CN1136067A - 酯衍生物、液晶组合物和液晶显示元件 - Google Patents
酯衍生物、液晶组合物和液晶显示元件 Download PDFInfo
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- CN1136067A CN1136067A CN96105985A CN96105985A CN1136067A CN 1136067 A CN1136067 A CN 1136067A CN 96105985 A CN96105985 A CN 96105985A CN 96105985 A CN96105985 A CN 96105985A CN 1136067 A CN1136067 A CN 1136067A
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- phenylene
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- 239000000203 mixture Substances 0.000 title claims abstract description 174
- 150000001875 compounds Chemical class 0.000 title claims abstract description 137
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 91
- 239000007788 liquid Substances 0.000 title claims abstract description 43
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 38
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- -1 4-cyclohexylidene Chemical group 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 12
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 abstract 1
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 34
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 22
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- 238000000034 method Methods 0.000 description 21
- 230000000704 physical effect Effects 0.000 description 21
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- 239000004990 Smectic liquid crystal Substances 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
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- 230000002829 reductive effect Effects 0.000 description 13
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- 239000007795 chemical reaction product Substances 0.000 description 9
- 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 9
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- 230000003287 optical effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- 150000002148 esters Chemical class 0.000 description 5
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- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 239000003153 chemical reaction reagent Substances 0.000 description 3
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- CPSYYLWYCFQWMK-UHFFFAOYSA-N 2-fluoro-4-(propoxymethyl)benzoyl chloride Chemical compound CCCOCC1=CC=C(C(Cl)=O)C(F)=C1 CPSYYLWYCFQWMK-UHFFFAOYSA-N 0.000 description 2
- GOMSYKAATAQBRT-UHFFFAOYSA-N 4-(butoxymethyl)benzoyl chloride Chemical compound CCCCOCC1=CC=C(C(Cl)=O)C=C1 GOMSYKAATAQBRT-UHFFFAOYSA-N 0.000 description 2
- YRKALCQZNLVXNM-UHFFFAOYSA-N 4-(pentoxymethyl)benzoyl chloride Chemical compound CCCCCOCC1=CC=C(C(Cl)=O)C=C1 YRKALCQZNLVXNM-UHFFFAOYSA-N 0.000 description 2
- WOYPUSSSRAPAOQ-UHFFFAOYSA-N 4-(propoxymethyl)benzoyl chloride Chemical compound CCCOCC1=CC=C(C(Cl)=O)C=C1 WOYPUSSSRAPAOQ-UHFFFAOYSA-N 0.000 description 2
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 2
- NXAYNWHPPQEMSL-SAABIXHNSA-N CCCCOC[C@H]1CC[C@H](CCc2ccc(cc2)C(Cl)=O)CC1 Chemical compound CCCCOC[C@H]1CC[C@H](CCc2ccc(cc2)C(Cl)=O)CC1 NXAYNWHPPQEMSL-SAABIXHNSA-N 0.000 description 2
- JLHSAZYUGYFLQO-HDJSIYSDSA-N CCCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(Cl)=O Chemical compound CCCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(Cl)=O JLHSAZYUGYFLQO-HDJSIYSDSA-N 0.000 description 2
- KKDLQWYXDNSYKS-JOCQHMNTSA-N CCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(Cl)=O Chemical compound CCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(Cl)=O KKDLQWYXDNSYKS-JOCQHMNTSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- RNJCXDJXPXWMDK-UHFFFAOYSA-N [AlH3].COCCO[Na] Chemical compound [AlH3].COCCO[Na] RNJCXDJXPXWMDK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001979 organolithium group Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 229920000642 polymer Polymers 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 description 1
- GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
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- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical group OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical group C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5982295 | 1995-02-22 | ||
| JP59822/95 | 1995-02-22 | ||
| JP138625/95 | 1995-05-12 | ||
| JP13862595 | 1995-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1136067A true CN1136067A (zh) | 1996-11-20 |
Family
ID=26400899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96105985A Pending CN1136067A (zh) | 1995-02-22 | 1996-02-20 | 酯衍生物、液晶组合物和液晶显示元件 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5820784A (cg-RX-API-DMAC10.html) |
| EP (3) | EP0728830B1 (cg-RX-API-DMAC10.html) |
| KR (1) | KR100294288B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN1136067A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE212333T1 (cg-RX-API-DMAC10.html) |
| DE (2) | DE69608013T2 (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102511082A (zh) * | 2009-09-16 | 2012-06-20 | 株式会社半导体能源研究所 | 半导体器件及其制造方法 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0184869B1 (ko) * | 1989-12-06 | 1999-05-15 | 위르겐 호이만 | 1,4-이치환된 2,6-디플루오로벤젠 화합물 및 액정 매질 |
| TW371312B (en) * | 1995-04-12 | 1999-10-01 | Chisso Corp | Fluorine-substituted liquid-crystal compound, liquid-crystal composition and liquid-crystal display device |
| JP3981411B2 (ja) * | 1995-08-01 | 2007-09-26 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 液晶媒体 |
| US6599589B1 (en) | 1999-09-30 | 2003-07-29 | Minolta Co., Ltd. | Liquid crystal composition and liquid crystal light display element using the same |
| DE19947954A1 (de) * | 1999-10-06 | 2001-04-12 | Merck Patent Gmbh | Flüssigkristalline Phenolester |
| DE19949333A1 (de) * | 1999-10-13 | 2001-04-19 | Merck Patent Gmbh | Esterverbindungen und deren Verwendung in flüssigkristallinen Medien |
| DE10111139A1 (de) * | 2000-04-07 | 2001-10-11 | Merck Patent Gmbh | Elektrooptische Flüssigkristallanzeige |
| DE10151913B4 (de) * | 2000-11-18 | 2011-01-05 | Merck Patent Gmbh | Nematische Flüssigkristallmischung und ihre Verwendung in Flüssigkristallanzeigen |
| JP4206687B2 (ja) * | 2002-04-09 | 2009-01-14 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777658A (en) * | 1980-11-04 | 1982-05-15 | Chisso Corp | 4'-cyanophenyl 4-(alpha-alkoxymethyl)benzoate |
| JPH0247979B2 (ja) * | 1982-09-28 | 1990-10-23 | Chisso Corp | Furuorobifuenirunoesuterujudotai |
| JPS59106451A (ja) * | 1982-12-08 | 1984-06-20 | Chisso Corp | シクロヘキサンカルボン酸−4′−シアノビフエニルエステル |
| JPH0247983B2 (ja) * | 1982-12-14 | 1990-10-23 | Chisso Corp | 44furuoroo4**hidorokishibifuenirunoesuterujudotai |
| JPS59128354A (ja) * | 1983-01-10 | 1984-07-24 | Chisso Corp | シクロヘキサンカルボン酸ハロゲノフエニルエステル誘導体 |
| US4661283A (en) * | 1984-03-02 | 1987-04-28 | Chisso Corporation | Benzoate derivatives having a large positive dielectric anisotropy value and liquid crystal compositions containing same |
| JPS6143150A (ja) * | 1984-08-06 | 1986-03-01 | Casio Comput Co Ltd | p−シアノビフエニル−〔p−(ω−アルコキシアルキル)〕−ベンゾエ−ト化合物および液晶組成物 |
| DE3729071A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | Substituierte phenoxypyridine |
| DE3909802A1 (de) * | 1988-07-27 | 1990-04-05 | Merck Patent Gmbh | Difluormethylverbindungen |
| US5324449A (en) * | 1987-09-25 | 1994-06-28 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Substituted phenyl trifluoromethyl ethers |
| US5387369A (en) * | 1988-10-20 | 1995-02-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Supertwist liquid crystal display |
| GB8910240D0 (en) * | 1989-05-04 | 1989-06-21 | Secr Defence | Phenyl esters and their use in liquid crystal materials |
| EP0438575B1 (de) * | 1989-08-12 | 1994-10-26 | MERCK PATENT GmbH | Benzolderivate und flüssigkristallines medium |
| US5271865A (en) * | 1990-02-13 | 1993-12-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline mixture of low viscosity |
| WO1991016291A1 (de) * | 1990-04-21 | 1991-10-31 | MERCK Patent Gesellschaft mit beschränkter Haftung | Phenylcyclohexane und flüssigkristallines medium |
| JP2796753B2 (ja) * | 1990-05-09 | 1998-09-10 | キヤノン株式会社 | カイラルスメクチック液晶組成物およびそれを使用した液晶素子 |
| US5213710A (en) * | 1990-09-26 | 1993-05-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Benzene derivatives and a liquid-crystalline medium |
| KR100198364B1 (ko) * | 1990-10-02 | 1999-06-15 | 플레믹 크리스티안 | 액정 매질 |
| DE59109091D1 (de) * | 1990-12-07 | 1999-03-04 | Merck Patent Gmbh | Supertwist-Flüssigkristallanzeige |
| US5409637A (en) * | 1991-02-20 | 1995-04-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Nematic liquid-crystal composition |
| JP3081006B2 (ja) * | 1991-03-05 | 2000-08-28 | セイミケミカル株式会社 | ジフルオロシアノ化合物、液晶組成物及び液晶電気光学素子 |
| GB2253402B (en) * | 1991-03-05 | 1994-10-19 | Merck Patent Gmbh | Nematic liquid-crystal composition |
| JP2807357B2 (ja) * | 1991-03-27 | 1998-10-08 | セイミケミカル株式会社 | トランスエチレン誘導体化合物、液晶組成物及び液晶電気光学素子 |
| JPH04360860A (ja) * | 1991-06-04 | 1992-12-14 | Seiko Epson Corp | エステル化合物及び液晶組成物及び液晶表示素子 |
| JPH0597772A (ja) * | 1991-10-07 | 1993-04-20 | Seiko Epson Corp | エステル化合物及び液晶組成物及び液晶表示素子 |
| GB2266714B (en) * | 1992-05-06 | 1995-11-29 | Merck Patent Gmbh | Alkoxymethylene compounds |
| JP2732335B2 (ja) * | 1992-05-28 | 1998-03-30 | チッソ株式会社 | 液晶組成物およびこの組成物を用いた液晶表示素子 |
| CN1085591A (zh) * | 1992-08-06 | 1994-04-20 | 窒素公司 | 液晶组合物以及利用该组合物来制作的液晶显示元件 |
| EP0681021B1 (en) * | 1994-05-06 | 1998-12-23 | Chisso Corporation | A liquid crystal composition |
| JP3579728B2 (ja) * | 1994-06-23 | 2004-10-20 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
| EP0708106B1 (en) * | 1994-10-20 | 2000-08-09 | Shin-Etsu Chemical Co., Ltd. | Novel silacyclohexane compounds, a liquid crystal composition comprising the same and a liquid crystal device comprising the composition |
-
1996
- 1996-02-20 CN CN96105985A patent/CN1136067A/zh active Pending
- 1996-02-22 KR KR1019960004100A patent/KR100294288B1/ko not_active Expired - Fee Related
- 1996-02-22 DE DE69608013T patent/DE69608013T2/de not_active Expired - Fee Related
- 1996-02-22 EP EP96102671A patent/EP0728830B1/en not_active Expired - Lifetime
- 1996-02-22 EP EP00103442A patent/EP1010687A2/en not_active Withdrawn
- 1996-02-22 US US08/606,032 patent/US5820784A/en not_active Expired - Fee Related
- 1996-02-22 US US08/605,776 patent/US5755994A/en not_active Expired - Lifetime
- 1996-02-22 EP EP96102672A patent/EP0738709B1/en not_active Expired - Lifetime
- 1996-02-22 AT AT96102672T patent/ATE212333T1/de not_active IP Right Cessation
- 1996-02-22 DE DE69618700T patent/DE69618700T2/de not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102511082A (zh) * | 2009-09-16 | 2012-06-20 | 株式会社半导体能源研究所 | 半导体器件及其制造方法 |
| CN102511082B (zh) * | 2009-09-16 | 2016-04-27 | 株式会社半导体能源研究所 | 半导体器件及其制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0728830B1 (en) | 2000-05-03 |
| DE69608013T2 (de) | 2000-11-02 |
| DE69618700D1 (de) | 2002-03-14 |
| EP0738709A2 (en) | 1996-10-23 |
| US5755994A (en) | 1998-05-26 |
| KR100294288B1 (ko) | 2001-09-17 |
| US5820784A (en) | 1998-10-13 |
| EP0738709A3 (en) | 1997-07-16 |
| EP0738709B1 (en) | 2002-01-23 |
| DE69608013D1 (de) | 2000-06-08 |
| DE69618700T2 (de) | 2002-09-12 |
| EP0728830A3 (cg-RX-API-DMAC10.html) | 1996-09-04 |
| ATE212333T1 (de) | 2002-02-15 |
| KR960031424A (ko) | 1996-09-17 |
| EP0728830A2 (en) | 1996-08-28 |
| EP1010687A2 (en) | 2000-06-21 |
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