DE10101022A1 - Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen - Google Patents
Fluorierte Aromaten und ihre Verwendung in FlüssigkristallmischungenInfo
- Publication number
- DE10101022A1 DE10101022A1 DE2001101022 DE10101022A DE10101022A1 DE 10101022 A1 DE10101022 A1 DE 10101022A1 DE 2001101022 DE2001101022 DE 2001101022 DE 10101022 A DE10101022 A DE 10101022A DE 10101022 A1 DE10101022 A1 DE 10101022A1
- Authority
- DE
- Germany
- Prior art keywords
- replaced
- liquid crystal
- straight
- chain
- carbon atoms
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- -1 cyclopropane-1,2-diyl Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000011159 matrix material Substances 0.000 claims description 16
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 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 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XSLGMCCYXVCFJE-UHFFFAOYSA-N 2-butoxy-1,8-difluoro-9h-fluorene Chemical compound C1=CC=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 XSLGMCCYXVCFJE-UHFFFAOYSA-N 0.000 description 10
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- SFRIUBIWEWMQLU-UHFFFAOYSA-N 3-butoxy-4,6-difluorodibenzofuran Chemical compound C1=CC=C2C3=CC=C(OCCCC)C(F)=C3OC2=C1F SFRIUBIWEWMQLU-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WYBPSCOKKHAONR-UHFFFAOYSA-N 1,8-difluoro-2-propyl-9h-fluorene Chemical compound C1=CC(F)=C2CC3=C(F)C(CCC)=CC=C3C2=C1 WYBPSCOKKHAONR-UHFFFAOYSA-N 0.000 description 8
- IYRVTRAXOGYGHE-UHFFFAOYSA-N 1,8-difluoro-9h-fluorene Chemical compound C12=CC=CC(F)=C2CC2=C1C=CC=C2F IYRVTRAXOGYGHE-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- LBGPIEMELJTABZ-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C2C(C=CC=C3F)=C3CC2=C1F Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C2C(C=CC=C3F)=C3CC2=C1F LBGPIEMELJTABZ-SHTZXODSSA-N 0.000 description 6
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- POPHQFBCQWIKSK-UHFFFAOYSA-N 1,8-difluorofluoren-9-one Chemical compound C12=CC=CC(F)=C2C(=O)C2=C1C=CC=C2F POPHQFBCQWIKSK-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- JNQQTLOOPAETMK-UHFFFAOYSA-N 4,6-difluoro-3-pentyldibenzofuran Chemical compound C1=CC=C2C3=CC=C(CCCCC)C(F)=C3OC2=C1F JNQQTLOOPAETMK-UHFFFAOYSA-N 0.000 description 4
- OCCXSCMDIKCVAV-UHFFFAOYSA-N 4,6-difluorodibenzofuran Chemical group O1C2=C(F)C=CC=C2C2=C1C(F)=CC=C2 OCCXSCMDIKCVAV-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006263 metalation reaction Methods 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- KSMJRPQSMUQVMV-UHFFFAOYSA-N (1,8-difluoro-9h-fluoren-2-yl)boronic acid Chemical compound C1=CC=C(F)C2=C1C1=CC=C(B(O)O)C(F)=C1C2 KSMJRPQSMUQVMV-UHFFFAOYSA-N 0.000 description 3
- NODROMSAAFOASE-UHFFFAOYSA-N (7-butoxy-1,8-difluoro-9h-fluoren-2-yl)boronic acid Chemical compound C1=CC(B(O)O)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 NODROMSAAFOASE-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FZXKSQJJGVGOOP-UHFFFAOYSA-N 1,8-difluoro-9h-fluoren-2-ol Chemical compound C1=CC=C(F)C2=C1C1=CC=C(O)C(F)=C1C2 FZXKSQJJGVGOOP-UHFFFAOYSA-N 0.000 description 2
- ZLRGHOAODDBQEI-UHFFFAOYSA-N 1-(7-butoxy-1,8-difluoro-9h-fluoren-2-yl)propan-1-ol Chemical compound C1=CC(C(O)CC)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 ZLRGHOAODDBQEI-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- RYLXHYHAMATFEI-UHFFFAOYSA-N 1-fluoro-8-(1-fluoro-2-methylhexyl)-9h-fluorene Chemical compound C1C(C(=CC=C2)F)=C2C2=C1C(C(F)C(C)CCCC)=CC=C2 RYLXHYHAMATFEI-UHFFFAOYSA-N 0.000 description 2
