WO2016017614A1 - ネマチック液晶組成物 - Google Patents
ネマチック液晶組成物 Download PDFInfo
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- WO2016017614A1 WO2016017614A1 PCT/JP2015/071323 JP2015071323W WO2016017614A1 WO 2016017614 A1 WO2016017614 A1 WO 2016017614A1 JP 2015071323 W JP2015071323 W JP 2015071323W WO 2016017614 A1 WO2016017614 A1 WO 2016017614A1
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- liquid crystal
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000004988 Nematic liquid crystal Substances 0.000 title description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 121
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000001153 fluoro group Chemical group F* 0.000 claims description 36
- -1 naphthalene-2,6-diyl Group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 10
- 125000005653 3,5-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:2])=C(F)C([H])=C1[*:1] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 125000005453 2,5-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C(F)=C([H])C([*:2])=C1F 0.000 claims 1
- 239000012071 phase Substances 0.000 abstract description 12
- 230000007704 transition Effects 0.000 abstract description 8
- 239000007791 liquid phase Substances 0.000 abstract description 5
- 230000007423 decrease Effects 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 0 Cc1cc(*)c(*)c(*)c1 Chemical compound Cc1cc(*)c(*)c(*)c1 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 125000003302 alkenyloxy group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 2
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 150000008423 fluorobenzenes Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical class C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C09K19/34—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0208—Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.)
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0216—Super Birefringence Effect (S.B.E.); Electrically Controlled Birefringence (E.C.B.)
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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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
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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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
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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
- G02F1/01—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
- G02F1/1362—Active matrix addressed cells
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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
- 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
- C09K2019/0466—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 linking chain being a -CF2O- chain
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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
- C09K19/10—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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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)
- C09K2019/3004—Cy-Cy
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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)
- C09K2019/301—Cy-Cy-Ph
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- C—CHEMISTRY; METALLURGY
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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)
- C09K2019/3025—Cy-Ph-Ph-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
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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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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13706—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having positive dielectric anisotropy
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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
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
- G02F2202/022—Materials and properties organic material polymeric
Definitions
- the present invention relates to a nematic liquid crystal composition having a positive dielectric anisotropy ( ⁇ ) useful as an electro-optical liquid crystal display material.
- Liquid crystal display elements are used in various measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, etc., including clocks and calculators.
- Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, VA type characterized by vertical alignment using TFT (thin film transistor) and horizontal alignment.
- the liquid crystal composition used in these liquid crystal display elements is stable against external factors such as moisture, air, heat, light, etc., and exhibits a liquid crystal phase in the widest possible temperature range centering on room temperature, and has low viscosity. And a low driving voltage is required.
- the liquid crystal composition has several to several tens of kinds of compounds in order to optimize the dielectric anisotropy ( ⁇ ) and the refractive index anisotropy ( ⁇ n) for each display element. It is composed of
- a liquid crystal composition having a negative ⁇ is used for a vertical alignment type display
- a liquid crystal composition having a positive ⁇ is used for a horizontal alignment type display such as a TN type, STN type, or IPS type.
- a driving method in which a liquid crystal composition having a positive ⁇ is vertically aligned when no voltage is applied and a lateral electric field is applied has been reported. The nature is further increasing. On the other hand, low voltage driving, high-speed response, and a wide operating temperature range are required in all driving systems.
- ⁇ is positive, the absolute value is large, the viscosity ( ⁇ ) is small, and a high nematic phase-isotropic liquid phase transition temperature (T ni ) is required.
- T ni nematic phase-isotropic liquid phase transition temperature
- the problems to be solved by the present invention are adjusted to desired dielectric anisotropy ( ⁇ ) and refractive index anisotropy ( ⁇ n), and decrease in nematic phase-isotropic liquid phase transition temperature (T ni ) and By suppressing the rise in the lower limit temperature of the nematic phase, the viscosity ( ⁇ ) is sufficiently low without deteriorating the temperature range of the nematic phase, and the response speed when used in a liquid crystal display device is fast and excellent in reliability.
- Another object is to provide a liquid crystal composition having a positive dielectric anisotropy ( ⁇ ).
- the present inventor has studied various fluorobenzene derivatives and found that the above problem can be solved by combining specific compounds, and has completed the present invention.
- the present invention is a liquid crystal composition having a positive dielectric anisotropy, wherein the liquid crystal composition has the general formula (LC0)
- R 01 represents an alkyl group having 1 to 15 carbon atoms, and one or two or more CH 2 groups in the alkyl group are —O—, —
- One or more of the alkyl groups may be substituted with CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O—, —OCF 2 —.
- the hydrogen atom of may be optionally substituted with halogen
- a 01 and A 02 are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4 -Phenylene group, 3,5-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, naphthalene-2,6-diyl group, Decahydronaphthalene-2,6-diyl group or 1,2,3,4 Represents tetrahydronaphthalene-2,6-diyl group, B 01 is one of the following structures
- X 01 , X 02 , X 05 , X 06 and X 07 each independently represent a hydrogen atom or a fluorine atom
- Y 01 and Y 02 each independently represent a chlorine atom, a cyano group or a fluorine atom
- Z 01 , Z 02 and Z 03 each independently represents a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, —, and —CF 3 or —OCF 3 .
- each of X 03 and X 04 independently represents a hydrogen atom or a fluorine atom; 01 and m 02 each independently represents an integer of 0 to 2, m 01 + m 02 each independently represents 0, 1 or 2, and a plurality of A 01 , A 02 , Z 01 and / or Z 03 are present. If they are the same, You can have me. ) Or a compound represented by general formula (LC1)
- R 11 and R 12 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is not directly adjacent to an oxygen atom.
