JP6519973B2 - ネマチック液晶組成物及びこれを用いた液晶表示素子 - Google Patents
ネマチック液晶組成物及びこれを用いた液晶表示素子 Download PDFInfo
- Publication number
- JP6519973B2 JP6519973B2 JP2014041639A JP2014041639A JP6519973B2 JP 6519973 B2 JP6519973 B2 JP 6519973B2 JP 2014041639 A JP2014041639 A JP 2014041639A JP 2014041639 A JP2014041639 A JP 2014041639A JP 6519973 B2 JP6519973 B2 JP 6519973B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- group
- general formula
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 154
- 239000000203 mixture Substances 0.000 title claims description 102
- 239000004988 Nematic liquid crystal Substances 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 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 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- -1 1,3-dithiane-2,5-diyl Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims 2
- 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 claims 1
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 18
- 230000000704 physical effect Effects 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 10
- 206010047571 Visual impairment Diseases 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 230000007547 defect Effects 0.000 description 6
- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 4
- 0 *CC(C(O*c1ccc(*)cc1)=O)=C Chemical compound *CC(C(O*c1ccc(*)cc1)=O)=C 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
-
- 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
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1343—Electrodes
- G02F1/13439—Electrodes characterised by their electrical, optical, physical properties; materials therefor; method of making
-
- 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
- G02F1/1368—Active matrix addressed cells in which the switching element is a three-electrode device
-
- 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
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—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
- C09K19/10—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
-
- 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)
- C09K2019/3004—Cy-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
- 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)
- C09K2019/3009—Cy-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)
- C09K2019/301—Cy-Cy-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)
- C09K2019/3016—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)
- C09K2019/3025—Cy-Ph-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)
- C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K2019/548—Macromolecular compounds stabilizing the alignment; Polymer stabilized alignment
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/0009—Materials therefor
- G02F1/0045—Liquid crystals characterised by their physical properties
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
Description
第一成分として、一般式(I)
第二成分として、一般式(II)
本願発明の液晶組成物において、一般式(I)で表される化合物を1種又は2種を含有するが好ましく、1種から5種含有することが更に好ましく、その含有量は0.001から1質量%であることが好ましく、0.001から0.1質量%が更に好ましく、0.001から0.05質量%が特に好ましい。
第二成分として使用する一般式(II)
一般式(II−a)から一般式(II−f)で表される化合物中、一般式(II−a)、一般式(II−c)及び一般式(II−d)が更に好ましい。
一般式(III)で表される化合物において、R31〜R32はお互い独立しては炭素原子数1から10のアルキル基、アルコキシ基、又は炭素原子数2から10のアルケニル基を表す。M31はトランス−1,4−シクロへキシレン基を表す。L31は単結合、−CH2CH2−又は、−CH2O−を表す。n31は0又は1を表す。
本願発明の液晶組成物は、また更に、一般式(IV−a)から一般式(IV−d)
(式中、R41〜R48はお互い独立しては炭素原子数1から10のアルキル基、アルコキシ基又は炭素原子数2から10のアルケニル基を表す。)
本願発明では一般式(IV−a)から一般式(IV−d)で表される化合物群から選ばれる化合物を含有することができるが、1種〜10種含有することが好ましく、1種〜8種含有することが特に好ましく、その含有量は5から80質量%であることが好ましく、10から70質量%であることが更に好ましく、20から60質量%であることが特に好ましい。
Sp1及びSp2はそれぞれ独立して、単結合、炭素原子数1〜8のアルキレン基又は−O−(CH2)s−
(式中、sは2から7の整数を表し、酸素原子は芳香環に結合するものとする。)を表し、
