DD289524A5 - Fluessigkristalline cyclopropylalkyl- oder-alkenyl-heterocyclen, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen - Google Patents
Fluessigkristalline cyclopropylalkyl- oder-alkenyl-heterocyclen, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen Download PDFInfo
- Publication number
- DD289524A5 DD289524A5 DD88322084A DD32208488A DD289524A5 DD 289524 A5 DD289524 A5 DD 289524A5 DD 88322084 A DD88322084 A DD 88322084A DD 32208488 A DD32208488 A DD 32208488A DD 289524 A5 DD289524 A5 DD 289524A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phase sequence
- cyclopropyl
- pyrimidine
- phenyl
- oxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000007788 liquid Substances 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 title description 44
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical class [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 title description 3
- -1 pyrimidin-2,5-diyl Chemical group 0.000 claims abstract description 39
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 3
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 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 description 2
- 239000003513 alkali Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 1
- 238000000819 phase cycle Methods 0.000 description 99
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 102100037158 Keratin, type I cytoskeletal 39 Human genes 0.000 description 3
- 101710183429 Keratin, type I cytoskeletal 39 Proteins 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- RSZOXKKXCBHWNB-RKDXNWHRSA-N (1R,2R)-2-hexylcyclopropane-1-carboxylic acid Chemical compound C(CCCCC)[C@H]1[C@@H](C1)C(=O)O RSZOXKKXCBHWNB-RKDXNWHRSA-N 0.000 description 2
- XYGUNTNTTDQAGL-UHFFFAOYSA-N 2-(4-decoxyphenyl)-5-octoxypyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 XYGUNTNTTDQAGL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IETWSNMXSKALFY-UHFFFAOYSA-N 5-octoxy-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 IETWSNMXSKALFY-UHFFFAOYSA-N 0.000 description 2
- IFZAIZAFLMXIKG-UHFFFAOYSA-N 7-cyclopropylheptanoic acid Chemical compound OC(=O)CCCCCCC1CC1 IFZAIZAFLMXIKG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102220597499 Formyltetrahydrofolate synthetase_K56T_mutation Human genes 0.000 description 2
- 102100028354 Keratin, type I cuticular Ha5 Human genes 0.000 description 2
- 101710150713 Keratin, type I cuticular Ha5 Proteins 0.000 description 2
- 102220577436 Stromal cell-derived factor 1_K48S_mutation Human genes 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 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
- DPPSUGSPUHMWEH-BYPYZUCNSA-N (2s)-2-fluoro-3-methylbutanoic acid Chemical compound CC(C)[C@H](F)C(O)=O DPPSUGSPUHMWEH-BYPYZUCNSA-N 0.000 description 1
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical class CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 1
- GZIGBJSUHIWOGQ-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-dodecoxypyrimidine Chemical compound N1=CC(OCCCCCCCCCCCC)=CN=C1C1=CC=C(OCCCC)C=C1 GZIGBJSUHIWOGQ-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
- DCKBKOTWLPKZBD-UHFFFAOYSA-N 2-(4-dodecoxyphenyl)-5-octoxypyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC=C(OCCCCCCCC)C=N1 DCKBKOTWLPKZBD-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
- BDTDHPKKEJERKY-UHFFFAOYSA-N 2-(9-cyclopropylnonoxy)-5-(4-decoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(C=N1)=CN=C1OCCCCCCCCCC1CC1 BDTDHPKKEJERKY-UHFFFAOYSA-N 0.000 description 1
