DE19919348B4 - Flüssigkristallines Medium - Google Patents
Flüssigkristallines Medium Download PDFInfo
- Publication number
- DE19919348B4 DE19919348B4 DE19919348A DE19919348A DE19919348B4 DE 19919348 B4 DE19919348 B4 DE 19919348B4 DE 19919348 A DE19919348 A DE 19919348A DE 19919348 A DE19919348 A DE 19919348A DE 19919348 B4 DE19919348 B4 DE 19919348B4
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- formula
- alkenyl
- alkyl
- radical
- 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 4
- -1 piperidine-1,4-diyl Chemical group 0.000 claims abstract description 110
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 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 1
- 239000004973 liquid crystal related substance Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 0 Cc(cc1)ccc1-c1ccc(-c2cc(F)cc(C*)c2)c(F)c1 Chemical compound Cc(cc1)ccc1-c1ccc(-c2cc(F)cc(C*)c2)c(F)c1 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 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 2
- 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 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000001911 terphenyls Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 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 description 1
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical group FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101150026303 HEX1 gene Proteins 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 1
- 102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 description 1
- 101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 description 1
- 108700017836 Prophet of Pit-1 Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000620457 Telestes souffia Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000004883 computer application Methods 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 101150047356 dec-1 gene Proteins 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 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 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3021—Cy-Ph-Ph-Cy
-
- 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)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19919348A DE19919348B4 (de) | 1998-04-30 | 1999-04-28 | Flüssigkristallines Medium |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19819392.0 | 1998-04-30 | ||
| DE19819392 | 1998-04-30 | ||
| DE19843582 | 1998-09-23 | ||
| DE19843582.7 | 1998-09-23 | ||
| DE19919348A DE19919348B4 (de) | 1998-04-30 | 1999-04-28 | Flüssigkristallines Medium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE19919348A1 DE19919348A1 (de) | 1999-11-04 |
| DE19919348B4 true DE19919348B4 (de) | 2009-11-05 |
Family
ID=26045877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19919348A Expired - Lifetime DE19919348B4 (de) | 1998-04-30 | 1999-04-28 | Flüssigkristallines Medium |
Country Status (3)
| Country | Link |
|---|---|
| US (6) | US6685996B2 (enExample) |
| JP (2) | JP5269274B2 (enExample) |
| DE (1) | DE19919348B4 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8252201B1 (en) | 2008-11-09 | 2012-08-28 | Military University of Technology | Liquid crystalline medium |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19919348B4 (de) * | 1998-04-30 | 2009-11-05 | Merck Patent Gmbh | Flüssigkristallines Medium |
| WO2001012751A1 (en) * | 1999-08-11 | 2001-02-22 | Merck Patent Gmbh | Liquid-crystalline medium |
| DE10032346A1 (de) * | 2000-07-04 | 2002-01-17 | Merck Patent Gmbh | Flüssigkristallines Medium |
| DE10060745A1 (de) * | 2000-12-07 | 2002-06-13 | Merck Patent Gmbh | Flüssigkristallines Medium |
