EP3898890A1 - Flüssigkristallines medium - Google Patents
Flüssigkristallines mediumInfo
- Publication number
- EP3898890A1 EP3898890A1 EP19829495.1A EP19829495A EP3898890A1 EP 3898890 A1 EP3898890 A1 EP 3898890A1 EP 19829495 A EP19829495 A EP 19829495A EP 3898890 A1 EP3898890 A1 EP 3898890A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- formula
- formulas
- medium according
- independently
- 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.)
- Pending
Links
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 34
- 150000001875 compounds Chemical class 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- -1 Methoxy ethoxy Chemical group 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000003381 stabilizer Substances 0.000 claims description 15
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 69
- 150000003254 radicals Chemical class 0.000 description 21
- 229920000728 polyester Polymers 0.000 description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 125000006850 spacer group Chemical group 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- ZYMKZMDQUPCXRP-UHFFFAOYSA-N fluoro prop-2-enoate Chemical compound FOC(=O)C=C ZYMKZMDQUPCXRP-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920001690 polydopamine Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical class C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 1
- WWQRDAMGSQVYAE-UHFFFAOYSA-N 2-ethenoxyprop-2-enoic acid Chemical compound OC(=O)C(=C)OC=C WWQRDAMGSQVYAE-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000599985 Beijerinckia mobilis Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100156282 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) vib-1 gene Proteins 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000620457 Telestes souffia Species 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000004883 computer application Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 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 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- 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
-
- 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
- C09K19/02—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.)
-
- 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
-
- 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
-
- 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
- C09K19/08—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
- C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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Definitions
- the present invention relates to a liquid-crystalline medium (LC medium), its use for electro-optical purposes and LC displays containing this medium.
- LC medium liquid-crystalline medium
- Liquid crystals are mainly used as dielectrics in display devices, since the optical properties of such substances can be influenced by an applied voltage.
- Electro-optical devices based on liquid crystals are well known to the person skilled in the art and can be based on various effects. Such devices are, for example, cells with dynamic scattering, DAP cells (deformation of aligned phases), guest / host cells, TN cells with a twisted nematic ("twisted nematic") structure, STN cells (“super-twisted nematic”) , SBE cells (“superbirefringence effect”) and OMI cells ("optical mode interference").
- the most common display devices are based on the Schadt-Flelfrich effect and have a twisted nematic structure.
- the liquid crystal materials must have good chemical and thermal stability and good stability against electric fields and electromagnetic radiation. Furthermore, the liquid crystal materials should have a low viscosity and give short response times, low threshold voltages and a high contrast in the cells.
- liquid crystals are generally used as mixtures of several components, it is important that the components are readily miscible with one another.
- dielectric anisotropy and optical anisotropy must meet different requirements depending on the cell type and application.
- materials for cells should also be twisted nematic structure have a positive dielectric anisotropy and a low electrical conductivity.
- LC media with large positive dielectric anisotropy, wide nematic phases, relatively low birefringence, very high specific
- Such matrix liquid crystal displays are known.
- active elements i.e. transistors
- non-linear elements for the individual switching of the individual pixels.
- active matrix where one has two types
- MOS Metal Oxide Semiconductor
- TFT Thin film transistors
- the TN effect is usually used as the electro-optical effect.
- TFTs made from compound semiconductors such as CdSe or TFT's based on polycrystalline or amorphous silicon The latter technology is being worked on with great intensity worldwide.
- the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counter electrode on the inside. Compared to the size of the pixel electrode, the TFT is very small and practically does not disturb the image.
- This technology can also be expanded for full color images are, wherein a mosaic of red, green and blue filters is arranged such that each filter element is opposite a switchable picture element.
- the TFT displays usually work as TN cells with crossed polarizers in transmission and are illuminated from behind.
- MLC displays of this type are particularly suitable for TV applications (e.g. pocket TVs) or for high-information displays for computer applications (laptops) and in automobile or aircraft construction.
- reflective liquid crystal displays are also of particular interest. These reflective liquid crystal displays use the ambient light for information display. This means that they consume significantly less energy than backlit liquid crystal displays with the appropriate size and resolution. Since the TN effect is characterized by a very good contrast, such reflective displays are also in bright
- Liquid crystals with small birefringence are even more important than with transmissive displays, since reflective displays are the effective ones
- Layer thickness that the light traverses is approximately twice as large as in transmissive displays with the same layer thickness.
- LC media are desired, which enable the following advantages in the cells:
- the invention has for its object LC media, in particular for the type MFK, TN, PS-TN, STN, ECB, OCB, IPS, PS-IPS, FFS, PS-FFS or to provide positive VA displays which do not or only show the disadvantages mentioned above, and preferably have fast switching times and low rotational viscosities with a high clearing point, and high dielectric anisotropy and a low threshold voltage.
- the invention relates to a liquid-crystalline (LC) medium, characterized in that it has a positive dielectric anisotropy and contains one or more compounds of the formula IA and one or more compounds of the formula IB
- R 1 and R 2 are each independently alkyl, alkoxy, oxaalkyl or fluoroalkyl, each having 1 to 8 carbon atoms, and wherein the LC medium no compounds selected from
- the LC medium according to the invention preferably does not contain any
- Another object of the present invention is the use of LC mixtures according to the invention as described above and below in electro-optical displays, in particular LC displays, preferably in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS, posi-VA and PS-posi-VA displays, as well as in FK windows and shutter glasses, especially for 3D applications.
- Another object of the invention is an electro-optical display, in particular an LC display, preferably of TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS, posi-VA or posi- PS-VA type, an FK window, or shutter glasses for 3D applications, containing an FK medium according to the invention.
- meogenic group is known to the person skilled in the art and is described in the literature, and means a group which, through the anisotropy of its attractive and repulsive interactions, contributes significantly to one in low molecular weight or polymeric substances
- LC liquid crystal
- mesogenic compounds do not necessarily have to have an LC phase themselves. It is also possible that mesogenic compounds only exhibit LC phase behavior after mixing with others Show compounds and / or after polymerization.
- Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units.
- spacer or "spacer group”, also referred to above and below as “Sp”, is known to the person skilled in the art and is described in the literature, see for example Pure Appl. Chem. 2001, 73 (5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. Unless otherwise stated, the term means
- reactive mesogen denotes a compound containing a mesogenic group and one or more functional groups which are suitable for the polymerization (also referred to as polymerizable group or group P).
- polymerizable compound denotes a monomeric polymerizable compound.
- Alkoxy radical can be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 carbon atoms and accordingly preferably means ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, furthermore methyl , Octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradedoxy.
- an alkyl radical is substituted at least once by flalogen, this radical is preferably straight-chain and flalogen is preferably F or CI. In the case of multiple substitution, flalogen is preferably F.
- the resulting residues also include perfluorinated residues. In the case of single substitution, the fluorine or chlorine substituent can be in any position, but preferably in the co-position.
- X ° is preferably F, CI or mono- or polypropylene alkyl or alkoxy radical having 1, 2 or 3 carbon atoms or mono- or polypropylene alkenyl radical having 2 or 3 carbon atoms.
- X ° is particularly preferably F, CI, CF3, CFIF 2 , OCF3,
- Carbon atoms especially the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups of 2 to 5 carbon atoms are generally preferred.
- fluoroalkyl preferably encompasses straight-chain groups with terminal fluorine, ie fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl. However, other positions of the fluorine are not excluded.
- oxaalkyl or "alkoxy” preferably includes straight-chain radicals of the formula C n Fl 2n + i -0- (CFl 2 ) m , where n and m each independently represent an integer from 1 to 6 m can also be 0 mean.
- the compounds of the formula IA are preferably selected from the following sub-formulas:
- the LC medium according to the invention contains one or more compounds of the formula IA, preferably selected from the group consisting of the formulas IA1 and IA2, particularly preferably selected from the group consisting of the formulas IA1 a, IA1 b and IA2a particularly preferably of the formula IA1 a and / or IA1 b.
- the individual concentration of each of these compounds is preferably 3 to 25% by weight, particularly preferably 5 to 20% by weight.
- the total concentration of these compounds is
- the compounds of the formula IB are preferably selected from the following sub-formula:
- the LC medium according to the invention contains one or more compounds of the formula IB, preferably selected from formula IB1, particularly preferably selected from the group consisting of the formulas IB1 a and IB1 b, very particularly preferably of the formula IB1 a.
- the individual concentration of each of these compounds is preferably 3 to 25% by weight, particularly preferably 8 to 20% by weight.
- the total concentration of these compounds is preferably 5 to 30% by weight, particularly preferably 8 to 25% by weight.
- the LC medium according to the invention contains one or more compounds of the formula IA, preferably of the formula IA1, very particularly preferably of the formula IA1 a and / or of the formula IA1 b, and one or more compounds of the formula IB, preferably of the formula IB1, very particularly preferably of the formula IB1 a.
- LC medium according to the invention one or more stabilizers.
- Preferred stabilizers are selected from the group consisting of the following formulas
- R a_d straight-chain or branched alkyl having 1 to 10 C atoms
- Particularly preferred stabilizers of the formula S3 are selected from formula S3A
- n2 is an integer from 1 to 12, and wherein one or more F1 atoms in the group (CF are optionally replaced by methyl, ethyl, propyl, butyl, pentyl or flexyl.
- Very particularly preferred stabilizers are selected from the group consisting of the following formulas
- this contains
- LC medium according to the invention one or more stabilizers selected from the group consisting of formula S1-1, S2-1, S3-1, S3-1, S3-3 and S4-1.
- LC medium according to the invention one or more stabilizers selected from Table D below.
- the concentration of the stabilizers in particular those of the formulas S1-S3 and their sub-formulas, and those of Table D, in which
- LC medium according to the invention is preferably 10 to 500 ppm, particularly preferably 20 to 100 ppm.
- the LC medium additionally contains one or more compounds selected from the following formulas:
- Preferred compounds of the formula II and III are those in which Y denotes H.
- R ° denotes alkyl having 1 to 6 C atoms, preferably ethyl or propyl, and X ° F or OCF 3 , preferably F.
- the LC medium additionally contains one or more compounds selected from the following formulas:
- R ° and X ° have the meaning given in formula II or one of the preferred meanings given above and below.
- Preferred compounds are those of the formulas 111, II2 and II3, particularly preferably those of the formulas 111 and II2.
- R ° preferably denotes alkyl having 1 to 6 C atoms, particularly preferably ethyl or propyl
- X ° preferably denotes F or OCF3, particularly preferably F.
- the LC medium contains one or more compounds of the formula II or their sub-formulas in which Y ° is CFI 3 .
- the LC medium preferably contains one or more compounds of the formula II selected from the following sub-formulas:
- R ° and X ° have the meaning given in formula II or one of the preferred meanings given above and below.
- Preferred compounds are those of the formulas IIA1, IIA2 and IIA3, those of the formulas IIA1 and IIA2 are particularly preferred.
- R ° preferably denotes alkyl having 1 to 6 C atoms, particularly preferably ethyl or propyl
- X ° preferably denotes F or OCF3, particularly preferably F.
- the LC medium contains one or more compounds of the formula III selected from the following sub-formulas:
- R ° and X ° have the meaning given in formula II or one of the preferred meanings given above and below.
- Preferred compounds are those of the formula 1111, III4, III6, 11116, 11119 and III20.
- R means
- alkyl with 1 to 6 carbon atoms particularly preferably ethyl or propyl
- X ° preferably denotes F or OCF 3 , particularly preferably F
- Y 2 preferably denotes F.
- the LC medium contains one or more compounds of the formula III or their sub-formulas as described above and below in which Y ° is CFI 3 .
- the LC medium preferably contains one or more compounds of the formula III selected from the following sub-formulas:
- R ° and X ° have the meaning given in formula III or one of the meanings given above and below.
