WO2012086504A1 - 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子 - Google Patents
重合性化合物含有液晶組成物及びそれを使用した液晶表示素子 Download PDFInfo
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- 0 Cc1c(*)c(*)c(*)c(-c2c(*)c(*)c(*)c(*)c2C)c1* Chemical compound Cc1c(*)c(*)c(*)c(-c2c(*)c(*)c(*)c(*)c2C)c1* 0.000 description 2
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- 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
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- 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
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- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
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- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
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- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/3001—Cyclohexane rings
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Definitions
- the present invention relates to a polymerizable compound-containing liquid crystal composition and a liquid crystal display device using the same.
- the PSA (Polymer Sustained Alignment) type liquid crystal display element has a structure in which a polymer structure is formed in the cell in order to control the pretilt angle of the liquid crystal molecules, and has been developed as a liquid crystal display element from high-speed response and high contrast. Has been promoted.
- a PSA type liquid crystal display device is produced by injecting a polymerizable compound-containing liquid crystal composition comprising a polymerizable compound and a liquid crystal compound between substrates, and applying a voltage to polymerize the polymerizable compound in a state where liquid crystal molecules are aligned. This is done by fixing the orientation of the liquid crystal molecules.
- a cause of image sticking which is a display defect of this PSA type liquid crystal display element, there are known impurities and changes in alignment of liquid crystal molecules (changes in pretilt angle).
- the structure of the polymer changes when the same pattern is displayed for a long time when the liquid crystal display element is configured.
- the pretilt angle may change. Therefore, a polymerizable compound that forms a polymer having a rigid structure in which the polymer structure does not change is required.
- a display element is configured using a polymerizable compound having a ring structure and a structure such as a 1,4-phenylene group having only a polymerizable functional group.
- Patent Document 1 See Patent Document 1 and the construction of a display element using a polymerizable compound having a biaryl structure (see Patent Document 2) have been studied.
- these polymerizable compounds have low compatibility with the liquid crystal compound, there is a problem such as precipitation of the polymerizable compound when the polymerizable compound-containing liquid crystal composition is prepared. It was necessary to improve compatibility.
- a problem to be solved by the present invention is a liquid crystal composition containing a polymerizable compound that does not cause display defects such as image sticking and has a low viscosity corresponding to a high-speed response without precipitation in a wide temperature range, and a display using the same
- An object of the present invention is to provide a liquid crystal display element having excellent display quality without unevenness.
- R 1 and R 2 are each independently the following formulas (R-1) to (R-15):
- X 1 to X 8 each independently represents a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom or a hydrogen atom, at least one of which represents a fluorine atom.
- R 3 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one or more hydrogen atoms present in these groups are substituted with fluorine atoms.
- R 4 represents an alkyl group or alkoxyl group having 1 to 10 carbon atoms, an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms, and one or more hydrogen atoms present in these groups are A polymerizable compound-containing liquid crystal composition containing one or more compounds represented by the formula (1), which may be substituted with a fluorine atom, and m is 0, 1 or 2. Provided liquid crystal display device.
- the polymerizable compound-containing liquid crystal composition of the present invention has excellent compatibility between the liquid crystal compound and the polymerizable compound, it maintains a nematic state without precipitation even when left at a low temperature for a long time. A wide driving temperature range is guaranteed.
- the liquid crystal composition of the present invention has a low viscosity, the response speed when the liquid crystal display element is formed is high, and it can be applied to 3D display and the like.
- the polymerizable compound of the present invention does not have a polymerization rate that is too fast or too slow during photopolymerization and is moderate, so that uniform and stable orientation control can be obtained, and there is little or no image sticking or display unevenness. Since a liquid crystal display element can be provided, the liquid crystal composition of the present invention is very useful.
- the polymerizable compound-containing liquid crystal composition of the present invention has a general formula (I) as a first component.
- R 1 and R 2 are each independently the following formulas (R-1) to (R-15):
- X 1 to X 8 each independently represents a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom or a hydrogen atom, at least one of which represents a fluorine atom.