- the alkyl group may be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- One or two or more hydrogen atoms therein may be optionally substituted with halogen
- a 11 to A 13 each independently represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
- 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, tetrahydropyran-2, 5-diyl group, 1,3-dioxane-2,5 Diyl group, 1,4-bicyclo [2.2.2] octylene group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl group, Z 11 and Z 12 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 — or —CF 2 O—, m 11 represents 0, 1 or 2, and when a pluralit
- ⁇ is positive and its absolute value and refractive index anisotropy ( ⁇ n) are adjusted to desired ones, while ⁇ is low, rotational viscosity ( ⁇ 1 ) is small, and liquid crystallinity. And a stable liquid crystal phase in a wide temperature range. In addition, it is chemically stable to heat, light, water, etc., and has good solubility, so that it has good phase stability at low temperatures.
- the liquid crystal composition of the present invention contains one or more compounds represented by the general formula (LC0) and one or more compounds represented by the general formula (LC1).
- the liquid crystal composition including the compound represented by the general formula (LC0) and the compound represented by the general formula (LC1) has a positive ⁇ and a desired absolute value and refractive index anisotropy ( ⁇ n).
- ⁇ n refractive index anisotropy
- R 01 is preferably an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms or a carbon atom.
- An alkenyl group having a number of 2 to 5 is particularly preferable.
- R 01 is preferably selected from groups represented by any one of formulas (R1) to (R5).
- a 01 and A 02 are each independently preferably a trans-1,4-cyclohexylene group, a naphthalene-2,6-diyl group or a 1,4-phenylene group for decreasing the viscosity.
- 1,4-cyclohexylene group is more preferable, and 3-fluoro-1,4-phenylene group and 3,5-difluoro-1,4-phenylene group are preferable for increasing ⁇ .
- 3,5-difluoro-1,4-phenylene group is more preferable, and in order to increase T 1 ⁇ i , a trans-1,4-cyclohexylene group or 1,4-phenylene group is preferable.
- B01 is for reducing the viscosity.
- X 01 , X 02 , X 05 , X 06 and X 07 are each independently preferably a hydrogen atom for decreasing the viscosity and increasing T 1 ⁇ i , and a fluorine atom for increasing ⁇ . It is preferable that
- B 01 is particularly preferably selected from any of the following partial structures.
- Y 01 and Y 02 are preferably a fluorine atom, —CF 3 , —OCF 3 , which improves the lower limit temperature of the nematic phase and favors the low-temperature operation and storage stability of the liquid crystal composition.
- a fluorine atom, a cyano group, —CF 3 or —OCF 3 is preferable, and in order to decrease the viscosity, a fluorine atom is preferable.
- a fluorine atom, —CF 3 or —OCF 3 is preferable.
- X 03 and X 04 are each independently a hydrogen atom or a fluorine atom, preferably a fluorine atom for increasing ⁇ , and preferably a fluorine atom for improving solubility. . At least one of X 03 and X 04 is preferably a fluorine atom, and both X 03 and X 04 are more preferably a fluorine atom from the viewpoint of ⁇ and solubility.
- Z 1 , Z 2 , and Z 3 are each independently —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CF ⁇ CF—, for decreasing the viscosity, It is preferably —CH 2 CH 2 —, —CH ⁇ CH—, —C ⁇ C— or a single bond, and is —CF 2 O—, —OCF 2 —, —CH 2 CH 2 — or a single bond. Is more preferably a single bond, and in order to increase T 1 ⁇ i , —C ⁇ C— or a single bond is preferable.
- m 01 and m 02 is preferably m 01 + m 02 is 0 or 1 when emphasizing eta, if m 01 + m 02 represents 1, m 01 represents 0, m 02 is 1 Is preferably represented.
- m 01 + m 02 is preferably 1 or 2.
- m 01 + m 02 is preferably 0 or 1.
- the number of F substitutions in the general formula (LC0) is preferably 2 to 7.
- the compound represented by the general formula (LC0) is preferably a compound satisfying at least one of the following matters.
- the liquid crystal compound represented by the general formula (LC0) is represented by the following general formula (LC0- a) to (LC0-j) (In the formula, R 01 , A 01 , A 02 , X 01 to X 07 , Y 01 and Y 02 are R 01 , A 01 , A 02 , X 01 to X 06 , Y 01 and Y in the general formula (LC0)).
- the liquid crystal composition of the present invention preferably contains one or more compounds represented by (LC0-a) to (LC0-i) as the compound represented by the general formula (LC0).
- the following general formulas (LC0-a1) to (LC0-a11) are more preferable, and the compounds represented by the general formula (0-a1) are more preferable. .
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compound represented by the general formula (LC0-b) the following general formulas (LC0-b1) to (LC0-b24) are more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-c) the following general formulas (LC0-c1) to (LC0-c17) are preferable, and the general formulas (LC0-c1) to (LC0-c3) are preferable. More preferred are general formula (LC0-c2) and general formula (LC0-c3).
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-d) the following general formulas (LC0-d1) to (LC0-d9) are more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-e) are more preferably the following general formulas (LC0-e1) to (LC0-e8), and the general formulas (LC0-e1) and (LC0-e8) Is more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-f) the following general formulas (LC0-f1) to (LC0-f6) are more preferable, and the general formula (LC0-f2) is more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compound represented by the general formula (LC0-g) the following general formula (LC0-g1) to general formula (LC0-g12) are more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-h) the following general formulas (LC0-h1) to (LC0-h4) are more preferable.
- R 01 represents the same meaning as R 01 in the general formula (LC0).
- the compounds represented by the general formula (LC0-i) the following general formulas (LC0-i1) to (LC0-i6) are more preferable.