| TW568947B (en) * | 2001-01-19 | 2004-01-01 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| DE10150198A1 (de) | 2001-10-12 | 2003-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium |
| EP1306418B1 (en) * | 2001-10-23 | 2008-06-04 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| TW574350B (en) | 2001-10-23 | 2004-02-01 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| EP1310542B1 (en) * | 2001-11-07 | 2007-04-18 | MERCK PATENT GmbH | Liquid crystalline compound, medium and display |
| DE60219569T2 (de) * | 2001-11-07 | 2007-12-27 | Merck Patent Gmbh | Flüssigkristalline Verbindung, flüssigkristallines Medium und Flüssigkristallanzeige |
| KR100977949B1 (ko) * | 2002-02-05 | 2010-08-24 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| DE10204607A1 (de) * | 2002-02-05 | 2003-08-07 | Merck Patent Gmbh | Flüssigkristallines Medium mit hoher Doppelbrechung und verbesserter UV-Stabilität |
| JP4206687B2 (ja) * | 2002-04-09 | 2009-01-14 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
| DE10247986A1 (de) | 2002-10-15 | 2004-04-29 | Merck Patent Gmbh | Photostabiles flüssigkristallines Medium |
| US7361388B2 (en) | 2003-05-27 | 2008-04-22 | Merck Patent Gmbh | Liquid-crystalline compounds having a tetrahydropyran ring |
| JP5039282B2 (ja) * | 2004-03-05 | 2012-10-03 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体 |
| KR101131089B1 (ko) * | 2004-06-18 | 2012-03-30 | 메르크 파텐트 게엠베하 | 액정 매질 |
| WO2005123879A1 (de) | 2004-06-18 | 2005-12-29 | Merck Patent Gmbh | Flüssigkristallines medium |
| EP1756248B1 (de) * | 2004-06-18 | 2008-12-03 | MERCK PATENT GmbH | Flüssigkristallines medium |
| KR101355300B1 (ko) * | 2004-11-26 | 2014-01-23 | 샤프 가부시키가이샤 | 액정 매질 |
| KR101148400B1 (ko) * | 2005-06-29 | 2012-05-23 | 엘지디스플레이 주식회사 | Ｉｐｓ 모드 액정표시소자 |
| US7674508B2 (en) | 2006-10-31 | 2010-03-09 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
| JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
| KR20120060817A (ko) * | 2009-06-29 | 2012-06-12 | 닛토덴코 가부시키가이샤 | 발광 아릴-헤테로아릴 화합물 |
| KR101986858B1 (ko) | 2011-06-01 | 2019-06-07 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| JP5850023B2 (ja) * | 2012-11-27 | 2016-02-03 | Jnc株式会社 | 末端にｃｆ２ｏｃｆ３を有する液晶化合物、液晶組成物および液晶表示素子 |
| JP6358034B2 (ja) * | 2013-12-12 | 2018-07-18 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR20170040101A (ko) * | 2015-10-02 | 2017-04-12 | 주식회사 동진쎄미켐 | 액정 조성물 |
| CN109722256B (zh) * | 2017-10-27 | 2021-08-10 | 北京八亿时空液晶科技股份有限公司 | 一种液晶组合物及其应用 |
| CN107794058B (zh) * | 2017-10-31 | 2021-08-10 | 晶美晟光电材料（南京）有限公司 | 一种液晶混合物及其应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4101543A1 (de) * | 1990-01-25 | 1991-08-01 | Merck Patent Gmbh | Halogenierte terphenyle und fluessigkristallines medium |
| DE4428766A1 (de) * | 1993-08-28 | 1995-03-02 | Merck Patent Gmbh | Benzolderivate und flüssigkristallines Medium |
| EP0832955A1 (en) * | 1996-09-25 | 1998-04-01 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
| EP0950651A1 (en) * | 1996-09-25 | 1999-10-20 | Chisso Corporation | Fluoroalkylated liquid-crystal compounds, liquid-crystal compositions, and liquid-crystal display elements |
| EP0989107A1 (en) * | 1996-09-25 | 2000-03-29 | Chisso Corporation | Terphenyl derivative, liquid-crystal composition, and liquid-crystal display element |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292454A (en) | 1989-05-26 | 1994-03-08 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Trifluorotoluene compounds, and a liquid crystalline medium |