- BEOKXLVVIGGYRI-UHFFFAOYSA-N 2-[4-(4-cyclopropylbutoxy)phenyl]-5-decylpyrimidine Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCC1CC1 BEOKXLVVIGGYRI-UHFFFAOYSA-N 0.000 description 1
- WFURSVSBAFBATR-UHFFFAOYSA-N 2-[4-(7-cyclopropylheptoxy)phenyl]-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCCC1CC1 WFURSVSBAFBATR-UHFFFAOYSA-N 0.000 description 1
- DDQHPMWQOXJXFN-UHFFFAOYSA-N 2-[4-(7-cyclopropylheptoxy)phenyl]-5-octylpyridine Chemical compound N1=CC(CCCCCCCC)=CC=C1C(C=C1)=CC=C1OCCCCCCCC1CC1 DDQHPMWQOXJXFN-UHFFFAOYSA-N 0.000 description 1
- UJMZNSFFOFLXLK-UHFFFAOYSA-N 2-[4-(8-cyclopropyloctoxy)phenyl]-5-decylpyrimidine Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCCCC1CC1 UJMZNSFFOFLXLK-UHFFFAOYSA-N 0.000 description 1
- GUWXCOWDCFCFRD-UHFFFAOYSA-N 2-[4-(8-cyclopropyloctoxy)phenyl]-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCCCC1CC1 GUWXCOWDCFCFRD-UHFFFAOYSA-N 0.000 description 1
- IYWAJVNNPGAOAA-UHFFFAOYSA-N 2-[4-(9-cyclopropylnonoxy)phenyl]-5-hexylpyrimidine Chemical compound N1=CC(CCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCCCCC1CC1 IYWAJVNNPGAOAA-UHFFFAOYSA-N 0.000 description 1
- XDHIFVUTCVJMHT-UHFFFAOYSA-N 2-[4-(9-cyclopropylnonoxy)phenyl]-5-octoxypyrimidine Chemical compound N1=CC(OCCCCCCCC)=CN=C1C(C=C1)=CC=C1OCCCCCCCCCC1CC1 XDHIFVUTCVJMHT-UHFFFAOYSA-N 0.000 description 1
- RHPNXDKLKKFPPD-UHFFFAOYSA-N 4-(5-heptoxypyrimidin-2-yl)phenol Chemical compound CCCCCCCOc1cnc(nc1)-c1ccc(O)cc1 RHPNXDKLKKFPPD-UHFFFAOYSA-N 0.000 description 1
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 1
- FZNOKCDLZNGIKK-UHFFFAOYSA-N 5-(11-cyclopropylundecoxy)-2-(4-dodecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCCCCC1CC1 FZNOKCDLZNGIKK-UHFFFAOYSA-N 0.000 description 1
- HXMSFFNOWLHDAK-UHFFFAOYSA-N 5-(5-cyclopropylpentoxy)-2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCC1CC1 HXMSFFNOWLHDAK-UHFFFAOYSA-N 0.000 description 1
- LFFPLAYCYSEISB-UHFFFAOYSA-N 5-(6-cyclopropylhexoxy)-2-(4-dodecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCC1CC1 LFFPLAYCYSEISB-UHFFFAOYSA-N 0.000 description 1
- DUGFARMIHDWISH-UHFFFAOYSA-N 5-(6-cyclopropylhexoxy)-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCC1CC1 DUGFARMIHDWISH-UHFFFAOYSA-N 0.000 description 1
- LZCMIYBXGULNMI-UHFFFAOYSA-N 5-(6-cyclopropylhexoxy)-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCC1CC1 LZCMIYBXGULNMI-UHFFFAOYSA-N 0.000 description 1
- LNUABJAXGGDQMP-UHFFFAOYSA-N 5-(7-cyclopropylheptoxy)-2-(4-decoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCC1CC1 LNUABJAXGGDQMP-UHFFFAOYSA-N 0.000 description 1
- LRSIQYKGDSAHAU-UHFFFAOYSA-N 5-(7-cyclopropylheptoxy)-2-(4-dodecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCC1CC1 LRSIQYKGDSAHAU-UHFFFAOYSA-N 0.000 description 1
- QSDWAVCAUQWCEH-UHFFFAOYSA-N 5-(7-cyclopropylheptoxy)-2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCC1CC1 QSDWAVCAUQWCEH-UHFFFAOYSA-N 0.000 description 1
- ZJCVFQNKRCKDDE-UHFFFAOYSA-N 5-(7-cyclopropylheptoxy)-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCC1CC1 ZJCVFQNKRCKDDE-UHFFFAOYSA-N 0.000 description 1
- PRCIMZWEKOLJPB-UHFFFAOYSA-N 5-(7-cyclopropylheptoxy)-2-(4-undecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCC1CC1 PRCIMZWEKOLJPB-UHFFFAOYSA-N 0.000 description 1
- RIIVWAYFAHVFQR-UHFFFAOYSA-N 5-(8-cyclopropyloctoxy)-2-(4-decoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCC1CC1 RIIVWAYFAHVFQR-UHFFFAOYSA-N 0.000 description 1
- SPRICEZXYTWDCM-UHFFFAOYSA-N 5-(8-cyclopropyloctoxy)-2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCC1CC1 SPRICEZXYTWDCM-UHFFFAOYSA-N 0.000 description 1
