WO2006068195A1 - ヘキセンジイン誘導体 - Google Patents
ヘキセンジイン誘導体 Download PDFInfo
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- WO2006068195A1 WO2006068195A1 PCT/JP2005/023522 JP2005023522W WO2006068195A1 WO 2006068195 A1 WO2006068195 A1 WO 2006068195A1 JP 2005023522 W JP2005023522 W JP 2005023522W WO 2006068195 A1 WO2006068195 A1 WO 2006068195A1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—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
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3021—Cy-Ph-Ph-Cy
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Definitions
- the present invention relates to a novel liquid crystal compound having a hexenediyne skeleton, a liquid crystal composition containing the compound, and use thereof.
- Liquid crystal elements are widely used in the field of display, as a display, etc., in the field of optical pickup, as a diffraction grating, a phase plate, and the like. These devices require various performances such as high contrast ratio, wide viewing angle, wide operating temperature range, high speed response, low operating voltage, chemical stability, etc. There is a need for downsizing. For this reason, physical properties such as refractive index anisotropy, dielectric anisotropy, and conductivity of liquid crystal materials used in liquid crystal elements are important. In particular, there is an increasing demand for materials having a large value of refractive index anisotropy. Yes.
- the product of the refractive index anisotropy value ( ⁇ ) of a liquid crystal material and the cell thickness (dl) needs to be a constant value.
- a method of obtaining a high-quality display without domain by reducing dl is adopted, and it has a large ⁇ value in order to adjust the ⁇ value of liquid crystal material to an optimal value.
- a liquid crystal compound having a large ⁇ value is extremely useful for producing a liquid crystal display device having a high response speed and good display quality. .
- a polarization diffraction element with high light utilization efficiency by forming a lattice-like rectangular structure on a transparent substrate and filling it with a liquid crystal material. ing.
- the first-order diffraction efficiency is maximized.
- polarization diffraction elements have been increasingly narrowed in the grating pitch p.
- a tolan derivative represented by the following formula (A) (see Patent Document 1).
- Patent Document 1 Japanese Patent Publication No. 1 502823
- Patent Document 2 JP-A-3-294386
- Patent Document 3 JP-A-6-312946
- Patent Document 4 JP-A-7-304694
- Non-Patent Document 1 The 'Molecular Crystal Liquid Crystal ", 1978, 48 Certificates, p 175 Non-Patent Document 2:.” Liquid Crystal] lambda 1993 years, 15 Certificates, p 529- 540
- each of the above compounds has a problem that the value of refractive index anisotropy is insufficient and the temperature range showing liquid crystallinity is narrow. Further, the compound represented by the formula (B) has a problem that it is thermally unstable.
- the present invention has been made to solve the above-described problems, and provides a novel liquid crystal compound having a hexenediin skeleton and a liquid crystal composition containing the liquid crystal compound. That is, the present invention has the following gist.
- R 2 each independently an alkyl group, an alkenyl group, an alkoxy group, a halogen atom, or a cyan group.
- at least one hydrogen atom in the alkyl group, the alkenyl group, and the alkoxy group may be substituted with a chlorine atom or a fluorine atom.
- Ring group A and ring group B each independently a trans 1,4-cyclohexylene group or a 1,4-phenylene group.
- hydrogen atoms in these ring groups may be substituted with chlorine atoms, fluorine atoms or methyl groups.
- X 1 and X 2 each independently a hydrogen atom or a fluorine atom.
- a liquid crystal composition comprising at least one liquid crystal compound according to ⁇ 1>, ⁇ 2> or ⁇ 3>.
- ⁇ 6> An optical element comprising the liquid crystal composition according to ⁇ 4> or ⁇ 5>.
- An optical element for an optical pickup comprising the liquid crystal composition according to ⁇ 4> or ⁇ 5>.
- the compound represented by formula (1) is also referred to as compound (1).
- the value of refractive index anisotropy is abbreviated as “ ⁇ ”.
- the description of the wavelength in the following means that it is in the range of the described value ⁇ 2 nm even if it is described as a single point value.
- the compound of the present invention is a novel liquid crystalline compound represented by the following formula (1).
- R 1 and R 2 each independently represents an alkyl group, an alkenyl group, an alkoxy group, a halogen atom, or a cyan group.
- R 1 and R 2 are each an alkyl group, an alkeninole group, or an alkoxy group, it is possible for these groups to have a straight-chain structure to expand the liquid crystal phase expression temperature range and to reduce ⁇ less. preferable.
- one or more of hydrogen atoms in these groups may be substituted with chlorine atoms or fluorine atoms.
