DE60109466T2 - Flüssigkristallmischung - Google Patents
Flüssigkristallmischung Download PDFInfo
- Publication number
- DE60109466T2 DE60109466T2 DE60109466T DE60109466T DE60109466T2 DE 60109466 T2 DE60109466 T2 DE 60109466T2 DE 60109466 T DE60109466 T DE 60109466T DE 60109466 T DE60109466 T DE 60109466T DE 60109466 T2 DE60109466 T2 DE 60109466T2
- Authority
- DE
- Germany
- Prior art keywords
- diyl
- optionally substituted
- atoms
- alkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000007788 liquid Substances 0.000 title description 3
- -1 cyclohexane-1,4-diyl Chemical group 0.000 claims description 109
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 239000004973 liquid crystal related substance Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011159 matrix material Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 239000012963 UV stabilizer Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 229910021647 smectite Inorganic materials 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 13
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 6
- MIKWCGJOXVQNJT-UHFFFAOYSA-N 4-(2,2,6,6-tetramethylpiperidin-4-yl)phenol Chemical compound C1C(C)(C)NC(C)(C)CC1C1=CC=C(O)C=C1 MIKWCGJOXVQNJT-UHFFFAOYSA-N 0.000 description 6
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- FGGXTQDATCWSFJ-UHFFFAOYSA-N 4-(2,2,6,6-tetramethylpiperidin-4-yl)cyclohexan-1-ol Chemical compound C1C(C)(C)NC(C)(C)CC1C1CCC(O)CC1 FGGXTQDATCWSFJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- GHJUORCGZFHNKG-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-one Chemical compound CN1C(C)(C)CC(=O)CC1(C)C GHJUORCGZFHNKG-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- LNZLKYDXPBRIOA-UHFFFAOYSA-N 4-(4-octylphenyl)benzoyl chloride Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(Cl)=O)C=C1 LNZLKYDXPBRIOA-UHFFFAOYSA-N 0.000 description 1
- OEABBNGVFWXEJP-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzoyl chloride Chemical compound C1CC(CCC)CCC1C1=CC=C(C(Cl)=O)C=C1 OEABBNGVFWXEJP-UHFFFAOYSA-N 0.000 description 1
- IQYGKXCPNZTVLL-UHFFFAOYSA-N 4-(5-hexylpyrimidin-2-yl)benzoyl chloride Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(C(Cl)=O)C=C1 IQYGKXCPNZTVLL-UHFFFAOYSA-N 0.000 description 1
- YXBOJGHBKKAPOG-UHFFFAOYSA-N 4-octoxybenzoyl chloride Chemical compound CCCCCCCCOC1=CC=C(C(Cl)=O)C=C1 YXBOJGHBKKAPOG-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- GMZABADCQVWQPS-JOCQHMNTSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(Br)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(Br)C=C1 GMZABADCQVWQPS-JOCQHMNTSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- LFVLUOAHQIVABZ-UHFFFAOYSA-N Iodofenphos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(I)C=C1Cl LFVLUOAHQIVABZ-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000448053 Toya Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- IXYUSDWFQQXDTP-UHFFFAOYSA-N methyl 4-(4-heptylphenyl)benzoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(=O)OC)C=C1 IXYUSDWFQQXDTP-UHFFFAOYSA-N 0.000 description 1
- RTTGTHPEVMEHEK-UHFFFAOYSA-N methyl 4-hexylbenzoate Chemical compound CCCCCCC1=CC=C(C(=O)OC)C=C1 RTTGTHPEVMEHEK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0266—Antiferroelectrics
-
- 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
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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00118736 | 2000-08-30 | ||
| EP00118736A EP1184442A1 (en) | 2000-08-30 | 2000-08-30 | Liquid crystal mixture |