- the lower limit in the composition is 0.1% by mass (hereinafter referred to as% in the composition). Is preferably contained in an amount of 0.3% or more, preferably 0.5% or more, preferably 0.8% or more, and preferably 1% or more. It is preferable to contain 2% or more, preferably 3% or more, preferably 4% or more, preferably 5% or more, preferably 6% or more.
- the upper limit is preferably 80% or less, preferably 70% or less, preferably 60% or less, and 55% or less. It is preferable to contain, preferably 50% or less, preferably 48% or less, preferably 45% or less, preferably 43% or less, and preferably 40% or less.
- R 11 and R 12 each independently represents an alkyl group having 1 to 15 carbon atoms, and one or more —CH 2 — in the alkyl group is such that an oxygen atom is not directly adjacent to each other. , —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —
- One or more hydrogen atoms may be optionally substituted with halogen, but may be an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkoxy having 1 to 8 carbon atoms.
- R 11 and R 12 are alkenyl groups, it is preferably selected from groups represented by any one of formulas (R1) to (R5).
- R 11 and R 12 are alkenyloxy groups, in order to reduce the viscosity, it is preferably an alkenyl group having 2 to 6 carbon atoms, and preferably selected from the group represented by the formula (R6) .
- R 14 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, one -CH 2 present in the group - or nonadjacent two or more -CH 2 - is It may be replaced by —O—, —COO—, —OCO— or —CO—, and a hydrogen atom present in these groups may be replaced with a fluorine atom. Represents a point.
- R 14 preferably represents a hydrogen atom or a methyl group.
- R 11 and R 12 are not particularly limited, but both represent an alkyl group, one represents an alkyl group, the other represents an alkenyl group, or one represents an alkyl group, and the other Preferably represents an alkoxy group, or one of them represents an alkyl group, and the other represents an alkenyloxy group.
- a 11 to A 13 are each independently one of the following structures:
- Z 11 and Z 12 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O— , -OCF 2 - or -CF 2 O-, a single bond, -CH 2 CH 2 -, - OCF 2 - or -CF 2 O-are more preferably a single bond is particularly preferred.
- m 11 preferably represents an integer of 1 or 2.
- a 11 and / or Z 11 may be the same or different.
- the compound represented by the general formula (LC1) is more preferably a compound represented by the following general formula (LC1-1) to general formula (LC1-39).
- the liquid crystal composition of the present invention preferably contains one or more compounds represented by (LC1-1) to (LC1-26) as the compound represented by the general formula (LC1), LC1-1) to (LC1-5), (LC1-7), (LC1-15), (LC1-16), (LC1-18), (LC1-21), (LC1-38) It is more preferable to contain one or more compounds.
- R 11 and R 12 each independently represents the same meaning as R 11 and R 12 in formula (LC1)), and are preferred.
- alkyl and alkyl * are each independently an alkyl group or alkoxy group having 1 to 5 carbon atoms
- alkylyl and alkenyl * are each independently an alkenyl group or alkenyloxy group having 2 to 5 carbon atoms. Represents.
- the content of the compound represented by the general formula (LC1) is preferably 1% or more, preferably 5% or more, and preferably 10% or more as a lower limit.
- 87% or less preferably 85% or less, preferably 83% or less, preferably 80% or less, preferably 88% or less, preferably 85% or less It is preferably contained, preferably 83% or less, preferably 80% or less, preferably 78% or less, preferably 75% or less, and 73% or less.
- 70% or less is preferable, 68% or less is preferable, and 65% or less is preferable.
- it contains than 63%, and preferably 60% or less.
- the content of the general formula (LC0) and the general formula (LC1) is preferably 5% or more, preferably 10% or more, and preferably 15% or more as the lower limit.
- the content is preferably 75% or more.
- the upper limit is preferably 100% or less, preferably 95% or less, preferably 90% or less, preferably 85% or less, and preferably 80% or less, 75% or less, preferably 70% or less, preferably 65% or less, preferably 60% or less, preferably 55% or less, preferably 50% or less
- the content is preferably 40% or less, and more preferably 30% or less.
- liquid crystal composition has the general formula (LC2)
- R 21 represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is —O—, so that an oxygen atom is not directly adjacent to each other.
- One or two of the alkyl groups may be substituted with —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- a 21 and A 22 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1, 4-phenylene group, 3,5-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl group, 1,4-bicyclo [2.2.2] octylene group, naphtha Down-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, B 21 is any of the following structures
- X 21 to X 25 each independently represents a hydrogen atom or a fluorine atom
- m 21 is 0 , 1, 2 or 3, and when there are a plurality of A 21 and / or Z 21 , they may be the same or different.
- R 21 is preferably an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms, and preferably a straight chain.
- R 21 is an alkenyl group, it is preferably selected from groups represented by any one of formulas (R1) to (R5).
- a 21 and A 22 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group Or a tetrahydropyran group is preferable.
- X 21 , X 22 , X 23 , X 24 and X 25 are each independently preferably a hydrogen atom for decreasing the viscosity and increasing T 1 ⁇ i , and a fluorine atom for increasing ⁇ . It is preferable that
- X 23 to X 25 are each independently a fluorine atom or a hydrogen atom, it is preferably selected from the following partial structures.
- Y 21 and Y 22 are particularly preferably used in combination of a fluorine atom, —CF 3 , and —OCF 3 , which improves the lower limit temperature of the nematic phase and favors the low-temperature operation and storage stability of the liquid crystal composition.
- B 21 is particularly preferably selected from any of the following partial structures.
- Z 21 and Z 22 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—.
- -OCF 2 - or -CF 2 O- is preferably a single bond, -OCH 2 -, - CH 2 O -, - OCF 2 - or -CF 2 O-are more preferred.
- m 21 preferably represents an integer of 0 to 2.
- a 21 and / or Z 21 may be the same or different.
