DE102011106314A1 - Flüssigkristallines Medium enthaltend Thiophenderivate - Google Patents
Flüssigkristallines Medium enthaltend Thiophenderivate Download PDFInfo
- Publication number
- DE102011106314A1 DE102011106314A1 DE102011106314A DE102011106314A DE102011106314A1 DE 102011106314 A1 DE102011106314 A1 DE 102011106314A1 DE 102011106314 A DE102011106314 A DE 102011106314A DE 102011106314 A DE102011106314 A DE 102011106314A DE 102011106314 A1 DE102011106314 A1 DE 102011106314A1
- Authority
- DE
- Germany
- Prior art keywords
- atoms
- compounds
- alkyl
- independently
- formula
- 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.)
- Withdrawn
Links
- 150000003577 thiophenes Chemical class 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- -1 cyclohexane-1,4-diyl Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 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 2
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 32
- 230000003287 optical effect Effects 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 description 52
- 210000004027 cell Anatomy 0.000 description 20
- 239000012071 phase Substances 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 12
- 0 *C(CC1)CCC1c(cc1*)cc(*)c1-c(cc1*)cc(F)c1OC=C(F)F Chemical compound *C(CC1)CCC1c(cc1*)cc(*)c1-c(cc1*)cc(F)c1OC=C(F)F 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BJNSEVYWWJWPJX-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylphenyl)phenyl]-5-ethenylthiophene Chemical compound C1=CC(CCC)=CC=C1C(C=C1F)=CC(F)=C1C1=CC=C(C=C)S1 BJNSEVYWWJWPJX-UHFFFAOYSA-N 0.000 description 3
- YJSNJQSUPJYSSV-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylphenyl)phenyl]-5-ethylthiophene Chemical compound C1=CC(CCC)=CC=C1C(C=C1F)=CC(F)=C1C1=CC=C(CC)S1 YJSNJQSUPJYSSV-UHFFFAOYSA-N 0.000 description 3
- GDBVVTJSGDEUPR-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylphenyl)phenyl]-5-propylthiophene Chemical compound S1C(CCC)=CC=C1C1=C(F)C=C(C=2C=CC(CCC)=CC=2)C=C1F GDBVVTJSGDEUPR-UHFFFAOYSA-N 0.000 description 3
- HYRYQZIGBWDHAD-UHFFFAOYSA-N 2-bromo-5-ethylthiophene Chemical compound CCC1=CC=C(Br)S1 HYRYQZIGBWDHAD-UHFFFAOYSA-N 0.000 description 3
- AZMSRFANKVHIEG-UHFFFAOYSA-N 2-bromo-5-propylthiophene Chemical compound CCCC1=CC=C(Br)S1 AZMSRFANKVHIEG-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 210000004263 induced pluripotent stem cell Anatomy 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- RJHFYYMQAHTWPW-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylcyclohexyl)phenyl]-5-ethylthiophene Chemical compound C1CC(CCC)CCC1C(C=C1F)=CC(F)=C1C1=CC=C(CC)S1 RJHFYYMQAHTWPW-UHFFFAOYSA-N 0.000 description 2
- MVMCNZDNEINZLE-UHFFFAOYSA-N 2-[3-fluoro-4-(4-pentylphenyl)phenyl]-5-hexylthiophene Chemical compound S1C(CCCCCC)=CC=C1C1=CC=C(C=2C=CC(CCCCC)=CC=2)C(F)=C1 MVMCNZDNEINZLE-UHFFFAOYSA-N 0.000 description 2
- ATMCJRZDWVJJKE-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)-2,6-difluorophenyl]-5-propylthiophene Chemical compound S1C(CCC)=CC=C1C1=C(F)C=C(C=2C=CC(CC)=CC=2)C=C1F ATMCJRZDWVJJKE-UHFFFAOYSA-N 0.000 description 2
- ZKKMOOLNYXTBTH-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)-3,5-difluorophenyl]-5-propylthiophene Chemical compound S1C(CCC)=CC=C1C1=CC(F)=C(C=2C=CC(CC)=CC=2)C(F)=C1 ZKKMOOLNYXTBTH-UHFFFAOYSA-N 0.000 description 2
- KIPWOOKIXYCLST-UHFFFAOYSA-N 2-ethyl-5-[4-(4-ethylphenyl)-2,6-difluorophenyl]thiophene Chemical compound S1C(CC)=CC=C1C1=C(F)C=C(C=2C=CC(CC)=CC=2)C=C1F KIPWOOKIXYCLST-UHFFFAOYSA-N 0.000 description 2
- YQTDQQVKDGUCKC-UHFFFAOYSA-N 2-ethyl-5-[4-(4-ethylphenyl)-3,5-difluorophenyl]thiophene Chemical compound S1C(CC)=CC=C1C1=CC(F)=C(C=2C=CC(CC)=CC=2)C(F)=C1 YQTDQQVKDGUCKC-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KOLJRVLDEBMHMC-UHFFFAOYSA-N [2,6-difluoro-4-(4-propylphenyl)phenyl]boronic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC(F)=C(B(O)O)C(F)=C1 KOLJRVLDEBMHMC-UHFFFAOYSA-N 0.000 description 2