- These polymer groups are cured by radical polymerization, radical addition polymerization, cationic polymerization and anionic polymerization.
- radical polymerization radical polymerization
- radical addition polymerization radical addition polymerization
- anionic polymerization anionic polymerization.
- the formula (R-1), formula (R-2), formula (R-4), formula (R-5), formula (R-7), formula (R— 11), (R-13) or (R-15) is preferred, (R-1) and (R-2) are more preferred, and (R-2) is particularly preferred.
- X 1 to X 8 each independently represents a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom or a hydrogen atom, and particularly preferably a fluorine atom.
- the structure of the biphenyl skeleton in general formula (I) is more preferably formula (I-11) to formula (I-14), and particularly preferably formula (I-11).
- the polymerizable compound containing a skeleton represented by the formulas (I-11) to (I-14) has an optimum alignment regulating power after polymerization for a PSA type liquid crystal display device, a good alignment state can be obtained. , Display unevenness is suppressed or does not occur at all.
- the polymerizable compound-containing liquid crystal composition of the present invention contains at least one polymerizable compound represented by the general formula (I), preferably 1 to 5 types, preferably 1 to 3 types. More preferably.
- the alignment control power with respect to a liquid-crystal composition will become weak.
- the content of the polymerizable compound represented by the general formula (I) is too large, the energy required for the polymerization increases, the amount of the polymerizable compound that remains without being polymerized increases, and the display is poor. Therefore, the content is preferably 0.01 to 2.00% by mass, more preferably 0.05 to 1.00% by mass, and 0.10 to 0.50% by mass. It is particularly preferred that
- R 3 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one or two or more hydrogen atoms present in these groups are fluorine atoms.
- R 4 represents an alkyl group or alkoxyl group having 1 to 10 carbon atoms, an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms, and one or two or more groups present in these groups
- a hydrogen atom may be substituted with a fluorine atom, and m represents 0, 1 or 2, but R 3 is linear and more preferably represents an alkyl group having 1 to 10 carbon atoms, and 1 carbon atom.
- R 4 represents a straight chain, more preferably represents an alkyl group having 1 to 5 carbon atoms or an alkoxyl group, and represents an alkoxyl group having 1 to 5 carbon atoms. Is particularly good More preferably, m represents 0 or 1.
- 1 type or 2 or more types of compounds represented by the general formula (II) are contained, more preferably 1 to 6 types, and particularly preferably 2 to 5 types.
- the content of the compound represented by the general formula (II) is preferably 5 to 35% by mass, more preferably 10 to 35% by mass, and 15 to 30% by mass. Particularly preferred.
- the general formula (II) is particularly preferably the general formula (II-A) and the general formula (II-B).
- the polymerizable compound-containing liquid crystal composition of the present invention further has the general formula (III)
- R 9 represents the same meaning as R 3 and R 10 represents the same meaning as R 4 ), and it is more preferable to contain one or more compounds represented by
- the compound represented by the general formula (III) contains one or more compounds, but one to six is more preferable, and two to five is particularly preferable.
- the content of the general formula (III) is preferably in the range of 5 to 35% by mass, more preferably in the range of 10 to 30% by mass, and particularly preferably in the range of 15 to 30% by mass.
- the general formula (III) is particularly preferably the general formula (III-A).
- the liquid crystal compound contained in the polymerizable compound-containing liquid crystal composition of the present invention does not have a partial structure in which heteroatoms such as —O—O—, —O—S—, and —S—S— are directly bonded to each other. .
- the compound which has an alkenyl group is not included, and it is more preferable that the side chain of all the liquid crystal compounds is an alkyl group or an alkoxyl group.
- the structure of the liquid crystal compound is preferably a cyclohexane ring, a benzene ring or a benzene ring substituted with fluorine, It is not preferable to contain a compound that is substituted with a chlorine atom even if it is the same halogen atom.
- the use of a liquid crystal compound substituted with a chlorine atom is also impractical because it causes display defects.
- a liquid crystal display device prepared using a liquid crystal composition containing general formulas (I), (II) and (III) has a low viscosity and can achieve a high-speed response.
