DE19748819A1 - Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen - Google Patents
Fluorierte Derivate des Phenanthrens und ihre Verwendung in FlüssigkristallmischungenInfo
- Publication number
- DE19748819A1 DE19748819A1 DE19748819A DE19748819A DE19748819A1 DE 19748819 A1 DE19748819 A1 DE 19748819A1 DE 19748819 A DE19748819 A DE 19748819A DE 19748819 A DE19748819 A DE 19748819A DE 19748819 A1 DE19748819 A1 DE 19748819A1
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- replaced
- formula
- crystal mixture
- 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
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 title claims abstract 5
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 cyclopropane-1,2-diyl Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 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 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical group CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006349 photocyclization reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000010949 copper Substances 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002987 phenanthrenes Chemical class 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000000185 1,3-diols Chemical class 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004519 manufacturing process Methods 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical class FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VWJSSJFLXRMYNV-UHFFFAOYSA-N 1-(3,4-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C(F)=C1 VWJSSJFLXRMYNV-UHFFFAOYSA-N 0.000 description 1
- DVTULTINXNWGJY-UHFFFAOYSA-N 1-Bromo-2,4,5-trifluorobenzene Chemical compound FC1=CC(F)=C(Br)C=C1F DVTULTINXNWGJY-UHFFFAOYSA-N 0.000 description 1
- MUUAQFJJUGVBGB-UHFFFAOYSA-N 1-bromo-2,3,4-trifluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1F MUUAQFJJUGVBGB-UHFFFAOYSA-N 0.000 description 1
- MGHBDQZXPCTTIH-UHFFFAOYSA-N 1-bromo-2,4-difluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1 MGHBDQZXPCTTIH-UHFFFAOYSA-N 0.000 description 1
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- YLNUVAIYEOLXRN-UHFFFAOYSA-N 1-ethynyl-4-fluoro-2-methoxybenzene Chemical compound COC1=CC(F)=CC=C1C#C YLNUVAIYEOLXRN-UHFFFAOYSA-N 0.000 description 1
- XWQXTRDNHNVTJU-SREVYHEPSA-N 1-fluoro-2-methoxy-4-[(z)-2-(3-methylphenyl)ethenyl]benzene Chemical compound C1=C(F)C(OC)=CC(\C=C/C=2C=C(C)C=CC=2)=C1 XWQXTRDNHNVTJU-SREVYHEPSA-N 0.000 description 1
- KOFLQGLXAAGOBW-UHFFFAOYSA-N 1-fluoro-2-methoxy-4-[2-(3-methylphenyl)ethynyl]benzene Chemical compound C1=C(F)C(OC)=CC(C#CC=2C=C(C)C=CC=2)=C1 KOFLQGLXAAGOBW-UHFFFAOYSA-N 0.000 description 1
- GTBXZWADMKOZQJ-UHFFFAOYSA-N 1-phenanthrol Chemical compound C1=CC2=CC=CC=C2C2=C1C(O)=CC=C2 GTBXZWADMKOZQJ-UHFFFAOYSA-N 0.000 description 1
- KHYLAAAVPPDCEJ-UHFFFAOYSA-N 2-(4-fluoro-3-methoxyphenyl)ethynyl-trimethylsilane Chemical compound COC1=CC(C#C[Si](C)(C)C)=CC=C1F KHYLAAAVPPDCEJ-UHFFFAOYSA-N 0.000 description 1
- VRLUSLNMNQAPOH-UHFFFAOYSA-N 2-cyclohexylpropanoic acid Chemical group OC(=O)C(C)C1CCCCC1 VRLUSLNMNQAPOH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BBZMJJNKBOEGKP-UHFFFAOYSA-N 3-fluoro-2-methoxy-7-methylphenanthrene Chemical compound C1=C(C)C=CC2=C(C=C(C(OC)=C3)F)C3=CC=C21 BBZMJJNKBOEGKP-UHFFFAOYSA-N 0.000 description 1
- SEVMQEIGENUPIE-UHFFFAOYSA-N 4-bromo-1-fluoro-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1F SEVMQEIGENUPIE-UHFFFAOYSA-N 0.000 description 1
- CJTIWGBQCVYTQE-UHFFFAOYSA-N 4-bromo-2-chloro-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Cl CJTIWGBQCVYTQE-UHFFFAOYSA-N 0.000 description 1
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 1
- YPTHSYKJDRMAJY-UHFFFAOYSA-N 5-bromo-2-fluorophenol Chemical compound OC1=CC(Br)=CC=C1F YPTHSYKJDRMAJY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 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
- 238000011161 development Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical group 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000005754 fluoropyridines Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical class FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000001564 phenyl benzoates Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical class OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- 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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19748819A DE19748819A1 (de) | 1997-11-05 | 1997-11-05 | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
| DE59812664T DE59812664D1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
| US09/530,665 US6482478B1 (en) | 1997-11-05 | 1998-11-05 | Fluorinated derivatives of phenanthrene and the utilization thereof in liquid crystal mixtures |
| PCT/EP1998/007080 WO1999024385A1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
| EP98961141A EP1028935B1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
| JP2000520400A JP2001522822A (ja) | 1997-11-05 | 1998-11-05 | フェナントレンのフッ素化誘導体、および液晶混合物におけるそれらの使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19748819A DE19748819A1 (de) | 1997-11-05 | 1997-11-05 | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19748819A1 true DE19748819A1 (de) | 1999-05-06 |
Family
ID=7847661
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19748819A Ceased DE19748819A1 (de) | 1997-11-05 | 1997-11-05 | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