| PCT/EP2001/009832 WO2002018515A1 (en) | 2000-08-30 | 2001-08-25 | Liquid crystal mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60109466D1 DE60109466D1 (de) | 2005-04-21 |
| DE60109466T2 true DE60109466T2 (de) | 2006-04-13 |
Family
ID=8169691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60109466T Expired - Lifetime DE60109466T2 (de) | 2000-08-30 | 2001-08-25 | Flüssigkristallmischung |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6958176B2 (enExample) |
| EP (2) | EP1184442A1 (enExample) |
| JP (1) | JP5269279B2 (enExample) |
| KR (2) | KR100989030B1 (enExample) |
| CN (1) | CN100497523C (enExample) |
| DE (1) | DE60109466T2 (enExample) |
| WO (1) | WO2002018515A1 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1184442A1 (en) * | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| US6824707B2 (en) | 2001-10-23 | 2004-11-30 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
| EP1367114A1 (en) * | 2002-04-11 | 2003-12-03 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
| WO2006034341A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| MX2007003327A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa. |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
| TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| AR051026A1 (es) | 2004-09-20 | 2006-12-13 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| CA2580855A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| US8541457B2 (en) | 2005-06-03 | 2013-09-24 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors |
| JP4935055B2 (ja) * | 2005-11-15 | 2012-05-23 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| US7782438B2 (en) * | 2006-06-13 | 2010-08-24 | Kent State University | Fast switching electro-optical devices using banana-shaped liquid crystals |
| AU2007288245A1 (en) | 2006-08-24 | 2008-02-28 | Novartis Ag | 2- (pyrazin-2-yl) -thiazole and 2- (1h-pyrazol-3-yl) -thiazole derivatives as well as related compounds as stearoyl-CoA desaturase (SCD) inhibitors for the treatment of metabolic, cardiovascular and other disorders |
| US20110101270A1 (en) * | 2008-04-22 | 2011-05-05 | Atsutaka Manabe | Liquid-crystalline medium |
| US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
| US8628685B2 (en) * | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
| US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8349210B2 (en) * | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8431039B2 (en) * | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
| JP2010230759A (ja) * | 2009-03-26 | 2010-10-14 | Sekisui Chem Co Ltd | 液晶シート |
| DE102011013007A1 (de) | 2010-04-01 | 2011-10-06 | Merck Patent Gmbh | Flüssigkristallines Medium und Elektrooptische Anzeige |
| KR102566087B1 (ko) | 2010-12-07 | 2023-08-14 | 메르크 파텐트 게엠베하 | 액정 매질 및 전기-광학 디스플레이 |
| KR101846042B1 (ko) * | 2010-12-10 | 2018-04-05 | 메르크 파텐트 게엠베하 | 액정 매질 및 전기 광학 디스플레이 |
| EP2514800B2 (de) | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| DE102012008570A1 (de) | 2011-04-21 | 2012-10-25 | Merck Patent Gmbh | Verbindungen und Flüssigkristallines Medium |
| CN104520762B (zh) * | 2012-06-25 | 2018-02-16 | 汉阳大学校产学协力团 | 液晶显示装置和驱动液晶显示装置的方法 |
| EP2722380B1 (de) | 2012-10-18 | 2018-02-21 | Merck Patent GmbH | Flüssigkristallines Medium, Methode zu seiner Stabilisierung und Flüssigkristallanzeige |
| EP3327103B1 (de) | 2012-10-18 | 2020-10-14 | Merck Patent GmbH | Flüssigkristallines medium, methode zu seiner stabilisierung und flüssigkristallanzeige |
| JP5692480B1 (ja) * | 2013-06-26 | 2015-04-01 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| WO2014208320A1 (ja) | 2013-06-26 | 2014-12-31 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR102068961B1 (ko) * | 2013-06-28 | 2020-01-22 | 엘지디스플레이 주식회사 | 액정 물질 및 이를 포함하는 액정표시장치 |