- X 26 and X 27 each independently represent a hydrogen atom or a fluorine atom
- Z 23 represents —OCH 2 —, —CH 2 O—, —OCF 2 — or —CF 2 O—
- 21 , A 21 , Z 21 , X 21 , X 22 , Y 21 and m 21 are each independently R 21 , A 21 , Z 21 , X 21 , X 22 , Y 21 and m 21 in the general formula (LC2). It is preferable to contain 1 type, or 2 or more types of the compound represented by this.
- X 26 and X 27 are preferably fluorine atoms, and at least one of X 026 and X 27 is preferably a fluorine atom, and more preferably both X 26 and X 27 are fluorine atoms.
- the compound represented by general formula (LC2-a) is a compound represented by general formula (LC2-a1) to general formula (LC2-a11).
- R 21 , X 21 , X 22 , X 26 , X 27 , and Y 21 have the same meanings as R 21 , X 21 , X 22 , X 26 , X 27 , and Y 21 in formula (LC2)).
- X 30 , X 31 , X 32 and X 33 each independently represent a hydrogen atom or a fluorine atom.
- R 21 , A 21 , A 22 , X 21 , X 22 , Y 21 and m 21 are each independently R 21 , A 21 , A 22 , X 21 , X 22 , Y 21 and m 21 have the same meaning. It is preferable to contain one or more compounds represented by
- the compound represented by the general formula (LC2-b) is a compound represented by the general formula (LC2-b1) to the general formula (LC2-b21).
- X 34 , X 35 , X 36 , X 37 , X 38 , X 39 , X 50 and X 51 each independently represent a hydrogen atom or a fluorine atom
- R 21 , X 21 , X 22 and Y 21 each independently represents one or more compounds represented by the same meaning as R 21 , X 21 , X 22 and Y 21 in formula (LC2-b)
- compounds other than the general formula (LC2-a) and the general formula (LC2-b) preferably include the following compounds.
- the content of the compound represented by the general formula (LC2) is preferably 1% or more, preferably 3% or more, and preferably 5% or more as a lower limit.
- the content is preferably 8% or more, more preferably 10% or more, and preferably 15% or more.
- the upper limit is preferably 50% or less, preferably 45% or less, preferably 40% or less, preferably 35% or less, and preferably 30% or less.
- the content is preferably 25% or less, and preferably 20% or less.
- the liquid crystal composition of the present invention preferably has a viscosity ⁇ at 20 ° C. of 20 mPa ⁇ s or less.
- the liquid crystal composition of the present invention can contain one or more optically active compounds. Any optically active compound can be used as long as the liquid crystal molecules can be twisted and aligned. Usually, since this twist changes with temperature, a plurality of optically active compounds can be used to obtain a desired temperature dependency. In order not to adversely affect the temperature range and viscosity of the nematic liquid crystal phase, it is preferable to select and use an optically active compound having a strong twisting effect.
- a liquid crystal such as cholesteric nonanate or a compound represented by the following general formulas (Ch-1) to (Ch-6) is preferably contained.
- R c1 , R c2 and R * each independently represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is an oxygen atom May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 — so that they are not directly adjacent,
- One or more hydrogen atoms in the alkyl group may be optionally substituted with halogen, provided that R * has at least one branched chain group or halogen substituent having optical activity
- Z c1 and Z c2 are each independently a single bond, —CH ⁇ CH—, —C ⁇ C—, —CH 2 CH 2 —, — (CH 2 ) 4 —, —COO—, —OCO—, —OCH 2 -, - CH 2 O - , - OCF 2 - or D
- D 3 and D 4 represent a cyclohexane ring or a benzene ring, and one or more of —CH 2 — in the cyclohexane ring is substituted with —O— so that the oxygen atom is not directly adjacent.
- one or more of —CH 2 CH 2 — in the ring note may be substituted with —CH ⁇ CH—, —CF 2 O— or —OCF 2 —.
- One or more —CH ⁇ may be substituted with —N ⁇ so that the nitrogen atoms are not directly adjacent, and one or more hydrogen atoms in the ring are substituted with F, Cl, CH 3 May be used).
- the liquid crystal composition of the present invention may contain one or more polymerizable compounds, and the polymerizable compound contains a benzene derivative, a triphenylene derivative, a truxene derivative, a phthalocyanine derivative or a cyclohexane derivative at the center of the molecule. And a discotic liquid crystal compound having a structure in which a linear alkyl group, a linear alkoxy group or a substituted benzoyloxy group is radially substituted as its side chain.
- the polymerizable compound is represented by the general formula (PC)
- P 1 represents a polymerizable functional group
- Sp 1 represents a spacer group having 0 to 20 carbon atoms
- Q p1 represents a single bond, —O—, —NH—, —NHCOO—, —OCONH— , —CH ⁇ CH—, —CO—, —COO—, —OCO—, —OCOO—, —OOCO—, —CH ⁇ CH—, —CH ⁇ CH—COO—, —OCO—CH ⁇ CH— or — C ⁇ C—
- p 1 and p 2 each independently represent 1, 2 or 3
- MG p represents a mesogenic group or a mesogenic support group
- R p1 represents a halogen atom, a cyano group or a carbon atom Represents an alkyl group of 1 to 25, and one or more CH 2 groups in the alkyl group are —O—, —S—, —NH—
- MG p in the polymerizable compound general formula (PC) has the following structure:
- C 01 to C 03 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3 -Dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine-2 , 5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene -2,7-diyl group, 9,10-dihydrophenanthrene-2,7
- Z p1 and Z p2 are each independently —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH ⁇ CH—, —C ⁇ C—.
- -CH CHCOO -
- - OCOCH CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COOCH 2 CH 2 -, - OCOCH 2 CH 2 -, - CONH -, - NHCO- Or a single bond
- 3 represents 0, 1 or 2.