| DE4027840A1 (de) | 1989-09-06 | 1991-03-07 | Merck Patent Gmbh | Fluorbenzolderivate und fluessigkristallines medium |
| US5308542A (en) | 1990-03-13 | 1994-05-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 4,4'-disubstituted 2',3-difluorobisphenyls and a liquid-crystalline medium |
| JPH04290859A (ja) * | 1991-03-20 | 1992-10-15 | Seiko Epson Corp | シクロヘキシルターフェニル誘導体及びそれを含有する液晶組成物及びそれを用いた液晶表示素子 |
| JP3347775B2 (ja) | 1992-11-11 | 2002-11-20 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ネマチック液晶混合物および弗素化クロルテルフェニル |
| US5326644A (en) | 1993-02-05 | 1994-07-05 | Avery Dennison Corporation | Repulpable pressure-sensitive adhesive compositions |
| KR100323836B1 (ko) * | 1993-05-10 | 2002-06-20 | 플레믹 크리스티안 | 벤젠유도체,이를포함하는액정매질및당해액정매질을포함하는전기광학액정디스플레이 |
| US5718840A (en) | 1993-05-10 | 1998-02-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Benzene derivatives, and liquid-crystalline medium |
| US5730904A (en) | 1993-05-19 | 1998-03-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Partially fluroinated benzene derivatives, and liquid-crystalline medium |
| DE4416272C2 (de) | 1993-05-19 | 2003-09-11 | Merck Patent Gmbh | Partiell fluorierte Benzolderivate |
| DE4334363A1 (de) * | 1993-10-08 | 1995-04-13 | Hoechst Ag | 3,4,5-Trifluorbenzole und ihre Verwendung in Flüssigkristallmischungen |
| JPH07138568A (ja) * | 1993-11-16 | 1995-05-30 | Seiko Epson Corp | 液晶組成物 |
| DE19513007A1 (de) | 1994-04-14 | 1995-10-19 | Merck Patent Gmbh | Hexafluorpropylether und flüssigkristallines Medium |
| GB9411233D0 (en) | 1994-06-04 | 1994-07-27 | Central Research Lab Ltd | Liquid crystal compositions |
| DE19528085A1 (de) * | 1994-08-06 | 1996-02-08 | Merck Patent Gmbh | Benzolderivate und flüssigkristallines Medium |
| GB2296253B (en) | 1994-12-22 | 1998-11-25 | Merck Patent Gmbh | Nematic liquid crystal mixtures |
| DE19504518A1 (de) | 1995-02-11 | 1996-08-14 | Merck Patent Gmbh | Partiell fluorierte Benzolderivate |
| JP3783246B2 (ja) * | 1995-07-18 | 2006-06-07 | 大日本インキ化学工業株式会社 | ｐ−テルフェニル誘導体 |
| JP3783248B2 (ja) * | 1995-07-25 | 2006-06-07 | 大日本インキ化学工業株式会社 | ４−（２−シクロヘキシル）プロピル−ｐ−テルフェニル誘導体 |
| JPH09143103A (ja) * | 1995-11-21 | 1997-06-03 | Dainippon Ink & Chem Inc | ４−（２−シクロヘキシル）エチルビフェニル誘導体 |
| US5762828A (en) | 1996-04-30 | 1998-06-09 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal medium |
| DE19919348B4 (de) * | 1998-04-30 | 2009-11-05 | Merck Patent Gmbh | Flüssigkristallines Medium |
| JP4534287B2 (ja) * | 1999-04-19 | 2010-09-01 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
| WO2001012751A1 (en) * | 1999-08-11 | 2001-02-22 | Merck Patent Gmbh | Liquid-crystalline medium |
| DE10032346A1 (de) * | 2000-07-04 | 2002-01-17 | Merck Patent Gmbh | Flüssigkristallines Medium |
| DE10060745A1 (de) * | 2000-12-07 | 2002-06-13 | Merck Patent Gmbh | Flüssigkristallines Medium |
| TW574350B (en) * | 2001-10-23 | 2004-02-01 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| DE60219569T2 (de) * | 2001-11-07 | 2007-12-27 | Merck Patent Gmbh | Flüssigkristalline Verbindung, flüssigkristallines Medium und Flüssigkristallanzeige |
| DE10312405B4 (de) * | 2002-04-16 | 2011-12-01 | Merck Patent Gmbh | Flüssigkristallines Medium mit hoher Doppelbrechung und Lichtstabilität und seine Verwendung |
-
1999
- 1999-04-28 DE DE19919348A patent/DE19919348B4/de not_active Expired - Lifetime
- 1999-04-30 JP JP12380799A patent/JP5269274B2/ja not_active Expired - Lifetime
-
2001
- 2001-07-02 US US09/895,199 patent/US6685996B2/en not_active Expired - Lifetime
- 2001-11-02 US US09/985,311 patent/US6565933B2/en not_active Expired - Lifetime