| KR101646637B1 (ko) | 2013-07-03 | 2016-08-08 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
| US9758726B2 (en) | 2013-07-12 | 2017-09-12 | Lg Chem, Ltd. | Liquid crystal cell |
| JP6459975B2 (ja) * | 2013-11-19 | 2019-01-30 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| US9969935B2 (en) | 2013-11-29 | 2018-05-15 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| JP6657639B2 (ja) * | 2014-08-05 | 2020-03-04 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| EP2993216B1 (de) | 2014-09-02 | 2017-07-26 | Merck Patent GmbH | Verbindungen und flüssigkristallines medium |
| WO2016035667A1 (ja) * | 2014-09-05 | 2016-03-10 | Dic株式会社 | 液晶組成物及びそれを使用した液晶表示素子 |
| JP6402907B2 (ja) * | 2014-09-24 | 2018-10-10 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| CN106795434A (zh) * | 2014-10-10 | 2017-05-31 | Dic株式会社 | 液晶组合物和使用其的液晶显示元件 |
| DE102015013980A1 (de) | 2014-11-11 | 2016-05-12 | Merck Patent Gmbh | Heterocyclische Verbindung, Flüssigkristallines Medium, Methode zu seiner Stabilisierung und Fküssigkristallanzeige |
| JP5850187B1 (ja) * | 2015-01-08 | 2016-02-03 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR102564639B1 (ko) * | 2015-01-19 | 2023-08-08 | 메르크 파텐트 게엠베하 | 중합가능한 화합물 및 액정 디스플레이에서 이의 용도 |
| DE102015003602A1 (de) | 2015-03-18 | 2016-09-22 | Merck Patent Gmbh | Flüssigkristalines Medium |
| JP6729556B2 (ja) * | 2015-03-24 | 2020-07-22 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| EP3093328B1 (de) | 2015-05-13 | 2018-06-13 | Merck Patent GmbH | Flüssigkristallines medium |
| WO2016192834A1 (de) * | 2015-05-29 | 2016-12-08 | Merck Patent Gmbh | Flüssigkristallines medium |
| US10329252B2 (en) | 2015-09-04 | 2019-06-25 | Dic Corporation | Stabilizer compound, liquid crystal composition, and display element |
| WO2017038617A1 (ja) | 2015-09-04 | 2017-03-09 | Dic株式会社 | 液晶組成物及びそれを使用した液晶表示素子 |
| JP6696411B2 (ja) * | 2015-12-03 | 2020-05-20 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| JP2017109939A (ja) * | 2015-12-15 | 2017-06-22 | Dic株式会社 | 安定剤化合物、液晶組成物及び表示素子 |
| DE102017006567A1 (de) * | 2016-08-05 | 2018-02-08 | Merck Patent Gmbh | Piperidin-derivate und flüssigkristallines medium |
| JP6790741B2 (ja) * | 2016-11-09 | 2020-11-25 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| DE102016122963B4 (de) * | 2016-11-29 | 2021-06-24 | Infineon Technologies Austria Ag | Halbleitervorrichtung mit einem bidirektionalen Schalter |
| JP6988829B2 (ja) * | 2016-12-26 | 2022-01-05 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| DE102018000109A1 (de) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Verbindungen und Flüssigkristallines Medium |
| DE102018000286A1 (de) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Verbindungen und flüssigkristallines medium |
| KR102355529B1 (ko) * | 2017-08-07 | 2022-01-26 | 삼성디스플레이 주식회사 | 유기 전계 발광 표시 장치 |
| JP2019094368A (ja) * | 2017-11-17 | 2019-06-20 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| CN112218933B (zh) | 2018-05-30 | 2025-12-12 | 默克专利股份有限公司 | 化合物和液晶介质 |
| WO2019228938A1 (en) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Compounds and liquid-crystalline medium |
| JP7115513B2 (ja) * | 2020-05-22 | 2022-08-09 | Dic株式会社 | 化合物、組成物及び表示素子 |
| CN113292514B (zh) * | 2021-04-07 | 2022-11-15 | 浙江华显光电科技有限公司 | 一种哌嗪衍生物及包含其的有机光电器件 |