- Sp 1 and Sp 2 are each independently an alkylene group
- the alkylene group may be substituted by one or more halogen atoms or CN, and one or two present in the group
- the above CH 2 groups are —O—, —S—, —NH—, —N (CH 3 ) —, —CO—, —COO—, —OCO—, —
- R p2 to R p6 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.
- PC polymerizable compound general formula
- p 4 are each independently represents 1, 2 or 3.
- Sp 1 , Sp 2 , Q p1 and Q p2 are preferably a single bond
- P 1 and P 2 are preferably the formula (PC0-a), and are an acryloyloxy group and a methacryloyloxy group. More preferably, p 1 + p 4 is preferably 2, 3 or 4, and R p1 is preferably H, F, CF 3 , OCF 3 , CH 3 or OCH 3 .
- compounds represented by general formula (PC1-2), general formula (PC1-3), general formula (PC1-4) and general formula (PC1-8) are preferred.
- MG p in the general formula (PC) is a discotic liquid crystal compound represented by the general formula (PC1) -9.
- R 7 independently represents P 1 -Sp 1 -Q p 1 or a substituent of the general formula (PC1-e), and R 81 and R 82 each independently represents a hydrogen atom, a halogen atom or methyl
- R 83 represents an alkoxy group having 1 to 20 carbon atoms, and at least one hydrogen atom in the alkoxy group is a substituent represented by the general formulas (PC0-a) to (PC0-d). Has been replaced.
- the amount of the polymerizable compound used is preferably 0.05 to 2.0% by mass.
- the liquid crystal composition containing the polymerizable compound of the present invention is prepared by polymerizing the polymerizable compound. At this time, it is required to reduce the unpolymerized component to a desired amount or less, and the liquid crystal composition contains a compound having a biphenyl group and / or a terphenyl group in the partial structure in the general formula (LC0).
- the compound represented by -68) is preferable, and one or more compounds are preferably selected and contained in an amount of 0.1 to 40% by mass. Further, they can be used together in the group consisting of polymerizable compounds represented by the general formula (PC1-1) to the general formula (PC1-3), the general formula (PC1-8) or the general formula (PC1-9). preferable.
- the liquid crystal composition may further contain one or more antioxidants, and may further contain one or more UV absorbers.
- the antioxidant is preferably selected from those represented by the following general formula (E-1) and / or general formula (E-2).
- R e1 represents an alkyl group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkyl group is —O—, so that an oxygen atom is not directly adjacent to each other.
- One or two of the alkyl groups may be substituted with —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O— or —OCF 2 —.
- the liquid crystal composition of the present invention can be used as a liquid crystal display element, particularly an active matrix driving liquid crystal display element, for example, TN mode, OCB mode, ECB mode, IPS (including FFS electrode) mode or VA-IPS mode (including FFS electrode).
- TN mode for example, TN mode, OCB mode, ECB mode, IPS (including FFS electrode) mode or VA-IPS mode (including FFS electrode).
- VA-IPS mode refers to a pixel electrode arranged on the same substrate surface by aligning a liquid crystal material ( ⁇ > 0) having a positive dielectric anisotropy perpendicular to the substrate surface when no voltage is applied. This is a method of driving liquid crystal molecules by a common electrode.
- Vc threshold voltage
- the VA method is expressed by the following equation.
- Vc is the Frederick transition (V)
- ⁇ is the circumference
- d cell is the distance between the first substrate and the second substrate ( ⁇ m)
- d gap is the distance between the pixel electrode and the common electrode ( ⁇ m)
- d ITO is the pixel electrode and / or common electrode width ( ⁇ m)
- ⁇ r1>, ⁇ r2>, and ⁇ r3> are extrapolated lengths ( ⁇ m)
- K11 is the spray elastic constant (N)
- K22 is the twist elasticity.
- Constant (N) represents the elastic constant (N) of the bend
- ⁇ represents the anisotropy of the dielectric constant.
- the following formula 4 is applied to the present invention.
- Vc is the Frederick transition (V)
- ⁇ is the circumference
- d cell is the distance between the first substrate and the second substrate ( ⁇ m)
- d gap is the distance between the pixel electrode and the common electrode ( ⁇ m)
- d ITO is the width of the pixel electrode and / or common electrode ( ⁇ m)
- ⁇ r>, ⁇ r ′>, ⁇ r3> are extrapolation lengths ( ⁇ m)
- K33 is the bend elastic constant (N)
- ⁇ is the dielectric constant represents the anisotropy.
- the cell configuration of several 4 the d gap as small as possible, by as large as possible a d ITO, lower driving voltage is Hakare large absolute value of ⁇ is the liquid crystal composition used , K33 can be selected to reduce the drive voltage.
- the liquid crystal display element produced using the liquid crystal composition of the present invention can be produced by rubbing treatment using polyimide or polyamide compound as a method for aligning liquid crystal molecules on the substrate surface. It can also be produced by a photo-alignment technique using chalcone, cinnamate, cinnamoyl compound or the like. Further, as a new alignment method, a method in which a polymerizable liquid crystal compound is incorporated in the alignment layer and the polymerizable liquid crystal compound is polymerized can also be applied.
- the liquid crystal composition of the present invention can adjust preferable ⁇ , K11, K33 and the like.
- the product ( ⁇ n ⁇ d) of the refractive index anisotropy ( ⁇ n) of the liquid crystal composition and the distance (d) between the first substrate and the second substrate of the display device is strongly related to viewing angle characteristics and response speed. . Therefore, the interval (d) tends to be as thin as 3 to 4 ⁇ m.
