CN101928199A - 一种双乙烯类液晶化合物及其制备方法 - Google Patents
一种双乙烯类液晶化合物及其制备方法 Download PDFInfo
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- CN101928199A CN101928199A CN2010102448616A CN201010244861A CN101928199A CN 101928199 A CN101928199 A CN 101928199A CN 2010102448616 A CN2010102448616 A CN 2010102448616A CN 201010244861 A CN201010244861 A CN 201010244861A CN 101928199 A CN101928199 A CN 101928199A
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- divinyl
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 53
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 150000001336 alkenes Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 238000007239 Wittig reaction Methods 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 230000008859 change Effects 0.000 claims abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 18
- -1 aliphatic alcohols Chemical class 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003849 aromatic solvent Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- 235000009518 sodium iodide Nutrition 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- SRJQTHAZUNRMPR-UYQKXTDMSA-N spinosyn A Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRJQTHAZUNRMPR-UYQKXTDMSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 6
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 230000006837 decompression Effects 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical class CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- KKWVSPRXEUBOHT-UHFFFAOYSA-N CC1=CC=CC=C1.[AlH3] Chemical compound CC1=CC=CC=C1.[AlH3] KKWVSPRXEUBOHT-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VNXUIRXHRSJUNQ-UHFFFAOYSA-N bromoethane;triphenylphosphane Chemical compound CCBr.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VNXUIRXHRSJUNQ-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical class [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 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)
- Liquid Crystal Substances (AREA)
Abstract
Description
Claims (10)
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CN 201010244861 CN101928199B (zh) | 2010-08-04 | 2010-08-04 | 一种双乙烯类液晶化合物及其制备方法 |
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CN 201010244861 CN101928199B (zh) | 2010-08-04 | 2010-08-04 | 一种双乙烯类液晶化合物及其制备方法 |
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CN101928199A true CN101928199A (zh) | 2010-12-29 |
CN101928199B CN101928199B (zh) | 2013-02-13 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102807468A (zh) * | 2012-07-19 | 2012-12-05 | 烟台万润精细化工股份有限公司 | 一种丙基邻氟苯类化合物的制备方法 |
CN104610978A (zh) * | 2015-02-09 | 2015-05-13 | 石家庄诚志永华显示材料有限公司 | 液晶化合物及包含该化合物的液晶介质 |
CN106190172A (zh) * | 2015-05-29 | 2016-12-07 | 三星显示有限公司 | 液晶组合物以及包含其的液晶显示设备 |
WO2017126275A1 (ja) * | 2016-01-20 | 2017-07-27 | Jnc株式会社 | 2原子結合基と2,3-ジフルオロフェニレンを有する4環液晶性化合物、液晶組成物および液晶表示素子 |
CN108559526A (zh) * | 2018-06-06 | 2018-09-21 | 江苏创拓新材料有限公司 | 高纯度含双键液晶单体的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002193852A (ja) * | 2000-12-19 | 2002-07-10 | Merck Patent Gmbh | 負のdc異方性のアルケニル化合物と液晶性媒体 |
CN1436761A (zh) * | 2002-02-06 | 2003-08-20 | 清华大学 | 一种烷基环己基炔类液晶及其生产方法 |
JP2005272351A (ja) * | 2004-03-24 | 2005-10-06 | Yuichiro Haramoto | スチリル誘導体及びその製造方法 |
-
2010
- 2010-08-04 CN CN 201010244861 patent/CN101928199B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002193852A (ja) * | 2000-12-19 | 2002-07-10 | Merck Patent Gmbh | 負のdc異方性のアルケニル化合物と液晶性媒体 |
CN1436761A (zh) * | 2002-02-06 | 2003-08-20 | 清华大学 | 一种烷基环己基炔类液晶及其生产方法 |
JP2005272351A (ja) * | 2004-03-24 | 2005-10-06 | Yuichiro Haramoto | スチリル誘導体及びその製造方法 |
Non-Patent Citations (1)
Title |
---|
李洪胜: "双烯基液晶化合物的合成及其性能研究", 《河北科技大学硕士学位论文》, 10 March 2010 (2010-03-10), pages 33 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102807468A (zh) * | 2012-07-19 | 2012-12-05 | 烟台万润精细化工股份有限公司 | 一种丙基邻氟苯类化合物的制备方法 |
CN102807468B (zh) * | 2012-07-19 | 2014-12-10 | 烟台万润精细化工股份有限公司 | 一种丙基邻氟苯类化合物的制备方法 |
CN104610978A (zh) * | 2015-02-09 | 2015-05-13 | 石家庄诚志永华显示材料有限公司 | 液晶化合物及包含该化合物的液晶介质 |
CN106190172A (zh) * | 2015-05-29 | 2016-12-07 | 三星显示有限公司 | 液晶组合物以及包含其的液晶显示设备 |
WO2017126275A1 (ja) * | 2016-01-20 | 2017-07-27 | Jnc株式会社 | 2原子結合基と2,3-ジフルオロフェニレンを有する4環液晶性化合物、液晶組成物および液晶表示素子 |
KR20180101346A (ko) | 2016-01-20 | 2018-09-12 | 제이엔씨 주식회사 | 2원자 결합기와 2,3-디플루오로페닐렌을 가지는 4환 액정성 화합물, 액정 조성물 및 액정 표시 소자 |
JPWO2017126275A1 (ja) * | 2016-01-20 | 2018-11-08 | Jnc株式会社 | 2原子結合基と2,3−ジフルオロフェニレンを有する4環液晶性化合物、液晶組成物および液晶表示素子 |
CN108559526A (zh) * | 2018-06-06 | 2018-09-21 | 江苏创拓新材料有限公司 | 高纯度含双键液晶单体的制备方法 |
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Publication number | Publication date |
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CN101928199B (zh) | 2013-02-13 |
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