- WXHUASFUKDIAKN-UHFFFAOYSA-N 2-butoxy-1,8-difluoro-7-(4-pentylphenyl)-9h-fluorene Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C2C(C=CC(OCCCC)=C3F)=C3CC2=C1F WXHUASFUKDIAKN-UHFFFAOYSA-N 0.000 description 2
- DKQCYJHKYAXICU-UHFFFAOYSA-N 2-butoxy-1,8-difluoro-7-propyl-9h-fluorene Chemical compound C1=CC(CCC)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 DKQCYJHKYAXICU-UHFFFAOYSA-N 0.000 description 2
- HVIAEALBBMNFIW-UHFFFAOYSA-N 3-[9-(2-carboxyethyl)fluoren-9-yl]propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)(CCC(O)=O)C3=CC=CC=C3C2=C1 HVIAEALBBMNFIW-UHFFFAOYSA-N 0.000 description 2
- COWHDUMHYFLLER-UHFFFAOYSA-N 3-[9-(2-cyanoethyl)fluoren-9-yl]propanenitrile Chemical compound C1=CC=C2C(CCC#N)(CCC#N)C3=CC=CC=C3C2=C1 COWHDUMHYFLLER-UHFFFAOYSA-N 0.000 description 2
- NQEDLIZOPMNZMC-UHFFFAOYSA-N 4-propylcyclohexan-1-one Chemical compound CCCC1CCC(=O)CC1 NQEDLIZOPMNZMC-UHFFFAOYSA-N 0.000 description 2
- GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 2
- ZDMXGVWCSZQMIR-UHFFFAOYSA-N 7-butoxy-1,8-difluoro-9h-fluoren-2-ol Chemical compound C1=CC(O)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 ZDMXGVWCSZQMIR-UHFFFAOYSA-N 0.000 description 2
- UFTDIZWMRWPDAP-UHFFFAOYSA-N 9-oxofluorene-1,8-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2C(=O)C2=C1C=CC=C2C(=O)O UFTDIZWMRWPDAP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 150000003938 benzyl alcohols Chemical class 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 2
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- HBBGSNOHAGNQRQ-UHFFFAOYSA-N dibenzofuran-4,6-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2OC2=C1C=CC=C2C(=O)O HBBGSNOHAGNQRQ-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- WHDBZUDFOQNASQ-UHFFFAOYSA-N dibenzothiophene-4-carboxylic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C(=O)O WHDBZUDFOQNASQ-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 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
- ZHWFPPRUOLEOBE-UHFFFAOYSA-N 1,2-difluoro-3-octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC(F)=C1F ZHWFPPRUOLEOBE-UHFFFAOYSA-N 0.000 description 1
- WXDISAIOQGZAEV-UHFFFAOYSA-N 1,8-diaminofluoren-9-one Chemical compound C12=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N WXDISAIOQGZAEV-UHFFFAOYSA-N 0.000 description 1
- YRHFPDHKKQSAFC-UHFFFAOYSA-N 1,8-difluoro-2,7-dipropyl-9h-fluorene Chemical compound C1=C(CCC)C(F)=C2CC3=C(F)C(CCC)=CC=C3C2=C1 YRHFPDHKKQSAFC-UHFFFAOYSA-N 0.000 description 1
- NZTLRPBYWWCLCB-UHFFFAOYSA-N 1-(1,8-difluoro-9h-fluoren-2-yl)cyclohexan-1-ol Chemical compound C=1C=C(C2=C(C(=CC=C2)F)C2)C2=C(F)C=1C1(O)CCCCC1 NZTLRPBYWWCLCB-UHFFFAOYSA-N 0.000 description 1
- YXJJGVOXTGCLHG-UHFFFAOYSA-N 1-bromo-2,3-difluoro-4-octoxybenzene Chemical compound CCCCCCCCOC1=CC=C(Br)C(F)=C1F YXJJGVOXTGCLHG-UHFFFAOYSA-N 0.000 description 1
- PLRSROOKLLCMSX-UHFFFAOYSA-N 1-bromo-2-fluoro-4-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C(F)=C1 PLRSROOKLLCMSX-UHFFFAOYSA-N 0.000 description 1
- SGCJPYYTVBHQGE-UHFFFAOYSA-N 1-bromo-4-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C=C1 SGCJPYYTVBHQGE-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- WJRBIZJUWCBZCT-UHFFFAOYSA-N 1-fluorofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=CC=C2F WJRBIZJUWCBZCT-UHFFFAOYSA-N 0.000 description 1
- QCVHDBUWKNNURQ-UHFFFAOYSA-N 2,7-dibutoxy-1,8-difluoro-9h-fluorene Chemical compound C1=CC(OCCCC)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 QCVHDBUWKNNURQ-UHFFFAOYSA-N 0.000 description 1
- ASGKBAUXUXOKGG-UHFFFAOYSA-N 2-(2,3-difluoro-4-heptoxyphenyl)-5-nonylpyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCC)C(F)=C1F ASGKBAUXUXOKGG-UHFFFAOYSA-N 0.000 description 1
- OWBDECISILOCJX-UHFFFAOYSA-N 2-(2,3-difluoro-4-nonoxyphenyl)-5-nonylpyrimidine Chemical compound FC1=C(F)C(OCCCCCCCCC)=CC=C1C1=NC=C(CCCCCCCCC)C=N1 OWBDECISILOCJX-UHFFFAOYSA-N 0.000 description 1
- VQAJNBZLBNSACK-UHFFFAOYSA-N 2-(2,3-difluoro-4-octoxyphenyl)-5-nonylpyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C(F)=C1F VQAJNBZLBNSACK-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
- 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 1
- IHQUQNPGVVLDKR-UHFFFAOYSA-N 2-(4-heptoxyphenyl)-5-nonylpyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCC)C=C1 IHQUQNPGVVLDKR-UHFFFAOYSA-N 0.000 description 1
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- ATZLPEPWPJQANQ-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OCCCCCC)C=C1 ATZLPEPWPJQANQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- IEBFRHSLBJYXSF-UHFFFAOYSA-N 2-butoxy-1,8-difluoro-7-propoxy-9h-fluorene Chemical compound C1=CC(OCCC)=C(F)C2=C1C1=CC=C(OCCCC)C(F)=C1C2 IEBFRHSLBJYXSF-UHFFFAOYSA-N 0.000 description 1
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- YIUVWECPDLUPOE-UHFFFAOYSA-N 3-butoxy-4,6-difluoro-7-propyldibenzofuran Chemical compound CCCC1=CC=C2C3=CC=C(OCCCC)C(F)=C3OC2=C1F YIUVWECPDLUPOE-UHFFFAOYSA-N 0.000 description 1
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- HPEYDZLWXZGALH-AIJCFQAPSA-N 4-[4-[4-[(2s)-2-fluorooctoxy]phenyl]phenyl]-1-heptylcyclohexane-1-carbonitrile Chemical compound C1CC(CCCCCCC)(C#N)CCC1C1=CC=C(C=2C=CC(OC[C@@H](F)CCCCCC)=CC=2)C=C1 HPEYDZLWXZGALH-AIJCFQAPSA-N 0.000 description 1
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- LIIWGEPQAZKMBX-UHFFFAOYSA-N 5-decyl-2-(4-octoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C=C1 LIIWGEPQAZKMBX-UHFFFAOYSA-N 0.000 description 1
- GLBFRDAOJSRRJO-UHFFFAOYSA-N 5-hexoxy-2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=C(OCCCCCC)C=N1 GLBFRDAOJSRRJO-UHFFFAOYSA-N 0.000 description 1
- FMCGFINLOXSJPV-UHFFFAOYSA-N 5-nonyl-2-(4-octoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C=C1 FMCGFINLOXSJPV-UHFFFAOYSA-N 0.000 description 1
- PHQREJCPVUZOGR-UHFFFAOYSA-N 9,9-difluorofluorene Chemical compound C1=CC=C2C(F)(F)C3=CC=CC=C3C2=C1 PHQREJCPVUZOGR-UHFFFAOYSA-N 0.000 description 1
- DIUKWNVWEKCPHH-UHFFFAOYSA-N 9-oxofluorene-1,8-dicarboxamide Chemical compound C12=CC=CC(C(N)=O)=C2C(=O)C2=C1C=CC=C2C(=O)N DIUKWNVWEKCPHH-UHFFFAOYSA-N 0.000 description 1
- OMNUZVRKIQHPOJ-UHFFFAOYSA-N 9h-fluorene-1,8-dicarboxylic acid Chemical compound C1C(C(=CC=C2)C(O)=O)=C2C2=C1C(C(=O)O)=CC=C2 OMNUZVRKIQHPOJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 238000007045 Balz-Schiemann reaction Methods 0.000 description 1
- QXAYTDJGUAOTKH-MXVIHJGJSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C2C(C=CC(OCCCC)=C3F)=C3CC2=C1F Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C2C(C=CC(OCCCC)=C3F)=C3CC2=C1F QXAYTDJGUAOTKH-MXVIHJGJSA-N 0.000 description 1
- VISRVHFQLWKRAF-WGSAOQKQSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C2C3=CC=C(OCCCC)C(F)=C3OC2=C1F Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C2C3=CC=C(OCCCC)C(F)=C3OC2=C1F VISRVHFQLWKRAF-WGSAOQKQSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical class C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 1