- the product ( ⁇ n ⁇ d) is particularly preferably 0.31 to 0.33 in the case of the TN, ECB, IPS (liquid crystal alignment without application is substantially horizontal to the substrate surface) method. In the VA-IPS system, 0.20 to 0.59 is preferable in the case of vertical alignment with respect to both substrates, and 0.30 to 0.40 is particularly preferable.
- the refractive index anisotropy ( ⁇ n) of the liquid crystal composition suitable for each mode is 0.070 to 0.110.
- the liquid crystal composition of the present invention containing a compound represented by the general formula (PC) as a polymerizable compound was prepared by polymerizing a polymerizable compound contained in the liquid crystal composition with or without voltage application.
- a liquid crystal display element for TN mode, OCB mode, ECB mode, IPS mode or VA-IPS mode of polymer stabilization can be provided.
- a liquid crystal composition containing a polymerizable compound is sandwiched between two substrates, and the polymerizable compound in the liquid crystal composition is polymerized by energy such as ultraviolet rays with or without voltage applied. Can be produced.
- the orientation state of the liquid crystal molecules can be memorized by polymerizing the polymerizable compound, whereby the stability of the orientation state can be improved. In addition, an improvement in response speed can be expected.
- T NI Nematic phase-isotropic liquid phase transition temperature (° C)
- Tn lower limit temperature of nematic phase (° C)
- ⁇ dielectric constant in the direction perpendicular to the molecular long axis direction at 25 ° C.
- ⁇ dielectric anisotropy at 25 ° C.
- no refractive index for ordinary light at 25 ° C.
- ⁇ n refractive index anisotropic at 25 ° C.
- sex Vth Applied voltage (V) in a cell having a cell thickness of 6 ⁇ m in which the transmittance changes by 10% when a rectangular wave with a frequency of 1 KHz is applied at 25 ° C.
- the characteristics results when the liquid crystal composition is stored at ⁇ 20 ° C., ⁇ 25 ° C., ⁇ 30 ° C. and ⁇ 40 ° C. are shown in the table.
- the numbers in the table represent the storage time, ⁇ means that the same liquid crystal state was maintained after the storage time as before the storage, and x indicates that precipitation was observed after the storage time. (Examples 1 to 6)
- the prepared liquid crystal composition and its physical property values are shown below.
- the comparative examples were prepared so that the nematic phase-isotropic liquid phase transition temperature (T NI ) and the dielectric anisotropy ( ⁇ ) values at 25 ° C. were comparable.
- T NI nematic phase-isotropic liquid phase transition temperature
- ⁇ in Comparative Examples 1 and 2 is 18.4 mPa ⁇ s and 18.5 mPa ⁇ s, respectively. s.
- ⁇ 1 in Examples 1 to 6 is a value in the range of 68 mPa ⁇ s to 79 mPa ⁇ s
- ⁇ 1 in Comparative Examples 1 and 2 is 94 Pa ⁇ s and 87 Pa ⁇ s, respectively. It was. In addition, it was confirmed that the liquid crystal compositions of Examples 4 and 5 showed good phase stability even at low temperatures after precipitation was not observed after storage at ⁇ 30 ° C. for 168 hours, but the liquid crystal compositions of Comparative Examples 1 and 2 Precipitation was observed after 72 hours at ⁇ 30 ° C.