Z51は−OCH2−、−CH2O−、−COO−、−OCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CY1=CY2−(式中、Y1及びY2はそれぞれ独立して、フッ素原子又は水素原子を表す。)、−C≡C−又は単結合を表し、
M51は1,4−フェニレン基、トランスー1,4−シクロヘキシレン基又は単結合を表し、式中の全ての1,4−フェニレン基は、任意の水素原子がフッ素原子により置換されていても良い。)で表される二官能モノマーが好ましい。
これらの骨格を含む重合性化合物は重合後の配向規制力がPSA型液晶表示素子に最適であり、良好な配向状態が得られることから、表示ムラが抑制されるか、又は、全く発生しない。
本発明の液晶組成物にモノマーを添加する場合において、重合開始剤が存在しない場合でも重合は進行するが、重合を促進するために重合開始剤を含有していてもよい。重合開始剤としては、ベンゾインエーテル類、ベンゾフェノン類、アセトフェノン類、ベンジルケタール類、アシルフォスフィンオキサイド類等が挙げられる。
Δn :20℃における屈折率異方性
Δε :20℃における誘電率異方性
η :20℃における粘度(mPa・s)
γ1 :20℃における回転粘性(mPa・s)
VHR:周波数60Hz,印加電圧5Vの条件下で50℃における電圧保持率(%)
焼き付き:
液晶表示素子の焼き付き評価は、表示エリア内に所定の固定パターンを1200時間表示させた後に、全画面均一な表示を行ったときの固定パターンの残像のレベルを目視にて以下の4段階評価で行った。
○残像ごく僅かに有るも許容できるレベル
△残像有り許容できないレベル
×残像有りかなり劣悪
滴下痕 :
液晶表示装置の滴下痕の評価は、全面黒表示した場合における白く浮かび上がる滴下痕を目視にて以下の4段階評価で行った。
○残像ごく僅かに有るも許容できるレベル
△残像有り許容できないレベル
×残像有りかなり劣悪
尚、実施例において化合物の記載について以下の略号を用いる。
(側鎖)
-n -CnH2n+1 炭素原子数nの直鎖状アルキル基
n- CnH2n+1- 炭素原子数nの直鎖状アルキル基
-On -OCnH2n+1 炭素原子数nの直鎖状アルコキシ基
-V -CH=CH2
V- CH2=CH-
-V1 -CH=CH-CH3
(環構造)
以下に示される液晶組成物LC−1を調製し、その物性値を測定した。この結果を次の表に示す。
(比較例1)
実施例1に記載の式(I−c−1)で表される化合物を添加していない液晶組成物LC−1の初期のVHRは98.5%であったのに対し、150℃で1時間の高温放置後のVHRは、86.7%と初期に対して大きく低下した。
また、液晶組成物LC−1を用いてVA液晶表示素子を作製し、前述の方法により焼き付き及び滴下痕の測定したところ、以下に示すように実施例1と比べて劣る結果を示した。
一般式(II)で表される化合物を含有しない、以下に示される液晶組成物LC−Aを調製し、物性値を測定した。
また、液晶組成物LCM−2を用いてVA液晶表示素子を作製し、前述の方法により焼き付き及び滴下痕の測定したところ、以下に示すように実施例1に比べて劣る結果を示した。
(実施例2から実施例4)
次に示す液晶組成物LC−2〜LC−4を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−3〜LCM−5の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−3〜LCM−5を用いて作製したVA液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
次に示す液晶組成物LC−5を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−6の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−6を用いて作製したVA液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
実施例1に記載の液晶組成物LC−1及び実施例5に記載のLC−5の各々99.97%に対して、式(I−a−1)
液晶組成物LCM−7及びLCM−8の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−7及びLCM−8を用いて作製したVA液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
実施例1に記載の液晶組成物LC−1 99.97%に対して、式(I−b−1)
液晶組成物LCM−9の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−9を用いて作製したVA液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
実施例1に記載の液晶組成物LCM−1 99.7%に対して、
比較例1で使用した液晶組成物LC−1及び比較例2で使用したLCM−2の各々99.7%に対して、
本液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように実施例9に比べて劣る結果を示した。
実施例2〜4に記載の液晶組成物LCM−3〜5の各々99.7%に対して、
(実施例14から実施例4)
次に示す液晶組成物LC−6〜LC−29を調製し、その物性値を測定した。この結果を次の表に示す。
Claims (7)
- 第一成分として、一般式(I)
第二成分として、一般式(II−c)
一般式(II−d)
式(IV−a−1)
- 一般式(I)で表される化合物の含有量が0.001質量%から1質量%であり、一般式(II)で表される化合物の含有量が5質量%から30質量%である請求項1から3のいずれか一項に記載のネマチック液晶組成物。
- 一般式(V)
Sp1及びSp2はそれぞれ独立して、単結合、炭素原子数1〜8のアルキレン基又は−O−(CH2)s−
(式中、sは2から7の整数を表し、酸素原子は芳香環に結合するものとする。)を表し、
Z51は−OCH2−、−CH2O−、−COO−、−OCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CY1=CY2−(式中、Y1及びY2はそれぞれ独立して、フッ素原子又は水素原子を表す。)、−C≡C−又は単結合を表し、
M51は1,4−フェニレン基、トランス−1,4−シクロヘキシレン基又は単結合を表し、式中の全ての1,4−フェニレン基は、任意の水素原子がフッ素原子により置換されていても良い。)で表される重合性化合物を含有する請求項1から4のいずれか一項に記載のネマチック液晶組成物。 - 透明導電性材料からなる共通電極を具備した第一の基板と、透明導電性材料からなる画素電極と各画素に具備した画素電極を制御する薄膜トランジスターを具備した第二の基板と、前記第一の基板と第二の基板間に挟持された液晶組成物を有し、該液晶組成物中の液晶分子の電圧無印加時の配向が前記基板に対して略垂直である液晶表示素子であって、該液晶組成物として請求項1から5のいずれか一項に記載のネマチック液晶組成物を用いた液晶表示素子。
- 請求項5に記載の重合性化合物を含有するネマチック液晶組成物を用い、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モード液晶表示素子。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014041639A JP6519973B2 (ja) | 2013-03-06 | 2014-03-04 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013043988 | 2013-03-06 | ||
JP2013043988 | 2013-03-06 | ||
