DE112005000732T5 - Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige - Google Patents
Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige Download PDFInfo
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- DE112005000732T5 DE112005000732T5 DE112005000732T DE112005000732T DE112005000732T5 DE 112005000732 T5 DE112005000732 T5 DE 112005000732T5 DE 112005000732 T DE112005000732 T DE 112005000732T DE 112005000732 T DE112005000732 T DE 112005000732T DE 112005000732 T5 DE112005000732 T5 DE 112005000732T5
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 220
- 239000004973 liquid crystal related substance Substances 0.000 title description 55
- 125000005647 linker group Chemical group 0.000 claims abstract description 11
- -1 DR-2 and DR-3 Chemical compound 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- HBPXFHNNLMCUPA-UHFFFAOYSA-M molport-023-277-200 Chemical compound [Br-].C1N(C2)CN3CN2C[N+]1(CCO)C3 HBPXFHNNLMCUPA-UHFFFAOYSA-M 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- WCLNGBQPTVENHV-MKQVXYPISA-N cholesteryl nonanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCC)C1 WCLNGBQPTVENHV-MKQVXYPISA-N 0.000 description 123
- 239000000203 mixture Substances 0.000 description 123
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
- 125000003545 alkoxy group Chemical group 0.000 description 46
- 229910052736 halogen Inorganic materials 0.000 description 43
- 150000002367 halogens Chemical class 0.000 description 43
- 239000007787 solid Substances 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 125000003342 alkenyl group Chemical group 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 29
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- 0 C**(*)C(CC1)CCC1*(*)* Chemical compound C**(*)C(CC1)CCC1*(*)* 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 26
- 239000000306 component Substances 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- 238000000399 optical microscopy Methods 0.000 description 20
- 238000000819 phase cycle Methods 0.000 description 20
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 125000003302 alkenyloxy group Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 230000007704 transition Effects 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- HAQVFNUBVIRDKF-UHFFFAOYSA-N methyl 4-(4-benzhydryloxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C=C1)=CC=C1OC(C=1C=CC=CC=1)C1=CC=CC=C1 HAQVFNUBVIRDKF-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 235000015096 spirit Nutrition 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 230000005693 optoelectronics Effects 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 5
- WRLLBTKDSCJOBL-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl)methanol Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C(O)C1=C(F)C(F)=C(F)C(F)=C1F WRLLBTKDSCJOBL-UHFFFAOYSA-N 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UYCSYCNORWNNCM-UHFFFAOYSA-N 2-(2-fluoro-4-pentylphenyl)benzoic acid Chemical compound FC1=CC(CCCCC)=CC=C1C1=CC=CC=C1C(O)=O UYCSYCNORWNNCM-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- HBPAPDGVCPVONJ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)benzonitrile Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1C#N HBPAPDGVCPVONJ-UHFFFAOYSA-N 0.000 description 3
- ZNJRONVKWRHYBF-UHFFFAOYSA-N 2-[2-[2-(1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- BRDFFOUFZZDCLT-UHFFFAOYSA-N 1-benzhydryloxy-4-iodobenzene Chemical compound C1=CC(I)=CC=C1OC(C=1C=CC=CC=1)C1=CC=CC=C1 BRDFFOUFZZDCLT-UHFFFAOYSA-N 0.000 description 2
- NKAVDXBGTXDQCB-UHFFFAOYSA-N 2-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1C(O)=O NKAVDXBGTXDQCB-UHFFFAOYSA-N 0.000 description 2
- XAKMJTRJTQZTGT-UHFFFAOYSA-N 2-[4-(2-methylbutyl)phenyl]benzoic acid Chemical compound C1=CC(CC(C)CC)=CC=C1C1=CC=CC=C1C(O)=O XAKMJTRJTQZTGT-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 2
- SIJBDWPVNAYVGY-UHFFFAOYSA-N CC1(C)OCCO1 Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISFDFDOPKKJNNA-UHFFFAOYSA-N FC1=CC=C(C=C1)C(C1=CC=C(C=C1)F)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC Chemical compound FC1=CC=C(C=C1)C(C1=CC=C(C=C1)F)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC ISFDFDOPKKJNNA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DMGMCZRNMYQQQB-UHFFFAOYSA-N [4-(oxan-2-yloxy)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OC1OCCCC1 DMGMCZRNMYQQQB-UHFFFAOYSA-N 0.000 description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WCTZPQWLFWZYJE-UHFFFAOYSA-N bis(4-fluorophenyl)methanol Chemical compound C=1C=C(F)C=CC=1C(O)C1=CC=C(F)C=C1 WCTZPQWLFWZYJE-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- DUCQGUCBWHWEBT-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]methanol Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DUCQGUCBWHWEBT-UHFFFAOYSA-N 0.000 description 2
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011737 fluorine Chemical group 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 108700039708 galantide Proteins 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
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- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012533 medium component Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- SYUYIZNZGCNURJ-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1 SYUYIZNZGCNURJ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 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
- 239000012044 organic layer Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003973 paint Substances 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- ZAEQTGTVGUJEFV-UHFFFAOYSA-N phenylmethanesulfonate;pyridin-1-ium Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 ZAEQTGTVGUJEFV-UHFFFAOYSA-N 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001348 pyrrole-2,5-diyl group Chemical group N1C(=CC=C1*)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography 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
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000002604 ultrasonography Methods 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
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
-
- 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
- C09K19/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04007162 | 2004-03-25 | ||
| EP04007162.3 | 2004-03-25 | ||
| PCT/EP2005/002555 WO2005095544A1 (en) | 2004-03-25 | 2005-03-10 | Liquid crystal compounds, liquid crystal medium and liquid crystal display |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE112005000732T5 true DE112005000732T5 (de) | 2008-09-04 |
Family
ID=34962745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE112005000732T Withdrawn DE112005000732T5 (de) | 2004-03-25 | 2005-03-10 | Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2007530470A (https=) |
| KR (1) | KR20060135001A (https=) |
| DE (1) | DE112005000732T5 (https=) |
| TW (1) | TW200609333A (https=) |
| WO (1) | WO2005095544A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114517098A (zh) * | 2020-11-20 | 2022-05-20 | 默克专利股份有限公司 | 可聚合液晶材料和聚合的液晶膜 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI412824B (zh) * | 2010-08-20 | 2013-10-21 | Innolux Corp | 液晶混合物、液晶顯示器及其操作方法 |
| CN102675040B (zh) * | 2012-04-27 | 2015-02-04 | 石家庄诚志永华显示材料有限公司 | 多氟四联苯类液晶化合物及其制备方法与应用 |
| CN106083538B (zh) * | 2016-06-07 | 2019-05-28 | 阜阳欣奕华材料科技有限公司 | 一种化合物、液晶组合物及液晶显示器 |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| AU2021224588B2 (en) | 2020-02-18 | 2024-07-18 | Gilead Sciences, Inc. | Antiviral compounds |
| EP4323362B1 (en) | 2021-04-16 | 2025-05-07 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
| AU2022328698B2 (en) | 2021-08-18 | 2025-02-20 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
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| DE3534778A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale ester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| DE3534777A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Fluessigkristall-phase mit eine temperaturkompensation bewirkenden dotierstoffen |
| DE3534780A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| DE4342280A1 (de) | 1993-12-11 | 1995-06-14 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19541820A1 (de) | 1995-11-09 | 1997-05-15 | Consortium Elektrochem Ind | Chirale Dianhydrohexit-Derivate enthaltende flüssigkristalline Organosiloxane |
| EP1038941A1 (de) | 1999-03-25 | 2000-09-27 | Basf Aktiengesellschaft | Chirale Verbindungen und deren Verwendung als chirale Dotierstoffe zur Herstellung von cholesterische-fl-ssigkristallinen Zusammensetzungen |
| EP1111954A2 (en) | 1999-12-22 | 2001-06-27 | Nortel Networks Limited | Distributed optical switching device |
| WO2002006196A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds i |
| WO2002006265A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds iii |