- 2001-11-02 US US09/985,310 patent/US6669998B2/en not_active Expired - Lifetime
- 2001-11-02 US US09/985,349 patent/US6596350B2/en not_active Expired - Lifetime
-
2003
- 2003-04-04 US US10/406,212 patent/US6929833B2/en not_active Expired - Lifetime
- 2003-08-06 US US10/634,953 patent/US7029731B2/en not_active Expired - Lifetime
-
2010
- 2010-03-12 JP JP2010055905A patent/JP5550951B2/ja not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4101543A1 (de) * | 1990-01-25 | 1991-08-01 | Merck Patent Gmbh | Halogenierte terphenyle und fluessigkristallines medium |
| DE4428766A1 (de) * | 1993-08-28 | 1995-03-02 | Merck Patent Gmbh | Benzolderivate und flüssigkristallines Medium |
| EP0832955A1 (en) * | 1996-09-25 | 1998-04-01 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
| EP0950651A1 (en) * | 1996-09-25 | 1999-10-20 | Chisso Corporation | Fluoroalkylated liquid-crystal compounds, liquid-crystal compositions, and liquid-crystal display elements |
| EP0989107A1 (en) * | 1996-09-25 | 2000-03-29 | Chisso Corporation | Terphenyl derivative, liquid-crystal composition, and liquid-crystal display element |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8252201B1 (en) | 2008-11-09 | 2012-08-28 | Military University of Technology | Liquid crystalline medium |
Also Published As
| Publication number | Publication date |
|---|---|
| US6565933B2 (en) | 2003-05-20 |
| US6596350B2 (en) | 2003-07-22 |
| US6669998B2 (en) | 2003-12-30 |
| DE19919348A1 (de) | 1999-11-04 |
| JP2010163623A (ja) | 2010-07-29 |
| US20040094748A1 (en) | 2004-05-20 |
| US20020093004A1 (en) | 2002-07-18 |
| US20020061368A1 (en) | 2002-05-23 |
| US20020060311A1 (en) | 2002-05-23 |
| US6929833B2 (en) | 2005-08-16 |
| US6685996B2 (en) | 2004-02-03 |
| JP5550951B2 (ja) | 2014-07-16 |
| US20030064172A1 (en) | 2003-04-03 |
| JPH11349945A (ja) | 1999-12-21 |
| JP5269274B2 (ja) | 2013-08-21 |
| US7029731B2 (en) | 2006-04-18 |
| US20030203129A1 (en) | 2003-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE19919348B4 (de) | Flüssigkristallines Medium | |
| DE19961702B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| EP0775101A1 (de) | Benzolderivate und flüssigkristallines medium | |
| EP0847433B1 (de) | Flüssigkristallines medium | |
| DE19859421A1 (de) | Flüssigkristallines Medium | |
| EP1717293B1 (de) | Flüssigkristallines Medium | |
| DE10204790A1 (de) | Flüssigkristallines Medium | |
| DE10344474A1 (de) | Flüssigkristallines Medium | |
| EP1061113B1 (de) | Flüssigkristallines Medium | |
| DE19629812B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE10111572B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE19528665A1 (de) | Flüssigkristallines Medium | |
| DE102004024456A1 (de) | Flüssigkristallines Medium | |
| DE10002462B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE19961015A1 (de) | Flüssigkristallines Medium | |
| EP1199346B1 (de) | Flüssigkristallines Medium | |
| DE19650635B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE10058661A1 (de) | Flüssigkristallines Medium | |
| DE10008712B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE19811456B4 (de) | Flüssigkristallines Medium | |
| DE10340534B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| EP1971667B1 (de) | Flüssigkristallines medium | |
| DE10060744B4 (de) | Flüssigkristallines Medium und seine Verwendung | |
| DE10123986B4 (de) | Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige | |
| DE102006006116A1 (de) | Flüssigkristallines Medium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8364 | No opposition during term of opposition | ||
| R071 | Expiry of right |