- the light with respect to a short wavelength region of about 400 to 450 nm is used. Resistance There is an advantage of improving the performance.
- the number of carbon atoms of the alkyl group and the alkoxy group is also a point in the temperature range of the nematic phase:! To 10 is preferable, 2 to 8 is particularly preferable, 3 to 7 force, S is particularly preferable.
- the alkenyl group has 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms. Furthermore, since the alkenyl group has a large elastic constant ratio (K / K), when the carbon number is even,
- a group having a double bond from the carbon atom at the end of the kenyl chain toward the ring group is preferred.
- a group having a double bond from the second carbon atom to the ring group from the alkenyl chain end is preferable because the elastic constant ratio increases and the response speed increases.
- R 1 and R 2 are halogen atoms
- each of them is preferably a chlorine atom or a fluorine atom, particularly preferably a fluorine atom, from the viewpoint of shortening the absorption wavelength, increasing compatibility, and decreasing the viscosity.
- R 1 and R 2 are each a straight-chain alkyl group having from 10 to 10 carbon atoms, a straight-chain alkoxy group having from! To 10 carbon atoms, a straight-chain alkenyl group having from 2 to 10 carbon atoms, and a carbon number of 1
- a perfluoroalkyl group of ⁇ 6 or a perfluoroalkoxy group of 1 to 6 carbon atoms is preferred from the viewpoint of the nematic phase expression temperature range and the decrease in ⁇ .
- a straight-chain alkyl group having 3 to 7 carbon atoms or a straight-chain alkoxy group having 3 to 7 carbon atoms is particularly preferable because of the wide temperature range in which compound (1) exhibits liquid crystallinity.
- X 1 and X 2 are each independently a hydrogen atom or a fluorine atom, and at least one is preferably a fluorine atom. In the present invention, it is particularly preferable that both X 1 and X 2 are fluorine atoms from the viewpoint of shortening the absorption wavelength and increasing light resistance.
- the ring group ⁇ and the ring group ⁇ are each independently a trans 1,4_cyclohexylene group or a 1,4_funylene group.
- a hydrogen atom in the group which may be an unsubstituted group may be substituted with a chlorine atom, a fluorine atom or a methyl group.
- the number of substituents is 1 to 4, and in particular, one or two is preferable from the viewpoint of the nematic phase expression temperature range. Substituents are also preferred from the viewpoint of the nematic phase expression temperature range and the suppression of the decrease in ⁇ n.
- Cyclic group A and cyclic group B are 1, 4-F from the point that ⁇ of compound (1) can be increased.
- An enylene group is preferred.
- a trans 1,4-cyclohexylene group is preferable from the viewpoint that the transmittance of light to be used can be improved and the compatibility with other compounds can be enhanced.
- n 0 or 1.
- n When n is 0, the crystal-nematic phase transition point of the compound (1) can be lowered, and there is an advantage of excellent compatibility with other liquid crystal compounds.
- n 1 and ring group A and ring group B are trans-1,4-cyclohexylene groups, there is an advantage that the temperature range showing the liquid crystal phase with high light transmittance is widened.
- n 1, the cyclic group A is a trans 1,4-cyclohexylene group and the cyclic group B is a 1,4-phenylene group, a very large value of ⁇ is shown.
- Examples of the compound (1) include the following compounds (lFa) to (lFd), the following compounds (lHa) to (lHd), and the like. lFa), (lFc), (lFd), (lHa), (lHc), and (lHd) are preferred.
- the following compounds (lFa), (lFc), and (lFd) contain a cyclohexyl group, so that the absorption is shortened and it is advantageous in terms of light resistance. Meaning the same).
- R 5 and in the formula are each independently a linear alkyl group having from 10 to 10 carbon atoms or a linear alkoxy group having from 1 to 10 carbon atoms.
- R 5 and R 6 are each a straight chain having 3 to 7 carbon atoms, preferably a straight-chain alkyl group having 2 to 8 carbon atoms or a straight-chain alkoxy group having 2 to 8 carbon atoms, from the point of the nematic phase expression temperature range.
- a chain alkyl group or a linear alkoxy group having 3 to 7 carbon atoms is particularly preferred.
- Compound (1) of the present invention can be synthesized, for example, by the method shown below.
- Examples of the method for synthesizing the compound (1F) when both X 1 and X 2 are fluorine atoms in the compound (1) include the following methods. That is, the following compound (al) and the following compound (b) are coupled in the presence of a transition metal complex catalyst to obtain the following compound (cl). Next, there is a method of obtaining the compound (1F) by coupling the compound (cl) and the following compound (d) (wherein , Ring group A, ring group B, and n have the same meaning as described above. ).
