CN1134168A - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
- Publication number
- CN1134168A CN1134168A CN94194026A CN94194026A CN1134168A CN 1134168 A CN1134168 A CN 1134168A CN 94194026 A CN94194026 A CN 94194026A CN 94194026 A CN94194026 A CN 94194026A CN 1134168 A CN1134168 A CN 1134168A
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- CN
- China
- Prior art keywords
- coo
- oco
- liquid crystalline
- crystalline cpd
- hydroxyl
- Prior art date
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- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 125000006850 spacer group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000004973 liquid crystal related substance Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- 238000000034 method Methods 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 239000012071 phase Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- -1 Carboxyl acyl chloride Chemical class 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 150000001263 acyl chlorides Chemical class 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 229960004756 ethanol Drugs 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 11
- 239000004990 Smectic liquid crystal Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 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 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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 3
- 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 2
- GAECNRSTNDHUBE-UHFFFAOYSA-N 1-[4-(chloromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(CCl)C=C1 GAECNRSTNDHUBE-UHFFFAOYSA-N 0.000 description 2
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 2
- OKGMOHVZKYWVHL-UHFFFAOYSA-N 4-(5-octoxypyrimidin-2-yl)phenol Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(O)C=C1 OKGMOHVZKYWVHL-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
- PQAKXUJJORJOPW-UHFFFAOYSA-N C(CCCCCCCCCC)O.[O] Chemical compound C(CCCCCCCCCC)O.[O] PQAKXUJJORJOPW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YSNYZCPALUKLFL-UHFFFAOYSA-N [O].CCCCCCCCCCC Chemical compound [O].CCCCCCCCCCC YSNYZCPALUKLFL-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- QBOWIPYEPOVPGR-UHFFFAOYSA-N ethyl 3-chloro-4-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(Cl)=C1 QBOWIPYEPOVPGR-UHFFFAOYSA-N 0.000 description 2
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 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
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229960004839 potassium iodide Drugs 0.000 description 2
- 235000007715 potassium iodide Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- JFAXJRJMFOACBO-UHFFFAOYSA-N (4-hydroxyphenyl) benzoate Chemical compound C1=CC(O)=CC=C1OC(=O)C1=CC=CC=C1 JFAXJRJMFOACBO-UHFFFAOYSA-N 0.000 description 1
