DD232304A5 - Fluessigkristalline phase - Google Patents

Fluessigkristalline phase Download PDF

Info

Publication number: DD232304A5
Authority: DD; German Democratic Republic
Prior art keywords: trans; hexylpyrimidine; ester; cyanophenyl; acid
Prior art date: 1984-02-07

Application number

DD85273086A

Other languages

German (de)

English (en)

Inventor

Bernhard Scheuble

Georg Weber

Original Assignee

Merck Patent Gmbh,De

Priority date (The priority date 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 date listed.)

1984-02-07

Filing date

1985-02-06

Publication date

1986-01-22

1985-02-06 Application filed by Merck Patent Gmbh,De filed Critical Merck Patent Gmbh,De

1986-01-22 Publication of DD232304A5 publication Critical patent/DD232304A5/de

Links

239000007788 liquid Substances 0.000 title abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 35
239000004973 liquid crystal related substance Substances 0.000 claims abstract description 33
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 14
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
150000003230 pyrimidines Chemical class 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 abstract description 2
-1 pyrimidine-2,5-diyl Chemical group 0.000 description 83
150000002148 esters Chemical class 0.000 description 26
QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 17
RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 16
OGFGFVYUTGSNAF-UHFFFAOYSA-N 5-heptyl-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCC)C=N1 OGFGFVYUTGSNAF-UHFFFAOYSA-N 0.000 description 16
FJRQLNHSTIQROP-UHFFFAOYSA-N 5-hexyl-2-(4-pentoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(OCCCCC)C=C1 FJRQLNHSTIQROP-UHFFFAOYSA-N 0.000 description 14
RXBBPIPXHBOXOU-KESTWPANSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 RXBBPIPXHBOXOU-KESTWPANSA-N 0.000 description 13
AEEUYSFCGITNNH-UHFFFAOYSA-N 2-(4-heptoxyphenyl)-5-hexylpyrimidine Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=NC=C(CCCCCC)C=N1 AEEUYSFCGITNNH-UHFFFAOYSA-N 0.000 description 12
SSXIKUCDZOQOKB-UHFFFAOYSA-N 4-(5-pentyl-1,3-dioxan-2-yl)benzonitrile Chemical compound O1CC(CCCCC)COC1C1=CC=C(C#N)C=C1 SSXIKUCDZOQOKB-UHFFFAOYSA-N 0.000 description 12
WKHRWWOOFQQILG-UHFFFAOYSA-N 5-hexyl-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCCC)C=N1 WKHRWWOOFQQILG-UHFFFAOYSA-N 0.000 description 12
125000000217 alkyl group Chemical group 0.000 description 12
235000010290 biphenyl Nutrition 0.000 description 10
239000004305 biphenyl Substances 0.000 description 10
ZCZHIMLDHBRGMF-UHFFFAOYSA-N 4-(5-butyl-1,3-dioxan-2-yl)benzonitrile Chemical compound O1CC(CCCC)COC1C1=CC=C(C#N)C=C1 ZCZHIMLDHBRGMF-UHFFFAOYSA-N 0.000 description 9
JBTFOPFQDACQDB-UHFFFAOYSA-N 5-hexyl-2-(4-methoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(OC)C=C1 JBTFOPFQDACQDB-UHFFFAOYSA-N 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
DOALOUQODWWGEZ-UHFFFAOYSA-N 1-ethyl-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC(CC)=CC=2)C=C1 DOALOUQODWWGEZ-UHFFFAOYSA-N 0.000 description 7
XQQYMNZQNMFGAR-UHFFFAOYSA-N 2-(4-heptoxyphenyl)-5-heptylpyrimidine Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=NC=C(CCCCCCC)C=N1 XQQYMNZQNMFGAR-UHFFFAOYSA-N 0.000 description 7
239000005247 4-Ethyl-4'-(trans-4-propylcyclohexyl)biphenyl Substances 0.000 description 7
125000004430 oxygen atom Chemical group O* 0.000 description 7
LGCWNHQHPFBPBP-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-hexylpyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=C(CCCCCC)C=N1 LGCWNHQHPFBPBP-UHFFFAOYSA-N 0.000 description 6
YQQXBCJQEGWHRW-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-nonylpyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 YQQXBCJQEGWHRW-UHFFFAOYSA-N 0.000 description 6
CLLQLHCWZVQLNO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-nonylpyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OC)C=C1 CLLQLHCWZVQLNO-UHFFFAOYSA-N 0.000 description 6
GTPJWQZJAGFLRR-UHFFFAOYSA-N 2-(4-nonoxyphenyl)-5-nonylpyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCCC)C=N1 GTPJWQZJAGFLRR-UHFFFAOYSA-N 0.000 description 6
