DE102004004228A1 - Benzochromenderivate - Google Patents
Benzochromenderivate Download PDFInfo
- Publication number
- DE102004004228A1 DE102004004228A1 DE200410004228 DE102004004228A DE102004004228A1 DE 102004004228 A1 DE102004004228 A1 DE 102004004228A1 DE 200410004228 DE200410004228 DE 200410004228 DE 102004004228 A DE102004004228 A DE 102004004228A DE 102004004228 A1 DE102004004228 A1 DE 102004004228A1
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- compounds
- formula
- zli
- diyl
- 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.)
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 72
- VCDAWCBLCCVSKE-UHFFFAOYSA-N 2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=CCO2 VCDAWCBLCCVSKE-UHFFFAOYSA-N 0.000 title abstract description 5
- -1 piperidine-1,4-diyl Chemical group 0.000 claims abstract description 115
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 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 abstract 1
- 239000000203 mixture Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 22
- 239000012071 phase Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 0 *Oc(ccc(Br)c1)c1F Chemical compound *Oc(ccc(Br)c1)c1F 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003302 alkenyloxy group Chemical group 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- OCODJNASCDFXSR-UHFFFAOYSA-N 1-bromo-2-fluoro-4-iodobenzene Chemical compound FC1=CC(I)=CC=C1Br OCODJNASCDFXSR-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- AMTAVRYIRXKBQJ-UHFFFAOYSA-N 6-bromo-3-ethoxy-2-fluorobenzoic acid Chemical compound CCOC1=CC=C(Br)C(C(O)=O)=C1F AMTAVRYIRXKBQJ-UHFFFAOYSA-N 0.000 description 4
- DVAPVAYHSYQGCV-UHFFFAOYSA-N 8-ethoxy-4,7-difluoro-3-phenylmethoxybenzo[c]chromen-6-one Chemical compound FC1=C2OC(=O)C3=C(F)C(OCC)=CC=C3C2=CC=C1OCC1=CC=CC=C1 DVAPVAYHSYQGCV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
- PQYGFFABMUEQON-UHFFFAOYSA-N 1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene Chemical compound CCCCOC1=CC=C(Br)C(OCOCCOC)=C1F PQYGFFABMUEQON-UHFFFAOYSA-N 0.000 description 3
- NOCFJMVWLRFUDI-UHFFFAOYSA-N 3-butoxy-4,6,6,7-tetrafluoro-8-(4-pentylcyclohexyl)benzo[c]chromene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2(F)F)C2=C1F NOCFJMVWLRFUDI-UHFFFAOYSA-N 0.000 description 3
- PFCOCJSPOJYUGG-UHFFFAOYSA-N 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)benzo[c]chromen-6-one Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2=O)C2=C1F PFCOCJSPOJYUGG-UHFFFAOYSA-N 0.000 description 3
- CABLNMPDNZPSOT-UHFFFAOYSA-N 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)benzo[c]chromene-6-thione Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2=S)C2=C1F CABLNMPDNZPSOT-UHFFFAOYSA-N 0.000 description 3
- ZMTIHOQUIPYSQK-UHFFFAOYSA-N 4-bromo-1-ethoxy-2-fluorobenzene Chemical compound CCOC1=CC=C(Br)C=C1F ZMTIHOQUIPYSQK-UHFFFAOYSA-N 0.000 description 3
- KWDPNPVCQGEUKZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(4-pentylcyclohexen-1-yl)benzene Chemical compound C1C(CCCCC)CCC(C=2C(=CC(Br)=CC=2)F)=C1 KWDPNPVCQGEUKZ-UHFFFAOYSA-N 0.000 description 3
- KXFJNXXTTNGXTQ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C=C1F KXFJNXXTTNGXTQ-UHFFFAOYSA-N 0.000 description 3
- HCVUDNMNSPYSHS-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylmethoxybenzene Chemical compound FC1=CC(Br)=CC=C1OCC1=CC=CC=C1 HCVUDNMNSPYSHS-UHFFFAOYSA-N 0.000 description 3
- QNGVPYFPKLUQDX-UHFFFAOYSA-N 6-bromo-2-fluoro-3-methylbenzoic acid Chemical compound CC1=CC=C(Br)C(C(O)=O)=C1F QNGVPYFPKLUQDX-UHFFFAOYSA-N 0.000 description 3
- MKUCVRSKYGZIKK-UHFFFAOYSA-N 6-bromo-2-fluoro-3-pentylphenol Chemical compound CCCCCC1=CC=C(Br)C(O)=C1F MKUCVRSKYGZIKK-UHFFFAOYSA-N 0.000 description 3
