CN102992971A - 多氟代乙烷醚液晶化合物及其组合物 - Google Patents
多氟代乙烷醚液晶化合物及其组合物 Download PDFInfo
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- CN102992971A CN102992971A CN2012103828039A CN201210382803A CN102992971A CN 102992971 A CN102992971 A CN 102992971A CN 2012103828039 A CN2012103828039 A CN 2012103828039A CN 201210382803 A CN201210382803 A CN 201210382803A CN 102992971 A CN102992971 A CN 102992971A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 14
- VHPYNVZYZFYVII-UHFFFAOYSA-N fluoroethane Chemical compound [CH2]CF VHPYNVZYZFYVII-UHFFFAOYSA-N 0.000 title abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000010792 warming Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- -1 fluoro phenylenes Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
组分代码 | 重量百分数(%) | 性能参数测试结果 |
2CPWO2 | 8 | Δn=0.098 |
化合物13 | 10 | Δε=-3.4 |
3CWO4 | 13 | Cp=78 |
3CCWO2 | 10 | η=26.9mpa.s |
4CCWO2 | 6 | Vth=2.28V |
2PGP3 | 2 | |
3CC1OWO2 | 7 | |
2PWP3 | 4 | |
VCWO2 | 5 | |
3CCV | 30 | |
3CCV1 | 5 |
组分代码 | 重量百分数(%) | 性能参数测试结果 |
2CPWO2 | 8 | Δn=0.107 |
3CPWO2 | 10 | Δε=-3.0 |
3CWO4 | 13 | Cp=82 |
3CCWO2 | 10 | η=25mpa.s |
4CCWO2 | 6 | Vth=2.37V |
2PGP3 | 2 | |
3CC1OWO2 | 7 | |
2PWP3 | 4 | |
VCWO2 | 5 | |
3CCV | 30 | |
3CCV1 | 5 |
组分代码 | 重量百分数(%) | 性能参数测试结果 |
2PGP3 | 10 | △n=0.098 |
5CCGF | 3 | Cp=78℃ |
VCCP1 | 12 | η=27.9mpa.s |
3CCV | 38 | △ε=5.6 |
V2CCP1 | 11 | Vth=1.39 |
3CCV1 | 5 | |
3PUQUF | 6 | |
3CCUF | 3 | |
化合物4 | 8 | |
3CCPOCF3 | 4 |
组分代码 | 重量百分数(%) | 性能参数测试结果 |
2PGP3 | 10 | △n=0.109 |
5CCGF | 3 | Cp=82℃ |
VCCP1 | 12 | η=26.2mpa.s |
3CCV | 38 | △ε=5.2 |
V2CCP1 | 11 | Vth=1.46 |
3CCV1 | 5 | |
3PUQUF | 6 | |
3CCUF | 3 | |
3CPUF | 8 | |
3CCPOCF3 | 4 |
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201210382803.9A CN102992971B (zh) | 2012-10-11 | 2012-10-11 | 多氟代乙烷醚液晶化合物及其组合物 |
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Application Number | Priority Date | Filing Date | Title |
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CN201210382803.9A CN102992971B (zh) | 2012-10-11 | 2012-10-11 | 多氟代乙烷醚液晶化合物及其组合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102992971A true CN102992971A (zh) | 2013-03-27 |
CN102992971B CN102992971B (zh) | 2015-05-20 |
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CN201210382803.9A Active CN102992971B (zh) | 2012-10-11 | 2012-10-11 | 多氟代乙烷醚液晶化合物及其组合物 |
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Country | Link |
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CN (1) | CN102992971B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019202951A (ja) * | 2018-05-22 | 2019-11-28 | Jnc株式会社 | 液晶性化合物、液晶組成物および液晶表示素子 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0558936A (ja) * | 1991-09-04 | 1993-03-09 | Asahi Glass Co Ltd | パーフルオロアルカン誘導体化合物及びそれを含有する液晶組成物 |
JPH08109372A (ja) * | 1994-08-17 | 1996-04-30 | Asahi Chem Ind Co Ltd | 含フッ素潤滑剤よりなる冷媒組成物 |
-
2012
- 2012-10-11 CN CN201210382803.9A patent/CN102992971B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0558936A (ja) * | 1991-09-04 | 1993-03-09 | Asahi Glass Co Ltd | パーフルオロアルカン誘導体化合物及びそれを含有する液晶組成物 |
JPH08109372A (ja) * | 1994-08-17 | 1996-04-30 | Asahi Chem Ind Co Ltd | 含フッ素潤滑剤よりなる冷媒組成物 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019202951A (ja) * | 2018-05-22 | 2019-11-28 | Jnc株式会社 | 液晶性化合物、液晶組成物および液晶表示素子 |
JP7187819B2 (ja) | 2018-05-22 | 2022-12-13 | Jnc株式会社 | 液晶性化合物、液晶組成物および液晶表示素子 |
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Publication number | Publication date |
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CN102992971B (zh) | 2015-05-20 |
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Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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Effective date of registration: 20210707 Address after: Room 711, Building 2, Courtyard 1, Jinhang Middle Road, Shunyi District, Beijing 101300 Patentee after: Beijing culture science and technology finance leasing Limited by Share Ltd. Address before: 246000 No. 9, Xiang Zhang Road, Daguan District Economic Development Zone, Anqing, Anhui Patentee before: ANQING FEIKAI NEW MATERIAL Co.,Ltd. |
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Effective date of registration: 20230403 Address after: 246000 No. 9, Xiang Zhang Road, Daguan District Economic Development Zone, Anqing, Anhui Patentee after: ANQING FEIKAI NEW MATERIAL Co.,Ltd. Address before: Room 711, Building 2, Courtyard 1, Jinhang Middle Road, Shunyi District, Beijing 101300 Patentee before: Beijing culture science and technology finance leasing Limited by Share Ltd. |