TW200422385A - Chiral phenol derivative, liquid-crystal medium comprising same, process for the preparation of a liquid-crystal medium, and electro-optical liquid-crystal display - Google Patents
Chiral phenol derivative, liquid-crystal medium comprising same, process for the preparation of a liquid-crystal medium, and electro-optical liquid-crystal display Download PDFInfo
- Publication number
- TW200422385A TW200422385A TW92127688A TW92127688A TW200422385A TW 200422385 A TW200422385 A TW 200422385A TW 92127688 A TW92127688 A TW 92127688A TW 92127688 A TW92127688 A TW 92127688A TW 200422385 A TW200422385 A TW 200422385A
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- Prior art keywords
- liquid crystal
- patent application
- compounds
- chiral
- fluorine
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 72
- 150000002989 phenols Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 5
- 230000008569 process Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 239000002019 doping agent Substances 0.000 claims abstract description 12
- 239000003381 stabilizer Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- -1 hexahydropyridine-1,4-diyl Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RRTCFFFUTAGOSG-UHFFFAOYSA-N benzene;phenol Chemical group C1=CC=CC=C1.OC1=CC=CC=C1 RRTCFFFUTAGOSG-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
- 230000000694 effects Effects 0.000 description 12
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 12
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 7
- 239000003989 dielectric material Substances 0.000 description 7
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- LCOCAXHKNKUUGN-UHFFFAOYSA-N (3,5-difluoro-4-octan-2-yloxyphenyl)boronic acid Chemical compound CCCCCCC(C)OC1=C(F)C=C(B(O)O)C=C1F LCOCAXHKNKUUGN-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000766026 Coregonus nasus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- SJWFXCIHNDVPSH-QMMMGPOBSA-N (2S)-octan-2-ol Chemical compound CCCCCC[C@H](C)O SJWFXCIHNDVPSH-QMMMGPOBSA-N 0.000 description 1
- JPJGNZQDELRZGE-UHFFFAOYSA-N (phenyl-$l^{2}-phosphanyl)benzene Chemical compound C=1C=CC=CC=1[P]C1=CC=CC=C1 JPJGNZQDELRZGE-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- SSQQUEKFNSJLKX-UHFFFAOYSA-N 4-bromo-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(Br)=CC(C(C)(C)C)=C1O SSQQUEKFNSJLKX-UHFFFAOYSA-N 0.000 description 1
- FWJBXJQTDBYSAV-UHFFFAOYSA-N 5-bromo-1,3-difluoro-2-octan-2-yloxybenzene Chemical compound CCCCCCC(C)OC1=C(F)C=C(Br)C=C1F FWJBXJQTDBYSAV-UHFFFAOYSA-N 0.000 description 1
- ZVSXKFNTWOIGJI-UHFFFAOYSA-N 7-phenyl heptanoic acid Chemical compound OC(=O)CCCCCCC1=CC=CC=C1 ZVSXKFNTWOIGJI-UHFFFAOYSA-N 0.000 description 1
- 102100024873 Ceramide-1-phosphate transfer protein Human genes 0.000 description 1
- 101710189399 Ceramide-1-phosphate transfer protein Proteins 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OQLKNTOKMBVBKV-UHFFFAOYSA-N hexamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 OQLKNTOKMBVBKV-UHFFFAOYSA-N 0.000 description 1
- 229960001915 hexamidine Drugs 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
-
- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or 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
- C09K19/52—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
- C09K19/586—Optically active dopants; chiral dopants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002146657 DE10246657A1 (de) | 2002-10-07 | 2002-10-07 | Chirales Phenolderivat, dieses enthaltendes Flüssigkristallmedium, Verfahren zur Herstellung eines Flüssigkristallmediums und elektrooptische Flüssigkristallanzeige |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200422385A true TW200422385A (en) | 2004-11-01 |
Family
ID=32010322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW92127688A TW200422385A (en) | 2002-10-07 | 2003-10-06 | Chiral phenol derivative, liquid-crystal medium comprising same, process for the preparation of a liquid-crystal medium, and electro-optical liquid-crystal display |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7790929B2 (enExample) |
| EP (1) | EP1549599B1 (enExample) |
| JP (1) | JP4593279B2 (enExample) |
| AT (1) | ATE435849T1 (enExample) |
| AU (1) | AU2003283251A1 (enExample) |
| DE (3) | DE10246657A1 (enExample) |
| TW (1) | TW200422385A (enExample) |
| WO (1) | WO2004033406A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103110635A (zh) * | 2005-07-04 | 2013-05-22 | 海波因特制药有限责任公司 | 组胺h3受体拮抗剂 |
| TWI475099B (zh) * | 2009-09-30 | 2015-03-01 | Jnc Corp | 液晶組成物及液晶顯示元件 |
| US20120194755A1 (en) * | 2011-01-27 | 2012-08-02 | Reald Inc. | Ultrafast twisted nematic liquid crystal display |
| JP6186974B2 (ja) * | 2012-07-30 | 2017-08-30 | Jnc株式会社 | 液晶組成物、酸化防止剤および液晶表示素子 |
| US20150275086A1 (en) * | 2012-10-24 | 2015-10-01 | Dic Corporation | Nematic liquid crystal composition and liquid crystal display device using same |
| TWI597352B (zh) | 2012-11-08 | 2017-09-01 | Dainippon Ink & Chemicals | Nematic liquid crystal composition and liquid crystal display device using the same |
| KR102017601B1 (ko) | 2013-03-06 | 2019-09-09 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 및 이를 사용한 액정 표시 소자 |
| JP5522314B1 (ja) * | 2013-03-25 | 2014-06-18 | Ｄｉｃ株式会社 | 液晶組成物、液晶表示素子及び液晶ディスプレイ |
| TWI568837B (zh) * | 2013-03-26 | 2017-02-01 | 迪愛生股份有限公司 | 液晶組成物、液晶顯示元件及液晶顯示器 |
| KR20150070027A (ko) * | 2013-12-16 | 2015-06-24 | 메르크 파텐트 게엠베하 | 액정 매질 |
| US10400168B2 (en) * | 2014-10-09 | 2019-09-03 | Dic Corporation | Composition and liquid crystal display device using the same |
| US10584284B2 (en) * | 2014-11-10 | 2020-03-10 | Jnc Corporation | Antioxidant having difluoromethoxy group, liquid crystal composition, and liquid crystal display device |
| KR102218333B1 (ko) | 2016-06-07 | 2021-02-22 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| JPWO2018003653A1 (ja) * | 2016-06-27 | 2019-04-18 | Dic株式会社 | 重合性液晶組成物、それを用いた光学異方体及び液晶表示素子 |
| SG11201908820VA (en) | 2017-03-23 | 2019-10-30 | Jacobio Pharmaceuticals Co Ltd | Novel heterocyclic derivatives useful as shp2 inhibitors |
| CN108822550B (zh) * | 2018-07-01 | 2021-06-04 | 浙江鑫都文化用品股份有限公司 | 一种液晶弹性体新材料的制备方法 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038250A (en) * | 1971-08-25 | 1977-07-26 | Ciba-Geigy Corporation | Light protecting agents |
| US4067895A (en) * | 1972-04-28 | 1978-01-10 | Sandoz Ltd | N-(para-hydroxybiphenyl)amides |
| US4032547A (en) * | 1976-02-23 | 1977-06-28 | Gulf Research & Development Company | Quinone alkide synthesis system |
| EP0217239B1 (de) | 1985-09-30 | 1990-10-24 | Hoechst Aktiengesellschaft | Chirale Phenolester mesogener Carbonsäuren und ihre Verwendung als Dotierstoff in Flüssigkristal-Phasen |
| GB8614213D0 (en) * | 1986-06-11 | 1986-07-16 | Kodak Ltd | Photographic acetanilide couplers |
| WO1992008450A2 (fr) * | 1990-11-12 | 1992-05-29 | Fileco | UTILISATION ANTIVIRALE DE COMPOSE 2,6-DI-t-BUTYLPHENOL SUBSTITUE EN POSITION 4, NOTAMMENT VIS-A-VIS DES VIRUS DE L'HERPES ET DES PAPILLOMAVIRUS |
| JPH06107584A (ja) * | 1992-09-29 | 1994-04-19 | Yamakawa Yakuhin Kogyo Kk | 光学活性化合物、その製造方法およびそれを含有する液晶組成物並びに液晶素子 |
| DE19539141B4 (de) * | 1995-10-20 | 2016-07-07 | Merck Patent Gmbh | 2,6-Di-tert.-butylphenole |
| DE19816268A1 (de) * | 1998-04-11 | 1999-10-14 | Clariant Gmbh | Cholesterische Flüssigkristallpolymere mit erhöhter Wetterstabilität |
| DE10117224B4 (de) * | 2000-04-19 | 2015-12-31 | Merck Patent Gmbh | Verfahren zur Stabilisierung von Halogenaromaten |
| JP2002256267A (ja) * | 2000-12-27 | 2002-09-11 | Dainippon Ink & Chem Inc | 抗酸化性液晶組成物 |
-
2002
- 2002-10-07 DE DE2002146657 patent/DE10246657A1/de not_active Withdrawn
-
2003
- 2003-09-18 AU AU2003283251A patent/AU2003283251A1/en not_active Abandoned
- 2003-09-18 EP EP03775161A patent/EP1549599B1/de not_active Expired - Lifetime
- 2003-09-18 WO PCT/EP2003/010398 patent/WO2004033406A1/de not_active Ceased
- 2003-09-18 AT AT03775161T patent/ATE435849T1/de not_active IP Right Cessation
- 2003-09-18 DE DE10393154T patent/DE10393154D2/de not_active Ceased
- 2003-09-18 US US10/530,572 patent/US7790929B2/en not_active Expired - Fee Related
- 2003-09-18 DE DE50311691T patent/DE50311691D1/de not_active Expired - Lifetime
- 2003-09-18 JP JP2004542358A patent/JP4593279B2/ja not_active Expired - Fee Related
- 2003-10-06 TW TW92127688A patent/TW200422385A/zh unknown
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| Publication number | Publication date |
|---|---|
| US20060011888A1 (en) | 2006-01-19 |
| WO2004033406A1 (de) | 2004-04-22 |
| EP1549599B1 (de) | 2009-07-08 |
| DE50311691D1 (de) | 2009-08-20 |
| DE10246657A1 (de) | 2004-04-15 |
| US7790929B2 (en) | 2010-09-07 |
| JP4593279B2 (ja) | 2010-12-08 |
| AU2003283251A1 (en) | 2004-05-04 |
| JP2006502205A (ja) | 2006-01-19 |
| DE10393154D2 (de) | 2005-08-25 |
| ATE435849T1 (de) | 2009-07-15 |
| EP1549599A1 (de) | 2005-07-06 |
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