- the nematic phase-isotropic liquid phase transition temperature (T ni ) is preferably 60 to 120 ° C., more preferably 70 to 100 ° C., and particularly preferably 70 to 85 ° C.
- ⁇ at 25 ° C. is preferably ⁇ 2.0 to ⁇ 6.0, more preferably ⁇ 2.5 to ⁇ 5.0, and ⁇ 2.5 to ⁇ 3.5. Is particularly preferred.
- ⁇ n at 25 ° C. is preferably from 0.08 to 0.13, more preferably from 0.09 to 0.12. More specifically, it is preferably 0.10 to 0.12 when corresponding to a thin cell gap, and preferably 0.08 to 0.10 when corresponding to a thick cell gap.
- the viscosity at 20 ° C. is preferably 10 to 30 mPa ⁇ s, more preferably 10 to 25 mPa ⁇ s, and particularly preferably 10 to 20 mPa ⁇ s.
- the polymerizable compound-containing liquid crystal composition of the present invention may contain a normal nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, polymerizable monomer and the like in addition to the above-mentioned compounds.
- a normal nematic liquid crystal smectic liquid crystal
- cholesteric liquid crystal cholesteric liquid crystal
- antioxidant antioxidant
- ultraviolet absorber polymerizable monomer and the like
- polymerizable monomer polymerizable monomer and the like in addition to the above-mentioned compounds.
- compounds represented by general formula (IV-1) to general formula (IV-12) may be contained.
- the polymerizable compound-containing liquid crystal composition of the present invention undergoes polymerization even when no polymerization initiator is present, but may contain a polymerization initiator in order to accelerate the polymerization.
- the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.
- a stabilizer may be added in order to improve storage stability.
- the stabilizer examples include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, and the like. It is done.
- the polymerizable compound-containing liquid crystal composition of the present invention is useful for a liquid crystal display device, particularly useful for a liquid crystal display device for active matrix driving, and a liquid crystal display for PSA mode, PSVA mode, VA mode, IPS mode or ECB mode. It can be used for an element.
- the polymerizable compound-containing liquid crystal composition of the present invention is provided with liquid crystal alignment ability by polymerizing the polymerizable compound contained therein by ultraviolet irradiation, and controls the amount of light transmitted using the birefringence of the liquid crystal composition.
- liquid crystal display elements used for liquid crystal display elements.
- AM-LCD active matrix liquid crystal display element
- TN nematic liquid crystal display element
- STN-LCD super twisted nematic liquid crystal display element
- OCB-LCD and IPS-LCD in-plane switching liquid crystal display element
- the two substrates of the liquid crystal cell used in the liquid crystal display element can be made of a transparent material having flexibility such as glass or plastic, and one of them can be an opaque material such as silicon.
- a transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
- the color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method.
- a method for producing a color filter by a pigment dispersion method will be described as an example.
- a curable coloring composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this process for each of the three colors red, green, and blue, a pixel portion for a color filter can be created.
- a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.
- the substrate is opposed so that the transparent electrode layer is on the inside.
- the thickness of the obtained light control layer is 1 to 100 ⁇ m. More preferably, the thickness is 1.5 to 10 ⁇ m.
- the polarizing plate it is preferable to adjust the product of the refractive index anisotropy ⁇ n of the liquid crystal and the cell thickness d so that the contrast is maximized.
- the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good.
- a retardation film for widening the viewing angle can also be used.
- the spacer examples include glass particles, plastic particles, alumina particles, and a photoresist material.
- a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.
- a normal vacuum injection method or an ODF method can be used as a method of sandwiching the polymerizable compound-containing liquid crystal composition between the two substrates.
- an appropriate polymerization rate is desirable in order to obtain good alignment performance of liquid crystals. Therefore, active energy rays such as ultraviolet rays or electron beams are irradiated singly or in combination or sequentially.
- the method of polymerizing by is preferred.
- ultraviolet rays When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used.
