance (cell gap) between two glass substrates of 5 ⁇ m. A voltage was applied to this device in steps of 0.5 V in the range of 16 V to 19.5 V. After no application for 0.2 seconds, the application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds).
- the peak current (peak current) and peak time (peak time) of the transient current (transient current) generated by this application were measured.
- the rotational viscosity value was obtained from these measured values and the calculation formula (8) described on page 40 in the paper by M. Imai et al.
- the value of dielectric anisotropy necessary for this calculation was determined by the method described below using the element whose rotational viscosity was measured.
- Threshold voltage (Vth; measured at 25 ° C .; V): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement.
- the light source is a halogen lamp.
- a sample was put in a normally white mode TN device in which the distance between two glass substrates (cell gap) was about 0.45 mm / ⁇ n ( ⁇ m) and the twist angle was 80 degrees.
- the voltage (32 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 10V by 0.02V.
- the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured.
- a voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum and the transmittance was 0% when the light amount was the minimum.
- the threshold voltage is a voltage when the transmittance reaches 90%.
- Voltage holding ratio (VHR-1; 25 ° C .;%):
- the TN device used for the measurement has a polyimide alignment film, and the distance between two glass substrates (cell gap) is 5 ⁇ m. This element was sealed with an adhesive that was cured with ultraviolet rays after the sample was placed.
- the TN device was charged by applying a pulse voltage (60 microseconds at 5 V).
- the decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined.
- the area B is an area when it is not attenuated.
- the voltage holding ratio is a percentage of the area A with respect to the area B.
- Voltage holding ratio (VHR-2; 80 ° C .;%):
- the TN device used for the measurement has a polyimide alignment film, and the distance between two glass substrates (cell gap) is 5 ⁇ m. This element was sealed with an adhesive that was cured with ultraviolet rays after the sample was placed.
- the TN device was charged by applying a pulse voltage (60 microseconds at 5 V).
- the decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined.
- the area B is an area when it is not attenuated.
- the voltage holding ratio is a percentage of the area A with respect to the area B.
- VHR-3 Voltage holding ratio
- the TN device used for measurement has a polyimide alignment film, and the cell gap is 5 ⁇ m.
- a sample was injected into this element and irradiated with light for 20 minutes.
- the light source is an ultra high pressure mercury lamp USH-500D (manufactured by USHIO), and the distance between the element and the light source is 20 cm.
- the decreasing voltage was measured for 16.7 milliseconds.
- VHR-3 is preferably 90% or more, and more preferably 95% or more.
- VHR-4 Voltage holding ratio
- the TN device into which the sample was injected was heated in a constant temperature bath at 80 ° C. for 500 hours, and then the voltage holding ratio was measured to evaluate the stability against heat.
- a composition having a large VHR-4 has a large stability to heat.
- the decreasing voltage was measured for 16.7 milliseconds.
- the rise time ( ⁇ r: rise time; millisecond) is the time required for the transmittance to change from 90% to 10%.
- the fall time ( ⁇ f: fall time; millisecond) is the time required to change the transmittance from 10% to 90%.
- the response time is the sum of the rise time and the fall time thus obtained.
- Elastic constant (K; measured at 25 ° C .; pN): An HP4284A LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd. was used for the measurement. A sample was put in a horizontal alignment cell in which the distance between two glass substrates (cell gap) was 20 ⁇ m. A charge of 0 to 20 volts was applied to the cell, and the capacitance and applied voltage were measured. Fitting the measured values of capacitance (C) and applied voltage (V) using “Liquid Crystal Device Handbook” (Nikkan Kogyo Shimbun), formulas (2.98) and (2.101) on page 75 Thus, the values of K11 and K33 were obtained from the formula (2.99). Next, K22 was calculated from the equation (3.18) on page 171 using the values of K11 and K33 obtained earlier. The elastic constant is an average value of K11, K22, and K33 thus obtained.
- GC-14B gas chromatograph manufactured by Shimadzu Corporation was used for measurement.
- the carrier gas is helium (2 mL / min).
- the sample vaporization chamber was set at 280 ° C, and the detector (FID) was set at 300 ° C.
- capillary column DB-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m; stationary liquid phase is dimethylpolysiloxane; nonpolar) manufactured by Agilent Technologies Inc. was used.
- the column was held at 200 ° C. for 2 minutes and then heated to 280 ° C. at a rate of 5 ° C./min.
- a sample was prepared in an acetone solution (0.1% by weight), and 1 ⁇ L thereof was injected into the sample vaporization chamber.
- the recorder is a C-R5A Chromatopac manufactured by Shimadzu Corporation, or an equivalent product.
- the obtained gas chromatogram showed the peak retention time and peak area corresponding to the component compounds.