| KR20230146471A (ko) | 2022-04-12 | 2023-10-19 | 메르크 파텐트 게엠베하 | 액정 매질 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB849282A (en) * | 1957-08-27 | 1960-09-21 | May & Baker Ltd | Pharmaceutical compositions comprising substituted 1,2,3,6-tetrahydropyridines |
| US3663558A (en) * | 1969-09-27 | 1972-05-16 | Sankyo Co | Delta**3 piperidone enol ethers and a process for their preparation |
| GB1395159A (en) | 1971-11-30 | 1975-05-21 | Ciba Geigy Ag | Tetra-hydropyridine derivatives |
| BE792043A (fr) * | 1971-11-30 | 1973-05-29 | Ciba Geigy | Derives de la piperidine utilisables pour stabiliser des matieres organiques |
| GB1398412A (en) * | 1972-07-28 | 1975-06-18 | Ciba Geigy Ag | Piperidine derivatives |
| SU435235A1 (ru) * | 1972-08-31 | 1974-07-05 | А. Б. Шапиро, М. В. Судник, М. Ф. Романцев , Э. Г. Розанцев Институт химической физики СССР | СПОСОБ ПОЛУЧЕНИЯ ДИПИПЕРИДИНДИНИТРОКСИЛОВАлкАнового РЯДА |
| GB1403942A (en) | 1973-04-05 | 1975-08-28 | Ciba Geigy Ag | Piperidine derivatives |
| US3937711A (en) * | 1973-10-15 | 1976-02-10 | Ciba-Geigy Corporation | 4-(carboxamidoethyl) piperidines |
| DE2642461A1 (de) * | 1976-09-21 | 1978-03-30 | Bayer Ag | Permanent stabilisierte polymere |
| SU631516A1 (ru) | 1977-02-25 | 1978-11-05 | Предприятие П/Я А-7253 | Способ получени 4-(4-оксифенил)3,4-дегидро-2,2,6,6-тетраметилпиперидина |
| JPS5523169A (en) * | 1978-08-09 | 1980-02-19 | Seiko Epson Corp | Liquid crystal composition and display elements comprising it |
| JPS58168641A (ja) | 1982-03-30 | 1983-10-05 | Sumitomo Chem Co Ltd | 安定化ポリオレフイン樹脂組成物 |
| DE3220155A1 (de) * | 1982-05-28 | 1983-12-01 | Merck Patent Gmbh, 6100 Darmstadt | Piperidinderivate |
| JPS6067587A (ja) * | 1983-09-22 | 1985-04-17 | Adeka Argus Chem Co Ltd | 液晶組成物 |
| EP0323803A1 (de) * | 1987-12-30 | 1989-07-12 | Ciba-Geigy Ag | Stabilisierung von Lacken mit N-formylierten gehinderten Aminen |
| JP2636035B2 (ja) * | 1989-02-27 | 1997-07-30 | 松下電器産業株式会社 | 強誘電性液晶組成物および強誘電性液晶表示装置 |
| DE4027981A1 (de) | 1990-09-04 | 1992-04-30 | Merck Patent Gmbh | Matrix-fluessigkristallanzeige |
| JPH05117324A (ja) * | 1991-10-31 | 1993-05-14 | Mitsubishi Rayon Co Ltd | 液晶複合体並びに液晶光学装置及びその製造方法 |
| ES2129809T3 (es) * | 1994-02-28 | 1999-06-16 | Sumitomo Chemical Co | Composicion para resina poliolefinica y pelicula de resina. |
| CN1142242C (zh) | 1995-08-01 | 2004-03-17 | 默克专利股份有限公司 | 液晶介质 |
| JPH09291282A (ja) * | 1996-04-26 | 1997-11-11 | Sumitomo Chem Co Ltd | 安定化した液晶材料およびこれを用いた液晶素子 |
| JP3965726B2 (ja) * | 1997-07-04 | 2007-08-29 | 日立化成工業株式会社 | ウレタン樹脂組成物及びゲルコート層を有する成形品の製造法 |
| JPH11174642A (ja) * | 1997-12-10 | 1999-07-02 | Konica Corp | ハロゲン化銀カラー写真感光材料 |
| NL1012219C2 (nl) | 1998-06-19 | 2000-04-13 | Ciba Sc Holding Ag | Werkwijze voor de polymersitie van overzadigde polyalkylpiperidinen. |
| DE19857352A1 (de) | 1998-12-11 | 2000-06-15 | Clariant Gmbh | Ferroelektrische Aktivmatrix-Displays mit weitem Arbeitstemperaturbereich |
| AU7514700A (en) * | 1999-09-07 | 2001-04-10 | Syngenta Participations Ag | Cyanopiperidines |
| EP1184442A1 (en) * | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| JP2002256267A (ja) * | 2000-12-27 | 2002-09-11 | Dainippon Ink & Chem Inc | 抗酸化性液晶組成物 |
| US6824707B2 (en) * | 2001-10-23 | 2004-11-30 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
| EP2031681A1 (en) | 2007-08-31 | 2009-03-04 | The Technical University of Denmark | Horizontally graded structures for electrochemical and electronic devices |
| US8349210B2 (en) * | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
-
2000
- 2000-08-30 EP EP00118736A patent/EP1184442A1/en not_active Withdrawn
-
2001
- 2001-08-25 KR KR1020087004499A patent/KR100989030B1/ko not_active Expired - Lifetime