- the polymerization is performed in a state where the polymerizable compound-containing liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must be given appropriate transparency to the active energy rays. I must.
- the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization.
- a means for polymerization In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the polymerizable compound-containing liquid crystal composition.
- the alternating electric field to be applied is preferably an alternating current having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on a desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the MVA mode liquid crystal display element, the pretilt angle is preferably controlled from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.
- the temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the liquid crystal composition of the present invention is maintained. Polymerization is preferably performed at a temperature close to room temperature, that is, typically at a temperature of 15 to 35 ° C.
- a lamp for generating ultraviolet rays a metal halide lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, or the like can be used.
- a wavelength of the ultraviolet-rays to irradiate it is preferable to irradiate the ultraviolet-ray of the wavelength range which is not the absorption wavelength range of a liquid crystal composition, and it is preferable to cut and use an ultraviolet-ray as needed.
- Intensity of ultraviolet irradiation is preferably from 0.1mW / cm 2 ⁇ 100W / cm 2, 2mW / cm 2 ⁇ 50W / cm 2 is more preferable.
- the amount of energy of ultraviolet rays to be irradiated can be adjusted as appropriate, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2 .
- the intensity may be changed.
- the time for irradiating with ultraviolet rays is appropriately selected depending on the intensity of the irradiated ultraviolet rays, but is preferably from 10 seconds to 3600 seconds, and more preferably from 10 seconds to 600 seconds.
- the measured characteristics are as follows.
- T ni Nematic phase-isotropic liquid phase transition temperature (° C.) ⁇ n: refractive index anisotropy at 25 ° C. ⁇ : dielectric anisotropy at 25 ° C. ⁇ : viscosity at 20 ° C. (mPa ⁇ s)
- Example 1 The prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 1 contains 99.85% of the liquid crystal composition and 0.15% of the polymerizable compound represented by the general formula (I-11). ni : 75.5 ° C., ⁇ n: 0.107, ⁇ : ⁇ 3.0, ⁇ : 17.5 mPa ⁇ s.
- This polymerizable compound-containing liquid crystal composition is injected into a cell with ITO coated with a polyimide alignment film that induces homeotropic alignment with a cell gap of 3.5 ⁇ m by a vacuum injection method, and a 1.8 V rectangular wave is applied at a frequency of 1 kHz.
- a high-pressure mercury lamp through a filter that cuts out ultraviolet rays of 320 nm or less, the irradiation intensity of the cell surface was adjusted to 15 mW / cm 2 and irradiated for 600 seconds, and the polymerization property in the polymerizable compound-containing liquid crystal composition A vertically aligned liquid crystal display element obtained by polymerizing the compound was obtained.
- This liquid crystal display element (PSVA mode) showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle. (Example 2) The prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 2 contains 99.8% of the liquid crystal composition and 0.2% of the polymerizable compound represented by the general formula (I-11). ni : 75.5 ° C., ⁇ n: 0.107, ⁇ : ⁇ 3.0, ⁇ : 17.5 mPa ⁇ s.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle. (Example 3)
- the prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 3 contains 99.65% of the liquid crystal composition and 0.35% of the polymerizable compound represented by the general formula (I-11). ni : 75.4 ° C., ⁇ n: 0.107, ⁇ : ⁇ 3.0, ⁇ : 17.5 mPa ⁇ s.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle.
- Example 4 The prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 4 contains 99.6% of the liquid crystal composition and 0.4% of the polymerizable compound represented by the general formula (I-11). ni : 75.4 ° C., ⁇ n: 0.107, ⁇ : ⁇ 3.0, ⁇ : 17.5 mPa ⁇ s.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle.
- the prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Comparative Example 1 contains 99.8% of the liquid crystal composition of Example 1 and 0.2% of the polymerizable compound described in JP-A No. 2003-307720.
- Examples 1 to 4 maintained the nematic state for 2 weeks or 3 weeks at any temperature of ⁇ 40 ° C. and ⁇ 25 ° C.