- capillary column As a solvent for diluting the sample, chloroform, hexane or the like may be used.
- the following capillary column may be used.
- HP-1 from Agilent Technologies Inc. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), Rtx-1 from Restek Corporation (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), BP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m) manufactured by SGE International Pty.
- a capillary column CBP1-M50-025 length 50 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m
- Shimadzu Corporation may be used.
- the ratio of the liquid crystal compound contained in the composition may be calculated by the following method. Liquid crystalline compounds can be detected by gas chromatography. The area ratio of peaks in the gas chromatogram corresponds to the ratio (number of moles) of liquid crystal compounds. When the capillary column described above is used, the correction coefficient of each liquid crystal compound may be regarded as 1. Therefore, the ratio (% by weight) of the liquid crystal compound is calculated from the peak area ratio.
- the present invention will be described in detail by examples.
- the present invention is not limited by the following examples.
- the compounds in Comparative Examples and Examples were represented by symbols based on the definitions in Table 3 below.
- Table 3 the configuration regarding 1,4-cyclohexylene is trans.
- the number in parentheses after the symbol corresponds to the compound number.
- the symbol ( ⁇ ) means other liquid crystal compounds.
- the ratio (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the total weight of the liquid crystal composition, and the liquid crystal composition contains impurities.
- Example 3 was selected from the compositions disclosed in JP-A-57-154135. The reason is that this composition contains the compound (1-11-1). The components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- Example 4 was selected from the compositions disclosed in JP-A-57-185230. The reason is that this composition contains the compound (1-23-1). The components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- Example A was selected from the compositions disclosed in JP-A-4-501575. The reason is that this composition contains compound (1), compound (1-8-1), compound (1-12-1), and compound (1-23-1), and has the lowest viscosity. .
- the components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- Example A was selected from the compositions disclosed in JP-T-4-501576. This is because the composition contains compound (1), compound (1-8-1), compound (1-23-1), and compound (2-10-1). The components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- Example 5 was selected from the compositions disclosed in JP-T-4-505477. The reason is that this composition contains compound (1), compound (1-8-1), compound (1-12-1), and compound (1-23-1), and has the lowest viscosity. .
- the components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- 5-HB-F 11% 6-HB-F (1) 10% 7-HB-F (1) 16% 2-HHB-OCF3 (1-8-1) 9% 3-HHB-OCF3 (1-8-1) 12% 4-HHB-OCF3 (1-8-1) 7% 5-HHB-OCF3 (1-8-1) 12% 3-HBB (F) -F (1-23-1) 10% 5-HBB (F) -F (1-23-1) 13%
- Example 1 was selected from the compositions disclosed in JP-A-5-105876. The basis is that this composition contains compound (1), compound (1-8-1), compound (1-12-1), compound (1-15-1), and compound (1-24-1) This is because the viscosity is the smallest.
- the components and properties of this composition are as follows. Since there was no description about K and K / (eta), this composition was prepared and it measured by the method mentioned above.
- liquid crystal compositions used in the liquid crystal display elements of Examples 1 to 10 have a larger elastic constant than that of Comparative Examples 1 to 7. Therefore, the liquid crystal composition used in the liquid crystal display element according to the present invention has more excellent characteristics than the liquid crystal composition used in the liquid crystal display elements disclosed in Patent Documents 1 to 7.
- a liquid crystal composition satisfying at least one characteristic or having an appropriate balance regarding at least two characteristics becomes an AM element having a short response time, a large voltage holding ratio, a large contrast ratio, a long lifetime, and the like, and thus can be used for a liquid crystal projector, a liquid crystal television, and the like.