- XMGPGLGPKITSRY-UHFFFAOYSA-N 5-(8-cyclopropyloctoxy)-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCC1CC1 XMGPGLGPKITSRY-UHFFFAOYSA-N 0.000 description 1
- LOHPSNSKOGVCHP-UHFFFAOYSA-N 5-(8-cyclopropyloctoxy)-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCC1CC1 LOHPSNSKOGVCHP-UHFFFAOYSA-N 0.000 description 1
- GORKWYIJPQQTAP-UHFFFAOYSA-N 5-(9-cyclopropylnonoxy)-2-(4-dodecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCCC1CC1 GORKWYIJPQQTAP-UHFFFAOYSA-N 0.000 description 1
- AUDYWTNPVLWJSS-UHFFFAOYSA-N 5-(9-cyclopropylnonoxy)-2-(4-heptoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCCC1CC1 AUDYWTNPVLWJSS-UHFFFAOYSA-N 0.000 description 1
- YMPSOQLWNKQKTF-UHFFFAOYSA-N 5-(9-cyclopropylnonoxy)-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCCC1CC1 YMPSOQLWNKQKTF-UHFFFAOYSA-N 0.000 description 1
- YUWBBWQUXHNXBH-UHFFFAOYSA-N 5-(9-cyclopropylnonoxy)-2-(4-undecoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCCCCCCC1CC1 YUWBBWQUXHNXBH-UHFFFAOYSA-N 0.000 description 1
- ZHGXLZMDIXLXOZ-UHFFFAOYSA-N 5-(cyclopropylmethoxy)-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCC1CC1 ZHGXLZMDIXLXOZ-UHFFFAOYSA-N 0.000 description 1
- PTJWMZXBQOHTOJ-UHFFFAOYSA-N 5-[4-(7-cyclopropylheptoxy)phenyl]-2-octylsulfanylpyrimidine Chemical compound C1=NC(SCCCCCCCC)=NC=C1C(C=C1)=CC=C1OCCCCCCCC1CC1 PTJWMZXBQOHTOJ-UHFFFAOYSA-N 0.000 description 1
- FMZJEDPAJRSVTN-UHFFFAOYSA-N 5-[4-(9-cyclopropylnonoxy)phenyl]-2-decylsulfanylpyrimidine Chemical compound C1=NC(SCCCCCCCCCC)=NC=C1C(C=C1)=CC=C1OCCCCCCCCCC1CC1 FMZJEDPAJRSVTN-UHFFFAOYSA-N 0.000 description 1
- MEMVERAKXMCNAZ-UHFFFAOYSA-N 5-[4-(cyclopropylmethoxy)butoxy]-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(N=C1)=NC=C1OCCCCOCC1CC1 MEMVERAKXMCNAZ-UHFFFAOYSA-N 0.000 description 1
- WOSIIAKQLDNQEE-UHFFFAOYSA-N 5-decoxy-2-(4-octoxyphenyl)pyrimidine Chemical compound N1=CC(OCCCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C=C1 WOSIIAKQLDNQEE-UHFFFAOYSA-N 0.000 description 1
- SVQZDRNTCOLRJG-UHFFFAOYSA-N 5-dodecoxy-2-(4-octoxyphenyl)pyrimidine Chemical compound N1=CC(OCCCCCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C=C1 SVQZDRNTCOLRJG-UHFFFAOYSA-N 0.000 description 1
- WBLQPVYQPZDBHS-UHFFFAOYSA-N 9-cyclopropylnonan-1-ol Chemical compound OCCCCCCCCCC1CC1 WBLQPVYQPZDBHS-UHFFFAOYSA-N 0.000 description 1
- WHIKJKXCDJAJHF-UAPYVXQJSA-N CCCCC[C@H]1CC[C@@H](CC1)C(=O)Oc1ccc(cc1)-c1ncccn1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)C(=O)Oc1ccc(cc1)-c1ncccn1 WHIKJKXCDJAJHF-UAPYVXQJSA-N 0.000 description 1
- 102220586640 Cysteinyl leukotriene receptor 1_K54S_mutation Human genes 0.000 description 1
- 102100023131 Keratin, type I cuticular Ha1 Human genes 0.000 description 1
- 101710150717 Keratin, type I cuticular Ha1 Proteins 0.000 description 1
- 102100028355 Keratin, type I cuticular Ha4 Human genes 0.000 description 1
- 101710150715 Keratin, type I cuticular Ha4 Proteins 0.000 description 1
- 102100028341 Keratin, type I cuticular Ha6 Human genes 0.000 description 1
- 101710150527 Keratin, type I cuticular Ha6 Proteins 0.000 description 1
- 102100033511 Keratin, type I cytoskeletal 17 Human genes 0.000 description 1
- 101710183401 Keratin, type I cytoskeletal 17 Proteins 0.000 description 1
- 102100032703 Keratin, type I cytoskeletal 25 Human genes 0.000 description 1
- 101710183654 Keratin, type I cytoskeletal 25 Proteins 0.000 description 1
- 102100037157 Keratin, type I cytoskeletal 40 Human genes 0.000 description 1