- Transition metal complex catalysts include paradoxes such as PdCl [P (C H)] and Pd [P (C H)].
- Catalyst can be used. If necessary, copper salts such as copper iodide and copper bromide can be used together as a co-catalyst.
- copper salts such as copper iodide and copper bromide can be used together as a co-catalyst.
- solvent secondary amines, tertiary amines, and amides can be used, and specific examples include piperidine, piperazine, morpholine, pyridine, triethreamine, dimethylformamide and the like.
- the compound (1) of the present invention has the following highly conjugated structure (90), it exhibits a very large ⁇ value.
- the compound (1) of the present invention contains at least one trans 1,4-cyclohexane.
- a structure having a hexylene group is preferred. By having this structure, there is an advantage that the transmittance of light used is high, and an advantage that the temperature range showing liquid crystallinity is wide. Furthermore, when the compound (1) is mixed with another liquid crystal compound and used as a liquid crystal composition, the compatibility with the other liquid crystal compound is also improved.
- a trans isomer and a cis isomer may exist with respect to a carbon-carbon double bond site in the structure represented by the structure (90). It is preferable to include a trans isomer as a main component from the viewpoint that the temperature range in which the matic phase appears is wide.
- the ratio of the trans isomer to the cis isomer is 0.95 or more as the trans isomer / (trans isomer + cis isomer) when measured by gas chromatography, high performance liquid chromatography, NMR, etc. It is particularly preferable that it is 0.98 or more.
- the compound (1) when both X 1 and X 2 are fluorine atoms, the compound (1) has a transdifluorine hexacene diyne structure in which a fluorine atom is substituted at the trans position with respect to the double bond in the hexenediyne structure. Therefore, despite being highly conjugated, it does not absorb in the visible light region and has excellent light resistance. Another advantage is that the crystal-nematic phase transition point is low and the viscosity is low.
- the compound (1) of the present invention is preferably mixed with other liquid crystal compounds and used as a liquid crystal composition.
- other liquid crystalline compounds include the following compounds (wherein R 7 , R 8 and R 9 are each independently an alkyl group, an alkenyl group, or an alkyl group substituted with a halogen atom).
- Compound (1) can also be used as a mixture with a commercially available nematic liquid crystal composition.
- the amount of the compound (1) contained in the liquid crystal composition of the present invention is 0.5% by mass or more with respect to the liquid crystal composition, and 2 to 30% by mass is preferable 3 to 20% by mass. % Is particularly preferred. By using the compound (1) in an amount within the above range, the ⁇ value of the liquid crystal composition can be dramatically improved.
- the liquid crystal composition of the present invention may contain components other than the compound (1) and other liquid crystal compounds (hereinafter referred to as other components) depending on the application.
- other components include chiral agents, ultraviolet absorbers, antioxidants, light stabilizers, and dichroic dyes.
- the total amount of the compound (1) and other liquid crystal compounds contained in the liquid crystal composition (hereinafter referred to as “total amount of liquid crystal”) and the ratio of other components are preferably adjusted depending on the application.
- total amount of liquid crystal is based on the liquid crystal composition. 30 to 95% by mass is preferable, and 50 to 95% by mass is particularly preferable.
- the amount of the chiral agent is preferably 5 to 70% by mass, more preferably 5 to 70% by mass with respect to the liquid crystal composition.
- the total amount of liquid crystals is based on the liquid crystal composition.
- the amount of the dichroic dye is preferably from 1 to 20% by weight, particularly preferably from 3 to 18% by weight, based on the liquid crystal composition.
- the amount of these components is preferably 5% by mass or less based on the liquid crystal composition, and 2% by mass or less. Particularly preferred.
- the total amount of the liquid crystal is preferably 95 to 100% by mass, particularly preferably 98 to 100% by mass with respect to the liquid crystal composition.
- the compound (1) of the present invention can be used as PDLC (Polymer Dispersed Liquid Crystal) by being subjected to a polymerization reaction together with a polymerizable monomer such as attalylate or metatalylate.
- PDLC Polymer Dispersed Liquid Crystal
- liquid crystal composition of the present invention can be usefully used in display elements and optical elements. These elements can be created by a known method, for example, by the following method.
- a pair of laminates in which an electrode and an orientation film are laminated in this order on a transparent substrate are arranged so that the surfaces of the orientation films face each other, and the periphery on the laminate is sealed with a sealant to assemble the cell. .
- a transparent glass substrate and a transparent resin substrate are particularly preferable because they are preferably rigid.
- the thickness of the transparent substrate is preferably 0.2 to 1.5 mm, particularly preferably 0.3 to 1.1 mm.
- a transparent conductive film such as an ITO film or a SnO film is vaporized.