YWSBRIQSYKROHJ-UHFFFAOYSA-N 4-(5-ethyl-1,3-dioxan-2-yl)benzonitrile Chemical compound O1CC(CC)COC1C1=CC=C(C#N)C=C1 YWSBRIQSYKROHJ-UHFFFAOYSA-N 0.000 description 6
GQPFCPRCGONDNN-UHFFFAOYSA-N 4-(5-propyl-1,3-dioxan-2-yl)benzonitrile Chemical compound O1CC(CCC)COC1C1=CC=C(C#N)C=C1 GQPFCPRCGONDNN-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
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 5
LUCHFKBTWHPREI-UHFFFAOYSA-N 1-(4-propylcyclohexyl)-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C2CCC(CCC)CC2)C=C1 LUCHFKBTWHPREI-UHFFFAOYSA-N 0.000 description 5
URHKQYKCNSLHHG-UHFFFAOYSA-N 2-(4-heptoxyphenyl)-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OCCCCCCC)C=C1 URHKQYKCNSLHHG-UHFFFAOYSA-N 0.000 description 5
QKEBUASRTJNJJS-UHFFFAOYSA-N 4-[4-(4-pentylcyclohexyl)phenyl]benzonitrile Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-UHFFFAOYSA-N 0.000 description 5
BHNCKGFFWRYBIL-UHFFFAOYSA-N 5-heptyl-2-(4-hexoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 BHNCKGFFWRYBIL-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
JOLGXBQYTARJLD-UHFFFAOYSA-N 1-ethyl-4-[4-(4-pentylcyclohexyl)phenyl]benzene Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(CC)=CC=2)C=C1 JOLGXBQYTARJLD-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
RMAFJFORFGJHLD-UHFFFAOYSA-N 2-(4-octoxyphenyl)-5-pentylpyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(CCCCC)C=N1 RMAFJFORFGJHLD-UHFFFAOYSA-N 0.000 description 3
VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 description 3
VDIHYZOQBIZBHO-UHFFFAOYSA-N 5-heptyl-2-(4-methoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(OC)C=C1 VDIHYZOQBIZBHO-UHFFFAOYSA-N 0.000 description 3
NJSPPGNEZLZGRI-UHFFFAOYSA-N 5-hexyl-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(CCCCCC)C=N1 NJSPPGNEZLZGRI-UHFFFAOYSA-N 0.000 description 3
PJBOOKMLDPERRS-PCYFZWJMSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 PJBOOKMLDPERRS-PCYFZWJMSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 description 2
NBOMAZVNDYECTP-DANJKSSVSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 NBOMAZVNDYECTP-DANJKSSVSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
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 2
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000003860 storage Methods 0.000 description 2
PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 1
150000005481 1,2-diphenylethanes Chemical class 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
WQADWIOXOXRPLN-AZXPZELESA-N 1,3-dithiane Chemical group C1CS[13CH2]SC1 WQADWIOXOXRPLN-AZXPZELESA-N 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 1
LOSGWRGHABIGEP-UHFFFAOYSA-N 2-(4-decylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCCCCCC)=CC=C1C1=NC=C(C#N)C=N1 LOSGWRGHABIGEP-UHFFFAOYSA-N 0.000 description 1
ZKQPONVDUDTAOD-UHFFFAOYSA-N 2-(4-dodecylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C1=NC=C(C#N)C=N1 ZKQPONVDUDTAOD-UHFFFAOYSA-N 0.000 description 1
VLDUBPCOGIAADA-UHFFFAOYSA-N 2-(4-heptoxyphenyl)-4-hexylpyrimidine Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=NC=CC(CCCCCC)=N1 VLDUBPCOGIAADA-UHFFFAOYSA-N 0.000 description 1
IAVXKMCGCPQZLI-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-4-hexylpyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC(CCCCCC)=N1 IAVXKMCGCPQZLI-UHFFFAOYSA-N 0.000 description 1
IWZAFMARMJZJDW-UHFFFAOYSA-N 2-(4-nonoxyphenyl)-5-octylpyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCC)C=N1 IWZAFMARMJZJDW-UHFFFAOYSA-N 0.000 description 1
IFXLWKJINPVGJO-UHFFFAOYSA-N 2-(4-nonoxyphenyl)-5-pentylpyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCC)C=N1 IFXLWKJINPVGJO-UHFFFAOYSA-N 0.000 description 1
FCCMNDONFWAAMS-UHFFFAOYSA-N 2-(4-tridecylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCCCCCCCCC)=CC=C1C1=NC=C(C#N)C=N1 FCCMNDONFWAAMS-UHFFFAOYSA-N 0.000 description 1
XGICANQHHQJKKV-UHFFFAOYSA-N 2-(4-undecylphenyl)pyrimidine-5-carbonitrile Chemical compound C1=CC(CCCCCCCCCCC)=CC=C1C1=NC=C(C#N)C=N1 XGICANQHHQJKKV-UHFFFAOYSA-N 0.000 description 1
SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical class C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 1
IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical class C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-UHFFFAOYSA-N 0.000 description 1
YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical class C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 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
125000005917 3-methylpentyl group Chemical group 0.000 description 1
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NPDAPMMGPACKRH-UHFFFAOYSA-N 4-(5-ethylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CC)=CN=C1C1=CC=C(C#N)C=C1 NPDAPMMGPACKRH-UHFFFAOYSA-N 0.000 description 1
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HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 1
RIQBVSRGAKAWBX-UHFFFAOYSA-N 4-hexyl-2-(4-nonoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C1=NC=CC(CCCCCC)=N1 RIQBVSRGAKAWBX-UHFFFAOYSA-N 0.000 description 1
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125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
VLJJKDDNKBVZPX-UHFFFAOYSA-N 5-heptyl-2-(4-octoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NC=C(CCCCCCC)C=N1 VLJJKDDNKBVZPX-UHFFFAOYSA-N 0.000 description 1
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SKTSOKCXDMDTQW-UHFFFAOYSA-N 5-heptylpyrimidine Chemical compound CCCCCCCC1=CN=CN=C1 SKTSOKCXDMDTQW-UHFFFAOYSA-N 0.000 description 1
JAIZEOKRVZKODU-UHFFFAOYSA-N 5-pentylpyrimidine Chemical compound CCCCCC1=CN=CN=C1 JAIZEOKRVZKODU-UHFFFAOYSA-N 0.000 description 1
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IRQQATFJQUTPRH-UAPYVXQJSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=N1)CCCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=N1)CCCCC IRQQATFJQUTPRH-UAPYVXQJSA-N 0.000 description 1
MZTXVWPCCZGQOP-XUTJKUGGSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=N1)CCCCC Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=NC=C(C=N1)CCCCC MZTXVWPCCZGQOP-XUTJKUGGSA-N 0.000 description 1
OXBRRUNAAVNTOZ-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-SHTZXODSSA-N 0.000 description 1
VJMNQADPCKONIA-XUTJKUGGSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 VJMNQADPCKONIA-XUTJKUGGSA-N 0.000 description 1
QPNMXUDEFKSNID-CHDDOINTSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 QPNMXUDEFKSNID-CHDDOINTSA-N 0.000 description 1
MDUQZBFHDPNORI-HDJSIYSDSA-N CCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 Chemical compound CCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 MDUQZBFHDPNORI-HDJSIYSDSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
238000000149 argon plasma sintering Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000005452 bending Methods 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004074 biphenyls Chemical class 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
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 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
125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
BPSQMWSZGQGXHF-UHFFFAOYSA-N dodecyl-ethyl-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC BPSQMWSZGQGXHF-UHFFFAOYSA-N 0.000 description 1
239000002019 doping agent Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000005684 electric field Effects 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000374 eutectic mixture Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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 1
238000011835 investigation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
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 1
230000003287 optical effect Effects 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
238000002310 reflectometry Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
150000001608 tolans Chemical class 0.000 description 1
230000007704 transition Effects 0.000 description 1
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 1