Abstract
Description
ここで、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aは独立して、テトラヒドロピラン-2,5-ジイル、1,4-シクロへキシレン、1,3-ジオキサン-2,5-ジイル、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレン、3,5-ジフルオロ-1,4-フェニレン、または2,5-ピリミジンであり;Z1は独立して、単結合、エチレン、またはカルボニルオキシであり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、またはトリフルオロメトキシであり;mは、1、2、または3である。
1. 少なくとも一方が透明な一対の基板からなり、これらの基板間に挟持された液晶組成物を有する、配向層、偏光板および透明電極を備えた液晶表示素子であって、この液晶組成物が第一成分として式(1)で表される化合物の群から選択された少なくとも1つの化合物を含有し、そして正の誘電率異方性を有する液晶組成物である液晶表示素子。
ここで、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aは独立して、テトラヒドロピラン-2,5-ジイル、1,4-シクロへキシレン、1,3-ジオキサン-2,5-ジイル、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレン、3,5-ジフルオロ-1,4-フェニレン、または2,5-ピリミジンであり;Z1は独立して、単結合、エチレン、またはカルボニルオキシであり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、またはトリフルオロメトキシであり;mは、1、2、または3である。
ここで、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Bおよび環Cは独立して、1,4-シクロへキシレン、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレンまたは2,5-ジフルオロ-1,4-フェニレンであり;Z2は独立して、単結合、エチレン、またはカルボニルオキシであり;pは、1、2、または3である。
ここで、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルである。
環Bおよび環Cは独立して、1,4-シクロへキシレン、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレンまたは2,5-ジフルオロ-1,4-フェニレンであり、pが2または3である時の任意の2つの環Bは同じであっても、異なってもよい。好ましい環Bまたは環Cは、粘度を下げるために1,4-シクロへキシレンであり、光学異方性を上げるために1,4-フェニレンである。
PSA(polymer sustained alignment)モードの素子に適合させるために重合可能な化合物が組成物に混合される。重合可能な化合物の好ましい例はアクリレート、メタクリレート、ビニル化合物、ビニルオキシ化合物、プロペニルエーテル、エポキシ化合物(オキシラン、オキセタン)、ビニルケトンなどの重合可能な基を有する化合物である。特に好ましい例は、アクリレート、またはメタクリレートの誘導体である。重合可能な化合物の好ましい割合は、その効果を得るために、約0.05重量%以上であり、表示不良を防ぐために約10重量%以下である。さらに好ましい割合は、約0.1重量%から約2重量%の範囲である。重合可能な化合物は、好ましくは光重合開始剤などの適切な開始剤存在下でUV照射などにより重合する。重合のための適切な条件、開始剤の適切なタイプ、および適切な量は、当業者には既知であり、文献に記載されている。例えば光開始剤であるIrgacure651(登録商標)、Irgacure184(登録商標)、またはDarocure1173(登録商標)(Ciba Japan K.K.)がラジカル重合に対して適切である。重合可能な化合物は、好ましくは光重合開始剤を約0.1重量%から約5重量%の範囲で含む。特に好ましくは光重合開始剤を約1重量%から約3重量%の範囲で含む。
表3において、1,4-シクロヘキシレンに関する立体配置はトランスである。実施例において記号の後にあるかっこ内の番号は化合物の番号に対応する。(-)の記号はその他の液晶性化合物を意味する。液晶性化合物の割合(百分率)は、液晶組成物の全重量に基づいた重量百分率(重量%)であり、液晶組成物には不純物が含まれている。最後に、この液晶組成物を含有する液晶表示素子の特性値をまとめた。
特開昭57-154135号公報に開示された組成物の中から実施例3を選んだ。根拠は、この組成物が化合物(1-11-1)を含有しているからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
3-HB-C (-) 22.4%
5-HB-C (-) 33.6%
7-HB-C (-) 24%
3-HHB(F)-F (1-11-1) 20%
NI=61.5℃;Tc≦-15℃;Δε=9.3;Vth=1.58V;η=23.0mPa・s;K=12.0pN;K/η=0.52nN/Pa・s(nm2/s).
特開昭57-185230号公報に開示された組成物の中から実施例4を選んだ。根拠は、この組成物が化合物(1-23-1)を含有しているからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
3-HB-C (-) 23.4%
5-HB-C (-) 31.5%
7-HB-C (-) 23.4%
5-HBB-C (-) 11.7%
3-HBB(F)-F (1-23-1) 10%
NI=72.3℃;Tc≦-6℃;Vth=1.69V;η=27.6mPa・s;K=12.6pN;K/η=0.46nN/Pa・s(nm2/s).
特開平2-233626号公報に開示された組成物の中から応用例1を選んだ。根拠は、この組成物が化合物(1-3-1)および化合物(1-11-1)を含有しているからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
5-HB(F,F)-F (1-3-1) 15%
2-HHB(F)-F (1-11-1) 28.33%
3-HHB(F)-F (1-11-1) 28.33%
5-HHB(F)-F (1-11-1) 28.33%
NI=77.7℃;Vth=1.94V;η=17.9mPa・s;K=11.4pN;K/η=0.64nN/Pa・s(nm2/s).
特表平4-501575号公報に開示された組成物の中から例Aを選んだ。根拠は、この組成物が化合物(1)、化合物(1-8-1)、化合物(1-12-1)、および化合物(1-23-1)を含有し、最も粘度が小さいからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
5-HB-F (1) 10%
6-HB-F (1) 7%
7-HB-F (1) 15%
2-HHB-OCF3 (1-8-1) 10%
3-HHB-OCF3 (1-8-1) 12%
4-HHB-OCF3 (1-8-1) 8%
5-HHB-OCF3 (1-8-1) 12%
3-HHB(F,F)-F (1-12-1) 10%
3-HBB(F)-F (1-23-1) 16%
NI=64.0℃;Δn=0.080;Vth=1.61V;η=14.0mPa・s;K=9.4pN;K/η=0.67nN/Pa・s(nm2/s).
特表平4-501576号公報に開示された組成物の中から例Aを選んだ。根拠は、この組成物が化合物(1)、化合物(1-8-1)、化合物(1-23-1)、および化合物(2-10-1)を含有しているからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
5-HB-F (1) 8%
6-HB-F (1) 6%
7-HB-F (1) 5%
2-HHB-OCF3 (1-8-1) 6%
3-HHB-OCF3 (1-8-1) 9%
4-HHB-OCF3 (1-8-1) 6%
5-HHB-OCF3 (1-8-1) 9%
3-HBB(F)-F (1-23-1) 9%
5-HBB(F)-F (1-23-1) 8%
3-HH2B-OCF3 (1) 4%
5-HH2B-OCF3 (1) 4%
3-HB(F)BH-3 (2-10-1) 2%
5-HB(F)BH-3 (2-10-1) 2%
5-HB(F)BH-5 (2-10-1) 2%
3-HHB(F)B-OCF3 (1) 10%
3-HHB(F)B-F (1) 10%
NI=92.0℃;Vth=2.4V;η=14.0mPa・s;K=11.7pN;K/η=0.48nN/Pa・s(nm2/s).
特表平4-505477号公報に開示された組成物の中から実施例5を選んだ。根拠は、この組成物が化合物(1)、化合物(1-8-1)、化合物(1-12-1)、および化合物(1-23-1)を含有し、最も粘度が小さいからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
5-HB-F (1) 11%
6-HB-F (1) 10%
7-HB-F (1) 16%
2-HHB-OCF3 (1-8-1) 9%
3-HHB-OCF3 (1-8-1) 12%
4-HHB-OCF3 (1-8-1) 7%
5-HHB-OCF3 (1-8-1) 12%
3-HBB(F)-F (1-23-1) 10%
5-HBB(F)-F (1-23-1) 13%
NI=60.0℃;Δn=0.084;Vth=1.61V;η=12.0mPa・s;K=8.8pN;K/η=0.73nN/Pa・s(nm2/s).
特開平5-105876号公報に開示された組成物の中から実施例1を選んだ。根拠は、この組成物が化合物(1)、化合物(1-8-1)、化合物(1-12-1)、化合物(1-15-1)、および化合物(1-24-1)を含有し、最も粘度が小さいからである。この組成物の成分および特性は下記のとおりである。KおよびK/ηについての記載がなかったため、本組成物を調合し、上述した方法により測定した。
5-HB-F (1) 5%
7-HB-F (1) 5%
2-HHB-OCF3 (1-8-1) 7%
3-HHB-OCF3 (1-8-1) 7%
4-HHB-OCF3 (1-8-1) 7%
5-HHB-OCF3 (1-8-1) 8%
3-HH2B(F)-F (1-15-1) 8%
5-HH2B(F)-F (1-15-1) 8%
3-HBB(F,F)-F (1-24-1) 14%
5-HBB(F,F)-F (1-24-1) 13%
3-HHB(F,F)-F (1-12-1) 9%
5-HHB(F,F)-F (1-12-1) 9%
NI=85.0℃;Δn=0.092;Vth=1.58V;η=18.0mPa・s;K=11.0pN;K/η=0.61nN/Pa・s(nm2/s).
3-HHB(F,F)-F (1-12-1) 10%
4-HHB(F,F)-F (1-12-1) 6%
5-HHB(F,F)-F (1-12-1) 6%
3-HBB(F,F)-F (1-24-1) 30%
2-HHBB(F,F)-F (1-39-1) 2%
3-HHBB(F,F)-F (1-39-1) 4%
4-HHBB(F,F)-F (1-39-1) 3%
1V-HH-V (2-1-1) 11%
V-HH-2V (2-1-1) 14%
V2-HH-2V (2-1-1) 6%
V2-HHB-1 (2-5-1) 4%
3-HHEBH-3 (2-8-1) 4%
NI=94.4℃;Tc≦-20℃;Δn=0.097;Δε=5.7;Vth=1.71V;η=15.7mPa・s.γ1=90.4mPa・s;K=15.4pN;K/η=0.98nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.54;VHR-1=99.1%;VHR-2=97.9%;VHR-3=98.2%.