| DE59812664T Expired - Lifetime DE59812664D1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59812664T Expired - Lifetime DE59812664D1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6482478B1 (enExample) |
| EP (1) | EP1028935B1 (enExample) |
| JP (1) | JP2001522822A (enExample) |
| DE (2) | DE19748819A1 (enExample) |
| WO (1) | WO1999024385A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1162185A1 (de) * | 2000-06-08 | 2001-12-12 | MERCK PATENT GmbH | Hydrierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
| DE10225048B4 (de) * | 2001-06-07 | 2015-03-12 | Merck Patent Gmbh | Fluorierte (Dihydro)phenanthrenderivate und deren Verwendung in flüssigkristallinen Medien |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19825488A1 (de) * | 1998-06-08 | 1999-12-09 | Aventis Res & Tech Gmbh & Co | Monostabiles ferroelektrisches Aktivmatrix-Display |
| JP4644888B2 (ja) * | 1999-08-03 | 2011-03-09 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
| JP4605412B2 (ja) * | 1999-08-27 | 2011-01-05 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
| DE10002186B4 (de) | 2000-01-19 | 2018-01-18 | Merck Patent Gmbh | Disubstituierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| JP4826005B2 (ja) * | 2000-09-28 | 2011-11-30 | Ｄｉｃ株式会社 | 液晶性化合物の精製方法 |
| US6677479B2 (en) | 2001-11-13 | 2004-01-13 | Clariant Finance Lbvi Limited | Substituted fluoroaromatics, process for preparing them and their use |
| DE102004022728B4 (de) * | 2004-05-07 | 2018-08-23 | Merck Patent Gmbh | Fluorierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| EP1645610A1 (de) * | 2004-10-11 | 2006-04-12 | Covion Organic Semiconductors GmbH | Phenanthren-Derivate |
| KR101250667B1 (ko) * | 2005-03-24 | 2013-04-03 | 메르크 파텐트 게엠베하 | 액정 매질 |
| DE102005026651A1 (de) | 2005-06-09 | 2006-12-14 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| TWI507511B (zh) | 2013-11-05 | 2015-11-11 | Ind Tech Res Inst | 負介電異方性液晶化合物、液晶顯示器、與光電裝置 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0032362B1 (en) | 1980-01-10 | 1984-08-22 | Noel A. Clark | Chiral smectic liquid crystal electro-optical device and process of making the same |
| DE3920625A1 (de) | 1989-06-23 | 1991-01-03 | Hoechst Ag | Ferroelektrische fluessigkristallelemente mit hoher spontaner polarisation und geringer helixganghoehe |
| EP0405346B1 (de) | 1989-06-29 | 1995-09-20 | F. Hoffmann-La Roche Ag | Bistabile ferroelektrische Flüssigkristallanzeige |
| DE4222565A1 (de) * | 1992-07-09 | 1994-01-13 | Hoechst Ag | Meta-substituierte Sechsringaromaten zur Verwendung in Flüssigkristallmischungen |
| DE19500768C2 (de) | 1994-01-17 | 2003-11-20 | Aventis Res & Tech Gmbh & Co | Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| US5648021A (en) | 1994-01-17 | 1997-07-15 | Hoechst Aktiengesellschaft | Phenanthrene derivatives and their use in liquid-crystalline mixtures |
| DE4432970A1 (de) | 1994-09-16 | 1996-03-21 | Hoechst Ag | Tetracyclische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen |
| US5596047A (en) * | 1994-11-16 | 1997-01-21 | Cytec Technology Corp. | Water-dispersible and curable waterborne compositions containing 1,3,5-triazine carbamates |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| JPH0931459A (ja) * | 1995-07-17 | 1997-02-04 | Hoechst Ag | 新規な強誘電性液晶組成物 |
| DE19653008A1 (de) * | 1996-12-19 | 1998-06-25 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| 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 |
-
1997
- 1997-11-05 DE DE19748819A patent/DE19748819A1/de not_active Ceased
-
1998
- 1998-11-05 US US09/530,665 patent/US6482478B1/en not_active Expired - Lifetime
- 1998-11-05 EP EP98961141A patent/EP1028935B1/de not_active Expired - Lifetime
- 1998-11-05 DE DE59812664T patent/DE59812664D1/de not_active Expired - Lifetime
- 1998-11-05 WO PCT/EP1998/007080 patent/WO1999024385A1/de not_active Ceased
- 1998-11-05 JP JP2000520400A patent/JP2001522822A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1162185A1 (de) * | 2000-06-08 | 2001-12-12 | MERCK PATENT GmbH | Hydrierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
| DE10225048B4 (de) * | 2001-06-07 | 2015-03-12 | Merck Patent Gmbh | Fluorierte (Dihydro)phenanthrenderivate und deren Verwendung in flüssigkristallinen Medien |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001522822A (ja) | 2001-11-20 |
| DE59812664D1 (de) | 2005-04-21 |
| EP1028935B1 (de) | 2005-03-16 |
| EP1028935A1 (de) | 2000-08-23 |
| US6482478B1 (en) | 2002-11-19 |
| WO1999024385A1 (de) | 1999-05-20 |
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Legal Events
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| 8127 | New person/name/address of the applicant |
Owner name: AVENTIS RESEARCH & TECHNOLOGIES GMBH & CO KG, 6592 |
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| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: AZ ELECTRONIC MATERIALS (GERMANY) GMBH, 65203 WIES |
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| 8127 | New person/name/address of the applicant |
Owner name: MERCK PATENT GMBH, 64293 DARMSTADT, DE |
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| R002 | Refusal decision in examination/registration proceedings | ||
| R003 | Refusal decision now final |
Effective date: 20120901 |