DE69309855T2 - Eneyne konjugierte Derivate und Flüssigkristallzusammensetzung - Google Patents
Eneyne konjugierte Derivate und FlüssigkristallzusammensetzungInfo
- Publication number
- DE69309855T2 DE69309855T2 DE69309855T DE69309855T DE69309855T2 DE 69309855 T2 DE69309855 T2 DE 69309855T2 DE 69309855 T DE69309855 T DE 69309855T DE 69309855 T DE69309855 T DE 69309855T DE 69309855 T2 DE69309855 T2 DE 69309855T2
- Authority
- DE
- Germany
- Prior art keywords
- trans
- buten
- yne
- group
- cyclohexyl
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 163
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 96
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- -1 pyridine-2,5-diyl Chemical group 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 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 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims abstract description 5
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 5
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 abstract description 237
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 46
- 239000000463 material Substances 0.000 abstract description 19
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 description 87
- 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 description 66
- 230000000704 physical effect Effects 0.000 description 48
- 239000000243 solution Substances 0.000 description 43
- 239000013078 crystal Substances 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 230000008021 deposition Effects 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
- 102220124982 rs140149764 Human genes 0.000 description 20
- 102220168578 rs199904091 Human genes 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- XXUSEPRYHRDKFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 18
- 239000005254 4-(trans-4-Propylcyclohexyl)benzonitrile Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- PCAYLZGYISOBSR-UHFFFAOYSA-N 2-(4-pentylcyclohexyl)acetaldehyde Chemical compound CCCCCC1CCC(CC=O)CC1 PCAYLZGYISOBSR-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WDECTZREPSJUQW-UHFFFAOYSA-N 4-[4-(4-ethylcyclohexyl)cyclohexyl]-1,2-difluorobenzene Chemical compound C1CC(CC)CCC1C1CCC(C=2C=C(F)C(F)=CC=2)CC1 WDECTZREPSJUQW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YDVUSMRUBCJGAV-UHFFFAOYSA-N 1,2-difluoro-4-[4-(4-pentylcyclohexyl)cyclohexyl]benzene Chemical compound C1CC(CCCCC)CCC1C1CCC(C=2C=C(F)C(F)=CC=2)CC1 YDVUSMRUBCJGAV-UHFFFAOYSA-N 0.000 description 11
- FSWZOZXLWVWJAH-UHFFFAOYSA-N 1,2-difluoro-4-[4-(4-propylcyclohexyl)cyclohexyl]benzene Chemical compound C1CC(CCC)CCC1C1CCC(C=2C=C(F)C(F)=CC=2)CC1 FSWZOZXLWVWJAH-UHFFFAOYSA-N 0.000 description 11
- CBOZMZUOCWAUQX-UHFFFAOYSA-N 2-(4-propylcyclohexyl)acetaldehyde Chemical compound CCCC1CCC(CC=O)CC1 CBOZMZUOCWAUQX-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- YWDALJMLXXWXFP-UHFFFAOYSA-N 1-ethyl-4-[2-(4-methoxyphenyl)ethynyl]benzene Chemical group C1=CC(CC)=CC=C1C#CC1=CC=C(OC)C=C1 YWDALJMLXXWXFP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- SDESCXGEQILYTQ-UHFFFAOYSA-N 1-methyl-4-[4-(4-propylcyclohexyl)cyclohexyl]benzene Chemical compound C1CC(CCC)CCC1C1CCC(C=2C=CC(C)=CC=2)CC1 SDESCXGEQILYTQ-UHFFFAOYSA-N 0.000 description 8
