CN102659533B - 作为液晶介质的组分的茚衍生物及其制备方法和应用 - Google Patents
作为液晶介质的组分的茚衍生物及其制备方法和应用 Download PDFInfo
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- CN102659533B CN102659533B CN201210104215.9A CN201210104215A CN102659533B CN 102659533 B CN102659533 B CN 102659533B CN 201210104215 A CN201210104215 A CN 201210104215A CN 102659533 B CN102659533 B CN 102659533B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 210000002858 crystal cell Anatomy 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 6
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 5
- 230000004044 response Effects 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 12
- 239000012071 phase Substances 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
- 239000003208 petroleum Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- 239000013256 coordination polymer Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
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- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 210000004263 induced pluripotent stem cell Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 0 C*c1ccc(CC(*C2CCC(*)CC2)C2)c2c1 Chemical compound C*c1ccc(CC(*C2CCC(*)CC2)C2)c2c1 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Families Citing this family (5)
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CN102875339B (zh) * | 2012-09-27 | 2015-05-27 | 江苏和成显示科技股份有限公司 | 液晶化合物及其制备方法和应用 |
CN102994100B (zh) * | 2012-10-11 | 2015-04-15 | 江苏和成显示科技股份有限公司 | 液晶组合物和含有该液晶组合物的液晶显示器件 |
CN103351275B (zh) * | 2013-07-01 | 2015-06-10 | 江苏和成显示科技股份有限公司 | 包含多氟代茚满的液晶化合物及其组合物和应用 |
CN106675575B (zh) * | 2015-11-06 | 2018-12-18 | 江苏和成显示科技有限公司 | 一种介电负性液晶化合物及其制备方法与应用 |
CN108690640B (zh) * | 2018-07-17 | 2022-02-25 | 烟台显华化工科技有限公司 | 一种含茚环的化合物及液晶介质 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1026143A1 (en) * | 1997-10-24 | 2000-08-09 | Chisso Corporation | Novel liquid-crystal compounds having large negative value of permittivity anisotropy, liquid-crystal composition, and liquid-crystal display element |
US20030222243A1 (en) * | 2002-04-04 | 2003-12-04 | Merck Patent Gmbh | Fluorinated indenes and 1,7-dihydroindacenes of negative dielectric anisotrophy |
CN101665701A (zh) * | 2009-09-25 | 2010-03-10 | 北京八亿时空液晶材料科技有限公司 | 一种向列型液晶组合物 |
CN101735823A (zh) * | 2009-12-18 | 2010-06-16 | 北京八亿时空液晶材料科技有限公司 | 一种负介电各向异性液晶组合物 |
CN102153442A (zh) * | 2011-03-04 | 2011-08-17 | 石家庄诚志永华显示材料有限公司 | 烷基双环己基2、3-二氟苯丁烯类液晶化合物及其用途 |
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- 2012-04-10 CN CN201210104215.9A patent/CN102659533B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1026143A1 (en) * | 1997-10-24 | 2000-08-09 | Chisso Corporation | Novel liquid-crystal compounds having large negative value of permittivity anisotropy, liquid-crystal composition, and liquid-crystal display element |
US20030222243A1 (en) * | 2002-04-04 | 2003-12-04 | Merck Patent Gmbh | Fluorinated indenes and 1,7-dihydroindacenes of negative dielectric anisotrophy |
CN101665701A (zh) * | 2009-09-25 | 2010-03-10 | 北京八亿时空液晶材料科技有限公司 | 一种向列型液晶组合物 |
CN101735823A (zh) * | 2009-12-18 | 2010-06-16 | 北京八亿时空液晶材料科技有限公司 | 一种负介电各向异性液晶组合物 |
CN102153442A (zh) * | 2011-03-04 | 2011-08-17 | 石家庄诚志永华显示材料有限公司 | 烷基双环己基2、3-二氟苯丁烯类液晶化合物及其用途 |
Non-Patent Citations (1)
Title |
---|
用液晶基元修饰的联茚满烯二酮衍生物的合成;郭辉等;《有机化学》;20051231;第25卷;第327页 * |
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Inventor after: Liu Qi Inventor after: Gong Qiming Inventor after: Tan Yudong Inventor after: Chen Zhaoyuan Inventor after: You Shizhi Inventor after: Wang Junzhi Inventor after: You Huiru Inventor before: Liu Qi Inventor before: Gong Qiming Inventor before: Tan Yudong Inventor before: Chen Zhaoyuan Inventor before: You Shizhi |
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