- Preferred compounds are those of the formula IIIA1, IIIA4, IIIA6, IIIA16, IIIA19 and IIIA20.
- R ° preferably denotes alkyl having 1 to 6 C atoms, particularly preferably ethyl or propyl
- X ° preferably denotes F or OCF3, particularly preferably F
- Y 2 preferably denotes F.
- the LC medium additionally contains one or more compounds selected from the following formulas:
- R °, X ° and Y 1-4 have the meanings given above, and
- the compounds of the formula IV are preferably selected from the following formulas: F
- R ° and X ° have the meanings given above.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- the compounds of the formula IVa are preferably selected from the following sub-formula:
- R ° has the meaning given above and preferably means propyl or pentyl.
- the compounds of the formula IVc are preferably selected from the following sub-formulas: wherein R ° has the meaning given above and preferably means propyl or pentyl.
- the compound (s) of the formula IVc in particular of the formula IVc1, is (are) preferably present in the LC medium according to the invention in a concentration of 1-20% by weight, particularly preferably 2-15% by weight.
- the compounds of the formula V are preferably selected from the following sub-formulas:
- R ° and X ° have the meanings given above.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula Va1,
- alkyl has the meaning given in formula IA1 and preferably denotes ethyl, propyl or pentyl, very particularly preferably propyl.
- the compounds of the formula VI are preferably selected from the following sub-formulas: wherein R ° and X ° have the meanings given above.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula VIb1 and / or Much, in which "alkyl” has the meaning given in formula IA1 and preferably denotes ethyl, propyl or pentyl, very particularly preferably propyl.
- the compounds of the formula VII are preferably selected from the following sub-formulas:
- R ° and X ° have the meanings given above.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- the LC medium additionally contains one or more compounds of the following formula: wherein R °, X ° and Y 1-4 each independently have one of the meanings given above.
- X ° preferably denotes F, CI, CF3, OCF3 or OCFIF2.
- R ° preferably denotes alkyl, alkoxy, oxaalkyl or fluoroalkyl, each with 1 to 6 carbon atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula IXa, where R ° has the meaning given above.
- R ° preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula IX, in particular of the formula IXa, is (are) preferably present in the LC medium according to the invention in a concentration of 1-15% by weight, particularly preferably 2-10% by weight.
- the LC medium additionally contains one or more compounds of the formula X:
- R ° is preferably alkyl having 1 to 6 carbon atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula Xa, in which "alkyl” has the meaning given in formula IA1 and preferably denotes ethyl, propyl or pentyl, very particularly preferably propyl.
- the compound (s) of the formula X in particular of the formula Xa, is (are) preferably present in the LC medium according to the invention in a concentration of 0.5-10% by weight, particularly preferably 1-5% by weight.
- the LC medium additionally contains one or more compounds of the following formula:
- R ° and Y 2-4 each independently of one another have one of the meanings given above.
- R ° preferably denotes alkyl, alkoxy, oxaalkyl or fluoroalkyl, in each case with up to 6 C atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula Xla, where R ° has the meaning given above.
- R ° preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula XI, in particular of the formula Xla, is (are) preferably in an LC medium according to the invention in one
- the LC medium additionally contains one or more compounds of the formula XII: in which R 1 and R 2 have the meanings given in formula IA and are preferably alkyl having 1 to 6 carbon atoms.
- the LC medium additionally contains one or more compounds selected from the following formulas:
- R 1 and R 2 have the meanings given in formula IA and LH or F.
- R 1 and R 2 are each, independently of one another, alkyl or alkoxy having 1 to 6 carbon atoms.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula XlVa in which "alkyl” and “alkyl * " each independently of one another have the meaning given in formula IA1 and preferably mean ethyl, propyl or pentyl, very particularly preferably ethyl or propyl.
- the LC medium additionally contains one or more compounds of the formula XVI,
- Particularly preferred compounds of the formula XVI are those selected from the group of the following sub-formulas: wherein "alkyl” and “alkyl * " have the meaning given in formula IA1 and are preferably ethyl, propyl or pentyl.
- the compounds of the formulas XVIb are preferred.
- the compounds are particularly preferably selected from the following sub-formulas
- the LC medium contains one or more compounds selected from the following formulas:
- L, R 1 and R 2 have the meanings given above and preferably R 1 and R 2 each independently represent alkyl having 1 to 6 carbon atoms.
- Compounds of the formula XVI 11 in which LF is are particularly preferred. Are particularly preferred
- the LC medium additionally contains one or more compounds selected from the following formulas: wherein R ° and C ° each independently have one of the meanings given above and Y 1 -4 each independently represent H or F.
- X ° preferably denotes F, CI, CF 3 , OCF3 or OCHF2.
- R ° preferably denotes alkyl, alkoxy, oxaalkyl or fluoroalkyl, each with 1 to 6 carbon atoms.
- the LC medium particularly preferably contains one or more
- R ° has the meaning given above.
- R ° preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula XX in particular the formula XXa, is (are) preferably present in the LC medium according to the invention in a concentration of 1-15% by weight, particularly preferably 2-10% by weight.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula XXIa,
- R ° has the meaning given above.
- R ° preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula XXI, in particular of the formula XXIa, is (are) preferably in the media according to the invention in one Concentration of 1-15 wt.%, Particularly preferably 2-10 wt.% Contain.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula XXIIIa,
- R ° has the meaning given above.
- R ° preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula XXIII, in particular of the formula XXIIIa, is (are) preferably in an LC medium according to the invention in one
- the LC medium additionally contains one or more compounds of the formula XXIV,
- R ° and Y 1 6 have the meanings given above, s means 0 or 1
- X ° has the meaning given above or alkyl or alkoxy, preferably straight-chain, with 1 -6 carbon atoms, and means.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- X ° preferably denotes F;
- the compounds of the formula XXIV are preferably selected from the following sub-formulas:
- R °, X ° and Y 1 have the meanings given above.