Classifications

- 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
- 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
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines

Landscapes

Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Liquid Crystal Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD85273086A 1984-02-07 1985-02-06 Fluessigkristalline phase DD232304A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843404117 DE3404117A1 (de)	1984-02-07	1984-02-07	Fluessigkristalline phase

Publications (1)

Publication Number	Publication Date
DD232304A5 true DD232304A5 (de)	1986-01-22

Family

ID=6226908

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85273086A DD232304A5 (de)	1984-02-07	1985-02-06	Fluessigkristalline phase

Country Status (4)

Country	Link
EP (1)	EP0151446B1 (fr)
JP (1)	JPS60192787A (fr)
DD (1)	DD232304A5 (fr)
DE (2)	DE3404117A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3315295A1 (de) *	1983-04-27	1984-10-31	Merck Patent Gmbh, 6100 Darmstadt	Fluorhaltige pyrimidinderivate
US4788000A (en) *	1983-05-26	1988-11-29	Sharp Kabushiki Kaisha	Liquid-crystal composition
WO1986000087A1 (fr) *	1984-06-07	1986-01-03	Seiko Instruments & Electronics Ltd.	Compose de cristaux liquides
WO1986002375A1 (fr) *	1984-10-17	1986-04-24	MERCK Patent Gesellschaft mit beschränkter Haftung	Composition a base de cristaux liquides
DE3500897A1 (de) *	1985-01-12	1986-07-17	Merck Patent Gmbh, 6100 Darmstadt	Fluessigkristalline phase
DE3515374C2 (de) *	1985-04-27	1998-02-26	Hoechst Ag	Chirale getilte smektische flüssigkristalline Phasen und deren Verwendung in elektrooptischen Anzeigeelementen
DE3518734A1 (de) *	1985-05-24	1986-11-27	Merck Patent Gmbh, 6100 Darmstadt	Smektische fluessigkristalline phasen
WO1987001717A2 (fr) *	1985-09-18	1987-03-26	MERCK Patent Gesellschaft mit beschränkter Haftung	Phases smectiques a cristaux liquides
JPS62294664A (ja) *	1986-06-13	1987-12-22	Alps Electric Co Ltd	液晶性化合物
JPS62294663A (ja) *	1986-06-13	1987-12-22	Alps Electric Co Ltd	液晶性化合物
JP2508125B2 (ja) *	1986-09-09	1996-06-19	味の素株式会社	フェニルピリミジン化合物及びこれを含有してなる液晶組成物
JP2532886B2 (ja) *	1987-09-08	1996-09-11	チッソ株式会社	ネマチツク液晶組成物
DE3731639A1 (de) *	1987-09-19	1989-03-30	Hoechst Ag	Fluessigkristalline phenylpyrimidin-cyclohexancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallmischungen
EP0307880B1 (fr) *	1987-09-19	1994-01-12	Hoechst Aktiengesellschaft	Mélanges liquides cristallins ferro-électriques
US4913532A (en) *	1987-10-19	1990-04-03	Casio Computer Co., Ltd.	Liquid crystal composition and liquid crystal display device using the same
US4944577A (en) *	1987-10-19	1990-07-31	Casio Computer Co., Ltd.	Liquid crystal display device
JP2511478B2 (ja) *	1987-10-19	1996-06-26	カシオ計算機株式会社	時分割駆動用液晶組成物
JPH02503093A (ja) *	1987-10-19	1990-09-27	カシオ計算機株式会社	改良された液晶混合物
JPH02502921A (ja) *	1988-01-12	1990-09-13	メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング	改良された液晶混合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2815860A1 (de) *	1977-04-15	1978-10-19	Hoffmann La Roche	Fluessigkristalline mischungen
DD138558A1 (de) *	1977-12-08	1979-11-07	Frank Kuschel	Nematische fluessig-kristalline gemische