- WDWMIQICZJPVHB-UHFFFAOYSA-N 6-bromo-2-fluoro-3-phenylmethoxyphenol Chemical compound OC1=C(Br)C=CC(OCC=2C=CC=CC=2)=C1F WDWMIQICZJPVHB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- BVNDLKONNFGLBX-WKILWMFISA-N FC=1C(OCC)=CC=C(C2=CC=3)C=1COC2=C(F)C=3OC[C@H]1CC[C@H](C=C)CC1 Chemical compound FC=1C(OCC)=CC=C(C2=CC=3)C=1COC2=C(F)C=3OC[C@H]1CC[C@H](C=C)CC1 BVNDLKONNFGLBX-WKILWMFISA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 150000008648 triflates Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- GHQPLVWOWSSUHW-UHFFFAOYSA-N (6-bromo-2-fluoro-3-pentylphenyl) 6-bromo-2-fluoro-3-methylbenzoate Chemical compound CCCCCC1=CC=C(Br)C(OC(=O)C=2C(=C(C)C=CC=2Br)F)=C1F GHQPLVWOWSSUHW-UHFFFAOYSA-N 0.000 description 2
- TVDGCJHEEOTNED-UHFFFAOYSA-N (6-bromo-2-fluoro-3-phenylmethoxyphenyl) 6-bromo-3-ethoxy-2-fluorobenzoate Chemical compound CCOC1=CC=C(Br)C(C(=O)OC=2C(=C(OCC=3C=CC=CC=3)C=CC=2Br)F)=C1F TVDGCJHEEOTNED-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- DQJSFSVPQDIUOD-UHFFFAOYSA-N 2,3-difluoro-2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=C(F)C(F)O2 DQJSFSVPQDIUOD-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- HZUFMTWUPUVPDS-UHFFFAOYSA-N 4,7-difluoro-8-methyl-3-pentylbenzo[c]chromen-6-one Chemical compound CC1=CC=C2C3=CC=C(CCCCC)C(F)=C3OC(=O)C2=C1F HZUFMTWUPUVPDS-UHFFFAOYSA-N 0.000 description 2
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-UHFFFAOYSA-N 0.000 description 2
- YZFVUQSAJMLFOZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(Br)C=C1F YZFVUQSAJMLFOZ-UHFFFAOYSA-N 0.000 description 2
- NQHXLQOYPJHTGF-UHFFFAOYSA-N 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoic acid Chemical compound C1CC(CCCCC)CCC1C1=CC=C(Br)C(C(O)=O)=C1F NQHXLQOYPJHTGF-UHFFFAOYSA-N 0.000 description 2
- LFXZYFFWYVFNJA-UHFFFAOYSA-N 6-bromo-3-butoxy-2-fluorophenol Chemical compound CCCCOC1=CC=C(Br)C(O)=C1F LFXZYFFWYVFNJA-UHFFFAOYSA-N 0.000 description 2
- JTPHMYZEINFFSE-UHFFFAOYSA-N 8-ethoxy-4,6,6,7-tetrafluoro-3-pentylbenzo[c]chromene Chemical compound CCOC1=CC=C2C3=CC=C(CCCCC)C(F)=C3OC(F)(F)C2=C1F JTPHMYZEINFFSE-UHFFFAOYSA-N 0.000 description 2
- XISACNRTNATVPU-UHFFFAOYSA-N 8-ethoxy-4,7-difluoro-6h-benzo[c]chromen-3-ol Chemical compound OC1=CC=C2C3=CC=C(OCC)C(F)=C3COC2=C1F XISACNRTNATVPU-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- IOWLXRZVKTVUGK-HDJSIYSDSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Br)C=C1F Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Br)C=C1F IOWLXRZVKTVUGK-HDJSIYSDSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 238000006411 Negishi coupling reaction Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 150000002987 phenanthrenes Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 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
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 101150047356 dec-1 gene Proteins 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
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- JMRYOSQOYJBDOI-UHFFFAOYSA-N dilithium;di(propan-2-yl)azanide Chemical compound [Li+].CC(C)[N-]C(C)C.CC(C)N([Li])C(C)C JMRYOSQOYJBDOI-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 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
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- 230000005684 electric field Effects 0.000 description 1
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
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- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229940067606 lecithin Drugs 0.000 description 1
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- 239000002075 main ingredient Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
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- 238000006263 metalation reaction Methods 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
- LQBFYFBVRPVLMT-UHFFFAOYSA-N methyl 6-[4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)phenyl]-2-fluoro-3-(4-pentylcyclohexyl)benzoate Chemical compound C1CC(CCCCC)CCC1C(C(=C1C(=O)OC)F)=CC=C1C1=CC=C(OCCCC)C(F)=C1OCOCCOC LQBFYFBVRPVLMT-UHFFFAOYSA-N 0.000 description 1