- R ° preferably denotes alkyl having 1 to 6 carbon atoms.
- X ° is preferably F, and Y 1 is preferably F;
- R ° is straight-chain alkyl or alkenyl with 2 to 6 carbon atoms
- the LC medium additionally contains one or more compounds selected from the following formulas:
- R 1 and X ° have the meanings given above.
- R 1 preferably denotes alkyl having 1 to 6 carbon atoms.
- X ° preferably denotes F or CI.
- XXIV preferably denotes CI.
- the LC medium additionally contains one or more compounds selected from the following formulas:
- R 1 and X ° have the meanings given above.
- R 1 preferably denotes alkyl having 1 to 6 carbon atoms.
- X ° preferably means F.
- the LC medium preferably contains one or more
- the compounds of the formulas XXVI-XXIX are preferably present in the LC medium according to the invention in a concentration of 1-20% by weight, particularly preferably 1-15% by weight.
- the LC medium preferably contains at least one compound of the formula XXIX.
- the LC medium according to the invention particularly preferably contains one or more compounds of the formula XXIXa,
- R 1 has the meaning given above.
- R 1 preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl or n-pentyl, particularly preferably n-propyl.
- the compound (s) of the formula XXIX, in particular of the formula XXIXa, is (are) preferably present in the LC medium according to the invention in a concentration of 1-15% by weight, particularly preferably 2-10% by weight.
- the LC medium additionally contains one or more compounds selected from the following formulas
- R 1 and X ° have the meanings given above.
- R 1 preferably denotes alkyl having 1 to 6 carbon atoms.
- X ° preferably means F.
- the LC medium preferably contains one or more
- the compound (s) of the formulas XXX1 -XXX3 is (are) preferably present in the LC medium according to the invention in a concentration of 1-20% by weight, particularly preferably 1-15% by weight.
- the LC medium according to the invention contains no compounds of the formula IA or IB in which R 1 and / or R 2 are alkenyl, alkenyloxy, oxaalkenyl or
- the LC medium according to the invention preferably contains no compounds of the formula IA or IB in which R 1 and / or R 2 is an optionally fluorinated alkyl, alkoxy or
- the LC medium contains one or more compounds of the formula II, preferably selected from the group consisting of the formulas 111, II2 and II3, particularly preferably from formulas 111 and II2.
- the individual concentration of each of these compounds is
- Compounds is preferably 5 to 45% by weight.
- the LC medium contains one or more compounds of the formula III, preferably selected from the group consisting of the formula 1111, III4, III6, 11116, 11119 and III20, particularly preferably from the group consisting of the formula 1111, III6, II 116 and III20.
- the concentration of each of these compounds is preferably 2 to 15% by weight.
- the total concentration of these compounds is preferably from 5 to 30% by weight.
- the LC medium contains one or more compounds of the formula IV, preferably selected from formula IVa or IVc, particularly preferably from formula IVa1 or IVc1, very particularly preferably of the formula IVc1.
- the individual concentration of each of these compounds is preferably 2 to 15% by weight. The total concentration of this
- Compounds is preferably 5 to 20% by weight.
- the LC medium contains one or more compounds of the formula V, particularly preferably of the formula Va, very particularly preferably of the formula Va1.
- the individual concentration of each of these compounds is preferably 1 to 20% by weight.
- the total concentration of these compounds is preferably 5 to 20% by weight.
- the LC medium contains one or more compounds of the formula VI, particularly preferably selected from the formulas Vlb and Vle, very particularly preferably from the formulas Vlb1 and Much.
- the individual concentration of each of these compounds is preferably 1 to 20% by weight.
- the total concentration of these compounds is preferably 5 to 20% by weight.
- the LC medium contains one or more compounds of the formula XIII, particularly preferably of the formula XI III.
- the total concentration of these compounds is preferably 1 to 20% by weight.
- the LC medium contains one or more compounds of the formula XIV, particularly preferably of the formula XlVa.
- the concentration of each of these compounds is preferably 2 to 15% by weight.
- the total concentration of these compounds is preferably 5 to 20% by weight.
- the LC medium contains one or more compounds of the formula X, particularly preferably of the formula Xa.
- the individual concentration of each of these compounds is preferably 1 to 10% by weight.
- the total concentration of these compounds is preferably 2 to 15% by weight.
- the LC medium contains one or more compounds of the formula XI, particularly preferably of the formula Xla.
- the individual concentration of each of these compounds is preferably 5 to 25% by weight.
- the total concentration of these compounds is preferably 10 to 35% by weight.
- the LC medium contains one or more compounds of the formula XVIb, particularly preferably selected from the formulas XVIbl, XVIb2 and XVIb3.
- the individual concentration of each of these compounds is preferably 2 to 15% by weight.
- the total concentration of these compounds is preferably 10 to 35% by weight.
- the LC medium contains one or more compounds of the formula XVIc, particularly preferably selected from the formulas XVIc1, XVIc2 and XVIc3.
- the individual concentration of each of these compounds is preferably 2 to 10% by weight.
- the total concentration of these compounds is preferably 5 to 20% by weight.
- the LC medium contains one or more compounds selected from the group consisting of the formulas XVI11, XVII2 and XVII3, particularly preferably of the formula XVI 11 in which L is F and / or the formula XVII2 in which L is F.
- the individual concentration of each of these compounds is preferably 1 to 8% by weight.
- the total concentration of these compounds is preferably 2 to 10% by weight.
- the LC medium contains one or more compounds of the formula XX, particularly preferably of the formula XXa.
- the individual concentration of each of these compounds is preferably 2 to 10% by weight.
- the total concentration of these compounds is preferably 2 to 20% by weight.
- the LC medium contains one or more compounds of the formula XXI, particularly preferably of the formula XXIa.
- the concentration of each of these compounds is preferably 2 to 10% by weight.
- the total concentration of these compounds is
- the LC medium contains one or more compounds of the formula XXIII, particularly preferably of the formula XXIIIa.