- AJZZFYUOIDYMRC-UHFFFAOYSA-N 2-(4-ethylcyclohexyl)acetaldehyde Chemical compound CCC1CCC(CC=O)CC1 AJZZFYUOIDYMRC-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- FRGNOZUOTHMJSC-UHFFFAOYSA-N 1-ethoxy-4-ethynylbenzene Chemical group CCOC1=CC=C(C#C)C=C1 FRGNOZUOTHMJSC-UHFFFAOYSA-N 0.000 description 6
- BBHJTCADCKZYSO-UHFFFAOYSA-N 4-(4-ethylcyclohexyl)benzonitrile Chemical compound C1CC(CC)CCC1C1=CC=C(C#N)C=C1 BBHJTCADCKZYSO-UHFFFAOYSA-N 0.000 description 6
- FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 6
- 239000005243 4-(trans-4-Ethylcyclohexyl)benzonitrile Substances 0.000 description 6
- JPWFWALAPSXMKY-JEKGWRKSSA-N C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 JPWFWALAPSXMKY-JEKGWRKSSA-N 0.000 description 6
- IKODGORUTZMKPL-VVPTUSLJSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)F Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)F IKODGORUTZMKPL-VVPTUSLJSA-N 0.000 description 6
- HCEOYNJLLLJUGL-MLRKGSHFSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCC1=CC=CC=C1 Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCC1=CC=CC=C1 HCEOYNJLLLJUGL-MLRKGSHFSA-N 0.000 description 6
- PVSIRBOEJQROHD-CJTWGMGISA-N C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(OCC)cc1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(OCC)cc1 PVSIRBOEJQROHD-CJTWGMGISA-N 0.000 description 6
- BHTWGXDSKPGUDY-AQYVVDRMSA-N CCC[C@H]1CC[C@@H](CC1)c1ccc(C#Cc2ccc(CC)cc2)c(F)c1 Chemical group CCC[C@H]1CC[C@@H](CC1)c1ccc(C#Cc2ccc(CC)cc2)c(F)c1 BHTWGXDSKPGUDY-AQYVVDRMSA-N 0.000 description 6
- CBOZMZUOCWAUQX-XYPYZODXSA-N CCC[C@H]1CC[C@H](CC=O)CC1 Chemical compound CCC[C@H]1CC[C@H](CC=O)CC1 CBOZMZUOCWAUQX-XYPYZODXSA-N 0.000 description 6
- KIRZLOBNESQJMN-YOCNBXQISA-N CCC[C@H]1CC[C@H](CCc2ccc(cc2)C#Cc2ccc(CCC)cc2)CC1 Chemical group CCC[C@H]1CC[C@H](CCc2ccc(cc2)C#Cc2ccc(CCC)cc2)CC1 KIRZLOBNESQJMN-YOCNBXQISA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000007333 cyanation reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- ULERJJLPGXLNFM-UHFFFAOYSA-N 1-butyl-4-[2-(4-ethoxyphenyl)ethynyl]benzene Chemical group C1=CC(CCCC)=CC=C1C#CC1=CC=C(OCC)C=C1 ULERJJLPGXLNFM-UHFFFAOYSA-N 0.000 description 5
- GMUPOLFWZIYWQO-VVPTUSLJSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C#N)F Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C#N)F GMUPOLFWZIYWQO-VVPTUSLJSA-N 0.000 description 5
- NEEQBENYJBKNBW-TYTSCOMFSA-N C1C[C@@H](CC)CC[C@@H]1\C=C\C#Cc1ccc(CC)cc1 Chemical compound C1C[C@@H](CC)CC[C@@H]1\C=C\C#Cc1ccc(CC)cc1 NEEQBENYJBKNBW-TYTSCOMFSA-N 0.000 description 5
- PWQPSCOHMLMVPO-WKILWMFISA-N C1C[C@@H](CCC)CC[C@@H]1CCOC1=CC=CC=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1CCOC1=CC=CC=C1 PWQPSCOHMLMVPO-WKILWMFISA-N 0.000 description 5
- RANMDUIOFWAAOR-UBILZTTLSA-N C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(OC)cc1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(OC)cc1 RANMDUIOFWAAOR-UBILZTTLSA-N 0.000 description 5
- MKVLQYLIUKSYEB-ALOJWSFFSA-N CCC[C@H]1CC[C@H](CCc2ccc(cc2)C#Cc2ccc(CC)cc2)CC1 Chemical group CCC[C@H]1CC[C@H](CCc2ccc(cc2)C#Cc2ccc(CC)cc2)CC1 MKVLQYLIUKSYEB-ALOJWSFFSA-N 0.000 description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- DTCTZMNXSRZIJH-UZTDKSTPSA-N c1cc(CCCCC)ccc1C#C\C=C\[C@H]1CC[C@H](CC)CC1 Chemical compound c1cc(CCCCC)ccc1C#C\C=C\[C@H]1CC[C@H](CC)CC1 DTCTZMNXSRZIJH-UZTDKSTPSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001247 metal acetylides Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Substances FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 4