- NCRNCSZWOOYBQF-UHFFFAOYSA-N 1,1-Dimethoxydecane Chemical compound CCCCCCCCCC(OC)OC NCRNCSZWOOYBQF-UHFFFAOYSA-N 0.000 description 1
- WHSAZJZPFFJHKA-UHFFFAOYSA-N 2,2-dimethoxyethyl benzoate Chemical compound COC(OC)COC(=O)C1=CC=CC=C1 WHSAZJZPFFJHKA-UHFFFAOYSA-N 0.000 description 1
- MHSAUKQYUPPMRZ-UHFFFAOYSA-N 2-(4-hexoxyphenyl)pyrimidin-5-ol Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=C(O)C=N1 MHSAUKQYUPPMRZ-UHFFFAOYSA-N 0.000 description 1
- QSOVSKMNRYAVJR-UHFFFAOYSA-N 2-benzoyloxybenzoic acid Chemical group OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 QSOVSKMNRYAVJR-UHFFFAOYSA-N 0.000 description 1
- MDURQPNBPHBIFN-UHFFFAOYSA-N 2-pentoxyphenol Chemical compound CCCCCOC1=CC=CC=C1O MDURQPNBPHBIFN-UHFFFAOYSA-N 0.000 description 1
- NGRCAKOXBYIZJP-LLVKDONJSA-N 3-chloro-4-[(2r)-octan-2-yl]oxybenzoic acid Chemical compound CCCCCC[C@@H](C)OC1=CC=C(C(O)=O)C=C1Cl NGRCAKOXBYIZJP-LLVKDONJSA-N 0.000 description 1
- OUANAAHOQVMJCH-UHFFFAOYSA-N 4-benzoyloxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC(=O)C1=CC=CC=C1 OUANAAHOQVMJCH-UHFFFAOYSA-N 0.000 description 1
- RGRXSVOGSNDAHW-UHFFFAOYSA-N C(=O)O.C(CCCCCC)C1=CC=CC=C1 Chemical compound C(=O)O.C(CCCCCC)C1=CC=CC=C1 RGRXSVOGSNDAHW-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000405414 Rehmannia Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- NFJDWPJJWRNWNF-UHFFFAOYSA-N [4-(chloromethyl)phenyl] benzoate Chemical compound C1=CC(CCl)=CC=C1OC(=O)C1=CC=CC=C1 NFJDWPJJWRNWNF-UHFFFAOYSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 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
- 230000006837 decompression Effects 0.000 description 1
- 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 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 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
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
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Abstract
式I的液晶化合物，其中X是芳族或脂族环系，n是2到6间的整数，每个Y各自互相独立地为一个直接键，-COO-、-OCO-、-O-、-CONH或-CON(R)-，其中R是C1至C4烷基，A是间隔基团，M是介晶基团，和B是侧链；这些化合物尤其适用于显示或用于生产反光涂料。
X(-Y-A-Y-M-Y-B)n (I)
Description
已知有大量液晶化合物。但是它们一般不以类似玻璃的方式固化。具有液晶性质并以类似玻璃的方式固化的已知化合物公开于诸如DE-A 37 03 640、DE-A 38 27 603、DE-A 38 30 968和EP-A-504 660等。前三份申请所叙述的化合物的共同性质是它们甚至易于从玻璃态结晶，并因此在凝固状态下的取向不稳定。在结晶的情况下所采用的任何混合物也不再稳定，这是由于分子在晶体中形成混晶要求比在各向异性流体中对掺混性要求高得多。
EP-A-504 660中所述的化合物形成稳态玻璃体。它们具有很高的平行于分子长轴的偶极矩，并且形成向列型或近晶状A型相。沿分子长轴的偶极矩意谓着这些材料在电场中与分子长轴平行排列，因此它们不具有铁电特性，而且存在的螺旋超结构在电场中是不稳定的。
还已知具有一种确定结构并且其中介晶基团(mesogenic group)经一个间隔基团(spacer)与中心单元(central unit)键合的液晶体系(例如DE-A-40 11 811)。但是，这些材料虽然不以与玻璃类似的方式固化，但由于具有高度对称性，它们还是非常易于结晶。此外，Liquid Crystals 11(5)(1992)，779页描述了经一个间隔基团与中心单元键合的铁电液晶。这些材料具有对热、弱的酸碱和水不稳定的介晶结构(mesogenic structure)。
用作液晶铁电材料的理想化合物是那些在冷却过程中经历向列型、