- concentration of these compounds is preferably 0.5 to 5% by weight.
- the LC medium contains one or more compounds of the formula XXIX, particularly preferably of the formula XXIXa.
- concentration of these compounds is preferably 2 to 10% by weight.
- the LC medium contains one or more compounds of the formula IA, one or more compounds of the formula IB, one or more compounds selected from the group consisting of formulas II and III or their sub-formulas, preferably selected from the group consisting of formulas 111 , II2, II3, 1111, III4, III6, 11116, 11119 and III20, one or more compounds selected from the group consisting of the formulas IV to XI and XVIII to XXX3, preferably selected from the group consisting of the formulas IV, V, VI, VII, X, XI, XX, XXI and XXIII or their sub-formulas and one or more compounds selected from the group consisting of the formulas XII to XVI 13, preferably selected from the group consisting of the formulas XIII, XIV, XVI, XVII1 and XVII2 or their sub-formulas.
- the concentration of the compounds of the formulas II-XI and XVIII-XXX3 in the LC medium according to the invention is 30 to 60% by weight.
- LC medium according to the invention is 2 to 30% by weight.
- Base materials from other classes of compounds are added, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
- Mixtures according to the invention are particularly notable for high De values and thus have significantly faster switching lines than the mixtures from the prior art.
- the total amount of compounds of the above formulas in the mixtures according to the invention is not critical.
- the mixtures can therefore contain one or more other components for the purpose
- RMs reactive mesogens
- polymerization initiator Contain polymerization initiator, as described, for example, in US Pat. No. 6,781,665.
- the polymerization initiator e.g. Irgacure®651 (BASF) is preferably added to the mixture containing polymerizable compounds in amounts of 0 to 1%.
- Such mixtures can be used for so-called polymer stabilized (PS) modes in which one
- Polymerization of the reactive mesogens in the liquid crystalline mixture should be used, e.g. for PS-IPS-, PS-FFS, PS-TN, PS-VA- IPS.
- the prerequisite for this is that the liquid crystal mixture itself does not contain any polymerizable components.
- the liquid crystal mixture itself does not contain any polymerizable components.
- polymerizable compounds selected from the compounds of formula M.
- R a and R b P, P-Sp-, H, F, CI, Br, I, -CN, -N0 2 , -NCO, -NCS, -OCN, -SCN,
- -O-CO-, -O-CO-O- can be replaced so that O and / or S atoms are not directly linked to each other, and in which one or more Fl atoms are also replaced by F, CI, Br, I , CN, P or P-Sp-- can be replaced, and in which, if B 1 and / or B 2 contain a saturated C atom, R a and / or R b can also mean a radical which is linked to this saturated C atom via a spiro Linkage can be connected, wherein at least one of the radicals R a and R b is a group P or
- P-Sp- means or contains
- B 1 and B 2 are aromatic, heteroaromatic, alicyclic or
- heterocyclic group preferably with 4 to 25 ring atoms, preferably carbon atoms, which also fused
- Rings or can contain rings, and which can optionally be substituted one or more times by L,
- R ° and R 00 are each independently of one another H or alkyl having 1 to 12 carbon atoms, R x P, P-Sp, H, halogen, straight-chain, branched or
- cyclic alkyl having 1 to 25 carbon atoms, in which one or more non-adjacent CH2 groups are also represented by -0-, -S-,
- -CO-, -CO-O-, -O-CO-, -O-CO-O- can be replaced so that 0 and / or S atoms are not directly linked to each other, and in which one or more H -Atoms by F, CI, P or
- P-Sp- can be replaced, an optionally substituted aryl or aryloxy group with 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group with 2 to 40 C atoms, m 0, 1, 2, 3 or 4, n1 1, 2, 3 or 4.
- Preferred compounds of the formula M are those in which B 1 and B 2 , each independently of one another, selected from the group consisting of 1,4-phenylene, naphthalene-1,4-diyl, naphthalene-2, 6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavone, it being possible for one or more CH groups in these groups to be replaced by N, cyclohexane -1, 4-diyl, in which one or more non-adjacent CH2 groups can also be replaced by 0 and / or S, 1, 4-cyclohexenylene, bicyclo [1 .1 .1] pentane-1, 3-diyl, Bicyclo [2.2.2] octane-1,4-diyl, spiro [3.3] heptane-2,6-diyl,
- Particularly preferred compounds of the formula M are those in which B 1 and B 2 are each independently 1, 4-phenylene, 1, 3-phenylene, naphthalene-1, 4-diyl or naphthalene-2,6-diyl. Further particularly preferred compounds of the formula M are those in which one or both radicals R a and R b are P or P-Sp-.
- Particularly preferred compounds of the formula M are selected from the following formulas:
- P 1 to P 3 are each independently polymerizable
- Sp 1 to Sp 3 each independently of one another are a single bond or a spacer group, preferably with one of the meanings given above and below for Sp, and particularly preferably - (CF jp-i-, - (CF jp-iO-, - (CF jp -i-CO-O- or - (Ch jp-iO-CO-O-, in which p1 is an integer from 1 to 12, and in the latter groups the linkage to the adjacent ring takes place via the O atom, where one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - can also mean R aa ,
- R y and R z each independently of one another are Fl, F, CFI 3 or CF 3 , Z 1 -0-, -CO-, -C (R y R z ) -, or -CF2CF2-,
- Z 2 and Z 3 each independently of one another -CO-O-, -O-CO-, -CFI2O-,
- n 2, 3 or 4
- L is the same or different in each occurrence and has the meaning given above under formula M and preferably F, CI, CN, or straight-chain or branched, optionally single or multiple fluorinated, alkyl, alkoxy, alkenyl, alkynyl,
- X 1 to X 3 each independently of one another -CO-O-, -O-CO- or one
- the polymerizable compounds of the formulas M2, M13, M17, M22, M23, M24 and M30 are preferred.
- Compounds of the formulas M2 and M13 are particularly preferred.