JP2014041639A JP6519973B2 (ja) | 2013-03-06 | 2014-03-04 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014506389A Division JP5585745B1 (ja) | 2013-03-06 | 2013-10-31 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014140510A Division JP6394945B2 (ja) | 2013-03-06 | 2014-07-08 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014196474A JP2014196474A (ja) | 2014-10-16 |
JP6519973B2 true JP6519973B2 (ja) | 2019-05-29 |
Family
ID=51490860
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014506389A Active JP5585745B1 (ja) | 2013-03-06 | 2013-10-31 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
JP2014041639A Active JP6519973B2 (ja) | 2013-03-06 | 2014-03-04 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
JP2014140510A Active JP6394945B2 (ja) | 2013-03-06 | 2014-07-08 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
JP2018153538A Active JP6760340B2 (ja) | 2013-03-06 | 2018-08-17 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014506389A Active JP5585745B1 (ja) | 2013-03-06 | 2013-10-31 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014140510A Active JP6394945B2 (ja) | 2013-03-06 | 2014-07-08 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
JP2018153538A Active JP6760340B2 (ja) | 2013-03-06 | 2018-08-17 | ネマチック液晶組成物及びこれを用いた液晶表示素子 |
Country Status (6)
Country | Link |
---|---|
US (2) | US9745513B2 (ja) |
JP (4) | JP5585745B1 (ja) |
KR (3) | KR102017601B1 (ja) |
CN (1) | CN104284962B (ja) |
TW (1) | TWI488949B (ja) |
WO (1) | WO2014136315A1 (ja) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102017601B1 (ko) * | 2013-03-06 | 2019-09-09 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자 |
EP3070147B1 (en) * | 2013-11-13 | 2019-01-30 | JNC Corporation | Liquid crystal composition and liquid crystal display element |
KR20160082065A (ko) * | 2014-12-30 | 2016-07-08 | 주식회사 동진쎄미켐 | 액정 화합물 및 이를 포함하는 액정 조성물 |
EP3298105B1 (en) * | 2015-05-20 | 2019-03-20 | Merck Patent GmbH | Liquid-crystal medium |
US10633590B2 (en) * | 2015-09-04 | 2020-04-28 | Dic Corporation | Liquid crystal composition and liquid crystal display device including the same |
KR20180109930A (ko) * | 2016-02-19 | 2018-10-08 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
EP3487953A2 (en) * | 2016-07-20 | 2019-05-29 | Merck Patent GmbH | Switching layer for use in an optical switching element |
CN107815322B (zh) * | 2016-09-14 | 2021-01-26 | 江苏和成显示科技有限公司 | 液晶化合物、液晶组合物及显示器件 |
CN108239538B (zh) * | 2016-12-23 | 2022-02-08 | 江苏和成显示科技有限公司 | 一种介电各向异性为负的液晶组合物及其应用 |
CN108239545B (zh) * | 2016-12-23 | 2022-02-25 | 江苏和成显示科技有限公司 | 具有负介电各向异性的液晶组合物及其显示器件 |
CN108239542A (zh) * | 2016-12-23 | 2018-07-03 | 江苏和成显示科技有限公司 | 具有负介电各向异性的液晶组合物及其显示器件 |
WO2019181883A1 (ja) * | 2018-03-20 | 2019-09-26 | 日産化学株式会社 | 液晶表示素子 |
JP6564495B1 (ja) * | 2018-05-14 | 2019-08-21 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
CN110577832A (zh) * | 2018-06-11 | 2019-12-17 | 石家庄诚志永华显示材料有限公司 | 负介电各向异性液晶组合物、液晶显示元件及液晶显示器 |
CN111484856B (zh) * | 2019-01-29 | 2023-04-07 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及液晶显示元件、液晶显示器 |
CN111484855A (zh) * | 2019-01-29 | 2020-08-04 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及液晶显示元件、液晶显示器 |
JP7470058B2 (ja) | 2019-01-30 | 2024-04-17 | 武田薬品工業株式会社 | 複素環化合物 |
CN109913242A (zh) * | 2019-03-21 | 2019-06-21 | 深圳市华星光电技术有限公司 | 液晶材料及液晶显示面板 |
CN113773855A (zh) * | 2021-09-01 | 2021-12-10 | 重庆汉朗精工科技有限公司 | 一种负性液晶组合物及其应用 |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06235925A (ja) | 1993-02-10 | 1994-08-23 | Matsushita Electric Ind Co Ltd | 液晶表示素子の製造方法 |
JPH06238925A (ja) | 1993-02-22 | 1994-08-30 | Seiko Instr Inc | 通電転写記録装置 |
TW371312B (en) | 1995-04-12 | 1999-10-01 | Chisso Corp | Fluorine-substituted liquid-crystal compound, liquid-crystal composition and liquid-crystal display device |
DE19539141B4 (de) | 1995-10-20 | 2016-07-07 | Merck Patent Gmbh | 2,6-Di-tert.-butylphenole |