近晶状A型和近晶状C型的相变化的化合物。另外，这些材料应该具有高流动粘度以防止其显示是压敏的，并且尤其是应该对弱的酸碱稳定。此外最好具有与其它液晶化合物较好的掺混特性。
本发明的一个目的是提供新型的液晶化合物，这些化合物以类似玻璃的方式固化，并具有近晶状和向列型相，对温度和pH值的变化、对水均不敏感，并且具有高流动粘度。
我们已经发现这一目的通过下式I的化合物而实现
X(-Y-A-Y-M-Y-B)n I，其中X是芳族或脂族环系；n是2到6的整数；每个Y彼此互相独立地为直接键、-COO-、-OCO-、-O-、-CONH-或-CON(R)，其中R是C1至C4烷基；A是间隔基团；M是介晶基团；和B是侧链。
X优选是三取代的苯基或环己基，其中取代基特别是相互为间位。
在基团Y中，特别优选的是-OCO-、-O-和-COO-。
已知的用于间隔目的的所有间隔基团都可在此充当间隔基团，这些基团通常经酯或醚基团或经直接键与X相联。间隔基团一般具有2到30个碳原子，优选2到12个碳原子，并且可在链上被诸如O、S、NH或NCH3间隔。合适的间隔基团链的取代基是氟、氯、溴、氰基、甲基和乙基。
代表性的间隔基团的例子包括：
(CH2)p，(CH2CH2O)mCH2CH2，CH2CH2SCH2CH2，CH2CH2NHCH2CH2，或
其中m是1到3；和p是1到12。M可以是已知的介晶基团。特别合适的是含有芳基或杂芳基的基团。具体地说，介晶基团符合式III：
(-T-Y1)r-T III，其中每个T彼此互相独立地为芳基或杂芳基；每个Y1彼此互相独立地为O、COO、OCO、CH2O、OCH2、CH＝N、N＝CH或直接键，和r是1到3。r优选1或2。
T一般是芳香碳环或杂环系，并可以被氟、氯、溴、氰基、羟基或硝基取代，例如符合下列基本结构：
或
特别优选的介晶基团M的例子包括： 或
测链B的例子包括C2至C30烷基或链烯基，优选C2至C11烷基，其中基团可以是直链或支链，可以被O、OCO、COO、
NH或N(CH3)间隔1次或多次，并且可以被苯基、氟、氯、溴、氰基或羟基取代。
单个基团B的例子包括：C2H5、C3H7、C4H9、C5H11、C6H13、C7H15、C8H17、C9H19、C10H21、C11H23、C12H25、
CH2CH＝CH2，(CH2)7CH＝CH2或(CH2)8CH＝CH2.手性侧链B的例子包括： 
或
其中R1是C1至C12烷基，并可以是手性或非手性的，R2是R1、氟或氯。
优选的基团R1的例子为：CpH2p＋1，
或
其中p从1至12。为了制备式I化合物(其中与X相邻的Y是COO、CONH或
而且n是3)，式X(COCl)3的羧酰氯可以与下式的化合物用本身已知的方法反应。HO-A-Y-M-Y-B.H2N-A-Y-M-Y-B，或
对于n＝3并且Y＝与X相邻的OCO式X(OH)3的化合物可以类似地与式ClOC-A-Y-M-Y-B的化合物反应。
对于Y＝O，羟基可以与卤代烷基反应。
对于n≠3的化合物，则相应地应用，即一般的制备方法可从文献得知，可能被提及的一个例子是与二环己基碳二亚胺(DCC)反应制备酯。在实施例中给出了此反应的细节，其中的份数及百分数若无特殊说明则均以重量计。
式I的化合物是液晶性质的，而且根据结构不同可以形成近晶状、向列型或胆甾醇型相。它们适用于液晶化合物所有的常规用途。
新型化合物介于低分子量液晶化合物和聚合液晶化合物之间。与聚合物相比，它们能够再生地制得并且具有基本均一的结构，但又具有类似聚合物的粘性。
为了得到所需的性质，最好使用式I的化合物的混合物，这样这些混合物就有可能当即制得或通过机械混合来制备。
本新型化合物尤其适用于显示以及用于生产反光涂料。
实施例
实施例中所用的某些缩写说明如下：DCC： 二环己基碳二亚胺；PP： 4-吡咯烷基吡啶；DMAP：4-N，N-二甲基氨基吡啶；C： 晶相；Gl： 玻璃相；I： 各向同性相；S： 近晶状相；Sc： 近晶状C型相，介晶部分(mesogene)为铁电排列：
SA： 近晶状A型相；Sca：近晶状C型相，介晶部分(mesogene)为抗铁电排列；Sx： 未分类的近晶状相；Ch： 胆甾醇型相；N： 向列型相；*： 手性液晶相；Z： 包含基团X和Y的中心单元。
相转变温度用偏振光显微镜记录。温度控制在一个Mettler FP80/82显微镜的加热台上实现。自动偏振化用Miyasato等Jpn.J.Appl.Phys.22(1986)，L 230方法确定。实施例1
制备三{6-[4-(4-戊氧基苯氧羰基)苯氧基]己基}1，3，5-苯三甲酸酯a.4-苯甲酰氧基苯甲酸与亚硫酰氯反应
将4mol亚硫酰氯和0.2ml三乙胺加入1mol 4-苯甲酰氧基苯甲酸中，所得混合物加热至沸腾，直至气体逸出完全。残留的亚硫酰氯随后经真空蒸馏除去，并加入石油醚(沸程为50至60℃)使酰氯沉淀。残留的固体在40℃下减压干燥。产率：
。b.4-苯甲酰氧基苄基氯与戊氧基苯酚反应
将0.1mol 4-苯甲酰氧基苯甲基氯溶解在150ml甲苯中，混合物加热至沸腾，将溶解在50ml甲苯和0.2mol吡啶混合物中的0.11mol4-戊氧基苯酚溶液在1小时内逐滴加入其中。溶液再回流1小时，然后冷却，产品用水洗涤以除去溶剂，并在硅胶(甲苯/乙酸乙酯5∶1)上进行色谱分离。
产率：
。c.4-戊氧基苯基4-苯甲酰氧基苯甲酸酯的氢化
将16.9克(0.042mol)4-戊氧基苯基4-苯甲酰氧基苯甲酸酯导入250ml乙醇中，并在常温下在常压氢气氛中用阮内镍氢化。随后用抽吸法过滤掉催化剂，并用乙醇销毁。蒸发滤液，产品通过硅胶过滤净化。产率：
。
4-戊氧基苯基4-羟基苯甲酸酯与6-氯代-1-己醇反应
将0.07mol 4-戊氧基苯基4-羟基苯甲酸酯和0.08mol 6-氯代-1-己醇溶解在250ml DMF中。将0.15mol磨细的碳酸钾加入该溶液，反应混合物恒温于80℃。反应进程用薄层色谱法监测。达到完全转化后，产品用常规法后处理，最后用含有微量甲苯的乙醇重结晶。产率：
。
4-戊氧基苯基4-(6-羟基己氧基)苯甲酸酯与1，3，5-苯三酰氯反应
将0.02mol 1，3，5-苯三酰氯溶解于150ml甲苯中，将混合物加热至沸，将溶解于50ml甲苯和0.2mol吡啶的混合物中的0.063mol 4-戊氧基苯基4-(6-羟基己氧基)苯甲酸酯溶液于1小时内逐滴加入其中。溶液再回流1小时。反应完成后，混合物蒸发至干，产品用柱色谱(硅胶，甲苯/乙酸乙酯3∶1)净化。产品随后用含微量甲苯的乙醇重结晶。产率：