- trireactive compounds of the formulas M15 to M31 in particular M17, M18, M19, M22, M23, M24, M25, M30 and M31.
- L has one of the meanings given above and below, and preferably F, CI, CN, NO 2 , CH 3 , C2H5, C (CH 3 ) 3, CH (CH 3 ) 2, CH 2 CH (CH 3 ) C2H 5 , OCH 3I OC2H5, COCH 3 , COC2H5, COOCHs, COOC2H5, CF 3 , OCF 3 , OCHF 2 , OC2F5 or P- Sp-, particularly preferably F, CI, CN, CH 3 , C 2 H 5 , OCFI 3 , COCFI 3 , OCF 3 or P-Sp-, very particularly preferably F, CI, CH 3 , OCFI 3 , COCFI 3 or OCF 3 , in particular F or CH 3 .
- Preferred compounds of the formulas M1 to M31 are those in which P 1 , P 2 and P 3 represent an acrylate, methacrylate, oxetane or
- Further preferred compounds of the formulas M1 to M31 are those in which at least one of the radicals Sp 1 , Sp 2 and Sp 3 is a single bond and at least one of the radicals Sp 1 , Sp 2 and Sp 3 is different from a single bond.
- the LC medium preferably contains one, two or three polymerizable compounds of the formula M, preferably selected from the formulas M1 to M31, particularly preferably selected from Table E.
- the liquid-crystalline media according to the present application preferably contain a total of 0.01 to 3%, preferably 0.1 to 1.0%, particularly preferably 0.1 to 0.5%, of polymerizable compounds. It has been observed that the addition of one or more
- polymerizable compounds such as selected from formula M or Table E
- An LC medium according to the invention containing one or more such polymerizable compounds is particularly suitable for use in PSA displays, in which it has advantageous properties such as reduced image sticking, faster and more complete polymerization, rapid tilt angle generation, increased tilt stability after UV exposure, high reliability, high VFIR values after UV exposure, and high
- polymerizable compounds can also shift the UV absorption to longer wavelengths, so that polymerization is possible at longer UV wavelengths, which is advantageous for the
- the polymerizable group P is a group which is for a
- Polymerization reaction such as free-radical or ionic chain polymerization, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation to a main polymer chain, is suitable.
- Phenyl or alkyl with 1 to 5 carbon atoms means, in particular H, F, CI or CH 3 , W 2 and W 3 each independently of one another Fl or alkyl with 1 to 5 carbon atoms, in particular Fl, methyl, ethyl or n- Are propyl, W 4 , W 5 and W 6 each independently mean CI, oxaalkyl or oxacarbonylalkyl with 1 to 5 C atoms, W 7 and W 8 each independently represent Fl, CI or alkyl with 1 to 5 C atoms, Phe 1, 4-phenylene, which is optionally substituted with one or more L radicals other than P-Sp as defined above, ki, k 2 and k 3 each independently represent 0 or 1, Wz preferably 1, and WA represents an integer from 1 to 10.
- CH 2 CH-COO-
- CH 2 C (CH 3 ) -COO-
- Very particularly preferred groups P are vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxy, in particular acrylate and methacrylate.
- Sp is different from a single bond, it is preferably selected from the formula Sp'-X ', so that the remainder P-Sp- corresponds to the formula P- Sp'-X'-, where
- Sp 'de notes alkylene having 1 to 20, preferably 1 to 12, carbon atoms
- Y 2 and Y 3 each independently mean Fl, F, CI or CN. is preferably -0-, -S -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR ° - CO-, -NR ° -CO-NR ° - or a single bond.
- Typical spacing groups Sp ' are, for example - (CFH 2 ) PI -, - (CFH 2 CFH 2 0) qi - CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 - NH-CH 2 CH 2 - or - (SiR 00 R 000 -O) Pi -, where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 00 and R 000 are those given above Have meanings.
- Sp and -Sp “-X” - are - (CFH 2 ) PI -, - (CFH 2 ) pi -0-, - (CFI 2 ) pi-0-C0-, - (CFI 2 ) pi- C0-0-, - (CFI 2 ) pi-0-C0-0-, wherein p1 and q1 have the meanings given above.
- Ethyleneoxyethylene methyleneoxybutylene, ethylene thioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and
- P- Sp- is a radical with two or more polymerizable groups
- Multifunctional polymerizable residues Suitable residues of this type, as well as polymerizable compounds containing them and their Production is described for example in US 7,060,200 B1 or US 2006/0172090 A1. Multifunctional ones are particularly preferred
- X has one of the meanings given for X ', and
- P 1 5 each independently of one another of those specified for P.
- polymerizable compounds and RMs can be prepared analogously to the processes known to the person skilled in the art and described in standard works of organic chemistry, such as, for example, in Houben-Weyl, Methods of Organic Chemistry, Thieme-Verlag, Stuttgart. Further synthetic methods can be found in the documents cited above and below.
- such RMs are synthesized, for example, by esterification or etherification of 2,6-dihydroxynaphthalene or 4,4'-dihydroxybiphenyl with corresponding acids, acid derivatives, or halogenated compounds containing a group P, such as (meth) acrylic acid chloride or ( Meth) acrylic acid, in the presence of a dehydrating reagent such as DCC (dicyclohexylcarbodiimide).
- DCC diclohexylcarbodiimide
- the structure of the LC displays according to the invention corresponds to the geometry customary for PSA displays, as described in the prior art cited at the beginning. Geometries without protrusions are preferred, in particular those in which the electrode on the color filter side is also unstructured and only the electrode on the TFT side has slots. Particularly suitable and preferred
- Electrode structures for PS-VA displays are described, for example, in US 2006/0066793 A1.
- the LC mixtures and LC media according to the invention are suitable in principle for any type of PS or PSA display, in particular those based on LC media with negative dielectric anisotropy, particularly preferably for PSA-VA-, PSA-IPS- or PS- FFS ads.