- AHBZEUWPEXLUDW-UHFFFAOYSA-N [4-(4-ethylphenyl)-2,6-difluorophenyl]boronic acid Chemical compound C1=CC(CC)=CC=C1C1=CC(F)=C(B(O)O)C(F)=C1 AHBZEUWPEXLUDW-UHFFFAOYSA-N 0.000 description 2
- NBDQFQLQZZZPOF-UHFFFAOYSA-N [4-(4-ethylphenyl)-3,5-difluorophenyl]boronic acid Chemical compound C1=CC(CC)=CC=C1C1=C(F)C=C(B(O)O)C=C1F NBDQFQLQZZZPOF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 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 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 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
- WVSFYQJOKNIGRU-UHFFFAOYSA-N 2-bromo-1,3-difluoro-5-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC(F)=C(Br)C(F)=C1 WVSFYQJOKNIGRU-UHFFFAOYSA-N 0.000 description 1
- WJSIEDBETVAKKL-UHFFFAOYSA-N 2-bromo-5-ethenylthiophene Chemical compound BrC1=CC=C(C=C)S1 WJSIEDBETVAKKL-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
- BYMWTPNAGOZPEF-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(Br)C=C1F BYMWTPNAGOZPEF-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N Cc(cc1)ccc1Cl Chemical compound Cc(cc1)ccc1Cl NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- JZBUKOJEEZIBIC-UHFFFAOYSA-N Cc(cc1)ccc1[F](C)c(cc1)cc(F)c1[F]c(cc1F)cc(F)c1F Chemical compound Cc(cc1)ccc1[F](C)c(cc1)cc(F)c1[F]c(cc1F)cc(F)c1F JZBUKOJEEZIBIC-UHFFFAOYSA-N 0.000 description 1
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 description 1
- 101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 108700017836 Prophet of Pit-1 Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000620457 Telestes souffia Species 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004883 computer application Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 101150047356 dec-1 gene Proteins 0.000 description 1
- 230000003247 decreasing effect 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
- 238000013461 design Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 1
- QPMAGMWYRUSFJP-UHFFFAOYSA-N disodium;(5-hexylthiophen-2-yl)oxy-dioxidoborane Chemical compound [Na+].[Na+].CCCCCCC1=CC=C(OB([O-])[O-])S1 QPMAGMWYRUSFJP-UHFFFAOYSA-N 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
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 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
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 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
- 239000008096 xylene Substances 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- 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
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
-
- 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)
- C09K2019/3025—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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102011106314A DE102011106314A1 (de) | 2010-07-29 | 2011-07-01 | Flüssigkristallines Medium enthaltend Thiophenderivate |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010032617 | 2010-07-29 | ||
| DE102010032617.8 | 2010-07-29 | ||
| DE102011106314A DE102011106314A1 (de) | 2010-07-29 | 2011-07-01 | Flüssigkristallines Medium enthaltend Thiophenderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102011106314A1 true DE102011106314A1 (de) | 2012-02-02 |
Family
ID=44627712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102011106314A Withdrawn DE102011106314A1 (de) | 2010-07-29 | 2011-07-01 | Flüssigkristallines Medium enthaltend Thiophenderivate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8906261B2 (https=) |
| EP (1) | EP2598604B1 (https=) |
| JP (1) | JP5788508B2 (https=) |
| KR (1) | KR101868648B1 (https=) |
| CN (2) | CN107011920B (https=) |
| DE (1) | DE102011106314A1 (https=) |
| TW (1) | TWI513803B (https=) |
| WO (1) | WO2012013281A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022238453A1 (en) * | 2021-05-12 | 2022-11-17 | Merck Patent Gmbh | Liquid crystal medium and electronic component |
| US11739267B2 (en) | 2019-06-28 | 2023-08-29 | Merck Patent Gmbh | LC medium |
| WO2023198669A1 (en) * | 2022-04-12 | 2023-10-19 | Merck Patent Gmbh | Liquid-crystalline medium |
| DE102023131322A1 (de) | 2023-09-26 | 2025-03-27 | Tcl China Star Optoelectronics Technology Co., Ltd. | Flüssigkristallzusammensetzung und Anzeigepaneel |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI462992B (zh) * | 2011-04-18 | 2014-12-01 | Daxin Materials Corp | 液晶化合物 |
| JP6058644B2 (ja) | 2011-06-01 | 2017-01-11 | 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 | 液晶媒体および液晶ディスプレイ |
| DE102015003602A1 (de) * | 2015-03-18 | 2016-09-22 | Merck Patent Gmbh | Flüssigkristalines Medium |
| JP6801835B2 (ja) * | 2015-07-09 | 2020-12-16 | ミメトゲン ファーマシュウティカルズ インコーポレイテッドＭｉｍｅｔｏｇｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | β−ターンペプチド模倣環状塩の液相合成及び結晶化 |
| US20200347302A1 (en) * | 2018-01-24 | 2020-11-05 | Nitto Denko Corporation | Liquid crystal composition containing a five-membered heterocyclic ring, reverse-mode polymer dispersed liquid crystal element, and associated selectively dimmable device |
| CN110229679B (zh) * | 2018-03-06 | 2020-11-17 | 北京八亿时空液晶科技股份有限公司 | 一种液晶介质的自配向添加剂及其制备方法与应用 |
| US11447703B2 (en) * | 2018-06-29 | 2022-09-20 | Merck Patent Gmbh | Thiophene compound, liquid-crystalline medium and liquid-crystal display comprising the same |
| EP3763802B1 (en) * | 2018-07-12 | 2023-09-06 | Merck Patent GmbH | Thiophene compound, liquid-crystalline medium and liquid-crystal display comprising the same |
| TWI892895B (zh) * | 2019-12-20 | 2025-08-01 | 德商馬克專利公司 | 液晶介質及含彼之液晶顯示器 |
| JP2021187742A (ja) * | 2020-05-26 | 2021-12-13 | Jnc株式会社 | 化合物、液晶組成物および液晶表示素子 |
| CN112266794B (zh) * | 2020-09-30 | 2022-09-09 | 北京八亿时空液晶科技股份有限公司 | 一种含噻吩的液晶化合物及其制备方法和应用 |
| CN115197716A (zh) * | 2021-04-13 | 2022-10-18 | 默克专利股份有限公司 | 液晶介质 |
| WO2023180505A1 (en) | 2022-03-25 | 2023-09-28 | Merck Patent Gmbh | Liquid crystalline medium |
| KR20230146471A (ko) | 2022-04-12 | 2023-10-19 | 메르크 파텐트 게엠베하 | 액정 매질 |
| CN121666438A (zh) * | 2023-06-30 | 2026-03-13 | 默克专利股份有限公司 | 液晶介质 |
| CN117603708B (zh) * | 2023-09-27 | 2025-11-21 | 惠州华星光电显示有限公司 | 液晶组合物及显示面板 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022818A1 (de) | 1980-06-19 | 1982-01-14 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristall-anzeigeelement |
| WO2009129915A1 (de) | 2008-04-24 | 2009-10-29 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
| WO2010094455A1 (de) | 2009-02-19 | 2010-08-26 | Merck Patent Gmbh | Thiophen-verbindungen für flüssigkristalline medien |
| WO2010099853A1 (de) | 2009-02-19 | 2010-09-10 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04217973A (ja) * | 1990-07-16 | 1992-08-07 | Canon Inc | 液晶性化合物、これを含む液晶組成物およびこれを利用した液晶素子、表示装置 |
| JP3187611B2 (ja) * | 1993-05-17 | 2001-07-11 | キヤノン株式会社 | 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置 |
| WO2006022040A1 (ja) * | 2004-08-27 | 2006-03-02 | National Institute Of Advanced Industrial Science And Technology | １，４−ジチエニルベンゼン誘導体 |
| JP4749101B2 (ja) * | 2005-09-22 | 2011-08-17 | 株式会社Ａｄｅｋａ | チオフェン化合物、該化合物を含有してなる液晶組成物、及び液晶素子 |
-
2011
- 2011-07-01 WO PCT/EP2011/003271 patent/WO2012013281A1/de not_active Ceased
- 2011-07-01 KR KR1020137004966A patent/KR101868648B1/ko active Active
- 2011-07-01 JP JP2013520992A patent/JP5788508B2/ja active Active
- 2011-07-01 US US13/812,743 patent/US8906261B2/en active Active
- 2011-07-01 EP EP11728788.8A patent/EP2598604B1/de active Active
- 2011-07-01 CN CN201610948046.5A patent/CN107011920B/zh active Active
- 2011-07-01 DE DE102011106314A patent/DE102011106314A1/de not_active Withdrawn
- 2011-07-01 CN CN201180036766XA patent/CN103038312A/zh active Pending
- 2011-07-28 TW TW100126834A patent/TWI513803B/zh active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022818A1 (de) | 1980-06-19 | 1982-01-14 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristall-anzeigeelement |
| WO2009129915A1 (de) | 2008-04-24 | 2009-10-29 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
| WO2010094455A1 (de) | 2009-02-19 | 2010-08-26 | Merck Patent Gmbh | Thiophen-verbindungen für flüssigkristalline medien |
| WO2010099853A1 (de) | 2009-02-19 | 2010-09-10 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
Non-Patent Citations (6)
| Title |
|---|
| "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status Nov. 1997, Merck KGaA, Darmstadt, Deutschland |
| C. H. Gooch und H. A. Tarry, Electron. Lett. 10, 2-4, 1974; C. H. Gooch und H. A. Tarry, Appl. Phys., Vol. 8, 1575-1584, 1975 |
| G. Weber et al., Liquid Crystals 5, 1381 (1989) |
| S. Matsumoto et a]., Liquid Crystals 5, 1320 (1989); K. Niwa et al., Proc. SID Conference, San Francisco, June 1984, p. 304 (1984) |
| STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Adressing of Television Liquid Crystal Displays, p. 145 ff, Paris |
| TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141 ff, Paris |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11739267B2 (en) | 2019-06-28 | 2023-08-29 | Merck Patent Gmbh | LC medium |
| WO2022238453A1 (en) * | 2021-05-12 | 2022-11-17 | Merck Patent Gmbh | Liquid crystal medium and electronic component |
| WO2023198669A1 (en) * | 2022-04-12 | 2023-10-19 | Merck Patent Gmbh | Liquid-crystalline medium |
| DE102023131322A1 (de) | 2023-09-26 | 2025-03-27 | Tcl China Star Optoelectronics Technology Co., Ltd. | Flüssigkristallzusammensetzung und Anzeigepaneel |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101868648B1 (ko) | 2018-06-18 |
| US20130119312A1 (en) | 2013-05-16 |
| TWI513803B (zh) | 2015-12-21 |
| US8906261B2 (en) | 2014-12-09 |
| EP2598604B1 (de) | 2015-11-25 |
| TW201213516A (en) | 2012-04-01 |
| CN107011920A (zh) | 2017-08-04 |
| EP2598604A1 (de) | 2013-06-05 |
| JP5788508B2 (ja) | 2015-09-30 |
| CN103038312A (zh) | 2013-04-10 |
| WO2012013281A1 (de) | 2012-02-02 |
| KR20140002608A (ko) | 2014-01-08 |
| JP2013537571A (ja) | 2013-10-03 |
| CN107011920B (zh) | 2021-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2598604B1 (de) | Flüssigkristallines medium enthaltend thiophenderivate | |
| EP2250235B1 (de) | Flüssigkristallines medium | |
| EP2242819B1 (de) | Flüssigkristallines medium | |
| EP2057251B1 (de) | Flüssigkristallines medium | |
| EP2338952B1 (de) | Flüssigkristallines Medium | |
| EP2593528B1 (de) | Flüssigkristallines medium mit stabilisator | |
| EP3271440B1 (de) | Flüssigkristallines medium | |
| DE102007007143A1 (de) | Flüssigkristallines Medium | |
| DE102008062858A1 (de) | Flüssigkristallines Medium | |
| DE102014010908A1 (de) | Flüssigkristallines Medium | |
| EP2542648B1 (de) | Flüssigkristallines medium | |
| EP2248872B1 (de) | Flüssigkristallines Medium | |
| DE102011016189A1 (de) | Flüssigkristallines Medium | |
| EP1908812A1 (de) | Flüssigkristallines Medium | |
| DE102013016339A1 (de) | Flüssigkristallines Medium | |
| DE102011009337A1 (de) | Flüssigkristallines Medium | |
| EP2516589B1 (de) | Flüssigkristallines medium | |
| EP2646525B1 (de) | Flüssigkristallines medium | |
| DE102006006116B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE102013020566A1 (de) | Flüssigkristallines Medium | |
| DE102007042414A1 (de) | Flüssigkristallines Medium | |
| DE102007042415A1 (de) | Flüssigkristallines Medium | |
| DE102007045661A1 (de) | Flüssigkristallines Medium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R005 | Application deemed withdrawn due to failure to request examination |