- JMLXBCSKFMMFGF-UHFFFAOYSA-N 1-butoxy-4-ethynylbenzene Chemical group CCCCOC1=CC=C(C#C)C=C1 JMLXBCSKFMMFGF-UHFFFAOYSA-N 0.000 description 4
- QTVHHOAFERRCDG-UHFFFAOYSA-N 1-butyl-4-[2-(4-methoxyphenyl)ethynyl]benzene Chemical group C1=CC(CCCC)=CC=C1C#CC1=CC=C(OC)C=C1 QTVHHOAFERRCDG-UHFFFAOYSA-N 0.000 description 4
- ZNTJVJSUNSUMPP-UHFFFAOYSA-N 1-ethyl-4-ethynylbenzene Chemical group CCC1=CC=C(C#C)C=C1 ZNTJVJSUNSUMPP-UHFFFAOYSA-N 0.000 description 4
- KBIAVTUACPKPFJ-UHFFFAOYSA-N 1-ethynyl-4-methoxybenzene Chemical group COC1=CC=C(C#C)C=C1 KBIAVTUACPKPFJ-UHFFFAOYSA-N 0.000 description 4
- ULPSMBQBIIZGAI-UHFFFAOYSA-N 1-methoxy-4-[2-(4-pentylphenyl)ethynyl]benzene Chemical group C1=CC(CCCCC)=CC=C1C#CC1=CC=C(OC)C=C1 ULPSMBQBIIZGAI-UHFFFAOYSA-N 0.000 description 4
- NPCKVHHCQBJJIS-UHFFFAOYSA-N 1-methoxy-4-[2-(4-propylphenyl)ethynyl]benzene Chemical group C1=CC(CCC)=CC=C1C#CC1=CC=C(OC)C=C1 NPCKVHHCQBJJIS-UHFFFAOYSA-N 0.000 description 4
- MEIZMSPIBFTTTE-UHFFFAOYSA-N 2-fluoro-4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C(F)=C1 MEIZMSPIBFTTTE-UHFFFAOYSA-N 0.000 description 4
- UYCJPJVRKXHAJH-KUQADXENSA-N C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(C#N)cc1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1\C=C\C#Cc1ccc(C#N)cc1 UYCJPJVRKXHAJH-KUQADXENSA-N 0.000 description 4
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- WBQSLPCFNYMITM-CTYIDZIISA-N COC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#N Chemical compound COC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#N WBQSLPCFNYMITM-CTYIDZIISA-N 0.000 description 4
- MPDPNLWERBBJCT-OPMHRUBESA-N FC1=C(C#N)C=CC(=C1)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CC Chemical compound FC1=C(C#N)C=CC(=C1)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CC MPDPNLWERBBJCT-OPMHRUBESA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UGDKJBAHADKBHV-WHCACAGWSA-N c1cc(CCC)ccc1C#C\C=C\[C@H]1CC[C@H](CC)CC1 Chemical compound c1cc(CCC)ccc1C#C\C=C\[C@H]1CC[C@H](CC)CC1 UGDKJBAHADKBHV-WHCACAGWSA-N 0.000 description 4
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- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N tert-hexyl alcohol Natural products CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XCHBUTMOJMKQBK-DHZHZOJOSA-N trimethyl-[4-[(e)-4-(4-pentylcyclohexyl)but-3-en-1-ynyl]cyclohexyl]oxysilane Chemical compound C1CC(CCCCC)CCC1\C=C\C#CC1CCC(O[Si](C)(C)C)CC1 XCHBUTMOJMKQBK-DHZHZOJOSA-N 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
- C09K19/06—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
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
-
- 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
-
- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
-
- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
-
- 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
- C09K19/06—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
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
-
- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen 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
- C09K19/3441—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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—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 one nitrogen atom, e.g. pyridine