- 101710183583 Keratin, type I cytoskeletal 40 Proteins 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 102220554267 Protein dispatched homolog 1_K68S_mutation Human genes 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001840 cholesterol esters Chemical class 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- 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
-
- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pyridine Compounds (AREA)
- Liquid Crystal (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3739884 | 1987-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD289524A5 true DD289524A5 (de) | 1991-05-02 |
Family
ID=6341201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88322084A DD289524A5 (de) | 1987-11-25 | 1988-11-23 | Fluessigkristalline cyclopropylalkyl- oder-alkenyl-heterocyclen, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0318423B1 (fr) |
| JP (1) | JPH0751563B2 (fr) |
| KR (1) | KR970011278B1 (fr) |
| CN (1) | CN1022409C (fr) |
| AT (1) | ATE117996T1 (fr) |
| BR (1) | BR8806184A (fr) |
| DD (1) | DD289524A5 (fr) |
| DE (2) | DE3852931D1 (fr) |
| NO (2) | NO885236L (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3718174A1 (de) * | 1987-05-29 | 1988-12-15 | Hoechst Ag | Verwendung von optisch aktiven oxiran-2-carbonsaeureestern als dotierstoffe in fluessigkristallmischungen, diese enthaltende fluessigkristallmischungen und neue optisch aktive oxiran-2-carbonsaeureester |
| US5407599A (en) * | 1987-11-25 | 1995-04-18 | Hoechst Aktiengesellschaft | Cyclopropylaklyl or -alkenyl or heterocyclic compounds, process for their preparation and their use in liquid-crystalline mixtures |
| DE3915804A1 (de) * | 1989-05-13 | 1990-11-15 | Hoechst Ag | Cyclopropylalkyl- oder -alkenylverbindungen, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
| DE3925971A1 (de) * | 1989-08-05 | 1991-02-07 | Hoechst Ag | Fluessigkristalline, insbesondere ferroelektrische fluessigkristalline mischungen und ihre verwendung in elektrooptischen vorrichtungen |
| DE4027923A1 (de) * | 1989-09-05 | 1991-03-07 | Merck Patent Gmbh | Phenylcyclohexane und fluessigkristallines medium |
| JPH03193774A (ja) * | 1989-12-22 | 1991-08-23 | Canon Inc | 光学活性液晶化合物、これを含む液晶組成物およびこれを利用した液晶素子 |
| US5064564A (en) * | 1989-12-22 | 1991-11-12 | Dainippon Ink And Chemicals, Inc. | Optically active compound, intermediate therefor, process for producing the intermediate, and liquid-crystal composition |
| US5128061A (en) * | 1990-08-14 | 1992-07-07 | Optical Shields, Inc. | Phenyl-pyrimidine liquid crystal materials |
| DE4030579A1 (de) * | 1990-09-27 | 1992-04-02 | Hoechst Ag | Cyclohexylphenylpyrimidine, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
| DE4434754A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Ag | Neue Verbindungen zur Verwendung in Flüssigkristallmischungen |
| JPH0931064A (ja) * | 1995-07-17 | 1997-02-04 | Rolic Ag | アルコキシアルコキシ−置換の含窒素複素環化合物誘導体 |
| DE10145778B4 (de) | 2001-09-17 | 2012-07-19 | Merck Patent Gmbh | Fluorierte Anthracene und ihre Verwendung in Flüssigkristallmischungen und in Flüssigkristalldisplays |
| DE10145780B4 (de) | 2001-09-17 | 2012-10-04 | Merck Patent Gmbh | Fluorierte Cyclopenta[a]naphthaline und ihre Verwendung in Flüssigkristallmischungen und Displays |
| DE10145779B4 (de) | 2001-09-17 | 2012-11-15 | Merck Patent Gmbh | Fluorierte Cyclopenta[b]naphthaline und ihre Verwendung in Flüssigkristallmischungen |
| EP1556360B1 (fr) | 2002-10-30 | 2008-01-23 | Ciba SC Holding AG | Dispositif electroluminescent |
| US9923148B2 (en) | 2002-10-30 | 2018-03-20 | Udc Ireland Limited | Electroluminescent device |
| CN104531166B (zh) * | 2014-12-12 | 2016-09-07 | 石家庄诚志永华显示材料有限公司 | 含有环丙基的液晶化合物以及液晶混合物 |