- the person skilled in the art can, without inventive step, use suitable LC mixtures and LC media according to the invention in other displays of the PS or PSA type, for example in PS-TN or PS-OCB displays, which differ from those mentioned above Displays, for example, by their basic structure or by the type, arrangement or structure of the individual components used, such as the substrates,
- LC medium according to the invention comprises one or more chiral dopants, preferably in a concentration of 0.01 to 1% by weight, particularly preferably of 0.05 to 0.5% by weight.
- the chiral dopants are
- LC medium according to the invention is a racemate of one or more chiral dopants, preferably selected from the preferred chiral dopants mentioned above.
- SA-FFS or SA-FIB-FFS displays which can also be polymer-stabilized.
- SA-FFS or SA-HB-FFS display contains no orientation layers, in particular no polyimide orientation layers.
- SA additives are preferably selected from compounds containing a mesogenic group and a straight-chain or branched alkyl side chain which has a terminal polar anchor group which is preferably selected from the group consisting of flydroxy, carboxy, amino and thiol groups.
- Anchor group one or more polymerizable groups which are linked to the mesogenic group, optionally via spacer groups.
- These polymerizable SA additives can be used in the LC medium under the same or similar conditions as the polymerizable ones mentioned above
- Suitable and preferred SA additives are, for example, in US
- the present invention also relates to the use of the mixtures according to the invention in electro-optical displays and the use of the mixtures according to the invention in LC windows, shutter glasses, in particular for 3D applications, and in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS, posi-VA and PS-posi-VA displays.
- Another object of the invention is an electro-optical display, a FK window, shutter glasses for 3D applications, and a FK display of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS, posi-VA or posi-PS-VA type, containing an LC medium according to the invention.
- the invention also relates to electro-optical displays, such as. B.
- STN or MFK displays with two plane-parallel carrier plates, which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture in the cell with positive dielectric anisotropy and high specific resistance) which contain such media and the use of these media for electro-optical purposes.
- liquid crystal mixtures according to the invention enable a significant expansion of the available parameter space.
- the mixtures according to the invention can also be used in FFS, IPS, OCB and IPS displays.
- the liquid crystal mixtures according to the invention make it possible, while maintaining the nematic phase up to -20 ° C and preferably up to -30 ° C, particularly preferably up to -40 ° C, and the clearing point> 70 ° C, preferably> 72 ° C, rotational viscosities gi of ⁇ 110 mPa-s, particularly preferably ⁇ 100 mPa-s to achieve, which excellent MFK displays can be achieved with fast switching times.
- Rotational viscosities are determined at 20 ° C.
- the dielectric anisotropy of the liquid crystal mixtures De according to the invention is preferably> +7, particularly preferably> +8, particularly preferably> 10 at 20 ° C.
- the mixtures are also characterized by small operating voltages.
- the threshold voltage of the liquid-crystal mixtures according to the invention is preferably ⁇ 2.0 V.
- the birefringence ie the liquid-crystal mixtures according to the invention is preferably> 0.09, particularly preferably> 0.10 at 20 ° C.
- the nematic phase range of the liquid crystal mixtures according to the invention is preferably at least 90 °, in particular at least 100 ° wide. This area preferably extends at least from
- Mixtures according to the invention can also be used to achieve higher clearing points (e.g. above 100 ° C.) at higher threshold voltages or lower clearing points at lower threshold voltages while maintaining the other advantageous properties. Likewise, with viscosities correspondingly slightly increased, mixtures with a larger de and thus low thresholds can be obtained.
- the MFK displays according to the invention preferably operate in the first transmission minimum according to Gooch and Tarry [C. H. Gooch and FI.A. Tarry, electron. Lett. 10, 2-4, 1974; C. H. Gooch and FI.A. Tarry, Appl. Phys., Vol. 8, 1575-1584, 1975], where in addition to particularly favorable electro-optical properties, such as e.g. high steepness of the characteristic and low angle dependence of the contrast (DE-PS 30 22 818) with the same threshold voltage as in an analog display in the second minimum, a smaller dielectric anisotropy is sufficient.
- Flier notebook can be using the
- Mixtures according to the invention realize in the first minimum significantly higher specific resistances than with mixtures with cyan
- the light stability and UV stability of the mixtures according to the invention is considerably better, i.e. they show a significantly smaller decrease in HR under light or UV exposure.
- the construction of the MFK display according to the invention from polarizers, electrode base plates and electrodes with surface treatment corresponds to the design customary for such displays.
- the concept of the usual design is broad here and also includes all modifications and modifications of the MLC display, in particular also matrix display elements based on poly-Si TFT or MIM.
- liquid-crystal mixtures which can be used according to the invention are prepared in a conventional manner, for example by adding one or more compounds of the formula 1 and one or more compounds of the formula 2 to one or more compounds of the formulas 3 to 5 and one or more compounds of the formula 6 and / or 7 and optionally one or more II to XXVIII or mixed with further liquid-crystalline compounds and / or additives.
- the desired amount is used in a lesser amount
- Components dissolved in the components that make up the main constituent expediently at elevated temperature. It is also possible to dissolve the components in an organic solvent, e.g. in acetone, chloroform or methanol to mix and the solvent after
- the dielectrics can also further additives known to the person skilled in the art and described in the literature, such as, for. B.
- UV stabilizers such as Tinuvin ® , eg Tinuvin ® 770, from Ciba Chemicals, antioxidants, eg TEMPOL, microparticles, radical scavengers, nanoparticles, etc. contain.
- 0 to 15% pleochroic dyes or chiral dopants can be added.
- Suitable stabilizers and dopants are listed in Tables C and D below.
- n and m each independently mean 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, in particular 2, 3, 5, furthermore 0, 4, 6 , preferably not 0.
- Liquid-crystalline mixtures which, in addition to the compounds of the formulas 1 and 2 and (3 to 5) and 6 and / or 7, contain at least one, two, three, four or more compounds from Table B are particularly preferred.
- Table C shows possible dopants which are generally added to the mixtures according to the invention.