。相转变温度：Gl 35 Sx 83 SA 87 N 108 I
下列产物可按实施例1叙述的方法合成：
实施例9
4-己氧基苯基4-(6-羟基己氧基)苯甲酸酯与1，3，5-环己烷三酰氯反应
将0.02mol 1，3，5-环己烷三酰氯溶解于150ml甲苯中，混合物加热至沸，将溶解于50ml甲苯和0.2mol吡啶混合物中的0.063mol 4-己氧基苯基4-(6-羟基己氧基)苯甲酸酯溶液于1小时内逐滴加入。溶液再回流1小时。反应完成后，混合物被蒸发至干，产品用柱色谱净化(硅胶，甲苯/乙酸乙酯3∶1)。产品随后用含微量甲苯的乙醇重结晶。产率：
。
相转变温度：
C 101(SA 78 N 95)I实施例10至14按实施例9叙述的方法合成：
实施例15
无规混合的低聚介晶部分(oligomesogen)
将0.02mol 1，3，5-环己烷三酰氯溶解于150ml甲苯中，混合物加热至沸，将溶解于50ml甲苯和0.2mol吡啶混合物中的0.021mol 4-癸氧基苯基4-(6-羟基己氧基)苯甲酸酯、0.021mol 4-癸氧基苯基4-(8-羟基辛氧基)苯甲酸酯、0.021mol 4-己氧基苯基4-(8-羟基辛氧基)苯甲酸酯溶液逐滴在1小时内加入其中。溶液再回流1小时。反应完成后，混合物蒸发至干，产品用柱色谱(硅胶，甲苯/乙酸乙酯3∶1)净化。产品随后在50℃下于高真空
中干燥。
用该法制备的混合物理论上包含十种无规分布的不同的化合物，质谱图非常独特。产率：
。
飞行时间质谱法测得的质量(M+)
(不同种类的M+值可以从统计规律基础上可能的不同排布计算出来：全部质量的理论比例＝理论比例。
用飞行时间质谱法测定的质量比例已经被标准化为1488g/mol的M+峰上。)
| M+/g/mol | 1488 | 1516 | 1544 | 1572 | 1600 | 1628 | 1656 |
| 理论比例 | 1 | 3 | 6 | 7 | 6 | 3 | 1 |
| 实际比例 | 1 | 3.1 | 6 | 6.8 | 6 | 3.1 | 1 |
相转变温度：
G1 23 SA 77 N 82 I实施例16
三{11-[4-(4-庚基苯甲酰基)苯氧基]十一烷基}1，3，5-苯三甲酸盐a.4-苯甲酰氧基苯基4-庚基苯甲酸酯的制备
将10.0g(0.05mol)4-苯甲酰氧基苯酚与11.0g(0.05mol)4-庚基苯甲酸和0.75g(0.005mol)4-吡咯烷基吡啶一起溶解于250ml无水二氯甲烷中，在0-5℃下逐滴加入15.4g(0.075mol)DCC。混合物在室温下搅拌24小时后，生成的脲用抽吸法过滤掉，蒸发滤液，产品用柱色谱(硅胶，洗脱剂甲苯乙酸乙酯5∶1)而与残留物分离。产率：
。
b.4-羟基苯基4-甲基苯甲酸酯的制备
将16.9g(0.042mol)4-苯甲酰氧基苯基4-甲基苯甲酸酯加入250ml乙醇中，在室温下在常压氢气氛中用阮内镍氢化。催化剂随后用抽吸法过滤掉，并用乙醇销毁。蒸发滤液，产品通过硅胶过滤净化。产率：
。c.4-(11-羟基十一烷氧基)苯基4-甲基-苯甲酸酯的制备
将9.3g(0.042mol)4-羟基苯基4-甲基苯甲酸酯溶解于80ml无水二甲基甲酰胺(DMF)中，将6.8g(0.05mol)碳酸钾加入其中。将11.3g(0.045mol)11-溴代-1-十一烷醇随后加入，将混合物加热至80℃24小时。在这段时间内，再加入0.6g碳酸钾。后处理时，将反应混合物倒入冰水中，用稀盐酸酸化，沉淀用抽滤法过滤。将残留物溶解在乙酸乙酯中，用水洗涤，用硫酸钠干燥，并在减压条件下脱除溶剂。产品用柱色谱净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。d.三{11-[4-(甲基苯甲酰基)苯氧基]十一烷基} 1，3，5-苯三甲酸酯的制备
将0.82g(0.003mol)1，3，5-苯三酰氯溶解于215ml无水甲苯中，溶液加热至100℃。在此温度下将53ml无水甲苯、1.07g(0.013mol)吡啶和3.7g(0.0092mol)4-(11-羟基十一烷氧基)苯基4-甲基苯甲酸酯的溶液逐滴加入其中。混合物在该温度下搅拌24小时，然后将其冷却并倒入300ml冰水中。将3ml浓盐酸加入其中，分出有机相，用水洗数次，用硫酸钠干燥，并在减压条件下脱除溶剂。产品用柱色谱净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。蒸发后产品
用含微量甲苯的乙醇重结晶。产率：
。相行为：C91(S54 N76)I
化合物17至19按实施例16所述方法制备：
实施例20
1，3，5-苯三酰氯与乙基4-(3-羟基丙氧基)-，4-(6-羟基己氧基)-和4-(8-羟基辛氧基)联苯基-4′-羧酸酯反应
将11.29g(0.033mol)乙基4-(3-羟基丙氧基)-，4-(6-羟基己氧基)-和4-8-羟基辛氧基)联苯基4′-羧酸酯的混合物(以乙基4-(6-羟基己氧基)联苯基-4′-羧酸酯计)溶解于50ml无水二氯甲烷中，加入2.65g(0.01mol)1，3，5-苯三酰氯。将2.6g(0.033mol)吡啶加入其中，反应混合物在室温下搅拌过夜。随后加入5ml水和少许稀盐酸，有机相被分出，溶剂用蒸馏法分离掉，将残留物干燥。产量：8.55g。相转变温度：Gl 18 SA 133 I。实施例21a.乙基对羟基苯甲酸酯的氯化
将16.6g(0.1mol)乙基对羟基苯甲酸酯导入50ml无水二氯代甲烷中，将13.5g(0.1mol)硫酰氯加入其中。7.5g(0.1mol)二乙醚随后被逐滴加入其中。将温度升至30℃，HCl剧烈释出。混合物被搅拌过夜。由于TLC分析显示未反应的原料仍然存在，再加入6.75g(0.05mol)硫酰氯。1小时后，产生的固体用抽吸法过滤出，用水洗涤至呈中性后干燥。一氯化产品用柱色谱分离(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。b.乙基3-氯代-4-羟基苯甲酸酯用R-(-)-2-辛醇醚化
将4.5g(0.022mol)乙基3-氯代-4-羟基苯甲酸酯与2.9g
(0.022mol)R-(-)-2-辛醇一起溶解于35ml无水四氢呋喃中，将8.7g(0.033mol)三苯基膦加入其中。将5.6g(0.033mol)二乙基偶氮羧酸酯在0-10℃下用注射器逐滴缓慢加入其中。反应混合物在室温下搅拌24小时。