- Comparative Example 1 maintained the nematic state for only one week, and precipitation was confirmed in the second week. From this, Examples 1 to 4 maintain a nematic state over a wide temperature range, and are very useful in that stability at low temperature is maintained over a long period of two or three times as compared with Comparative Example 1. It was confirmed to be a polymerizable compound-containing liquid crystal composition.
- the polymerizable compound-containing liquid crystal composition shown in Comparative Example 2 is 99.8% of a liquid crystal composition not containing the compounds represented by the general formulas (II-A) and (II-B) of the present invention, and JP-A-2003 No. 307720, 0.2% of the polymerizable compound, T ni : 76.4 ° C., ⁇ n: 0.107, ⁇ : -2.9, ⁇ : 21.2 mPa ⁇ s there were. Since the viscosity is significantly increased, it is easily assumed that the response speed will be significantly deteriorated when the liquid crystal display device is used.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast, but the response speed was slow and was not practical. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle. (Example 5) The prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 5 contains 99.8% of the above liquid crystal composition and 0.2% of the polymerizable compound represented by the general formula (I-11). ni : 76.4 ° C., ⁇ n: 0.092, ⁇ : -2.9, ⁇ : 18.6 mPa ⁇ s.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle. (Example 6)
- the prepared polymerizable compound-containing liquid crystal composition and its physical property values are shown below.
- the polymerizable compound-containing liquid crystal composition shown in Example 6 contains 99.8% of the liquid crystal composition and 0.2% of the polymerizable compound represented by the general formula (I-11). ni : 76.3 ° C., ⁇ n: 0.091, ⁇ : -2.7, ⁇ : 18.4 mPa ⁇ s.
- a liquid crystal display device (PSVA mode) using this polymerizable compound-containing liquid crystal composition showed high contrast and was capable of high-speed response. Moreover, the alignment control force with respect to the liquid crystal compound of a polymeric compound was confirmed by the measurement of a pretilt angle. From the above, it was confirmed that the polymerizable compound-containing liquid crystal composition of the present invention maintained a nematic state in a wide temperature range, and the liquid crystal display device had a high-speed response.
Abstract
Description
本発明の重合性化合物含有液晶組成物は、更に一般式(III)
本発明の重合性化合物含有液晶組成物に含まれる液晶化合物において、-O-O-、-O-S-及び-S-S-等のヘテロ原子同士が直接結合する部分構造をとることはない。また、アルケニル基を有する化合物を含まないことが好ましく、全ての液晶化合物の側鎖がアルキル基又はアルコキシル基であることがより好ましい。また、焼き付きや表示ムラ等の表示不良を抑制するため、又は、全く発生させないためには、液晶化合物の構造中にはシクロヘキサン環、ベンゼン環又はフッ素で置換されたベンゼン環であることが好ましく、同じハロゲン原子であっても塩素原子で置換される化合物を含有することは好ましくない。塩素原子で置換された液晶化合物を用いることは表示不良の原因にもなるため、実用的ではない。
Δn :25℃における屈折率異方性
Δε :25℃における誘電率異方性
η :20℃における粘度(mPa・s)
(実施例1)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(実施例2)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(実施例3)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(実施例4)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(比較例1)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(実施例5)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
(実施例6)