3-HHB(F,F)-F (1-12-1) 10%
3-HBB(F,F)-F (1-24-1) 40%
2-HHBB(F,F)-F (1-39-1) 4%
3-HHBB(F,F)-F (1-39-1) 4%
4-HHBB(F,F)-F (1-39-1) 3%
V-HH-3 (2-1-1) 15%
1V-HH-V (2-1-1) 10%
1V2-HH-V1 (2-1-1) 5%
1V2-HH-2V1 (2-1-1) 3%
V-HHB-1 (2-5-1) 3%
2-BB(F)B-3 (2-7-1) 3%
NI=77.5℃;Tc≦-20℃;Δn=0.102;Δε=5.6;Vth=1.64V;η=13.8mPa・s.γ1=64.4mPa・s;K=13.3pN;K/η=0.96nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.55;VHR-1=99.0%;VHR-2=98.1%;VHR-3=98.0%.
3-HB-CL (1-1-1) 10%
3-HHB-CL (1-7-1) 4%
3-HHB(F)-F (1-11-1) 7%
3-HBB(F,F)-F (1-24-1) 25%
3-HHEBB-F (1-37-1) 3%
3-HH2BB(F,F)-F (1-41-1) 6%
4-HH2BB(F,F)-F (1-41-1) 4%
1V-HH-3 (2-1-1) 8%
V-HH-V (2-1-1) 10%
V-HH-2V (2-1-1) 15%
3-HBB-2 (2-6-1) 3%
1-BB(F)B-2V (2-7-1) 5%
NI=86.4℃;Tc≦-20℃;Δn=0.109;Δε=4.3;Vth=1.91V;η=12.7mPa・s.γ1=52.4mPa・s;K=13.4pN;K/η=1.06nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.53;VHR-1=99.1%;VHR-2=98.0%;VHR-3=98.1%.
1V2-BB-CL (1) 3%
7-HB(F)-F (1-2-1) 5%
7-HB(F,F)-F (1-3-1) 7%
3-HHB(F,F)-F (1-12-1) 10%
3-H2HB(F)-F (1-13-1) 5%
5-H2HB(F)-F (1-13-1) 5%
3-H2HB(F,F)-F (1-14-1) 6%
4-H2HB(F,F)-F (1-14-1) 5%
3-HH2B(F,F)-F (1-16-1) 12%
3-HBB-F (1-22-1) 5%
V-HH-5 (2-1-1) 9%
1V-HH-V (2-1-1) 8%
V2-HH-2V (2-1-1) 8%
V2-BB(F)B-1 (2-7-1) 4%
5-HBB(F)B-3 (2-11-1) 8%
NI=75.0℃;Tc≦-20℃;Δn=0.090;Δε=4.5;Vth=1.88V;η=13.7mPa・s.γ1=63.4mPa・s;K=13.7pN;K/η=1.00nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.63;VHR-1=99.0%;VHR-2=98.0%;VHR-3=98.0%.
5-H2B(F)-F (1-4-1) 7%
3-HHB-OCF3 (1-8-1) 10%
3-HHEB-F (1-17-1) 6%
5-HHEB-F (1-17-1) 5%
2-HBEB(F,F)-F (1-30-1) 3%
3-HBEB(F,F)-F (1-30-1) 4%
3-BB(F,F)B(F)-OCF3 (1-32-1) 8%
3-BBB(F,F)-F (1-33-1) 3%
3-BB2B(F,F)-F (1-36-1) 3%
V-HH-3 (2-1-1) 16%
V-HH-2V (2-1-1) 15%
1V2-HH-V (2-1-1) 5%
V-HHB-1 (2-5-1) 6%
5-HBBH-3 (2-9-1) 3%
5-HB(F)BH-3 (2-10-1) 6%
NI=91.0℃;Tc≦-20℃;Δn=0.097;Δε=4.9;Vth=1.89V;η=13.9mPa・s.γ1=64.4mPa・s;K=14.7pN;K/η=1.06nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.55;VHR-1=99.1%;VHR-2=98.1%;VHR-3=98.0%.
5-HEB-F (1-5-1) 3%
5-HEB(F,F)-F (1-6-1) 5%
3-HHB-F (1-9-1) 5%
2-HHEB(F,F)-F (1-18-1) 4%
3-HHEB(F,F)-F (1-18-1) 8%
3-HBB(F)-F (1-23-1) 9%
5-HBB(F)-F (1-23-1) 6%
5-HBEB-F (1-29-1) 4%
2-BB(F)B(F,F)-F (1-34-1) 4%
3-BB(F)B(F,F)-F (1-34-1) 10%
3-HHBB(F)-F (1-38-1) 4%
5-HHBB(F)-F (1-38-1) 4%
3-HH-O1 (2-1) 3%
3-HH-4 (2-1-1) 3%
1V-HH-V (2-1-1) 8%
V-HH-V (2-1-1) 10%
V-HH-2V (2-1-1) 10%
NI=78.4℃;Tc≦-20℃;Δn=0.101;Δε=5.8;Vth=1.64V;η=14.4mPa・s.γ1=70.1mPa・s;K=13.4pN;K/η=0.93nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.60;VHR-1=98.9%;VHR-2=98.0%;VHR-3=97.9%.