| WO2002006195A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds ii |
| WO2002034739A1 (en) | 2000-10-20 | 2002-05-02 | Merck Patent Gmbh | Chiral binaphthol derivatives |
| EP1262471A2 (de) | 2001-05-31 | 2002-12-04 | Bayer Ag | Fluor enthaltende Bisphenole, deren Herstellung, deren Vor- und Zwischenprodukte sowie deren Verwendung |
| DE10217273A1 (de) | 2001-05-16 | 2002-12-05 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, Anzeige und Medium |
| DE10241301A1 (de) | 2002-09-04 | 2004-03-18 | Merck Patent Gmbh | Elektroptisches Lichtsteuerlement, electrooptisches Anzeige und Medium |
| DE10253606A1 (de) | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| DE10313979A1 (de) | 2003-03-27 | 2004-10-07 | Merck Patent Gmbh | Elektrooptisches Lichsteuerelement, elektrooptische Anzeige und Steuermedium |
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| US6485798B1 (en) * | 1999-03-16 | 2002-11-26 | Fuji Photo Film Co., Ltd. | Optical compensatory sheet comprising substrate and optically anisotropic layer |
| US6495484B1 (en) * | 2000-08-28 | 2002-12-17 | Univation Technologies, Llc | Catalyst system and its use in a polymerization process |
| EP1477547B1 (en) * | 2003-05-09 | 2006-06-14 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
-
2005
- 2005-03-10 KR KR1020067019668A patent/KR20060135001A/ko not_active Abandoned
- 2005-03-10 JP JP2007504292A patent/JP2007530470A/ja not_active Ceased
- 2005-03-10 DE DE112005000732T patent/DE112005000732T5/de not_active Withdrawn
- 2005-03-10 WO PCT/EP2005/002555 patent/WO2005095544A1/en not_active Ceased
- 2005-03-24 TW TW094109181A patent/TW200609333A/zh unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3534778A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale ester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| DE3534777A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Fluessigkristall-phase mit eine temperaturkompensation bewirkenden dotierstoffen |
| DE3534780A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| DE4342280A1 (de) | 1993-12-11 | 1995-06-14 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19541820A1 (de) | 1995-11-09 | 1997-05-15 | Consortium Elektrochem Ind | Chirale Dianhydrohexit-Derivate enthaltende flüssigkristalline Organosiloxane |
| EP1038941A1 (de) | 1999-03-25 | 2000-09-27 | Basf Aktiengesellschaft | Chirale Verbindungen und deren Verwendung als chirale Dotierstoffe zur Herstellung von cholesterische-fl-ssigkristallinen Zusammensetzungen |
| EP1111954A2 (en) | 1999-12-22 | 2001-06-27 | Nortel Networks Limited | Distributed optical switching device |
| WO2002006265A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds iii |
| WO2002006196A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds i |
| WO2002006195A1 (en) | 2000-07-13 | 2002-01-24 | Merck Patent Gmbh | Chiral compounds ii |
| WO2002034739A1 (en) | 2000-10-20 | 2002-05-02 | Merck Patent Gmbh | Chiral binaphthol derivatives |
| DE10217273A1 (de) | 2001-05-16 | 2002-12-05 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, Anzeige und Medium |
| EP1262471A2 (de) | 2001-05-31 | 2002-12-04 | Bayer Ag | Fluor enthaltende Bisphenole, deren Herstellung, deren Vor- und Zwischenprodukte sowie deren Verwendung |
| DE10241301A1 (de) | 2002-09-04 | 2004-03-18 | Merck Patent Gmbh | Elektroptisches Lichtsteuerlement, electrooptisches Anzeige und Medium |
| DE10253606A1 (de) | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| DE10313979A1 (de) | 2003-03-27 | 2004-10-07 | Merck Patent Gmbh | Elektrooptisches Lichsteuerelement, elektrooptische Anzeige und Steuermedium |
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| "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Stand Nov. 1997, Merck KGaA, Deutschland |
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| H. Kelker und R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980 |
| H. S. Kitzerow, "The Effekt of Electric Fields an Blue Phases", Mol. Cryst. Liq. Cryst. (1991), Bd. 202, S. 51-83 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114517098A (zh) * | 2020-11-20 | 2022-05-20 | 默克专利股份有限公司 | 可聚合液晶材料和聚合的液晶膜 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200609333A (en) | 2006-03-16 |
| JP2007530470A (ja) | 2007-11-01 |
| KR20060135001A (ko) | 2006-12-28 |
| WO2005095544A1 (en) | 2005-10-13 |
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