- Example 1 to 6 configured using the compound represented by the general formula (LC0) of the present application are the same as the liquid crystal compositions of Comparative Examples 1 and 2 configured without using the general formula (LC0). In comparison, it can be seen that ⁇ 1 can be greatly reduced and the low-temperature storage stability is excellent. (Examples 7 to 10) The prepared liquid crystal composition and its physical property values are shown below.
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Abstract
Description
・m01が0で、m02が1である化合物
・m01が1で、m02が0である化合物
・m01が2であって、複数のZ01が単結合である化合物
・Z02が単結合である化合物
・Z01、Z02及びZ03が単結合である化合物
一般式(LC0)で表される液晶化合物は、下記一般式(LC0-a)から(LC0-j)
(式中、R01、A01、A02、X01からX07、Y01及びY02は一般式(LC0)におけるR01、A01、A02、X01からX06、Y01及びY02と同じ意味を表し、X08からX13は水素原子又はフッ素原子を表す。)で表される化合物であることがより好ましい。本発明の液晶組成物は、一般式(LC0)で表される化合物として、(LC0-a)から(LC0-i)で表される化合物を1種又は2種以上含有することが好ましい。
一般式(LC0-b)で表される化合物としては、下記一般式(LC0-b1)~一般式(LC0-b24)がより好ましい。
一般式(LC0-c)で表される化合物としては、下記一般式(LC0-c1)~一般式(LC0-c17)が好ましく、一般式(LC0-c1)~一般式(LC0-c3)がより好ましく、一般式(LC0-c2)及び一般式(LC0-c3)が更に好ましい。
一般式(LC0-d)で表される化合物としては、下記一般式(LC0-d1)~一般式(LC0-d9)がより好ましい。
一般式(LC0-e)で表される化合物としては、下記一般式(LC0-e1)~一般式(LC0-e8)がより好ましく、一般式(LC0-e1)及び一般式(LC0-e8)が更に好ましい。
一般式(LC0-f)で表される化合物としては、下記一般式(LC0-f1)~一般式(LC0-f6)がより好ましく、一般式(LC0-f2)である事が更に好ましい。
一般式(LC0-g)で表される化合物としては、下記一般式(LC0-g1)~一般式(LC0-g12)がより好ましい。
一般式(LC0-h)で表される化合物としては、下記一般式(LC0-h1)~一般式(LC0-h4)がより好ましい。
一般式(LC0-i)で表される化合物としては、下記一般式(LC0-i1)~一般式(LC0-i6)がより好ましい。
本発明の液晶組成物において一般式(LC0)で表される化合物の含有量が少ないとその効果が現れないため、組成物中に下限値として、0.1質量%(以下組成物中の%は質量%を表す。)以上含有することが好ましく、0.3%以上含有することが好ましく、0.5%以上含有することが好ましく、0.8%以上含有することが好ましく、1%以上含有することが好ましく、2%以上含有することが好ましく、3%以上含有することが好ましく、4%以上含有することが好ましく、5%以上含有することが好ましく、6%以上含有することが好ましく、7%以上含有することが好ましく、8%以上含有することが好ましく、9%以上含有することが好ましく、10%以上含有することが好ましく、13%以上含有することが好ましく、15%以上含有することが好ましく、18%以上含有することが好ましく、20%以上含有することが好ましい。又、含有量が多いと析出等の問題を引き起こすため、上限値としては、80%以下含有することが好ましく、70%以下含有することが好ましく、60%以下含有することが好ましく、55%以下含有することが好ましく、50%以下含有することが好ましく、48%以下含有することが好ましく、45%以下含有することが好ましく、43%以下含有することが好ましく、40%以下含有することが好ましく、38%以下含有することが好ましく、37%以下含有することが好ましく、35%以下含有することが好ましく、32%以下含有することが好ましく、30%以下含有することが好ましく、28%以下含有することが好ましく、25%以下含有することが好ましく、23%以下含有することが好ましく、20%以下含有することが好ましい。一般式(1)で表される化合物は1種のみで使用することもできるが、2種以上の化合物を同時に使用してもよい。
R11及びR12がアルケニルオキシ基の場合、粘度を低下させる為には、炭素原子数2~6のアルケニル基である事が好ましく、式(R6)で表される基から選ばれることが好ましい。
本発明の液晶組成物において、一般式(LC1)で表される化合物の含有量は、下限値として、1%以上含有することが好ましく、5%以上含有することが好ましく、10%以上含有することが好ましく、15%以上含有することが好ましく、18%以上含有することが好ましく、20%以上含有することが好ましく、25%以上含有することが好ましく、28%以上含有することが好ましく、30%以上含有することが好ましく、33%以上含有することが好ましく、35%以上含有することが好ましく、38%以上含有することが好ましく、40%以上含有することが好ましく、43%以上含有することが好ましく、45%以上含有することが好ましく、48%以上含有することが好ましく、50%以上含有することが好ましく、53%以上含有することが好ましく、55%以上含有することが好ましく、58%以上含有することが好ましく、60%以上含有することが好ましい。また、上限値としては、99%以下含有することが好ましく、98%以下含有することが好ましく、95%以下含有することが好ましく、93%以下含有することが好ましく、90%以下含有することが好ましく、87%以下含有することが好ましく、85%以下含有することが好ましく、83%以下含有することが好ましく、80%以下含有することが好ましく、88%以下含有することが好ましく、85%以下含有することが好ましく、83%以以下含有することが好ましく、80%以下含有することが好ましく、78%以下含有することが好ましく、75%以下含有することが好ましく、73%以下含有することが好ましく、70%以下含有することが好ましく、68%以下含有することが好ましく、65%以下含有することが好ましく、63%以下含有することが好ましく、60%以下含有することが好ましい。一般式(1)で表される化合物は1種のみで使用することもできるが、2種以上の化合物を同時に使用してもよい。
R21は炭素原子数1~8のアルキル基、炭素原子数2~8のアルケニル基又は炭素原子数1~8のアルコキシ基であることが好ましく、直鎖であることが好ましい。R21がアルケニル基の場合、式(R1)から式(R5)のいずれかで表される基から選ばれることが好ましい。
A21及びA22はそれぞれ独立してトランス-1,4-シクロヘキシレン基、1,4-フェニレン基、3-フルオロ-1,4-フェニレン基、3,5-ジフルオロ-1,4-フェニレン基又はテトラヒドロピラン基が好ましい。
で表される化合物を少なくとも一種含有することが好ましく、(LC2-a4)~(LC2-a6)、(LC2-a10)、(LC2-a11)で表される化合物を少なくとも一種含有することがより好ましい。
