JPS6069045A - ジ置換エタン並びに液晶材料及び装置に於けるその使用 - Google Patents
ジ置換エタン並びに液晶材料及び装置に於けるその使用Info
- Publication number
- JPS6069045A JPS6069045A JP1180984A JP1180984A JPS6069045A JP S6069045 A JPS6069045 A JP S6069045A JP 1180984 A JP1180984 A JP 1180984A JP 1180984 A JP1180984 A JP 1180984A JP S6069045 A JPS6069045 A JP S6069045A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl group
- liquid crystal
- compounds
- mixture
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims description 86
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 60
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 125
- 239000000203 mixture Substances 0.000 claims description 107
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 230000005684 electric field Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 230000000694 effects Effects 0.000 description 35
- 239000004990 Smectic liquid crystal Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000004093 cyano group Chemical group *C#N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 19
- 230000008859 change Effects 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000007704 transition Effects 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- -1 di-substituted ethane Chemical class 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000003098 cholesteric effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- 239000007818 Grignard reagent Substances 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000374 eutectic mixture Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000008520 organization Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000000039 congener Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 235000015096 spirit Nutrition 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- JTNGTRJQFQXTLA-UHFFFAOYSA-N 2-(4-pentylcyclohexyl)acetyl chloride Chemical compound CCCCCC1CCC(CC(Cl)=O)CC1 JTNGTRJQFQXTLA-UHFFFAOYSA-N 0.000 description 2
- LWAPZSAZOVPOIO-UHFFFAOYSA-N 2-(4-propylcyclohexyl)acetyl chloride Chemical compound CCCC1CCC(CC(Cl)=O)CC1 LWAPZSAZOVPOIO-UHFFFAOYSA-N 0.000 description 2
- GEBUSPQBSWYLBN-UHFFFAOYSA-N 4-ethyl-2-fluoro-1-phenylbenzene Chemical group FC1=CC(CC)=CC=C1C1=CC=CC=C1 GEBUSPQBSWYLBN-UHFFFAOYSA-N 0.000 description 2
- OXMZZKBMFGEIKR-XYPYZODXSA-N C(CCC)[C@@H]1CC[C@H](CC1)CC(=O)Cl Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CC(=O)Cl OXMZZKBMFGEIKR-XYPYZODXSA-N 0.000 description 2
- LWAPZSAZOVPOIO-MGCOHNPYSA-N CCC[C@H]1CC[C@H](CC(Cl)=O)CC1 Chemical compound CCC[C@H]1CC[C@H](CC(Cl)=O)CC1 LWAPZSAZOVPOIO-MGCOHNPYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 210000003127 knee Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HIQULLQAUHZSSJ-UHFFFAOYSA-N 1-(2-methylbutyl)-2-phenylbenzene Chemical group CCC(C)CC1=CC=CC=C1C1=CC=CC=C1 HIQULLQAUHZSSJ-UHFFFAOYSA-N 0.000 description 1
- KRCZDDKSWIWWGR-UHFFFAOYSA-N 1-(3-fluoro-4-phenylphenyl)-4-propylcyclohexan-1-ol Chemical compound C1CC(CCC)CCC1(O)C1=CC=C(C=2C=CC=CC=2)C(F)=C1 KRCZDDKSWIWWGR-UHFFFAOYSA-N 0.000 description 1
- DLMYHUARHITGIJ-UHFFFAOYSA-N 1-ethyl-2-phenylbenzene Chemical group CCC1=CC=CC=C1C1=CC=CC=C1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 1
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- URJIMSMUIDZLTA-UHFFFAOYSA-N 2-(2-phenylphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC=C1C1=CC=CC=C1 URJIMSMUIDZLTA-UHFFFAOYSA-N 0.000 description 1
- YFNHOTZVDNNLFV-UHFFFAOYSA-N 2-(4-ethylcyclohexyl)acetyl chloride Chemical compound CCC1CCC(CC(Cl)=O)CC1 YFNHOTZVDNNLFV-UHFFFAOYSA-N 0.000 description 1
- QXTDWCATDIBLAL-UHFFFAOYSA-N 2-(4-pentylphenyl)benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=CC=C1C#N QXTDWCATDIBLAL-UHFFFAOYSA-N 0.000 description 1
- KLYUOIDZTZVDLE-UHFFFAOYSA-N 2-fluoro-1-phenyl-4-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC=C(C=2C=CC=CC=2)C(F)=C1 KLYUOIDZTZVDLE-UHFFFAOYSA-N 0.000 description 1
- GIWWLDRRWWDXJH-UHFFFAOYSA-N 2-methylbutyl benzenesulfonate Chemical compound CCC(C)COS(=O)(=O)C1=CC=CC=C1 GIWWLDRRWWDXJH-UHFFFAOYSA-N 0.000 description 1
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 1
- 239000005215 4-Cyano-4'-n-octyloxybiphenyl Substances 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 101000725988 Drosophila melanogaster COP9 signalosome complex subunit 3 Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- NQSUQAQPOPPGIN-UHFFFAOYSA-M [Br-].FC1=CC([Mg+])=CC=C1C1=CC=CC=C1 Chemical compound [Br-].FC1=CC([Mg+])=CC=C1C1=CC=CC=C1 NQSUQAQPOPPGIN-UHFFFAOYSA-M 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000013473 artificial intelligence Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013526 supercooled liquid Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8302119 | 1983-01-26 | ||
| GB838302119A GB8302119D0 (en) | 1983-01-26 | 1983-01-26 | Disubstituted ethanes |
| GB8328370 | 1983-10-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6069045A true JPS6069045A (ja) | 1985-04-19 |
| JPH0225894B2 JPH0225894B2 (enrdf_load_stackoverflow) | 1990-06-06 |
Family
ID=10536967
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1180984A Granted JPS6069045A (ja) | 1983-01-26 | 1984-01-25 | ジ置換エタン並びに液晶材料及び装置に於けるその使用 |
| JP1181084A Granted JPS6069046A (ja) | 1983-01-26 | 1984-01-25 | 液晶化合物の製造用ビフェニル類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1181084A Granted JPS6069046A (ja) | 1983-01-26 | 1984-01-25 | 液晶化合物の製造用ビフェニル類 |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS6069045A (enrdf_load_stackoverflow) |
| GB (1) | GB8302119D0 (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61282328A (ja) * | 1985-06-10 | 1986-12-12 | Chisso Corp | シクロヘキサン誘導体 |
| JPS6268883A (ja) * | 1985-08-26 | 1987-03-28 | コミサリヤ・ア・レネルジ・アトミク | １−（アルキルシクロヘキシル）−２−（アルキルフルオロビフエニリル）エタンを含むネマチツク液晶混合物 |
| JPH1072384A (ja) * | 1996-08-28 | 1998-03-17 | Chisso Corp | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| WO2009145101A1 (ja) * | 2008-05-29 | 2009-12-03 | チッソ株式会社 | フッ素原子を有する液晶性四環化合物、液晶組成物、及び液晶表示素子 |
| JP2010111686A (ja) * | 2009-12-24 | 2010-05-20 | Chisso Corp | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| WO2015016093A1 (en) * | 2013-07-30 | 2015-02-05 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57114532A (en) * | 1980-11-10 | 1982-07-16 | Merck Patent Gmbh | Fluorine-containiing cyclohexylbiphenyl derivatives, dielectric body containing them and electronic optical display element |
| JPS57165326A (en) * | 1981-04-03 | 1982-10-12 | Asahi Glass Co Ltd | Trans-4-alkyl-(4'-fluorobiphenyl-4)cyclohexane |
| JPS59155485A (ja) * | 1983-02-22 | 1984-09-04 | Canon Inc | 液晶組成物 |
| JPS6048945A (ja) * | 1983-08-27 | 1985-03-16 | Chisso Corp | シクロヘキシルビフエニルのフッ素化物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1460295A (en) * | 1973-06-01 | 1976-12-31 | Boots Co Ltd | Biphenyls and diphenyl ethers |
-
1983
- 1983-01-26 GB GB838302119A patent/GB8302119D0/en active Pending
-
1984
- 1984-01-25 JP JP1180984A patent/JPS6069045A/ja active Granted
- 1984-01-25 JP JP1181084A patent/JPS6069046A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57114532A (en) * | 1980-11-10 | 1982-07-16 | Merck Patent Gmbh | Fluorine-containiing cyclohexylbiphenyl derivatives, dielectric body containing them and electronic optical display element |
| JPS57165326A (en) * | 1981-04-03 | 1982-10-12 | Asahi Glass Co Ltd | Trans-4-alkyl-(4'-fluorobiphenyl-4)cyclohexane |
| JPS59155485A (ja) * | 1983-02-22 | 1984-09-04 | Canon Inc | 液晶組成物 |
| JPS6048945A (ja) * | 1983-08-27 | 1985-03-16 | Chisso Corp | シクロヘキシルビフエニルのフッ素化物 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61282328A (ja) * | 1985-06-10 | 1986-12-12 | Chisso Corp | シクロヘキサン誘導体 |
| JPS6268883A (ja) * | 1985-08-26 | 1987-03-28 | コミサリヤ・ア・レネルジ・アトミク | １−（アルキルシクロヘキシル）−２−（アルキルフルオロビフエニリル）エタンを含むネマチツク液晶混合物 |
| JPH1072384A (ja) * | 1996-08-28 | 1998-03-17 | Chisso Corp | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| WO2009145101A1 (ja) * | 2008-05-29 | 2009-12-03 | チッソ株式会社 | フッ素原子を有する液晶性四環化合物、液晶組成物、及び液晶表示素子 |
| JP5531954B2 (ja) * | 2008-05-29 | 2014-06-25 | Ｊｎｃ株式会社 | フッ素原子を有する液晶性四環化合物、液晶組成物、及び液晶表示素子 |
| JP2010111686A (ja) * | 2009-12-24 | 2010-05-20 | Chisso Corp | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| WO2015016093A1 (en) * | 2013-07-30 | 2015-02-05 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
| JP2015044797A (ja) * | 2013-07-30 | 2015-03-12 | 株式会社半導体エネルギー研究所 | 有機化合物、液晶組成物、液晶素子及び液晶表示装置 |
| US9580651B2 (en) | 2013-07-30 | 2017-02-28 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8302119D0 (en) | 1983-03-02 |
| JPH0446251B2 (enrdf_load_stackoverflow) | 1992-07-29 |
| JPH0225894B2 (enrdf_load_stackoverflow) | 1990-06-06 |
| JPS6069046A (ja) | 1985-04-19 |
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Legal Events
| Date | Code | Title | Description |
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| EXPY | Cancellation because of completion of term |