US6380555B1 (en) | 1999-12-24 | 2002-04-30 | Micron Technology, Inc. | Bumped semiconductor component having test pads, and method and system for testing bumped semiconductor components |
DE10117224B4 (de) | 2000-04-19 | 2015-12-31 | Merck Patent Gmbh | Verfahren zur Stabilisierung von Halogenaromaten |
US6977704B2 (en) | 2001-03-30 | 2005-12-20 | Fujitsu Display Technologies Corporation | Liquid crystal display |
DE10150198A1 (de) | 2001-10-12 | 2003-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium |
DE10216197B4 (de) | 2002-04-12 | 2013-02-07 | Merck Patent Gmbh | Flüssigkristallmedium und und seine Verwendung in einer elektrooptischen Anzeige |
DE10246657A1 (de) | 2002-10-07 | 2004-04-15 | Merck Patent Gmbh | Chirales Phenolderivat, dieses enthaltendes Flüssigkristallmedium, Verfahren zur Herstellung eines Flüssigkristallmediums und elektrooptische Flüssigkristallanzeige |
JP2006169472A (ja) | 2004-12-20 | 2006-06-29 | Chisso Corp | 液晶組成物および液晶表示素子 |
JP4876402B2 (ja) | 2005-02-16 | 2012-02-15 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
DE602006002184D1 (de) | 2005-06-22 | 2008-09-25 | Chisso Corp | Flüssigkristallzusammensetzung und Flüssigkristallanzeige |
JP5092287B2 (ja) | 2005-06-22 | 2012-12-05 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
JP4972888B2 (ja) | 2005-07-13 | 2012-07-11 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
KR101432959B1 (ko) | 2005-08-09 | 2014-08-21 | 메르크 파텐트 게엠베하 | 액정 매질 |
US7749403B2 (en) | 2006-01-06 | 2010-07-06 | Chisso Corporation | Monofluorinated terphenyl compound having alkenyl, liquid crystal composition, and liquid crystal display device |
CN101351432B (zh) | 2006-01-06 | 2011-08-31 | 智索株式会社 | 具有烯基的单氟化联三苯化合物、液晶组成物及液晶显示元件 |
WO2007108307A1 (ja) * | 2006-03-20 | 2007-09-27 | Chisso Corporation | 液晶組成物および液晶表示素子 |
US7595100B2 (en) | 2006-06-29 | 2009-09-29 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
JP5813287B2 (ja) | 2006-07-19 | 2015-11-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 液晶媒体 |
ATE486113T1 (de) | 2006-09-06 | 2010-11-15 | Chisso Corp | Chlorfluorbenzol-flüssigkristallverbindung, flüssigkristallzusammensetzung und flüssigkristallanzeigevorrichtung |
JP5163018B2 (ja) * | 2006-09-06 | 2013-03-13 | Jnc株式会社 | クロロフルオロベンゼン系液晶性化合物、液晶組成物および液晶表示素子 |
JP5051358B2 (ja) | 2007-05-17 | 2012-10-17 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
US8114310B2 (en) | 2007-10-22 | 2012-02-14 | Merck Patent Gmbh | Liquid-crystal display |
WO2009129911A1 (de) * | 2008-04-22 | 2009-10-29 | Merck Patent Gmbh, | Flüssigkristallines medium |
DE102008064171A1 (de) | 2008-12-22 | 2010-07-01 | Merck Patent Gmbh | Flüssigkristallines Medium |
WO2010072302A1 (de) | 2008-12-22 | 2010-07-01 | Merck Patent Gmbh | Flüssigkristallanzeige |
CN102292412B (zh) | 2009-01-22 | 2014-04-09 | Jnc株式会社 | 液晶组成物以及液晶显示元件 |
DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
JP5903890B2 (ja) * | 2009-11-09 | 2016-04-13 | Jnc株式会社 | 液晶表示素子、液晶組成物及び配向剤並びに液晶表示素子の製造方法及びその使用 |
EP2652088B1 (de) * | 2010-12-17 | 2014-10-15 | Merck Patent GmbH | Flüssigkristallines medium |
EP2514800B2 (de) | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
JP6056234B2 (ja) * | 2011-07-27 | 2017-01-11 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
DE102012024126A1 (de) * | 2011-12-20 | 2013-06-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
KR101316708B1 (ko) | 2012-04-26 | 2013-10-10 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자 |
US9150787B2 (en) | 2012-07-06 | 2015-10-06 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
US9045684B2 (en) | 2012-07-30 | 2015-06-02 | Jnc Corporation | Liquid crystal composition, antioxidant and liquid crystal display device |
