CN102898288B - Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof - Google Patents
Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof Download PDFInfo
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- CN102898288B CN102898288B CN201210388534.7A CN201210388534A CN102898288B CN 102898288 B CN102898288 B CN 102898288B CN 201210388534 A CN201210388534 A CN 201210388534A CN 102898288 B CN102898288 B CN 102898288B
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- liquid
- liquid crystal
- crystal composition
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- crystalline cpd
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 77
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- MNCPYCODYCPASZ-UHFFFAOYSA-N 2-(2,2-difluoroethenoxy)-1,1-difluoroethene Chemical compound FC(F)=COC=C(F)F MNCPYCODYCPASZ-UHFFFAOYSA-N 0.000 title abstract 2
- 239000007788 liquid Substances 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 8
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 229960000935 dehydrated alcohol Drugs 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- -1 sodium hydride form sodium salt Chemical class 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 5
- XLEILMCZKMFZTO-UHFFFAOYSA-N 2,3-difluorooxirane Chemical class FC1OC1F XLEILMCZKMFZTO-UHFFFAOYSA-N 0.000 description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JLGADZLAECENGR-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Br)Br JLGADZLAECENGR-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000002769 thiazolinyl group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000004991 Lytropic liquid crystal Substances 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 230000018199 S phase Effects 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OPPWASLOVKWHCT-UHFFFAOYSA-N boric acid;phenol Chemical compound OB(O)O.OC1=CC=CC=C1 OPPWASLOVKWHCT-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Abstract
Description
Claims (8)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210388534.7A CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
TW102136572A TWI499661B (en) | 2012-10-13 | 2013-10-09 | A liquid crystal compound having difluoro-vinyl diether-based structure, a liquid crystal composition comprising said compound and applicaton thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210388534.7A CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
Publications (2)
Publication Number | Publication Date |
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CN102898288A CN102898288A (en) | 2013-01-30 |
CN102898288B true CN102898288B (en) | 2014-08-13 |
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CN201210388534.7A Active CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
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CN (1) | CN102898288B (en) |
TW (1) | TWI499661B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104402683A (en) * | 2014-11-21 | 2015-03-11 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal mixture containing same |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103361074B (en) * | 2013-07-01 | 2015-08-26 | 江苏和成新材料有限公司 | Comprise polyfluoro for the liquid crystalline cpd of unsaturated indenes ring and composition thereof and application |
CN109061976A (en) * | 2017-06-13 | 2018-12-21 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
CN109085725A (en) * | 2017-06-13 | 2018-12-25 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
Family Cites Families (1)
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US8349414B2 (en) * | 2008-10-27 | 2013-01-08 | Jnc Corporation | Liquid crystal composition and liquid crystal display element |
-
2012
- 2012-10-13 CN CN201210388534.7A patent/CN102898288B/en active Active
-
2013
- 2013-10-09 TW TW102136572A patent/TWI499661B/en active
Non-Patent Citations (5)
Title |
---|
AlexeiI.Mushtaetal..Synthesisandsomechemicalpropertiesof1-aryloxy-2-chloro-1 2-difluoroethenes.《Journal of Fluorine Chemistry》.2005 |
Biomolecular Chemistry》.2011,(第9期),4842-4849. * |
Justin D.Moody et al..Synthesis of internal fluorinated alkenes via facile aryloxylation of substituted phenols with aryl trifluorovinyl ethers.《Organic & Biomolecular Chemistry》.2011,(第9期),4842-4849. |
Justin D.Moody et al..Synthesis of internal fluorinated alkenes via facile aryloxylation of substituted phenols with aryl trifluorovinyl ethers.《Organic & * |
Synthesis and some chemical properties of 1-aryloxy-2-chloro-1,2-difluoroethenes;Alexei I.Mushta et al.;《Journal of Fluorine Chemistry》;20050725;第126卷;1307-1311 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104402683A (en) * | 2014-11-21 | 2015-03-11 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal mixture containing same |
CN104402683B (en) * | 2014-11-21 | 2017-02-01 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal mixture containing same |
Also Published As
Publication number | Publication date |
---|---|
CN102898288A (en) | 2013-01-30 |
TW201414812A (en) | 2014-04-16 |
TWI499661B (en) | 2015-09-11 |
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C53 | Correction of patent of invention or patent application | ||
CB03 | Change of inventor or designer information |
Inventor after: Ruan Qunqi Inventor after: Huang Wanyu Inventor after: Shi Zhibing Inventor after: Tan Yudong Inventor after: Fang Yuanfei Inventor after: Chu Zhulong Inventor after: Huang Wei Inventor after: Ding Wenquan Inventor after: Ding Yan Inventor after: Wang Junzhi Inventor before: Ruan Qunqi Inventor before: Shi Zhibing Inventor before: Tan Yudong Inventor before: Fang Yuanfei Inventor before: Chu Zhulong Inventor before: Huang Wei Inventor before: Ding Wenquan Inventor before: Ding Yan |
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Free format text: CORRECT: INVENTOR; FROM: RUAN QUNQI SHI ZHIBING TAN YUDONG FANG YUANFEI CHUZHULONG HUANG WEI DING WENQUAN DING YAN TO: RUAN QUNQI SHI ZHIBING TAN YUDONG FANG YUANFEI CHUZHULONG HUANG WEI DING WENQUAN DING YAN WANG JUNZHI HUANG WANYU |
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Owner name: DAXING MATERIALS CORP. Effective date: 20140516 |
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Effective date of registration: 20140516 Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Applicant after: Daxin Materials Corp. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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Address after: East side of Yangtze River bridge, Yangzhong, Yangzhong, Jiangsu Co-patentee after: Daxin Materials Corp. Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Co-patentee before: Daxin Materials Corp. Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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Address after: Building 2, Sino Japan Cooperation Innovation Park, No. 16, Zidan Road, Qinhuai District, Nanjing, Jiangsu Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Patentee after: Daxin Materials Corp. Address before: 212212 east side of Yangzhong Yangtze River Bridge, Yangzhong City, Jiangsu Province Patentee before: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Patentee before: Daxin Materials Corp. |