| CN104593009A (zh) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其在液晶显示中的应用 |
| CN107177360A (zh) * | 2015-02-15 | 2017-09-19 | 石家庄诚志永华显示材料有限公司 | 含有环丙基的负介电各向异性液晶介质及其应用 |
| CN104593008B (zh) * | 2015-02-15 | 2017-01-04 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
| CN104593012A (zh) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | 一种液晶组合物 |
| CN104650925B (zh) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | 液晶介质 |
| CN104593003B (zh) * | 2015-02-15 | 2017-01-04 | 石家庄诚志永华显示材料有限公司 | 液晶介质 |
| CN104593010A (zh) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
| CN107267158A (zh) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | 含有环丙基的负介电各向异性液晶介质及其应用 |
| CN104650928A (zh) * | 2015-02-15 | 2015-05-27 | 石家庄诚志永华显示材料有限公司 | 一种含有环丙基化合物的液晶组合物 |
| CN104593005B (zh) * | 2015-02-15 | 2017-01-11 | 石家庄诚志永华显示材料有限公司 | 一种含有二氧六环结构的液晶组合物 |
| CN104593007B (zh) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
| CN104593004B (zh) * | 2015-02-15 | 2017-05-24 | 石家庄诚志永华显示材料有限公司 | 液晶组合物 |
| CN104593013B (zh) * | 2015-02-15 | 2016-12-07 | 石家庄诚志永华显示材料有限公司 | 一种液晶介质 |
| CN104593001A (zh) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
| CN104650923B (zh) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
| CN107286951B (zh) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| CN107286952B (zh) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| CN107345142B (zh) * | 2016-05-06 | 2020-02-21 | 北京八亿时空液晶科技股份有限公司 | 一种含有萘环的负介电各向异性液晶组合物及其应用 |
| CN107400516B (zh) * | 2016-05-19 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | 一种环丙基类负介电各向异性的液晶化合物及其应用 |
| CN107523314B (zh) * | 2016-06-20 | 2019-09-20 | 北京八亿时空液晶科技股份有限公司 | 一种含有环丙基醚类负介电液晶组合物及其应用 |
| CN107586545B (zh) * | 2016-07-06 | 2019-08-23 | 北京八亿时空液晶科技股份有限公司 | 一种快响应负介电各向异性液晶组合物及其应用 |
| CN109097066B (zh) * | 2017-06-20 | 2021-12-21 | 江苏和成显示科技有限公司 | 近晶相液晶组合物及其在液晶显示器件中应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3782531T2 (de) * | 1986-04-21 | 1993-05-06 | Ajinomoto Kk | Optisch aktive verbindung und fluessigkristalline zusammensetzung. |
-
1988
- 1988-11-21 CN CN88108037A patent/CN1022409C/zh not_active Expired - Fee Related
- 1988-11-22 AT AT88710048T patent/ATE117996T1/de not_active IP Right Cessation
- 1988-11-22 DE DE3852931T patent/DE3852931D1/de not_active Expired - Lifetime
- 1988-11-22 DE DE3839330A patent/DE3839330A1/de not_active Withdrawn
- 1988-11-22 EP EP88710048A patent/EP0318423B1/fr not_active Expired - Lifetime
- 1988-11-23 DD DD88322084A patent/DD289524A5/de not_active IP Right Cessation
- 1988-11-24 KR KR1019880015462A patent/KR970011278B1/ko not_active Expired - Fee Related
- 1988-11-24 BR BR888806184A patent/BR8806184A/pt not_active Application Discontinuation
- 1988-11-24 NO NO88885236A patent/NO885236L/no unknown
- 1988-11-24 JP JP63294826A patent/JPH0751563B2/ja not_active Expired - Lifetime
-
1989
- 1989-06-14 NO NO892472A patent/NO892472D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR970011278B1 (ko) | 1997-07-09 |
| KR890008111A (ko) | 1989-07-08 |
| EP0318423B1 (fr) | 1995-02-01 |
| DE3852931D1 (de) | 1995-03-16 |
| EP0318423A2 (fr) | 1989-05-31 |
| CN1039019A (zh) | 1990-01-24 |
| NO885236L (no) | 1989-05-26 |
| NO885236D0 (no) | 1988-11-24 |
| JPH01165573A (ja) | 1989-06-29 |
| CN1022409C (zh) | 1993-10-13 |
| ATE117996T1 (de) | 1995-02-15 |
| NO892472D0 (no) | 1989-06-14 |
| DE3839330A1 (de) | 1989-06-08 |
| JPH0751563B2 (ja) | 1995-06-05 |
| EP0318423A3 (en) | 1990-08-08 |
| NO892472L (no) | 1989-05-26 |
| BR8806184A (pt) | 1989-08-15 |
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