以下に、調製した重合性化合物含有液晶組成物とその物性値を示す。
以上のことから、本発明の重合性化合物含有液晶組成物は、広い温度範囲でネマチック状態を維持し、また、その液晶表示素子は高速応答であることが確認された。
Claims (17)
- 第一成分として、一般式(I)
- 一般式(I)が一般式(I-1)である請求項1に記載の重合性化合物含有液晶組成物。
- 一般式(I)において、R1及びR2がそれぞれ独立して式(R-1)又は(R-2)である請求項1から3のいずれかに記載の重合性化合物含有液晶組成物。
- 一般式(I)において、R1及びR2が式(R-2)である請求項1から3のいずれかに記載の重合性化合物含有液晶組成物。
- 一般式(I)で表される化合物の含有量が0.01質量%から2.0質量%である請求項1から8のいずれかに記載の重合性化合物含有液晶組成物。
- 一般式(II)で表される化合物の含有量が5質量%から35質量%である請求項1から9のいずれかに記載の重合性化合物含有液晶組成物。
- 一般式(III)で表される化合物の含有量が5質量%から35質量%である請求項1から10のいずれかに記載の重合性化合物含有液晶組成物。
- 一般式(I-1)で表される重合性化合物及び一般式(II-A)及び(II-B)及び一般式(III-A)で表される化合物を同時に含有する請求項1から11のいずれかに記載の重合性化合物含有液晶組成物。
- 25℃における誘電率異方性Δεが-6.0から-2.0の範囲であり、25℃における屈折率異方性Δnが0.08から0.13の範囲であり、20℃における粘度(η)が10から30 mPa・sの範囲であり、ネマチック相-等方性液体相転移温度(Tni)が60℃から120℃の範囲である請求項1から12のいずれかに記載の重合性化合物含有液晶組成物。
- 請求項1から13のいずれかに記載の重合性化合物含有液晶組成物を用いたことを特徴とする液晶表示素子。
- アクティブマトリックス駆動である請求項14に記載の液晶表示素子。
- PSAモード、PSVAモード、VAモード、IPSモード又はECBモードである請求項14又は15に記載の液晶表示素子。
- プレチルト角が85から89.9度である請求項14から16のいずれかに記載の液晶表示素子。
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US13/995,879 US9080101B2 (en) | 2010-12-24 | 2011-12-15 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
KR1020137008422A KR101369914B1 (ko) | 2010-12-24 | 2011-12-15 | 중합성 화합물 함유 액정 조성물 및 그것을 사용한 액정 표시 소자 |
JP2012517019A JP5196073B2 (ja) | 2010-12-24 | 2011-12-15 | 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子 |
EP11851082.5A EP2657318B1 (en) | 2010-12-24 | 2011-12-15 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
CN201180051489.XA CN103180410B (zh) | 2010-12-24 | 2011-12-15 | 含有聚合性化合物的液晶组合物以及使用其的液晶显示元件 |
US14/727,323 US9353312B2 (en) | 2010-12-24 | 2015-06-01 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
US15/147,095 US9777220B2 (en) | 2010-12-24 | 2016-05-05 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
US15/693,947 US10308873B2 (en) | 2010-12-24 | 2017-09-01 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
US16/381,455 US10934488B2 (en) | 2010-12-24 | 2019-04-11 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
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US14/727,323 Continuation US9353312B2 (en) | 2010-12-24 | 2015-06-01 | Polymerizable compound-containing liquid crystal composition and liquid crystal display device using the same |
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Also Published As
Publication number | Publication date |
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EP2657318A4 (en) | 2014-07-09 |
EP2952554A1 (en) | 2015-12-09 |
KR20130043693A (ko) | 2013-04-30 |
KR101369914B1 (ko) | 2014-03-06 |
TW201233785A (en) | 2012-08-16 |
EP2657318B1 (en) | 2015-10-21 |
JPWO2012086504A1 (ja) | 2014-05-22 |
EP2952554B1 (en) | 2017-03-01 |
EP2657318A1 (en) | 2013-10-30 |
CN104673327B (zh) | 2018-06-08 |
US20160244672A1 (en) | 2016-08-25 |
CN103180410A (zh) | 2013-06-26 |
US10308873B2 (en) | 2019-06-04 |
US9080101B2 (en) | 2015-07-14 |
US20190233730A1 (en) | 2019-08-01 |
US10934488B2 (en) | 2021-03-02 |
JP5196073B2 (ja) | 2013-05-15 |
US20170362509A1 (en) | 2017-12-21 |
TWI464248B (zh) | 2014-12-11 |
CN103180410B (zh) | 2016-06-15 |
CN104673327A (zh) | 2015-06-03 |
US20150259601A1 (en) | 2015-09-17 |
US9777220B2 (en) | 2017-10-03 |
US20130334462A1 (en) | 2013-12-19 |
US9353312B2 (en) | 2016-05-31 |
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