- VAAJKJJSHYQHAO-QAQDUYKDSA-N FC1=C(C=CC=2C3=CC=C(C(=C3CC1=2)F)[C@@H]1CC[C@H](CC1)CCC)CCC Chemical compound FC1=C(C=CC=2C3=CC=C(C(=C3CC1=2)F)[C@@H]1CC[C@H](CC1)CCC)CCC VAAJKJJSHYQHAO-QAQDUYKDSA-N 0.000 description 1
- PQPFHZNIMOHNRU-IYARVYRRSA-N FC=1C(OCCCC)=CC=C2C=1CC(C=1F)=C2C=CC=1[C@H]1CC[C@H](CCC)CC1 Chemical compound FC=1C(OCCCC)=CC=C2C=1CC(C=1F)=C2C=CC=1[C@H]1CC[C@H](CCC)CC1 PQPFHZNIMOHNRU-IYARVYRRSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical class BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 150000005700 bromopyrimidines Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical group OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical class O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- BSMAWCXKHJSJIB-UHFFFAOYSA-N dibenzofuran-4-carboxylic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2C(=O)O BSMAWCXKHJSJIB-UHFFFAOYSA-N 0.000 description 1
- QUSHMOLWMISFKF-UHFFFAOYSA-N dibenzothiophene-4,6-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2SC2=C1C=CC=C2C(=O)O QUSHMOLWMISFKF-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- UVIAJPBGCLEQFR-UHFFFAOYSA-N pentacyclo[8.7.1.11,5.014,18.09,19]nonadeca-5,7,9(19),10(18),11,13-hexaene-4,15-dione Chemical compound C1CC(=O)C(C2=3)=CC=CC=3C3=CC=CC4=C3C12CCC4=O UVIAJPBGCLEQFR-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical class Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0225—Ferroelectric
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- 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
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/582—Electrically active dopants, e.g. charge transfer agents
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/582—Electrically active dopants, e.g. charge transfer agents
- C09K19/584—Electrically active dopants, e.g. charge transfer agents having a condensed ring system; macrocyclic compounds
-
- 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
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Furan Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001101022 DE10101022A1 (de) | 2001-01-11 | 2001-01-11 | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen |
| JP2002556142A JP4379857B2 (ja) | 2001-01-11 | 2002-01-10 | フッ素化芳香族化合物および液晶混合物におけるこの使用 |
| EP02715410.3A EP1349822B1 (de) | 2001-01-11 | 2002-01-10 | Fluorierte aromaten und ihre verwendung in flüssigkristallmischungen |
| US10/466,135 US7018685B2 (en) | 2001-01-11 | 2002-01-10 | Fluorinated aromatic compounds and the use of the same in liquid crystal mixtures |
| PCT/EP2002/000191 WO2002055463A1 (de) | 2001-01-11 | 2002-01-10 | Fluorierte aromaten und ihre verwendung in flüssigkristallmischungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001101022 DE10101022A1 (de) | 2001-01-11 | 2001-01-11 | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10101022A1 true DE10101022A1 (de) | 2002-07-18 |
Family
ID=7670266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2001101022 Ceased DE10101022A1 (de) | 2001-01-11 | 2001-01-11 | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1349822B1 (enExample) |
| JP (1) | JP4379857B2 (enExample) |
| DE (1) | DE10101022A1 (enExample) |
| WO (1) | WO2002055463A1 (enExample) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7018685B2 (en) * | 2001-01-11 | 2006-03-28 | Merck Patent Gmbh | Fluorinated aromatic compounds and the use of the same in liquid crystal mixtures |