- NRZIJCCVRBHFCO-UHFFFAOYSA-N methyl 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoate Chemical compound C1CC(CCCCC)CCC1C1=CC=C(Br)C(C(=O)OC)=C1F NRZIJCCVRBHFCO-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N methyl tert-butyl ether Substances COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 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
- LLYKPZOWCPVRPD-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine;n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=CC=N1 LLYKPZOWCPVRPD-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
- 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium 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
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition 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
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
- 229940102001 zinc bromide Drugs 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200410004228 DE102004004228A1 (de) | 2003-02-25 | 2004-01-28 | Benzochromenderivate |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10308266 | 2003-02-25 | ||
| DE10308266.2 | 2003-02-25 | ||
| DE200410004228 DE102004004228A1 (de) | 2003-02-25 | 2004-01-28 | Benzochromenderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004004228A1 true DE102004004228A1 (de) | 2004-09-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE200410004228 Withdrawn DE102004004228A1 (de) | 2003-02-25 | 2004-01-28 | Benzochromenderivate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7326447B2 (https=) |
| EP (1) | EP1618101B1 (https=) |
| JP (1) | JP4860464B2 (https=) |
| KR (1) | KR101133905B1 (https=) |
| DE (1) | DE102004004228A1 (https=) |
| TW (1) | TWI338034B (https=) |
| WO (1) | WO2004076438A2 (https=) |
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| WO2007079830A1 (de) * | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Oxaphenanthren-derivate |
| WO2007079842A1 (de) | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Benzochromenderivate zur verwendung in flüssigkristallmedien und als therapeutische wirkstoffe |
| WO2007079840A3 (de) * | 2005-12-22 | 2007-09-13 | Merck Patent Gmbh | Benzochromenderivate |
| DE102008054350A1 (de) | 2007-11-27 | 2009-05-28 | Merck Patent Gmbh | Benzo[f]chromen- und Pyrano[3,2-f]chromen-Derivate |
| DE102006057027B4 (de) | 2005-12-22 | 2023-07-06 | Merck Patent Gmbh | Benzochromenderivate |
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| JP4403307B2 (ja) * | 2003-03-28 | 2010-01-27 | Ｄｉｃ株式会社 | ６員環ラクトン骨格を有する化合物を含有する液晶組成物 |
| DE10337346A1 (de) * | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
| CN1989225B (zh) | 2004-07-02 | 2012-07-11 | 默克专利股份有限公司 | 液晶介质和包含该液晶介质的电光学显示器 |
| JP5015774B2 (ja) * | 2004-07-29 | 2012-08-29 | 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 | ジフルオロ置換複素環化合物および液晶媒体における構成要素としてのその使用 |
| JP2008522958A (ja) * | 2004-10-07 | 2008-07-03 | 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 ハフトング | クロマン誘導体類、それらの調製方法、およびそれらの使用 |
| USRE46558E1 (en) | 2005-04-28 | 2017-09-26 | Paloma Pharmaceuticals, Inc. | Compositions and methods to treat diseases characterized by cellular proliferation and angiogenesis |
| EP1958945B1 (en) * | 2005-12-08 | 2014-11-12 | JNC Corporation | Compound having hydrocoumarin skeleton, liquid crystal composition and liquid crystal display element |
| BRPI0708318A2 (pt) * | 2006-02-28 | 2011-05-24 | Paloma Pharmaceuticals, Inc. | composições e uso de compostos para tratar doenças caracterizadas por proliferação celular e angiogênese |
| US20110021618A1 (en) * | 2008-03-25 | 2011-01-27 | Paloma Pharmaceuticals, Inc. | Methods of treating fibrotic disorders |