3-HHB(F)-OCF3 (1-10-1) 7%
3-HBB(F,F)-F (1-24-1) 12%
2-HB(F)B(F,F)-F (1-25-1) 4%
3-HB(F)B(F,F)-F (1-25-1) 12%
3-H2BB(F,F)-F (1-27-1) 5%
3-HHB(F)B(F,F)-F (1-40-1) 4%
5-HHB(F)B(F,F)-F (1-40-1) 3%
1V2-HH-V (2-1-1) 6%
1V-HH-V (2-1-1) 8%
V-HH-2V (2-1-1) 12%
3-HB-O2 (2-2-1) 6%
3-HHEH-5 (2-4-1) 3%
VFF-HHB-1 (2-5) 10%
3-HHB-1 (2-5-1) 4%
1V-HBB-2 (2-6-1) 4%
NI=82.9℃;Tc≦-20℃;Δn=0.103;Δε=5.9;Vth=1.67V;η=13.6mPa・s.γ1=63.8mPa・s;K=13.9pN;K/η=1.02nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.54;VHR-1=99.0%;VHR-2=97.9%;VHR-3=98.2%.
3-HHB(F,F)-F (1-12-1) 10%
3-HH2B(F)-F (1-15-1) 8%
3-H2BB(F)-F (1-26-1) 7%
3-HB(F)EB-OCF3 (1-28-1) 8%
3-HH2BB(F,F)-F (1-41-1) 4%
4-HH2BB(F,F)-F (1-41-1) 4%
1V2-HH-V (2-1-1) 6%
1V-HH-V (2-1-1) 8%
V-HH-2V (2-1-1) 16%
7-HB-1 (2-2-1) 3%
V2-BB-1 (2-3-1) 4%
1V2-BB-1 (2-3-1) 6%
3-HHB-O1 (2-5-1) 4%
V2-HHB-1 (2-5-1) 6%
1-BB(F)B-2V (2-7-1) 6%
NI=91.7℃;Tc≦-20℃;Δn=0.111;Δε=4.3;Vth=2.05V;η=11.2mPa・s.γ1=51.7mPa・s;K=13.4pN;K/η=1.20nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.54;VHR-1=99.0%;VHR-2=98.1%;VHR-3=98.0%.
3-HGB(F,F)-F (1-19-1) 3%
3-H2GB(F,F)-F (1-20-1) 5%
5-GHB(F,F)-F (1-21-1) 10%
3-HBB(F,F)-F (1-24-1) 10%
2-HHBB(F,F)-F (1-39-1) 3%
3-HHBB(F,F)-F (1-39-1) 4%
3-HH-VFF (2-1) 9%
1V-HH-3 (2-1-1) 6%
V-HH-V (2-1-1) 10%
V-HH-2V (2-1-1) 11%
1V2-BB-1 (2-3-1) 4%
V-HHB-1 (2-5-1) 7%
1-BB(F)B-2V (2-7-1) 5%
2-BB(F)B-2V (2-7-1) 5%
3-HHEBH-5 (2-8-1) 4%
1O1-HBBH-5 (-) 4%
NI=95.3℃;Tc≦-20℃;Δn=0.110;Δε=5.5;Vth=1.81V;η=13.8mPa・s.γ1=64.5mPa・s;K=14.2pN;K/η=1.03nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.54;VHR-1=99.1%;VHR-2=98.1%;VHR-3=98.1%.
1-BB(F)B-2V (2-7-1) 5%
3-HBB(F,F)-F (1-24-1) 20%
3-BB(F)B(F,F)-F (1-34-1) 8%
V-HH-3 (2-1-1) 15%
V-HH-V (2-1-1) 10%
V-HH-2V (2-1-1) 10%
V2-HHB-1 (2-5-1) 5%
5-HBB(F)B-3 (2-11-1) 4%
3-H2HB(F,F)-F (1-14-1) 6%
3-BB(F,F)B-F (1-31-1) 4%
3-B2BB(F,F)-F (1-35-1) 5%
3-HHB(F)B(F,F)-F (1-40-1) 4%
3-HH2BB(F,F)-F (1-41-1) 4%
NI=80.3℃;Tc≦-20℃;Δn=0.118;Δε=6.0;Vth=1.60V;η=14.3mPa・s.γ1=67.9mPa・s;K=13.8pN;K/η=0.97nN/Pa・s(nm2/s);Δε(5kHz)/Δε(50Hz)=0.56;VHR-1=99.1%;VHR-2=98.1%;VHR-3=98.2%.
Claims (27)
- 少なくとも一方が透明な一対の基板からなり、これらの基板間に挟持された液晶組成物を有する、配向層、偏光板および透明電極を備えた液晶表示素子であって、この液晶組成物が第一成分として式(1)で表される化合物の群から選択された少なくとも1つの化合物を含有し、そして正の誘電率異方性を有する液晶組成物である液晶表示素子。
ここで、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aは独立して、テトラヒドロピラン-2,5-ジイル、1,4-シクロへキシレン、1,3-ジオキサン-2,5-ジイル、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレン、3,5-ジフルオロ-1,4-フェニレン、または2,5-ピリミジンであり;Z1は独立して、単結合、エチレン、またはカルボニルオキシであり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、またはトリフルオロメトキシであり;mは、1、2、または3である。 - 液晶組成物の第一成分が式(1-1)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-7)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-11)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-12)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-22)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-23)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-24)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が式(1-34)で表される化合物の群から選択された少なくとも1つの化合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が、式(1-1)で表される化合物の群から選択された少なくとも1つの化合物、および式(1-7)で表される化合物の群から選択された少なくとも1つの化合物の混合物である請求項2に記載の液晶表示素子。
- 液晶組成物の第一成分が、式(1-12)で表される化合物の群から選択された少なくとも1つの化合物、および式(1-24)で表される化合物の群から選択された少なくとも1つの化合物の混合物である請求項2に記載の液晶表示素子。
- 液晶組成物が、液晶組成物の全重量に基づいて、第一成分の割合が10重量%から70重量%の範囲である請求項1から12のいずれか1項に記載の液晶表示素子。
- 液晶組成物が、第二成分として式(2)で表される化合物の群から選択された少なくとも1つの化合物をさらに含有する、請求項1から13のいずれか1項に記載の液晶表示素子。
ここで、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または任意の水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Bおよび環Cは独立して、1,4-シクロへキシレン、1,4-フェニレン、2-フルオロ-1,4-フェニレン、3-フルオロ-1,4-フェニレンまたは2,5-ジフルオロ-1,4-フェニレンであり;Z2は独立して、単結合、エチレン、またはカルボニルオキシであり;pは、1、2、または3である。 - 液晶組成物の第二成分が式(2-1)で表される化合物の群から選択された少なくとも1つの化合物である請求項15に記載の液晶表示素子。
- 液晶組成物の第二成分が、式(2-1)で表される化合物の群から選択された少なくとも1つの化合物、および式(2-5)で表される化合物の群から選択された少なくとも1つの化合物の混合物である請求項15に記載の液晶表示素子。
- 液晶組成物の第二成分が、式(2-1)で表される化合物の群から選択された少なくとも1つの化合物、および式(2-7)で表される化合物の群から選択された少なくとも1つの化合物の混合物である請求項15に記載の液晶表示素子。
- 液晶組成物の第二成分が、式(2-1)で表される化合物の群から選択された少なくとも1つの化合物、式(2-5)で表される化合物の群から選択された少なくとも1つの化合物、および式(2-7)で表される化合物の群から選択された少なくとも1つの化合物の混合物である請求項15に記載の液晶表示素子。
- 液晶組成物が、液晶組成物の全重量に基づいて、第二成分の割合が30重量%から90重量%の範囲である請求項14から19のいずれか1項に記載の液晶表示素子。
- 液晶表示素子の動作モードが、TNモード、OCBモード、IPSモード、またはPSAモードであり、液晶表示素子の駆動方式がアクティブマトリックス方式である請求項1から20のいずれか1項に記載の液晶表示素子。
- 請求項1から21のいずれか1項に記載の液晶表示素子中に含まれる液晶組成物。
- 弾性定数(K)が13pN以上であり、そして弾性定数(K)と粘度(η)の比が0.8nN/Pa・s(nm2/s)以上である請求項22に記載の液晶組成物。
- -20℃における誘電率異方性の周波数依存性(Δε(5kHz)/Δε(50Hz)が0.50以上である請求項22または23のいずれか1項に記載の液晶組成物。
- ネマチック相の上限温度が70℃以上であり、波長589nmにおける光学異方性(25℃)が0.08以上であり、そして周波数1kHzにおける誘電率異方性(25℃)が2以上である請求項22から24のいずれか1項に記載の液晶組成物。
- 実質的に第一成分および第二成分のみからなる請求項22から25のいずれか1項に記載の液晶組成物。
- 請求項22から26のいずれか1項に記載の液晶組成物の液晶表示素子への使用。
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JPWO2016052006A1 (ja) * | 2014-10-03 | 2017-04-27 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
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KR20160132230A (ko) * | 2015-05-07 | 2016-11-17 | 삼성디스플레이 주식회사 | 액정 조성물 및 이를 포함하는 액정 표시 장치 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008280337A (ja) * | 2008-04-08 | 2008-11-20 | Chisso Corp | ナフタレン環を有する液晶性化合物、液晶組成物および液晶表示素子 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3660505A (en) | 1969-08-27 | 1972-05-02 | Exxon Research Engineering Co | Hindered alkenyl phenols from quinone methide |
JPS57154135A (en) | 1981-03-04 | 1982-09-22 | Chisso Corp | 1,2-difluoro-4-(trans-4'-(trans-4"-alkylcyclohexyl)cyclo- hexyl)benzene |