| US7087272B2 (en) * | 2001-03-30 | 2006-08-08 | Merck Patent Gmbh | Fluorinated fluorene derivatives |
| CN1912052A (zh) * | 2005-08-09 | 2007-02-14 | 默克专利股份有限公司 | 液晶介质 |
| CN107868667A (zh) * | 2016-09-23 | 2018-04-03 | 默克专利股份有限公司 | 液晶介质和包含其的液晶显示器 |
| CN111592890A (zh) * | 2019-02-20 | 2020-08-28 | 北京八亿时空液晶科技股份有限公司 | 一种液晶化合物及其制备方法与应用 |
| CN113528152A (zh) * | 2020-04-21 | 2021-10-22 | 江苏和成新材料有限公司 | 液晶化合物及其液晶组合物和液晶显示器件 |
| CN113684037A (zh) * | 2017-10-31 | 2021-11-23 | 晶美晟光电材料（南京）有限公司 | 含有二苯并噻吩结构的液晶化合物以及包含该液晶化合物的液晶混合物 |
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| US4976887A (en) * | 1988-01-21 | 1990-12-11 | Kabushiki Kaisha Toshiba | Optically active liquid crystal compound and method of manufacturing the same, liquid crystal composition containing the same and liquid crystal display device |
| JP4048570B2 (ja) * | 1997-02-25 | 2008-02-20 | チッソ株式会社 | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| DE19720289A1 (de) * | 1997-05-15 | 1998-11-19 | Hoechst Ag | Fluorierte 9H-Fluoren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| WO2001010803A1 (fr) * | 1999-08-03 | 2001-02-15 | Dainippon Ink And Chemicals, Inc. | Compose de cycles accoles |
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2001
- 2001-01-11 DE DE2001101022 patent/DE10101022A1/de not_active Ceased
-
2002
- 2002-01-10 JP JP2002556142A patent/JP4379857B2/ja not_active Expired - Fee Related
- 2002-01-10 WO PCT/EP2002/000191 patent/WO2002055463A1/de not_active Ceased
- 2002-01-10 EP EP02715410.3A patent/EP1349822B1/de not_active Expired - Lifetime
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| US7018685B2 (en) * | 2001-01-11 | 2006-03-28 | Merck Patent Gmbh | Fluorinated aromatic compounds and the use of the same in liquid crystal mixtures |
| US7087272B2 (en) * | 2001-03-30 | 2006-08-08 | Merck Patent Gmbh | Fluorinated fluorene derivatives |
| DE10115955B4 (de) * | 2001-03-30 | 2017-10-19 | Merck Patent Gmbh | Fluorierte Fluoren-Derivate |
| CN1912052A (zh) * | 2005-08-09 | 2007-02-14 | 默克专利股份有限公司 | 液晶介质 |
| US7371437B2 (en) * | 2005-08-09 | 2008-05-13 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN1912052B (zh) * | 2005-08-09 | 2013-01-30 | 默克专利股份有限公司 | 液晶介质 |
| CN107868667A (zh) * | 2016-09-23 | 2018-04-03 | 默克专利股份有限公司 | 液晶介质和包含其的液晶显示器 |
| CN113913197A (zh) * | 2017-01-22 | 2022-01-11 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及包含该液晶组合物的液晶显示元件或液晶显示器 |
| CN113684037A (zh) * | 2017-10-31 | 2021-11-23 | 晶美晟光电材料（南京）有限公司 | 含有二苯并噻吩结构的液晶化合物以及包含该液晶化合物的液晶混合物 |
| CN111592890A (zh) * | 2019-02-20 | 2020-08-28 | 北京八亿时空液晶科技股份有限公司 | 一种液晶化合物及其制备方法与应用 |
| CN113528152A (zh) * | 2020-04-21 | 2021-10-22 | 江苏和成新材料有限公司 | 液晶化合物及其液晶组合物和液晶显示器件 |
| CN113528152B (zh) * | 2020-04-21 | 2023-08-04 | 江苏和成新材料有限公司 | 液晶化合物及其液晶组合物和液晶显示器件 |
| CN113913194A (zh) * | 2021-10-22 | 2022-01-11 | 北京云基科技有限公司 | 一种含氟液晶化合物及其应用 |
| US11788010B2 (en) | 2021-11-01 | 2023-10-17 | Jiangsu Hecheng Display Technology Co., Ltd. | Liquid crystal composition and liquid crystal display device comprising the same |
| US12460133B2 (en) | 2021-11-01 | 2025-11-04 | Jiangsu Hecheng Display Technology Co., Ltd. | Liquid crystal compound, liquid crystal composition thereof, and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1349822B1 (de) | 2016-09-28 |
| JP4379857B2 (ja) | 2009-12-09 |
| JP2004529867A (ja) | 2004-09-30 |
| EP1349822A1 (de) | 2003-10-08 |
| WO2002055463A1 (de) | 2002-07-18 |
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