-
- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29975692 | 1992-11-10 | ||
| JP4400893 | 1993-03-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69309855D1 DE69309855D1 (de) | 1997-05-22 |
| DE69309855T2 true DE69309855T2 (de) | 1997-09-11 |
Family
ID=26383854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69309855T Expired - Fee Related DE69309855T2 (de) | 1992-11-10 | 1993-11-10 | Eneyne konjugierte Derivate und Flüssigkristallzusammensetzung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5370819A (enExample) |
| EP (1) | EP0597701B1 (enExample) |
| KR (1) | KR940011410A (enExample) |
| AT (1) | ATE151810T1 (enExample) |
| DE (1) | DE69309855T2 (enExample) |
| TW (1) | TW253905B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5554316A (en) * | 1994-03-16 | 1996-09-10 | Chisso Corporation | Hexenediyne derivative and a liquid crystal composition |
| JPH08259474A (ja) * | 1995-03-23 | 1996-10-08 | Chisso Corp | 共役炭素鎖を有する液晶性化合物および液晶組成物 |
| GB2306479B (en) * | 1995-10-31 | 1999-05-26 | Shinetsu Chemical Co | A silacyclohexane compound a process for producing the same and a liquid crystal composition comprising the same |
| EP0947501A1 (en) * | 1996-11-28 | 1999-10-06 | Chisso Corporation | Conjugated nitrile derivatives, liquid crystal compounds, and liquid crystal display elements |
| JPH10245349A (ja) * | 1997-02-28 | 1998-09-14 | Chisso Corp | 不飽和炭化水素基を有する液晶性化合物、液晶組成物および液晶表示素子 |
| US6366330B1 (en) | 1997-05-23 | 2002-04-02 | Kent Displays Incorporated | Cholesteric liquid crystal display that prevents image sticking |
| US6172720B1 (en) | 1997-05-23 | 2001-01-09 | Kent Displays Incorporated | Low viscosity liquid crystal material |
| US6468443B1 (en) | 2000-07-21 | 2002-10-22 | Raytheon Company | Colorless and low viscosity compounds for low voltage liquid crystal operation |
| JPWO2006068195A1 (ja) * | 2004-12-22 | 2008-06-12 | 旭硝子株式会社 | ヘキセンジイン誘導体 |
| US8822628B2 (en) | 2012-09-24 | 2014-09-02 | Ticona Llc | Crosslinkable liquid crystalline polymer |
| WO2014047015A1 (en) | 2012-09-24 | 2014-03-27 | Ticona Llc | Crosslinkable aromatic polyester |
| US8853342B2 (en) | 2012-09-24 | 2014-10-07 | Ticona Llc | Crosslinkable liquid crystalline polymer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4615962A (en) * | 1979-06-25 | 1986-10-07 | University Patents, Inc. | Diacetylenes having liquid crystal phases |
| DE3901266A1 (de) * | 1989-01-18 | 1990-07-19 | Merck Patent Gmbh | Fluorhaltige aromaten |
-
1993
- 1993-11-09 TW TW082109401A patent/TW253905B/zh active
- 1993-11-10 DE DE69309855T patent/DE69309855T2/de not_active Expired - Fee Related
- 1993-11-10 EP EP93308996A patent/EP0597701B1/en not_active Expired - Lifetime
- 1993-11-10 US US08/149,942 patent/US5370819A/en not_active Expired - Fee Related
- 1993-11-10 KR KR1019930023783A patent/KR940011410A/ko not_active Withdrawn
- 1993-11-10 AT AT93308996T patent/ATE151810T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0597701A1 (en) | 1994-05-18 |
| DE69309855D1 (de) | 1997-05-22 |
| EP0597701B1 (en) | 1997-04-16 |
| KR940011410A (ko) | 1994-06-21 |
| ATE151810T1 (de) | 1997-05-15 |
| US5370819A (en) | 1994-12-06 |
| TW253905B (enExample) | 1995-08-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |