JPH0572912B2 - - Google Patents

Info

Publication number

JPH0572912B2

JPH0572912B2 JP62153792A JP15379287A JPH0572912B2 JP H0572912 B2 JPH0572912 B2 JP H0572912B2 JP 62153792 A JP62153792 A JP 62153792A JP 15379287 A JP15379287 A JP 15379287A JP H0572912 B2 JPH0572912 B2 JP H0572912B2

Authority

JP

Japan

Prior art keywords

group

compound

phase

liquid crystal

formula

Prior art date

1987-06-19

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.)

Expired - Fee Related

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• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 150000001875 compounds Chemical class 0.000 description 33
• 239000012071 phase Substances 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 239000004973 liquid crystal related substance Substances 0.000 description 11
• 239000004990 Smectic liquid crystal Substances 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• -1 phenol compound Chemical class 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 239000000203 mixture Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 230000007704 transition Effects 0.000 description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 230000005621 ferroelectricity Effects 0.000 description 4
• 230000010287 polarization Effects 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 230000002269 spontaneous effect Effects 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
• 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
• 238000010898 silica gel chromatography Methods 0.000 description 3
• 239000004988 Nematic liquid crystal Substances 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 239000012530 fluid Substances 0.000 description 2
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 238000002329 infrared spectrum Methods 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 238000000034 method Methods 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
• 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 2
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 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 description 2
• 125000000913 palmityl 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])C([H])([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 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 230000005684 electric field Effects 0.000 description 1
• 238000005401 electroluminescence Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000004043 responsiveness Effects 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1