本発明の液晶組成物において、一般式(LC2)で表される化合物の含有量は、下限値として、1%以上含有することが好ましく、3%以上含有することが好ましく、5%以上含有することが好ましく、8%以上含有することが好ましく、10%以上含有することが好ましく15%以上含有することが好ましい。また、上限値としては、50%以下含有することが好ましく、45%以下含有することが好ましく、40%以下含有することが好ましく、35%以下含有することが好ましく、30%以下含有することが好ましく、25%以下含有することが好ましく、20%以下含有することが好ましい。一般式(1)で表される化合物は1種のみで使用することもできるが、2種以上の化合物を同時に使用してもよい。
より好ましくは、重合性化合物一般式(PC)におけるMGpが以下の構造
(式中、C01~C03はそれぞれ独立して1,4-フェニレン基、1,4-シクロヘキシレン基、1,4-シクロヘキセニル基、テトラヒドロピラン-2,5-ジイル基、1,3-ジオキサン-2,5-ジイル基、テトラヒドロチオピラン-2,5-ジイル基、1,4-ビシクロ(2,2,2)オクチレン基、デカヒドロナフタレン-2,6-ジイル基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ピラジン-2,5-ジイル基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基又はフルオレン2,7-ジイル基を表し、1,4-フェニレン基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基及びフルオレン-2,7-ジイル基は置換基として1個以上のF、Cl、CF3、OCF3、シアノ基、炭素原子数1~8のアルキル基、アルコキシ基、アルカノイル基、アルカノイルオキシ基、炭素原子数2~8のアルケニル基、アルケニルオキシ基、アルケノイル基又はアルケノイルオキシ基を有していても良く、Zp1及びZp2はそれぞれ独立して-COO-、-OCO-、-CH2CH2-、-OCH2-、-CH2O-、-CH=CH-、-C≡C-、-CH=CHCOO-、-OCOCH=CH-、-CH2CH2COO-、-CH2CH2OCO-、-COOCH2CH2-、-OCOCH2CH2-、-CONH-、-NHCO-又は単結合を表し、p3は0、1又は2を表す。)
ここで、Sp1及びSp2はそれぞれ独立してアルキレン基である場合、該アルキレン基は1つ以上のハロゲン原子又はCNにより置換されていても良く、この基中に存在する1つ又は2つ以上のCH2基はO原子が直接隣接しないように-O-、-S-、-NH-、-N(CH3)-、-CO-、-COO-、-OCO-、-OCOO-、-SCO-、-COS-又は-C≡C-により置き換えられていてもよい。また、P1及びP2はそれぞれ独立して下記の一般式
(式中、Rp2からRp6はそれぞれ独立して水素原子、ハロゲン原子又は炭素原子数1~5のアルキル基を表す。)
より具体的には、重合性化合物一般式(PC)が一般式(PC0-1)から一般式(PC0-6)
重合性化合物の使用量は好ましくは0.05~2.0質量%である。
Ze1、Ze2はそれぞれ独立して単結合、-CH=CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-COO-、-OCO-、-OCH2-、-CH2O-、-OCF2-又は-CF2O-を表し
E1はシクロヘキサン環又はベンゼン環を表し、シクロヘキサン環中の1つ又は2つ以上の-CH2-は酸素原子が直接隣接しないように-O-で置換されていてもよく、また該環注の1つ又は2つ以上の-CH2CH2-は-CH=CH-、-CF2O-又は-OCF2-で置換されていてもよく、ベンゼン環中の1つ又は2つ以上の-CH=は窒素原子が直接隣接しないように、-N=で置換されていてもよく、該環中の1つ以上の水素原子がF、Cl、CH3で置換されていてもよく、q1は0、1、2又は3を表す。)
本発明の液晶組成物は、液晶表示素子特にアクティブマトリックス駆動用液晶表示素子として、例えばTNモード、OCBモード、ECBモード、IPS(FFS電極を含む)モード又はVA-IPSモード(FFS電極を含む)に使用することが出来る。ここで、VA-IPSモードとは、電圧無印加時に、誘電率異方性が正の液晶材料(Δε>0)を基板面に対し垂直に配向させ、同一基板面上に配置した画素電極と共通電極により液晶分子を駆動する方法であり、画素電極と共通電極で発生する湾曲電界の方向に液晶分子が配列することから、容易に画素分割やマルチドメインを形成することができ、応答にも優れる利点がある。非特許文献Proc.13th IDW,97(1997)、Proc.13th IDW,175(1997)、SID Sym.Digest,319(1998)、SID Sym.Digest,838(1998)、SID Sym.Digest,1085(1998)、SID Sym.Digest,334(2000)、Eurodisplay Proc.,142(2009)によれば、EOC、VA-IPSなど種々の呼称がされているが、本発明においては以下「VA-IPS」と略称する。
一方、VA-IPS方式においては、本発明等は下記数4が適用される。
TN-I :ネマチック相-等方性液体相転移温度(℃)
T-n :ネマチック相の下限温度(℃)
ε⊥ :25℃での分子長軸方向に対し垂直な方向の誘電率
Δε :25℃での誘電率異方性
no :25℃での常光に対する屈折率
Δn :25℃での屈折率異方性
Vth :25℃での周波数1KHzの矩形波を印加した時の透過率が10%変化するセル厚6μmのセルでの印加電圧(V)
η :20℃でのバルク粘性(mPa・s)
γ1 :回転粘性(mPa・s)
K11/pN:スプレイの弾性定数(N)
K22/pN:ツイストの弾性定数(N)
K33/pN:ベンドの弾性定数(N)
化合物記載に下記の略号を使用する。
(実施例1~6)
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
(実施例7~10)
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
以下に、調製した液晶組成物とその物性値を示す。
Claims (11)
- 正の誘電率異方性を有する液晶組成物であって、前記液晶組成物が一般式(LC0)
- 一般式(LC2)
- 一般式(LC1)で表される化合物を20~99質量%含有する請求項1から4のいずれか一項に記載の液晶組成物。
- 一般式(LC0)で表される化合物を1~50質量%含有する請求項1から5のいずれか一項に記載の液晶組成物。
- 重合性化合物を1種又は2種以上含有する請求項1から6のいずれか一項に記載の液晶組成物。
- 請求項1から7のいずれか一項に記載の液晶組成物を用いた液晶表示素子。
- 請求項1から7のいずれか一項に記載の液晶組成物を用いたアクティブマトリックス駆動用液晶表示素子。
- 請求項1から6のいずれか一項に記載の液晶組成物を用いたTNモード、OCBモード、ECBモード、IPSモード又はVA-IPSモード用液晶表示素子。
- 請求項7に記載の液晶組成物を用い、電圧印加下あるいは電圧無印加下で該液晶組成物中に含有する重合性化合物を重合させて作製した高分子安定化のTNモード、OCBモード、ECBモード、IPSモード又はVA-IPSモード用液晶表示素子。
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TWI648384B (zh) | 2019-01-21 |
TW201615808A (zh) | 2016-05-01 |
JPWO2016017614A1 (ja) | 2017-04-27 |
JP5910800B1 (ja) | 2016-04-27 |
US10000700B2 (en) | 2018-06-19 |
US20170198219A1 (en) | 2017-07-13 |
CN106459765A (zh) | 2017-02-22 |
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