- a film-like transparent electrode that is laminated on the surface of the transparent substrate by a method such as deposition or sputtering is preferred.
- the film-like transparent electrode is preferably patterned by a method such as photolithography or wet etching according to the application.
- An alignment film is laminated on the surface of the electrode.
- a method for laminating the alignment film a known method can be adopted, a method in which a polyamic acid solution is applied to the surface on which the transparent substrate electrode is laminated and then baked, and a soluble polyimide solution is laminated on the transparent substrate electrode. Examples include a method of volatilizing the solvent after coating on the surface, and a method of obliquely depositing an inorganic material such as SiO.
- the surface of the alignment film made of an organic material such as polyimide is preferably rubbed.
- a pair of the laminates is prepared, and a sealing agent such as an epoxy resin is annularly applied to the peripheral portion of the surface on the side where the alignment film is formed in at least one of the laminates.
- a spacer for obtaining a desired cell gap, conductive fine particles serving as a conductive path for applying a voltage, and the like can be mixed in advance.
- the cell gap is particularly preferably from 1 to 20 / im, from the viewpoint of response speed and productivity, from 3 to 10 ⁇ m.
- the annular coating portion of the sealant is provided with at least a discontinuous portion serving as an injection port for injecting the liquid crystal composition. By injecting the injection liquid crystal composition, the liquid crystal element is formed. Produced.
- the configuration of the liquid crystal element is not limited to the above-described configuration.
- a phase plate or the like in which an antireflection film may be laminated on the surface opposite to the surface on which the electrodes of the transparent substrate are laminated is laminated.
- An uneven rectangular structure may be provided on the surface of the substrate.
- the optical element of the present invention is useful as an optical element used for laser light in the field of optical pickup, such as a display in the display field, a production television, and the like.
- the optical element include a phase plate, a diffraction element, and a liquid crystal lens.
- the optical element is suitable for a phase-diffraction element and a polarization diffraction element in which a lattice-shaped rectangular structure is formed and filled with a liquid crystal material.
- the optical element of the present invention as an optical element of an optical pickup having a laser light source and a photodetector, an optical element, and an objective lens, it is possible to exhibit excellent characteristics in downsizing and short wavelength. .
- GC-MS gas chromatography / mass spectrometry
- THF tetrahydrofuran
- L liter
- the transition temperature from the crystal of the compound (lFa_la) to the nematic phase was 70.6 ° C, and the transition temperature from the nematic phase to the isotropic phase was 220 ° C. Further, the refractive index anisotropy value ( ⁇ ) of the compound (lFa-la) with respect to the laser beam having a wavelength of 589 nm was 0 ⁇ 455, and ⁇ with respect to the laser beam having a wavelength of 405 nm was 0.754. .
- Nematic liquid crystal (Merck, product number: ZLI1565, refractive index anisotropy with respect to laser light with a wavelength of 589 nm is 0.118) and the compound obtained in Example 1 (lFa_la) 19: 6 (mass ratio) )
- the transition temperature from the crystal of liquid crystal composition 1 to the nematic phase was ⁇ 2 ° C, and the transition temperature from the nematic phase to the isotropic phase was 108.4 ° C.
- ⁇ with respect to laser light having a wavelength of 589 nm of liquid crystal composition 1 was 0.388
- ⁇ with respect to laser light having a wavelength of 405 nm was 0.630.
- JC1041xx manufactured by Chisso Corporation
- the compound compound (1 Fa-la) obtained in Example 1 were mixed at a ratio of 19: 1 (mass ratio) to obtain liquid crystal composition 2.
- Liquid crystal composition 2 has good compatibility, and crystal precipitation and Phase separation was not observed.
- a nematic phase was developed at 25 ° C, and 1 was shown at 119, confirming that liquid crystallinity was exhibited.
- ⁇ with respect to the laser beam having a wavelength of 589 nm of the liquid crystal composition 2 was 0.173
- ⁇ with respect to the laser beam having a wavelength of 405 nm was 0.199.
- Two transparent glass substrates having a length of 100 mm, a width of 100 mm, and a thickness of 0.53 mm were prepared.
- a 15 nm thick ITO transparent conductive film was formed on each surface, and then patterned by photolithography and wet etching to produce a transparent electrode.
- a polyamic acid solution manufactured by Nissan Chemical Co., product number: SE510
- SE510 polyamic acid solution
- An epoxy sealant (an epoxy sealant was coated with a fiber spacer with a diameter of 3.2 ⁇ m and conductive coating on the peripheral edge of the surface on which one polyimide alignment film of the laminate was laminated. Acrylic spheres were added.) Were printed by the screen method. Next, the other laminate is laminated so that the polyimide alignment film faces each other and the bonding angle is about 180 degrees, and is crimped at a pressure of 6 ⁇ 10 4 N / m 2 , and at 170 ° C. Heat-cured. After heating and curing, the cell was cooled and cut into 5 mm length and 5 mm width.