混合物随后在旋转蒸发器中蒸发，残留物用柱色谱净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。c.R-(-)3-氯代-4-(2-辛氧基)苯甲酸酯的制备
将5.38g(0.017mol)乙基R-(-)-3-氯代-4-(2-辛氧基)苯甲酸酯溶解于80ml乙醇中，加入1.46g(0.026mol)KOH。混合物回流3小时；溶液随后用浓盐酸酸化，加入乙酸乙酯，沉淀物用抽吸法过滤掉。弃去残留物，蒸发滤液以得到所需的产品。产率：
。d.4-羟基-4′-(11-羟基十一烷氧基)联苯基与3，4-二氢吡喃反应
将42.72g(0.12mol)4-羟基-4′-(11-羟基十一烷氧基)联苯溶解于200ml无水氯仿中，加入10滴浓盐酸，随后在0-5℃下逐滴加入10.08g(0.12mol)3，4-二氢吡喃，混合物被缓慢温热至室温。2个小时后，再滴加5.0g 3，4-二氢吡喃，混合物温热至40℃，直至反应原料再不能被检测出。反应混合物随后用NaCO3溶液振摇2次进行萃取，有机相被分出，并用Na2CO3干燥。溶剂经蒸馏除去，粗产品用柱色谱净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。e.R-(-)-3-氯代-4-(2-辛氧基)苯甲酸与4-羟基
-4′-[1-(2-四氢吡喃基)十一烷氧基]联苯反应
将4.4g(0.01mol)R-(-)-3-氯代-4-(2-辛氧基)苯甲酸与2.9g(0.01mol)4-羟基-4′-[1-(2-四氢吡喃基)十一烷氧基]联苯一起溶解于80ml无水二氯甲烷中，加入0.15g(0.001mol)4-吡咯烷基吡啶。将3.08g(0.015mol)二环己基碳化二亚胺溶解于3ml无水二氯甲烷中，然后在0-5℃下被逐滴加入其中，随后将混合物在室温下搅拌24小时。形成的脲用抽吸法过滤掉，蒸发滤液，所需产品用柱色谱净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。f.四氢吡喃保护基团的脱除
将4.2g(0.006mol)在e中制备的化合物溶于50ml无水乙醇中，加入三滴浓盐酸，混合物在30℃下搅拌约18小时。沉淀的产品用抽吸法过滤出，并用柱色谱法净化(硅胶，洗脱剂甲苯/乙酸乙酯5∶1)。产率：
。g.1，3，5-苯三酰氯和4-(1-羟基十一烷氧基)联苯基R-(-)-3-氯代-4-(2-辛氧基)苯甲酸酯制备低聚介晶部分
反应和反应产物的净化方法与实施例1所述类似。产率：
。
相行为特征：C84(Gl 35 Sx *78) Sc *104 Ch 109 I
在T＝90℃下自动偏振化：105nC cm-2实施例22
由1，3，5-环己烷三酰氯和4-(1-羟基十一烷氧基)联苯基
R-(-)-3-氯代-4-(2-辛氧基)苯甲酸酯制备低聚介晶部分。
反应以与实施例8所述类似的方法进行。产率：
。相行为特征：C 90(Gl 35 Sx84)Sca *104 I在T＝90℃下自动偏振化：90nC cm-2下列化合物按实施例21和22所述合成：
实施例26a.4-羟基苯甲酸与乙酸酐反应
将153g(1.5mol)乙酸酐溶于150ml冰醋酸中，加入138.0g(1.0mol)4-羟基苯甲酸和10滴浓硫酸。混合物温热至59℃，并进一步回流2小时。
混合物冷却后，加入少许冰醋酸，产品用抽吸法过滤出，用少许冰醋酸和水洗涤，然后干燥。产率：
。b.4-羧基苯基乙酸酯与亚硫酰氯反应
将130.5g(0.73mol)4-羧基苯基乙酸酯在室温下导入172.6g(1.45mol)亚硫酰氯中，再加入86.3g(0.73mol)亚硫酰氯，将混合物回流2小时。随后用水喷射真空蒸馏法除去亚硫酰氯，残留物在油泵真空中蒸馏。产率：128.8g，沸点109-112℃/2毫巴，89％。c.乙基辛酸酯与水合肼反应
将214.3g(1.25mol)乙基辛酸酯溶于225ml乙醇中，然后在剧烈搅拌下缓慢加入到回流温度下的125.0g(2.5mol)水合肼溶解于170ml乙醇的溶液中。形成的残留物用抽吸法过滤出，并用乙醇重结晶。产率：143.4g，熔点：85-86℃，73％。
d.辛基酰肼与4-乙酰基苄基氯反应
将53.7g(0.34mol)辛基酰肼导入400ml无水吡啶中，将67.4g(0.34mol)熔融态4-乙酰基苄基氯在10℃剧烈搅拌下加入其中。温度升至30℃。混合物在室温下再搅拌2小时，然后倒至1.0kg的冰上，残留物用抽吸法过滤出，用水洗涤后干燥。产率：112.1g，99％。e.闭环制备2-庚基-5-(4-羟基苄基)-1，3，5-噻二唑
将64.0g(0.2mol)由d.制得的产品溶于1.0升无水甲苯中，加入96.0g(0.26mol)Lawesson试剂。在剧烈搅拌下逐滴加入20ml吡啶，混合物回流4小时。混合物在旋转蒸发器上蒸发，将粗品溶于500ml吡啶，加入44.0g(0.1mol)P4S10。混合物在60℃下搅拌2小时，再在80℃下搅拌4小时，然后冷却，加入50ml乙醇，将混合物倒至4.0kg冰上。混合物搅拌1小时后，用抽吸法过滤出固体，用水洗涤并用600ml甲醇搅拌，将溶解于400ml甲醇的26.35g(0.4mol)85％浓度的KOH溶液加入其中。混合物回流30分钟后，溶剂在常压下用蒸馏法除去，将残留物溶于600ml水中，用浓盐酸沉淀，并用抽吸法过滤，用水洗涤后干燥。产率：28.9g，熔点：72-73℃，52％。f.2-庚基-5-(4-羟基苯基)-1，3，5-噻二唑与11-溴代十一烷醇反应
将19.1g(0.073mol)2-庚基-5-(4-羟基苯基)-1，3，5-噻二唑溶于50ml无水DMF中，加入18.4g(0.073mol)11-溴代-十一烷醇、10.1g(0.073mol)粉末状碳酸钾和12.2g(0.07mol)碘化钾。混合物在80℃下搅拌7小时后，再加入3.68g(0.0124mol)11-溴代十一烷醇、2.0g(0.0146mol)碳酸钾和2.44g(0.0146mol)
碘化钾，混合物再在80℃下搅拌8小时。残留物用抽吸法过滤并用DMF洗涤，有机相用水搅拌，得到的残留过过滤。产品用水洗涤后干燥。产率：25.6g，熔点：82-83℃，82％。g.2-庚基-5-[4-(1 1-羟基十一烷氧基)苯基]-1，3，5-噻二唑与1，3，5-苯三酰氯反应
反应以与实施例1所述类似的方法进行。产率：
。
相转变温度：C 114(Sc 84 SA 99)I实施例27至29按实施例26所述的方法合成。 
实施例30a.2-(4-羟基苯基)-5-辛基嘧啶
将137.7ml(1.5mol)POCl3在冰冷却下加到135g(1.85mol)DMF中，混合物随后在室温下搅拌15分钟。将202g(1mol)癸醛缩二甲醇溶于500ml DMF中后，再逐滴加入其中，加完后混合物再搅拌约3小时。随后加入262.5g(1mol)4-苯甲酰氧基苯甲脒，混合物再搅拌1小时。随后缓慢加入1.1升三乙胺，在此过程中温度升至约70℃。为了使之易于搅拌，加入约700ml DMF，随后在常压下蒸馏除去三乙胺。将残留物倒入到约6升冰水中。用水洗涤沉淀产物，并用2.5升异丁醇重结晶，然后溶解于1升乙酸乙酯中，并加入10gPd/C(10％)在常压下氢化，直至停止吸收氢气。用抽吸法过滤掉催化剂，蒸发滤液得到的残留物在50℃下减压干燥。产率：
。b.8-[4-(5-辛基嘧啶-2-基)苯氧基]辛-1-醇
将42.0g(0.14mol)2-(4-羟苯基)-5-辛基嘧啶溶于400ml DMF中，加入38.7g(0.28mol)K2CO3和36.0g(0.21mol)8-氯代辛-1-醇。混合物随后被加热至100℃，同时TLC监控直至
反应完全。将混合物倒入3升冰水中，用抽吸法过滤出沉淀产物，用水洗涤，减压后干燥并用环己烷重结晶。产率：
。c.三{8-[4-(5-辛基嘧啶-2-基)苯氧基]辛基}1，3，5-三羧酸酯
8-[4-(5-辛基嘧啶-2-基)苯氧基]辛-1-醇与1，3，5-苯三酰氯反应以与实施例1类似的方法进行。产率：
。相行为特征：C91(SA90)I。实施例31
三{8-[4-(5-辛基嘧啶-2-基)苯氧基]辛基}1，3，5-环己烷三甲酸酯
8-[4-(5-辛基嘧啶-2-基)苯氧基]辛-1-醇与1，3，5-环己烷三甲酸反应以类似于实施例9所述的方法进行。产率：
。相行为特征：C78(SA75)I。
下列化合物以类似于实施例30或31的方法合成： 
实施例39
一种含嘧啶分晶部分的混合的低聚介晶部分的合成
本合成过程以类似于实施例30所述的方法进行，使用0.0024mol1，3，5-苯三酰氯，0.0027mol 8-[4-(5-辛基嘧啶-2-基)苯氧基]辛-1-醇，0.0027mol 8-[4-(5-辛基嘧啶-2-基)苯氧基]己-1-醇和0.0027mol 8-[4-(5-辛基嘧啶-2-基)苯氧基]十一烷-1-醇。产率：
。相行为特征：Gl＜25 SA71-82 I。
实施例40至42的化合物以类似实施例30的方法合成，实施例41和42包含一个癸基侧链。 
实施例43
实施例43的合成以类似于实施例30的方式进行。a.)4-(5-辛基嘧啶-2-基)苯基12-羟基十二烷酸酯
将0.034mol 2-(4-羟基苯基)-5-辛基嘧啶、0.051molDCC和0.1g DMAP在CH2Cl2中在室温下搅拌24小时。随后将溶剂用蒸馏法除去，残留物用环己烷重结晶。产率：
。b)三{11-[4-(5-辛基嘧啶-2-基)苯氧羰基]十一烷基}1，3，5-苯三甲酸酯
方法类似于实施例30，使用0.05mol 1，3，5-苯三酰氯和0.015mol4-(5-辛基嘧啶-2-基)苯基12-羟基十二烷酸酯。产率：
。
相转变温度：G1 28 SC 56 SA 72 I实施例44
实施例44的合成以类似于实施例30的方式进行。a.)2-(4-羟基苯基)-5-辛氧基嘧啶
使用0.1mol 4-苯甲酰氧基苯甲脒和0.1mol 2-辛氧基乙醛缩二甲醇。产率：
。b.)8-[4-(5-辛氧基嘧啶-2-基)苯氧基]辛-1-醇
使用0.009mol 2-(4-羟基苯基)-5-辛氧基嘧啶和0.014mol6-氯代辛-1-醇。产率：
。c.)三{8-[4-(5-辛氧基嘧啶-2-基)苯氧基]辛基}1，3，5-苯三甲酸酯
使用0.0025mol 1，3，5-苯三酰氯和0.0075mol 8-[4-(5-辛氧基嘧啶-2-基)苯氧基]辛-1-醇。在Al2O3(洗脱剂CH2Cl2)柱色谱分离后的产率：
。
相行为特征：Gl 86 SA 114 I。实施例45
实施例45的合成以与实施例30类似的方式进行。a)2-(4-己基氧苯基)嘧啶-5-醇
使用0.1mol 4-己氧基苯甲脒和0.1mol 2-苯甲酰氧基乙醛缩二甲醇。产率：
。b)6-[2-(4-己氧基苯基)嘧啶-5-氧基]己-1-醇
使用0.013mol 2-(4-己氧基苯基)-5-羟基嘧啶和0.020mol 6-氯代己-1-醇。产率：
。c)三{6-[2-(4-己氧基苯基)嘧啶-5-氧基]己基}1，3，5-苯三甲酸酯
使用0.003mol 1，3，5-苯三酰氯和0.01mol 6-[2-(4-己氧基苯基)嘧啶-5-氧基]己-1-醇。产率：
。相转变温度：C 36 SA 120 N 122 I。
权利要求书
按照条约第19条的修改
1.式I的液晶化合物：
X(-Y-A-Y-M-Y-B)3 I，
其中
X是芳族或脂族环系；
每个Y各自互相独立地为一个直接键、-COO-、-OCO-、-O-、-CONH-或-CON(R)，其中R是C1至C4烷基；
A是间隔基团；
M是介晶基团(mesogenic grouP)；和
B是侧链。
2.根据权利要求1的式I的液晶化合物，其中Y是O、COO或OCO。
3.根据权利要求1的式I的液晶化合物，包括具有2到12个碳原子的间隔基团。
4.根据权利要求1的式I的液晶化合物，其中M是
(T-Y1)r-T，
其中
每个T各自相互独立地为芳基或杂芳基；
每个Y1各自相互独立地为O、COO、OCO、CH2O、OCH2、或一个直接键，以及
r为1到3。
5.根据权利要求1的式I的液晶化合物，其中B是C2到C11烷基或链烯基，它们可以被O、OCO、COO、
NH或N(CH3)基团间隔，并且可以被苯基、氟、氯、溴、氰基或羟基取代。
6.根据权利要求5的液晶化合物，其中Y1是COO、OCO或一个直接键。
7.根据权利要求6的液晶化合物，其中B是经O、COO或OCO键合的C3至C11烷基，它们可以被O间隔一次或多次，并且优选是非支链的。
8.根据权利要求6的液晶化合物，其中B是经O、COO或OCO键合的手性C3至C11烷基，它们可以被氟、氯、溴、氰基或羟基取代，并且可以被O、COO、OCO或
间隔。
9.根据权利要求9的液晶化合物，其中B是经O、COO或OCO键合的手性C3至C11烷基，它们可以被氟、氯、溴或羟基取代，并且可以被O或COO间隔。
10.根据权利要求1到10的任一项的化合物的应用，单独地、与其它的这类化合物的混合物的形式或以与其它种类液晶一起用于信息的光学显示设备。
Claims (11)
1.式I的液晶化合物：
X(-Y-A-Y-M-Y-B)n I，
其中
X是芳族或脂族环系；
n是2到6的整数；
每个Y各自互相独立地为一个直接键、-COO-、-OCO-、-O-、-CONH-或-CON(R)，其中R是C1至C4烷基；
A是间隔基团；
M是介晶基团(mesogenic group)；和
B是侧链。
2.根据权利要求1的式I的液晶化合物，其中n为3。
3.根据权利要求1的式I的液晶化合物，其中Y是O、COO或OCO。
4.根据权利要求1的式I的液晶化合物，包括具有2到12个碳原子的间隔基团。
5.根据权利要求1的式I的液晶化合物，其中M是
(T-Y1)r-T，
其中
每个T各自相互独立地为芳基或杂芳基；
每个Y1各自相互独立地为O、COO、OCO、CH2O、OCH2、CH＝N、
N＝CH或一个直接键，以及
r为1到3。
6.根据权利要求1的式I的液晶化合物，其中B是C2到C11烷基或链烯基，它们可以被O、OCO、COO、
NH或N(CH3)基团间隔，并且可以被苯基、氟、氯、溴、氰基或羟基取代。
7.根据权利要求5的液晶化合物，其中Y1是COO、OCO或一个直接键。
8.根据权利要求6的液晶化合物，其中B是经O、COO或OCO键合的C3至C11烷基，它们可以被O间隔一次或多次，并且优选是非支链的。
9.根据权利要求6的液晶化合物，其中B是经O、COO或OCO键合的手性C3至C11烷基，它们可以被氟、氯、溴、氰基或羟基取代，并且可以被O、COO、OCO或
间隔。
10.根据权利要求9的液晶化合物，其中B是经O、COO或OCO键合的手性C3至C11烷基，它们可以被氟、氯、溴或羟基取代，并且可以被O或COO间隔。
11.根据权利要求1到10的任一项的化合物的应用，单独地、与其它的这类化合物的混合物的形式或以与其它种类液晶一起用于信息的光学显示设备。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4332733.8 | 1993-09-25 | ||
| DE4332733A DE4332733A1 (de) | 1993-09-25 | 1993-09-25 | Flüssigkristalline Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1134168A true CN1134168A (zh) | 1996-10-23 |
Family
ID=6498653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94194026A Pending CN1134168A (zh) | 1993-09-25 | 1994-09-14 | 液晶化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5804097A (zh) |
| EP (1) | EP0720641B1 (zh) |
| JP (1) | JPH09504788A (zh) |
| KR (1) | KR960704995A (zh) |
| CN (1) | CN1134168A (zh) |
| DE (2) | DE4332733A1 (zh) |
| WO (1) | WO1995008604A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115349006A (zh) * | 2020-03-27 | 2022-11-15 | 光学转变有限公司 | 介晶化合物 |
| CN115349006B (zh) * | 2020-03-27 | 2024-10-29 | 光学转变有限公司 | 介晶化合物 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996030351A1 (de) * | 1995-03-24 | 1996-10-03 | Basf Aktiengesellschaft | Flüssigkristalline verbindungen |
| DE19520704A1 (de) * | 1995-06-09 | 1996-12-12 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19649056A1 (de) * | 1996-11-27 | 1998-05-28 | Basf Ag | Polymerisierbare Oligomesogene |
| US6194481B1 (en) * | 1999-05-19 | 2001-02-27 | Board Of Regents Of The University Of Texas System | Mechanically strong and transparent or translucent composites made using zirconium oxide nanoparticles |
| JP4536891B2 (ja) * | 2000-09-14 | 2010-09-01 | 共同印刷株式会社 | 新規化合物およびこれを含有する可逆性感熱記録材料、可逆性感熱記録媒体 |
| US20040199004A1 (en) * | 2001-01-23 | 2004-10-07 | Southwest Research Institute | Novel mesogens |
| US7041234B2 (en) | 2001-01-23 | 2006-05-09 | Southwest Research Institute | Methods for synthesis of liquid crystals |
| US7147800B2 (en) * | 2001-01-23 | 2006-12-12 | Southwest Research Institute | Selective ether cleavage synthesis of liquid crystals |
| ATE312069T1 (de) * | 2001-03-07 | 2005-12-15 | Univ Texas | Verbundharze mit ultraniedriger schrumpfung auf grundlage von mischungen nematischer flüssigkristallmonomere |