TWI597352B (zh) * | 2012-11-08 | 2017-09-01 | Dainippon Ink & Chemicals | Nematic liquid crystal composition and liquid crystal display device using the same |
JP6248557B2 (ja) * | 2012-11-16 | 2017-12-20 | Jnc株式会社 | ビニルオキシを有する液晶性化合物、液晶組成物および液晶表示素子 |
JP6255975B2 (ja) * | 2012-12-27 | 2018-01-10 | Jnc株式会社 | 液晶組成物、酸化防止剤および液晶表示素子 |
KR102017601B1 (ko) * | 2013-03-06 | 2019-09-09 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자 |
-
2013
- 2013-10-31 KR KR1020157033720A patent/KR102017601B1/ko active IP Right Grant
- 2013-10-31 KR KR1020147026858A patent/KR20140127364A/ko active Application Filing
- 2013-10-31 JP JP2014506389A patent/JP5585745B1/ja active Active
- 2013-10-31 KR KR1020197025237A patent/KR102117336B1/ko active IP Right Grant
- 2013-10-31 US US14/773,067 patent/US9745513B2/en active Active
- 2013-10-31 CN CN201380022446.8A patent/CN104284962B/zh active Active
- 2013-10-31 WO PCT/JP2013/079561 patent/WO2014136315A1/ja active Application Filing
-
2014
- 2014-02-17 TW TW103105078A patent/TWI488949B/zh not_active IP Right Cessation
- 2014-03-04 JP JP2014041639A patent/JP6519973B2/ja active Active
- 2014-07-08 JP JP2014140510A patent/JP6394945B2/ja active Active
-
2017
- 2017-08-22 US US15/682,744 patent/US10316251B2/en active Active
-
2018
- 2018-08-17 JP JP2018153538A patent/JP6760340B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP5585745B1 (ja) | 2014-09-10 |
KR20150143859A (ko) | 2015-12-23 |
WO2014136315A1 (ja) | 2014-09-12 |
TW201437337A (zh) | 2014-10-01 |
US9745513B2 (en) | 2017-08-29 |
US20160009995A1 (en) | 2016-01-14 |
JP2019014893A (ja) | 2019-01-31 |
JP2014196474A (ja) | 2014-10-16 |
JP2014208842A (ja) | 2014-11-06 |
KR102117336B1 (ko) | 2020-06-01 |
JP6760340B2 (ja) | 2020-09-23 |
KR20140127364A (ko) | 2014-11-03 |
JP6394945B2 (ja) | 2018-09-26 |
KR20190107732A (ko) | 2019-09-20 |
US10316251B2 (en) | 2019-06-11 |
CN104284962B (zh) | 2016-02-24 |
CN104284962A (zh) | 2015-01-14 |
US20170349829A1 (en) | 2017-12-07 |
KR102017601B1 (ko) | 2019-09-09 |
JPWO2014136315A1 (ja) | 2017-02-09 |
TWI488949B (zh) | 2015-06-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6760340B2 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
JP5561570B2 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
TWI452119B (zh) | 向列型液晶組成物及使用其之液晶顯示元件 | |
KR101369396B1 (ko) | 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자 | |
JP5900718B1 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
JP5170602B1 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
TWI596192B (zh) | A nematic liquid crystal composition, and a liquid crystal display device using the nematic liquid crystal composition | |
JP5170603B1 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
TWI597352B (zh) | Nematic liquid crystal composition and liquid crystal display device using the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160920 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20171221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180216 |
|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7421 Effective date: 20180220 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180508 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180619 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20181204 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190107 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20190116 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190402 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190415 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6519973 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |