JPH09508401A - フェナントリジン誘導体およびそれらの液晶混合物における使用 - Google Patents
フェナントリジン誘導体およびそれらの液晶混合物における使用Info
- Publication number
- JPH09508401A JPH09508401A JP7520367A JP52036795A JPH09508401A JP H09508401 A JPH09508401 A JP H09508401A JP 7520367 A JP7520367 A JP 7520367A JP 52036795 A JP52036795 A JP 52036795A JP H09508401 A JPH09508401 A JP H09508401A
- Authority
- JP
- Japan
- Prior art keywords
- diyl
- liquid crystal
- substituted
- different
- alkyl group
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 150000005053 phenanthridines Chemical class 0.000 title claims abstract description 12
- 239000004973 liquid crystal related substance Substances 0.000 title description 35
- -1 pyrimidine-2,5-diyl Chemical group 0.000 claims abstract description 55
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 6
- 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 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical compound C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000010287 polarization Effects 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 150000000185 1,3-diols Chemical class 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000004862 dioxolanes Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005447 octyloxy 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])O* 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QMYSXXQDOZTXAE-WHFBIAKZSA-N (2s,3s)-2-chloro-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@H](Cl)C(O)=O QMYSXXQDOZTXAE-WHFBIAKZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GWWBKZJNSZGFCF-UHFFFAOYSA-N 1-fluoro-2-octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1F GWWBKZJNSZGFCF-UHFFFAOYSA-N 0.000 description 1
- IBYIRCIVTGUDNK-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(OCCCC)C=C1 IBYIRCIVTGUDNK-UHFFFAOYSA-N 0.000 description 1
- WSTRYHDQRWAJAU-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(OCC)C=C1 WSTRYHDQRWAJAU-UHFFFAOYSA-N 0.000 description 1
- HOAGGFRICQSSLG-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 HOAGGFRICQSSLG-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- WJOLFIJLWNIWJH-UHFFFAOYSA-N 4-fluoro-3-octoxyphenanthridine Chemical compound C1=CC=C2C3=CC=C(OCCCCCCCC)C(F)=C3N=CC2=C1 WJOLFIJLWNIWJH-UHFFFAOYSA-N 0.000 description 1
- ODLNBXFCLHWPHW-DEOSSOPVSA-N 5-[4-[(3s)-3,7-dimethyloct-6-enoxy]phenyl]-2-octoxypyrimidine Chemical compound C1=NC(OCCCCCCCC)=NC=C1C1=CC=C(OCC[C@@H](C)CCC=C(C)C)C=C1 ODLNBXFCLHWPHW-DEOSSOPVSA-N 0.000 description 1
- GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
- XAYBLZUVLOZTIN-UHFFFAOYSA-N 7-fluoro-3,8-dihexoxyphenanthridine Chemical compound CCCCCCOC1=CC=C2C3=CC=C(OCCCCCC)C=C3N=CC2=C1F XAYBLZUVLOZTIN-UHFFFAOYSA-N 0.000 description 1
- TZHZZJYBRSFBJE-UHFFFAOYSA-N 8-heptoxy-3-octoxybenzo[c][1,8]naphthyridine Chemical compound CCCCCCCOC1=CC=C2C3=CC=C(OCCCCCCCC)N=C3N=CC2=C1 TZHZZJYBRSFBJE-UHFFFAOYSA-N 0.000 description 1
- MYABQDZMZUJXJX-UHFFFAOYSA-N 8-methoxy-3-octoxybenzo[c][1,8]naphthyridine Chemical compound COC1=CC=C2C3=CC=C(OCCCCCCCC)N=C3N=CC2=C1 MYABQDZMZUJXJX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- WRWHVYFIFFLHMH-UHFFFAOYSA-N butyl-[4-(7-fluoro-8-octoxyphenanthridin-1-yl)oxybutan-2-yl]-dimethylsilane Chemical compound C1=CC(OCCC(C)[Si](C)(C)CCCC)=C2C3=CC=C(OCCCCCCCC)C(F)=C3C=NC2=C1 WRWHVYFIFFLHMH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002012 dioxanes Chemical class 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- ZIZBBPVOSQIWBA-UHFFFAOYSA-N n-(3-methoxyphenyl)-1-phenylmethanimine Chemical compound COC1=CC=CC(N=CC=2C=CC=CC=2)=C1 ZIZBBPVOSQIWBA-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 1種類または2種類以上の式(I): [式中、記号および添字は次の意味を有する: E1およびE2は、同一または異なり、−N−、−CF−または−CH−であり; R1およびR2は、同一または異なり、炭素数1〜20の直鎖もしくは分枝鎖のア ルキル基(不整炭素を有していても有していなくてもよい)であり、ここで1個 またはそれ以上の−CH2−基が、−O−、−S−、−C≡C−、シクロプロパ ン−1,2−ジイルまたは−Si(CH3)2−で置換されていてもよいが、ただ し酸素原子およびイオウ原子は互いに直接結合せず、さらに、アルキル基の1個 またはそれ以上の水素原子がフッ素で置換されていてもよく、または下記のいず れかのキラル基(光学的に活性であるかまたはラヤミ体である): であり;あるいは、R1およびR2の一方は水素であり; R3、R4、R5、R6およびR7は、同一または異なり、水素または炭素数1〜 16の直鎖もしくは分枝鎖のアルキル基(不整炭素を有していても有していなく てもよい)であり、ここで1個の−CH2−基が−O−で置換されていてもよく 、さらに、アルキル基の1個またはそれ以上の水素原子がフッ素で置換されてい ても よく;あるいはR4およびR5は、ジオキソラン系に結合する場合には、一緒にな って−(CH2)4−または−(CH2)5−を形成してもよく; Qは、−CH2−O−、−CO−O−または単結合であり; M1およびM2は、同一または異なり、−CO−O−、−O−CO−、−CH2− O−、−O−CH2−、−CH2−CH2−、−C≡C−または単結合であり; A1およびA2は、同一または異なり、1個またはそれ以上の水素原子がFで置換 されていてもよい1,4−フェニレン、トランス−1,4−シクロヘキシレン、 ピリミジン−2,5−ジイル、1個の水素原子がFで置換されていてもよいピリ ジン−2,5−ジイル、1,3,4−チアジアゾール−2,5−ジイル、1,3 −ジオキサン−2,5−ジイル、1,3−ジチアン−2,5−ジイル、1,3− チアゾール−2,4−ジイル、1,3−チアゾール−2,5−ジイル、チオフェ ン−2,4−ジイルまたはチオフェン−2,5−ジイルであり; mおよびnは、0または1であり、但しこれらの合計は最大1である] のフェナントリジン誘導体を含む強誘電性液晶混合物。 2. 式(I)において、基: が次のいずれかの意味: を有する化合物を含む、請求項1記載の強誘電性液晶混合物。 3. 式(I)において、R1およびR2が炭素数1〜16の直鎖もしくは分枝鎖 のアルキル基(不整炭素を有していても有していなくてもよい)であり、ここで 1個またはそれ以上の−CH2−基が、−O−、シクロプロパン−1,2−ジイ ル または−Si(CH3)2−で置換されていてもよいが、ただし酸素原子は互いに 直接結合せず、さらに、アルキル基の1個またはそれ以上の水素原子がFで置換 されていてもよい、請求項1または2に記載の強誘電性液晶混合物。 4. 式(I)において、R1およびR2が炭素数1〜10の直鎖もしくは分枝鎖 のアルキル基であり、ここで少なくともさらに2つの−CH2−基で環から離れ ている1個の−CH2−基が−Si(CH3)2−で置換されていてもよい、次の 群: からの化合物を含む、請求項1〜3のいずれかに記載の強誘電性液晶混合物。 5. 2〜20成分を含み、1〜10種類の式(I)の化合物を含む、請求項1 〜4のいずれかに記載の強誘電性液晶混合物。 6. 0.01〜80重量%の1種類または2種類以上の式(I)の化合物を含 む、請求項1〜5のいずれかに記載の強誘電性液晶混合物。 7. 請求項1〜6のいずれかに記載の強誘電性液晶混合物の、電気光学的スイ ッチングおよび/またはディスプレイ素子における使用。 8. 請求項1〜6のいずれかに記載の強誘電性液晶混合物を含む、電気光学的 スイッチングおよび/またはディスプレイ素子。 9. 式(Ia): [式中、記号および添字は次の意味を有する: E1およびE2は、同一または異なり、−N−、−CF−または−CH−であり; R1およびR2は、同一または異なり、炭素数1〜20の直鎖もしくは分枝鎖のア ルキル基(不整炭素を有していても有していなくてもよい)であり、ここで1個 またはそれ以上の−CH2−基が、−O−、−S−、−C≡C−、シクロプロパ ン−1,2−ジイルまたは−Si(CH3)2−で置換されていてもよいが、ただ し酸素原子およびイオウ原子は互いに直接結合せず、さらに、アルキル基の1個 またはそれ以上の水素原子がフッ素で置換されていてもよく、または下記のいず れかのキラル基(光学的に活性であるかまたはラセミ体である): であり: R3、R4、R5、R6およびR7は、同一または異なり、水素または炭素数1〜 1 6の直鎖もしくは分枝鎖のアルキル基(不整炭素を有していても有していなくて もよい)であり、ここで1個の−CH2−基が−O−で置換されていてもよく、 さらに、アルキル基の1個またはそれ以上の水素原子がフッ素で置換されていて もよく;あるいはR4およびR5は、ジオキソラン系に結合する場合には、一緒に なって−(CH2)4−または−(CH2)5−を形成してもよく; Qは、−CH2−O−、−CO−O−または単結合であり; M1およびM2は、同一または異なり、−CO−O−、−O−CO−、−CH2− O−、−O−CH2−、−CH2−CH2−、−C≡C−または単結合であり; A1およびA2は、同一または異なり、1個またはそれ以上の水素原子がFで置換 されていてもよい1,4−フェニレン、トランス−1,4−シクロヘキシレン、 ピリミジン−2,5−ジイル、1個の水素原子がFで置換されていてもよいピリ ジン−2,5−ジイル、1,3,4−チアジアゾール−2,5−ジイル、1,3 −ジオキサン−2,5−ジイル、1,3−ジチアン−2,5−ジイル、1,3− チアゾール−2,4−ジイル、1,3−チアゾール-2,5−ジイル、チオフェ ン−2,4−ジイルまたはチオフェン−2,5−ジイルであり; mおよびnは、0または1であり、但しこれらの合計は最大1である] のフェナントリジン誘導体。
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JP8520367A JP3014457B2 (ja) | 1994-12-28 | 1995-12-27 | 新規キヌクリジン誘導体及びその医薬組成物 |
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JP8520367A JP3014457B2 (ja) | 1994-12-28 | 1995-12-27 | 新規キヌクリジン誘導体及びその医薬組成物 |
PCT/JP1995/002713 WO1996020194A1 (fr) | 1994-12-28 | 1995-12-27 | Nouveaux derives de quinuclidine et composition pharmaceutique les contenant |
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JP2001316670A (ja) * | 2000-05-02 | 2001-11-16 | Dainippon Ink & Chem Inc | 液晶組成物 |
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