| DE10229169B4 (de) * | 2002-06-28 | 2011-08-11 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 80686 | Neue diskotische Verbindungen und Verfahren zur Herstellung optisch anisotroper Elemente |
| WO2004083335A2 (en) * | 2003-03-21 | 2004-09-30 | University Of Rochester | Glassy chiral-nematic liquid crystals and optical devices containing same |
| GB0319401D0 (en) * | 2003-08-19 | 2003-09-17 | Univ Hull | Materials |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2579217A1 (fr) * | 1985-03-22 | 1986-09-26 | Merck Patent Gmbh | Composes carbocycliques, leur preparation, leur utilisation en tant que composants de phases a cristaux liquides discotiques et elements d'affichage a cristaux liquides contenant de tels composes |
| DE3513795A1 (de) * | 1985-04-17 | 1986-10-23 | Basf Ag, 6700 Ludwigshafen | Amphiphile fluessigkristalline verbindungen |
| DD247227A1 (de) * | 1986-03-05 | 1987-07-01 | Univ Halle Wittenberg | Glasartige nematische fluessigkristalle |
| DD265155A1 (de) * | 1987-09-24 | 1989-02-22 | Univ Halle Wittenberg | Nematische fluessigkristalle mit glasphasen |
| DE3827603A1 (de) * | 1988-08-13 | 1990-03-15 | Hoechst Ag | Chirale smektische fluessigkristalle und diese enthaltende glasartige materialien zur darstellung und speicherung von information |
| DE4011812A1 (de) * | 1990-04-12 | 1991-10-17 | Consortium Elektrochem Ind | Tetrasubstituierte methane mit fluessigkristallinen eigenschaften |
| DE4108627A1 (de) * | 1991-03-16 | 1992-09-17 | Basf Ag | Fluessigkristalline verbindungen |
-
1993
- 1993-09-25 DE DE4332733A patent/DE4332733A1/de not_active Withdrawn
-
1994
- 1994-09-14 KR KR1019960701537A patent/KR960704995A/ko not_active Application Discontinuation
- 1994-09-14 WO PCT/EP1994/003069 patent/WO1995008604A1/de not_active Application Discontinuation
- 1994-09-14 JP JP7509540A patent/JPH09504788A/ja active Pending
- 1994-09-14 CN CN94194026A patent/CN1134168A/zh active Pending
- 1994-09-14 US US08/648,134 patent/US5804097A/en not_active Expired - Fee Related
- 1994-09-14 EP EP94927612A patent/EP0720641B1/de not_active Expired - Lifetime
- 1994-09-14 DE DE59406690T patent/DE59406690D1/de not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115349006A (zh) * | 2020-03-27 | 2022-11-15 | 光学转变有限公司 | 介晶化合物 |
| CN115349006B (zh) * | 2020-03-27 | 2024-10-29 | 光学转变有限公司 | 介晶化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5804097A (en) | 1998-09-08 |
| JPH09504788A (ja) | 1997-05-13 |
| WO1995008604A1 (de) | 1995-03-30 |
| DE59406690D1 (de) | 1998-09-17 |
| EP0720641B1 (de) | 1998-08-12 |
| KR960704995A (ko) | 1996-10-09 |
| DE4332733A1 (de) | 1995-03-30 |
| EP0720641A1 (de) | 1996-07-10 |
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