JPS57185230A (en) | 1981-05-06 | 1982-11-15 | Chisso Corp | 3,4-difluoro-4'-(trans-4"-alkylcyclohexyl)biphenyl |
JPS59176221A (ja) | 1983-03-16 | 1984-10-05 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | アルケニル化合物 |
JP2696557B2 (ja) | 1989-03-07 | 1998-01-14 | チッソ株式会社 | トリフルオロベンゼン誘導体 |
DE4027315A1 (de) | 1989-08-30 | 1991-03-07 | Merck Patent Gmbh | Halogenierte benzolderivate und fluessigkristallines medium |
DE59010895D1 (de) | 1989-09-06 | 2000-02-24 | Merck Patent Gmbh | Fluorbenzolderivate und flüssigkristallines Medium |
US5389289A (en) | 1990-03-09 | 1995-02-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline medium |
JP3043065B2 (ja) | 1990-03-09 | 2000-05-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 液晶媒体 |
JP2795327B2 (ja) | 1991-03-04 | 1998-09-10 | シャープ株式会社 | ネマチック液晶組成物 |
TW262553B (ja) * | 1994-03-17 | 1995-11-11 | Hitachi Seisakusyo Kk | |
EP0925268A1 (en) * | 1996-09-27 | 1999-06-30 | Chisso Corporation | Compound having alkadienyl group as side chain, and liquid crystal composition using same |
DE102004058002B4 (de) * | 2003-12-17 | 2014-01-09 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung |
JP5098249B2 (ja) * | 2006-08-07 | 2012-12-12 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
JP5657193B2 (ja) * | 2006-11-28 | 2015-01-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 液晶媒体 |
TWI472598B (zh) * | 2009-09-24 | 2015-02-11 | Jnc Corp | 液晶組成物以及液晶顯示元件 |
TWI461513B (zh) * | 2009-11-17 | 2014-11-21 | Jnc Corp | 液晶組成物及液晶顯示元件 |
-
2010
- 2010-04-23 TW TW099112850A patent/TWI461512B/zh active
- 2010-05-06 DE DE112010001973T patent/DE112010001973T8/de not_active Expired - Fee Related
- 2010-05-06 CN CN201080020089.8A patent/CN102421872B/zh not_active Expired - Fee Related
- 2010-05-06 US US13/319,687 patent/US8512821B2/en not_active Expired - Fee Related
- 2010-05-06 WO PCT/JP2010/057748 patent/WO2010131594A1/ja active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008280337A (ja) * | 2008-04-08 | 2008-11-20 | Chisso Corp | ナフタレン環を有する液晶性化合物、液晶組成物および液晶表示素子 |
Non-Patent Citations (1)
Title |
---|
YASOJI SUZUKI: "Kyo kara Monoshiri Series Tokoton Yasashii Ekisho no Hon", THE NIKKAN KOGYO SHINBUN, 2008, pages 54 - 55, 94-95 * |
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JPWO2016021333A1 (ja) * | 2014-08-04 | 2017-06-01 | Jnc株式会社 | 液晶表示素子 |
US10782566B2 (en) | 2014-08-04 | 2020-09-22 | Jnc Corporation | Liquid crystal display device |
JPWO2016052006A1 (ja) * | 2014-10-03 | 2017-04-27 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
WO2016098637A1 (ja) * | 2014-12-18 | 2016-06-23 | Dic株式会社 | 液晶組成物及びこれを用いた液晶表示素子 |
US10344211B2 (en) | 2014-12-18 | 2019-07-09 | Dic Corporation | Liquid crystal composition and liquid crystal display element using same |
JPWO2016098637A1 (ja) * | 2014-12-18 | 2017-07-20 | Dic株式会社 | 液晶組成物及びこれを用いた液晶表示素子 |
WO2017163663A1 (ja) | 2016-03-25 | 2017-09-28 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
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US8512821B2 (en) | 2013-08-20 |
TW201040247A (en) | 2010-11-16 |
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CN102421872B (zh) | 2014-03-19 |
DE112010001973T5 (de) | 2013-04-11 |
US20120069275A1 (en) | 2012-03-22 |
CN102421872A (zh) | 2012-04-18 |
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