- the liquid crystal composition 2 obtained in Example 3 was injected into the cell, and the injection port was sealed using a thermosetting adhesive to produce an optical element.
- the liquid crystal molecules in the optical element were horizontally aligned along the rubbing direction.
- the optical element was irradiated with laser light having a wavelength of 405 nm and an intensity of 30 mW for 7000 hours.
- the polarization direction of the laser beam was made parallel to the rubbing direction of the liquid crystal molecules.
- the optical element which has no change in characteristics before and after laser light irradiation, showed good light resistance.
- the compound of the present invention is a compound that is stable under use conditions in which the temperature range showing a liquid crystal phase with a large refractive index anisotropy value is wide. Since the compound can prepare a liquid crystal composition having a sufficiently large refractive index anisotropy even when used in a small amount, it can be usefully used as a material for optical elements such as display elements, diffraction elements, and phase plates. It should be noted that the entire contents of the Japanese Patent Application No. 2004-371368, filed on December 22, 2004, and the claims and the abstract are cited herein as the disclosure of the specification of the present invention. It is something that is incorporated.
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Abstract
Description
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Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2006549036A JPWO2006068195A1 (ja) | 2004-12-22 | 2005-12-21 | ヘキセンジイン誘導体 |
US11/767,215 US7374700B2 (en) | 2004-12-22 | 2007-06-22 | Hexenediyne derivative |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2004371368 | 2004-12-22 | ||
JP2004-371368 | 2004-12-22 |
Related Child Applications (1)
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US11/767,215 Continuation US7374700B2 (en) | 2004-12-22 | 2007-06-22 | Hexenediyne derivative |
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WO2006068195A1 true WO2006068195A1 (ja) | 2006-06-29 |
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PCT/JP2005/023522 WO2006068195A1 (ja) | 2004-12-22 | 2005-12-21 | ヘキセンジイン誘導体 |
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US (1) | US7374700B2 (ja) |
JP (1) | JPWO2006068195A1 (ja) |
WO (1) | WO2006068195A1 (ja) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06263661A (ja) * | 1992-09-04 | 1994-09-20 | Asahi Glass Co Ltd | ジフルオロ誘導体化合物およびそれを含有する液晶組成物 |
JPH06312946A (ja) * | 1992-11-10 | 1994-11-08 | Chisso Corp | 共役エンイン誘導体および液晶組成物 |
JPH07304694A (ja) * | 1994-03-16 | 1995-11-21 | Chisso Corp | ヘキセンジイン誘導体および液晶組成物 |
JPH10265531A (ja) * | 1997-01-23 | 1998-10-06 | Asahi Glass Co Ltd | 液晶高分子、偏光ホログラム素子および光ピックアップモジュール |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5419851A (en) * | 1992-09-04 | 1995-05-30 | Asahi Glass Company Ltd. | Difluoro-derivative compounds and liquid crystal compositions containing them |
TW253905B (ja) * | 1992-11-10 | 1995-08-11 | Chisso Corp | |
US5554316A (en) * | 1994-03-16 | 1996-09-10 | Chisso Corporation | Hexenediyne derivative and a liquid crystal composition |
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2005
- 2005-12-21 JP JP2006549036A patent/JPWO2006068195A1/ja active Pending
- 2005-12-21 WO PCT/JP2005/023522 patent/WO2006068195A1/ja active Application Filing
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2007
- 2007-06-22 US US11/767,215 patent/US7374700B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06263661A (ja) * | 1992-09-04 | 1994-09-20 | Asahi Glass Co Ltd | ジフルオロ誘導体化合物およびそれを含有する液晶組成物 |
JPH06312946A (ja) * | 1992-11-10 | 1994-11-08 | Chisso Corp | 共役エンイン誘導体および液晶組成物 |
JPH07304694A (ja) * | 1994-03-16 | 1995-11-21 | Chisso Corp | ヘキセンジイン誘導体および液晶組成物 |
JPH10265531A (ja) * | 1997-01-23 | 1998-10-06 | Asahi Glass Co Ltd | 液晶高分子、偏光ホログラム素子および光ピックアップモジュール |
Also Published As
Publication number | Publication date |
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JPWO2006068195A1 (ja) | 2008-06-12 |
US20070241310A1 (en) | 2007-10-18 |
US7374700B2 (en) | 2008-05-20 |
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