1984
- 1984-02-07 DE DE19843404117 patent/DE3404117A1/de not_active Withdrawn
1985
- 1985-01-26 EP EP85100810A patent/EP0151446B1/fr not_active Expired - Lifetime
- 1985-01-26 DE DE8585100810T patent/DE3579708D1/de not_active Expired - Fee Related
- 1985-02-06 DD DD85273086A patent/DD232304A5/de not_active IP Right Cessation
- 1985-02-07 JP JP60021020A patent/JPS60192787A/ja active Pending

Also Published As

Publication number	Publication date
JPS60192787A (ja)	1985-10-01
EP0151446B1 (fr)	1990-09-19
DE3579708D1 (de)	1990-10-25
DE3404117A1 (de)	1985-08-08
EP0151446A3 (en)	1986-10-29
EP0151446A2 (fr)	1985-08-14

Legal Events

Date	Code	Title	Description
1994-01-27	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

Publication	Publication Date	Title
EP0149208B1 (fr)	1988-05-04	Dérivés d'éthane
EP0152808B1 (fr)	1990-09-12	Hétérocycles azotés
EP0306505B1 (fr)	1993-03-24	Derives d'acetylene comme composants de phases de cristaux liquides
EP0182054B1 (fr)	1990-03-07	Composés hétérocycliques
EP0199004B1 (fr)	1989-09-06	Dérivés de la pyrimidine
EP0264435B1 (fr)	1992-03-04	Phases smectiques de cristaux liquides
EP0281611B1 (fr)	1993-11-24	Phases de cristaux liquides pour elements electro-optiques d'affichage fondes sur l'effet ecb
EP0256097B1 (fr)	1990-08-01	Composés vinyliques et phase liquide cristalline
EP0138006A2 (fr)	1985-04-24	Phase liquide-cristalline
EP0308438B1 (fr)	1993-09-29	Phase liquide cristalline contenant des tolanes
EP0215800B1 (fr)	1990-04-04	Pyrimidines
DD232304A5 (de)	1986-01-22	Fluessigkristalline phase
EP0168043A2 (fr)	1986-01-15	Phase liquide cristalline
EP0149209B1 (fr)	1988-03-02	Phase de cristal liquide
EP0158137B1 (fr)	1990-01-10	Pyrimidines
DE3807861A1 (de)	1989-09-21	2,3-difluorbiphenyle
EP0226592B1 (fr)	1989-09-06	Phase cristalline liquide
EP0135062B1 (fr)	1987-11-25	Cyclohexyldioxanes
DE3523185A1 (de)	1986-01-23	Fluessigkristall-phase
EP0184068A1 (fr)	1986-06-11	Nitriles d'acides carboxyliques
DE3814346A1 (de)	1989-11-09	Pyridinderivate, ihre verwendung als komponenten fluessigkristalliner phasen, entsprechende fluessigkristallphasen und sie enthaltende fluessigkristallanzeigeelemente
DD243937A5 (de)	1987-03-18	Fluessigkristalline phase enthaltend cyclohexanderivate
DE3434335A1 (de)	1986-03-27	Fluessigkristalline phase
DE4338348B4 (de)	2006-05-11	2,6-Disubstituierte Benzotrifluoride
DE3711306A1 (de)	1988-10-20	Tolanderivate und verwendung von carbonitrilen in fluessigkristallinen phasen fuer anzeigeelemente basierend auf dem ecb-effekt