- 2001-08-25 WO PCT/EP2001/009832 patent/WO2002018515A1/en not_active Ceased
- 2001-08-25 US US10/363,009 patent/US6958176B2/en not_active Expired - Lifetime
- 2001-08-25 EP EP01969650A patent/EP1319054B1/en not_active Expired - Lifetime
- 2001-08-25 CN CNB01813680XA patent/CN100497523C/zh not_active Expired - Lifetime
- 2001-08-25 DE DE60109466T patent/DE60109466T2/de not_active Expired - Lifetime
- 2001-08-25 JP JP2002524018A patent/JP5269279B2/ja not_active Expired - Fee Related
- 2001-08-25 KR KR1020037002809A patent/KR100890345B1/ko not_active Expired - Lifetime
-
2005
- 2005-08-11 US US11/201,605 patent/US9388338B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1457355A (zh) | 2003-11-19 |
| US6958176B2 (en) | 2005-10-25 |
| US20060011886A1 (en) | 2006-01-19 |
| KR20080023367A (ko) | 2008-03-13 |
| EP1319054A1 (en) | 2003-06-18 |
| US9388338B2 (en) | 2016-07-12 |
| DE60109466D1 (de) | 2005-04-21 |
| WO2002018515A1 (en) | 2002-03-07 |
| EP1184442A1 (en) | 2002-03-06 |
| CN100497523C (zh) | 2009-06-10 |
| KR100890345B1 (ko) | 2009-03-25 |
| US20040085490A1 (en) | 2004-05-06 |
| KR100989030B1 (ko) | 2010-10-25 |
| JP5269279B2 (ja) | 2013-08-21 |
| EP1319054B1 (en) | 2005-03-16 |
| JP2004507607A (ja) | 2004-03-11 |
| KR20030041979A (ko) | 2003-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60109466T2 (de) | Flüssigkristallmischung | |
| DE3789151T2 (de) | Fluoralkanderivat und Flüssigkristallmischung. | |
| DE3856314T2 (de) | Mesomorphische Verbindung, Flüssigkristallzusammensetzung und Flüssigkristallvorrichtung | |
| DE10101022A1 (de) | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen | |
| DE69426358T2 (de) | Verbindungen zur verwendung in flüssigkristallzusammensetzungen | |
| EP0238576B1 (de) | Stickstoffhaltige heterocyclische verbindungen | |
| DE4024190C2 (enExample) | ||
| DE69312777T2 (de) | Carboxylic-Säureester-Verbindung, flüssigkristallines Material, flüssigkristalline Zusammensetzungen und flüssigkristallines Element | |
| EP0321504A1 (de) | Chirale aryloxypropionsäureester und ihre verwendung als dotierstoff in flüssigkristall-phasen. | |
| EP1223210B1 (de) | Mehrfach fluorierte Fluorene und ihre Verwendung in Flüssigkristallmischungen | |
| DE69317512T2 (de) | Flüssigkristallverbindung, Zusammensetzung und Vorrichtung | |
| EP0883618B1 (de) | Difluorphenylpyrimidylpyridin-derivate und ihre verwendung in flüssigkristallinen mischungen | |
| EP0428665B1 (de) | Fluorphenylpyrimidine | |
| EP0475444B1 (de) | Die Verwendung von 4-Fluor-pyrimidin-Derivaten als Komponente für ferroelektrische Flüssigkristallmischungen und ihre Herstellung | |
| DE4245018B4 (de) | Flüssigkristalline Verbindungen | |
| DE4338348B4 (de) | 2,6-Disubstituierte Benzotrifluoride | |
| EP0438811A2 (de) | Ester von 3-Halogen- bzw. 3-Cyano-substituierten 2-Methylalkancarbonsäuren und ihre Verwendung als Dotierstoffe in flüssigkristallinen Mischungen | |
| EP0433826B1 (de) | Fluorphenylpyridine | |
| EP0267276B1 (de) | Smektische flüssigkristalline phasen enthaltend bicyclooctanester | |
| DE4118279C2 (de) | 2-(2-Fluorphenyl)-pyrimidine | |
| WO1991002722A1 (de) | 5-oxy-2-phenylpyridine und flüssigkristallines medium | |
| DE19648171A1 (de) | Difluorphenylpyrimidylpyridin-Derivate und ihre Verwendung in flüssigkristallinen Mischungen | |
| DE4116750A1 (de) | Optisch aktive 1,3-dioxolane als dotierungskomponenten in fluessigkristallmischungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: MERCK PATENT GMBH, 64293 DARMSTADT, DE |
|
| 8364 | No opposition during term of opposition |