| DE102009022309A1 (de) | 2009-05-22 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| EP2669263B1 (en) | 2010-12-21 | 2017-11-22 | JNC Corporation | Compound containing dihydrophenanthrene, liquid crystal composition and liquid crystal display device |
| WO2012112791A1 (en) | 2011-02-16 | 2012-08-23 | Paloma Pharmaceuticals, Inc. | Radiation countermeasure agents |
| EP2514800B2 (de) * | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| JP5983393B2 (ja) | 2012-01-27 | 2016-08-31 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| TWI452122B (zh) | 2012-02-24 | 2014-09-11 | Dainippon Ink & Chemicals | 液晶組成物 |
| CN104610217A (zh) * | 2015-02-09 | 2015-05-13 | 石家庄诚志永华显示材料有限公司 | 含有环戊基的二苯并吡喃酮衍生物的液晶化合物及其应用 |
| CN105647543A (zh) * | 2016-01-13 | 2016-06-08 | 石家庄诚志永华显示材料有限公司 | 液晶组合物 |
| JP6738044B2 (ja) | 2016-07-22 | 2020-08-12 | Jnc株式会社 | ベンゾピラン骨格を有する液晶性化合物、液晶組成物、および液晶表示素子 |
| CN107253942B (zh) * | 2017-06-19 | 2019-07-12 | 清华大学 | 侧向二氟亚甲基醚桥键双末端烷基环己基联苯衍生物及其制备方法与应用 |
| CN108018048B (zh) * | 2017-12-15 | 2021-11-05 | 石家庄诚志永华显示材料有限公司 | 一种负介电各项异性液晶组合物 |
| CN111484475B (zh) * | 2019-01-28 | 2022-11-04 | 北京八亿时空液晶科技股份有限公司 | 一种液晶化合物及其制备方法与应用 |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR95364E (fr) * | 1967-08-11 | 1970-09-11 | Ugine Kuhlmann | Nouveaux colorants méthiniques et leurs procédés de préparation. |
| US5648021A (en) * | 1994-01-17 | 1997-07-15 | Hoechst Aktiengesellschaft | Phenanthrene derivatives and their use in liquid-crystalline mixtures |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| JP4048570B2 (ja) * | 1997-02-25 | 2008-02-20 | チッソ株式会社 | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| JP4449105B2 (ja) * | 1999-07-12 | 2010-04-14 | チッソ株式会社 | ジベンゾピラン−６−オン誘導体およびそれを含む液晶組成物 |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
-
2004
- 2004-01-28 EP EP04705793.0A patent/EP1618101B1/de not_active Expired - Lifetime
- 2004-01-28 JP JP2006501636A patent/JP4860464B2/ja not_active Expired - Fee Related
- 2004-01-28 KR KR1020057015682A patent/KR101133905B1/ko not_active Expired - Fee Related
- 2004-01-28 DE DE200410004228 patent/DE102004004228A1/de not_active Withdrawn
- 2004-01-28 WO PCT/EP2004/000731 patent/WO2004076438A2/de not_active Ceased
- 2004-01-28 US US10/546,801 patent/US7326447B2/en not_active Expired - Lifetime
- 2004-02-24 TW TW093104656A patent/TWI338034B/zh not_active IP Right Cessation
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007079830A1 (de) * | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Oxaphenanthren-derivate |
| WO2007079842A1 (de) | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Benzochromenderivate zur verwendung in flüssigkristallmedien und als therapeutische wirkstoffe |
| WO2007079840A3 (de) * | 2005-12-22 | 2007-09-13 | Merck Patent Gmbh | Benzochromenderivate |
| US7824745B2 (en) | 2005-12-22 | 2010-11-02 | Merck Patent Gmbh | Benzochromene derivatives |
| US7998541B2 (en) * | 2005-12-22 | 2011-08-16 | Merck Patent Gmbh | Benzochromene derivatives for use in liquid crystal media and as therapeutic active substances |
| US8133887B2 (en) | 2005-12-22 | 2012-03-13 | Merck Patent Gmbh | Oxaphenanthrene derivatives |
| CN101346366B (zh) * | 2005-12-22 | 2012-11-21 | 默克专利股份有限公司 | 苯并色烯衍生物 |
| DE102006057027B4 (de) | 2005-12-22 | 2023-07-06 | Merck Patent Gmbh | Benzochromenderivate |
| DE102008054350A1 (de) | 2007-11-27 | 2009-05-28 | Merck Patent Gmbh | Benzo[f]chromen- und Pyrano[3,2-f]chromen-Derivate |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006520327A (ja) | 2006-09-07 |
| WO2004076438A3 (de) | 2005-02-24 |
| WO2004076438A2 (de) | 2004-09-10 |
| TW200418958A (en) | 2004-10-01 |
| EP1618101B1 (de) | 2017-12-20 |
| US20060177603A1 (en) | 2006-08-10 |
| KR20050115872A (ko) | 2005-12-08 |
| US7326447B2 (en) | 2008-02-05 |
| TWI338034B (en) | 2011-03-01 |
| JP4860464B2 (ja) | 2012-01-25 |
| EP1618101A2 (de) | 2006-01-25 |
| KR101133905B1 (ko) | 2012-04-10 |
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