- the mixtures contain 0 to 10% by weight, in particular 0.01 to 5% by weight and particularly preferably 0.01 to 3% by weight, of dopants.
- Stabilizers which can be added, for example, to the mixtures according to the invention in amounts of 0 to 10% by weight are mentioned below.
- n 1, 2, 3, 4, 5, 6 or 7
- Table E lists sample compounds which can preferably be used as reactive mesogenic compounds in the LC media according to the present invention. If the mixtures according to the invention contain one or more reactive compounds, they are preferably used in amounts of 0.01 to 5% by weight.
- An initiator or a mixture of two or more initiators may have to be added for the polymerization. The initiator or the initiator mixture is preferably added in amounts of 0.001 to 2% by weight, based on the mixture.
- a suitable initiator is, for example, Irgacure®651 (from BASF). RM-39
- the LC medium according to the invention contains one or more polymerizable compounds from Table E, preferably selected from the polymerizable compounds of the formulas RM-1 to RM-144, particularly preferably from the formulas RM-1, RM-4, RM- 8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-
- Table F shows SA additives which can preferably be used in the media according to the invention:
- the LC medium according to the invention contains one or more SA additives selected from the formulas SA-1 to SA-44, particularly preferably from the formulas SA-14 to SA-34 and SA-44, very particularly preferably from the Formulas SA-20 to SA-34 and SA-44.
- SA additives selected from the formulas SA-1 to SA-44, particularly preferably from the formulas SA-14 to SA-34 and SA-44, very particularly preferably from the Formulas SA-20 to SA-34 and SA-44.
- V10 the voltage (V) for 10% transmission (viewing direction perpendicular to the plate surface), (threshold voltage), determined in a TN
- LTS is the storage or low temperature stability in hours (h), measured in suitable test cells at a temperature of -20 ° C, unless explicitly stated otherwise.
- CCGU-3-F 5.5% gi 75 mPas CCQU-2-F 5.5% Vio 1.43 V CCQU-3-F 4.0% LTS 1000 h CCQU-5-F 4.0%
- Example 16 0.04% of the following compound is added as a stabilizer to the mixture from Example 2:
- VHR voltage holding ratio
- the VHR is measured as described above.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102018010212 | 2018-12-20 | ||
| PCT/EP2019/085543 WO2020127193A1 (de) | 2018-12-20 | 2019-12-17 | Flüssigkristallines medium |
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| EP3898890A1 true EP3898890A1 (de) | 2021-10-27 |
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| US (1) | US11920075B2 (ja) |
| EP (1) | EP3898890A1 (ja) |
| JP (1) | JP2022514872A (ja) |
| KR (1) | KR20210104826A (ja) |
| CN (1) | CN113195682A (ja) |
| DE (1) | DE102019008296A1 (ja) |
| WO (1) | WO2020127193A1 (ja) |
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| DE3022818C2 (de) | 1980-06-19 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Flüssigkristall-Anzeigeelement |
| EP0713515B1 (en) * | 1993-08-11 | 1997-11-26 | MERCK PATENT GmbH | Supertwist liquid-crystal display |
| US7060200B1 (en) | 1999-09-03 | 2006-06-13 | Merck Patent Gmbh | Multireactive polymerizable mesogenic compounds |
| TWI250353B (en) | 2002-02-04 | 2006-03-01 | Sharp Kk | Liquid crystal display and method of manufacturing the same |
| EP1378557B1 (de) | 2002-07-06 | 2007-02-21 | MERCK PATENT GmbH | Flüssigkristallines Medium |
| JP4387276B2 (ja) | 2004-09-24 | 2009-12-16 | シャープ株式会社 | 液晶表示装置 |
| US7527746B2 (en) | 2005-01-28 | 2009-05-05 | Chisso Corporation | Liquid crystal polyfunctional acrylate derivative and polymer thereof |
| DE102011108708A1 (de) | 2010-09-25 | 2012-03-29 | Merck Patent Gmbh | Flüssigkristallanzeigen und flüssigkristalline Medien mit homöotroper Ausrichtung |
| US9382479B2 (en) | 2012-02-03 | 2016-07-05 | Jnc Corporation | Liquid crystal compound, liquid crystal composition and liquid crystal display device |
| EP2703472B1 (de) * | 2012-08-31 | 2018-07-04 | Merck Patent GmbH | Flüssigkristallines Medium |
| US9674945B2 (en) | 2012-09-21 | 2017-06-06 | Intel Corporation | Heterogeneous integration of microfluidic devices in package structures |
| DE102013016399A1 (de) * | 2012-10-22 | 2014-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium |
| KR20150070027A (ko) | 2013-12-16 | 2015-06-24 | 메르크 파텐트 게엠베하 | 액정 매질 |
| EP3730590A1 (de) | 2014-03-10 | 2020-10-28 | Merck Patent GmbH | Flüssigkristalline medien mit homöotroper ausrichtung |
| TWI708770B (zh) | 2015-06-08 | 2020-11-01 | 日商捷恩智股份有限公司 | 具有苯并噻吩的液晶性化合物、液晶組成物及液晶顯示元件 |
| CN107709520B (zh) * | 2015-06-26 | 2021-07-30 | 默克专利股份有限公司 | 含可聚合化合物的液晶介质 |
| US10570335B2 (en) * | 2015-06-26 | 2020-02-25 | Merck Patetn Gmbh | Liquid crystal medium containing polymerisable compounds |
| CN114702966A (zh) * | 2015-08-05 | 2022-07-05 | 默克专利股份有限公司 | 液晶介质 |
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| WO2020127193A1 (de) | 2020-06-25 |
| DE102019008296A1 (de) | 2020-06-25 |
| US20220112426A1 (en) | 2022-04-14 |
| US11920075B2 (en) | 2024-03-05 |
| JP2022514872A (ja) | 2022-02-16 |
| KR20210104826A (ko) | 2021-08-25 |
| CN113195682A (zh) | 2021-07-30 |
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