TWI633172B - 炔基二苯乙炔化物、含彼之液晶混合物及用於高頻科技之組件 - Google Patents
炔基二苯乙炔化物、含彼之液晶混合物及用於高頻科技之組件 Download PDFInfo
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- TWI633172B TWI633172B TW103129089A TW103129089A TWI633172B TW I633172 B TWI633172 B TW I633172B TW 103129089 A TW103129089 A TW 103129089A TW 103129089 A TW103129089 A TW 103129089A TW I633172 B TWI633172 B TW I633172B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 65
- 238000005516 engineering process Methods 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 title description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 239000012071 phase Substances 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- FOOMDVGBZOQRGU-UHFFFAOYSA-N 1-[2-(4-butylphenyl)ethynyl]-2,3-dimethyl-4-prop-1-ynylbenzene Chemical compound C(CCC)C1=CC=C(C=C1)C#CC1=C(C(=C(C=C1)C#CC)C)C FOOMDVGBZOQRGU-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
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- 238000002044 microwave spectrum Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000010363 phase shift Effects 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- MZTFVMMWOFPNLF-UHFFFAOYSA-N 1-[2-(4-but-1-ynylphenyl)ethynyl]-2,3-dimethyl-4-prop-1-ynylbenzene Chemical compound C(#CCC)C1=CC=C(C=C1)C#CC1=C(C(=C(C=C1)C#CC)C)C MZTFVMMWOFPNLF-UHFFFAOYSA-N 0.000 description 1
- KDUHKRMAISJIHL-UHFFFAOYSA-N 1-[2-(4-butylphenyl)ethynyl]-2-methyl-4-prop-1-ynylbenzene Chemical compound C(CCC)C1=CC=C(C=C1)C#CC1=C(C=C(C=C1)C#CC)C KDUHKRMAISJIHL-UHFFFAOYSA-N 0.000 description 1
- KWPPEEFSTJZLEN-UHFFFAOYSA-N 1-bromo-2,3-dimethyl-4-prop-1-ynylbenzene Chemical compound BrC1=C(C(=C(C=C1)C#CC)C)C KWPPEEFSTJZLEN-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- HHMQEMKXBWBIKF-UHFFFAOYSA-N 4-[2-(4-butylphenyl)ethynyl]-2-methyl-1-prop-1-ynylbenzene Chemical compound C(CCC)C1=CC=C(C=C1)C#CC1=CC(=C(C=C1)C#CC)C HHMQEMKXBWBIKF-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- KPWBVVGSAADWIM-UHFFFAOYSA-N BrC1=CC(=C(C=C1)C#CC)C Chemical compound BrC1=CC(=C(C=C1)C#CC)C KPWBVVGSAADWIM-UHFFFAOYSA-N 0.000 description 1
- BHAGICBWIKOWJG-UHFFFAOYSA-N CC#Cc1ccc(Br)c(C)c1 Chemical compound CC#Cc1ccc(Br)c(C)c1 BHAGICBWIKOWJG-UHFFFAOYSA-N 0.000 description 1
- SYCKDCYFMUSTMI-UHFFFAOYSA-N CC1=C(C=CC(=C1C)C#CC)C#C Chemical group CC1=C(C=CC(=C1C)C#CC)C#C SYCKDCYFMUSTMI-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 239000004642 Polyimide Substances 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
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
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- C07C15/18—Polycyclic non-condensed hydrocarbons containing at least one group with formula
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/47—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
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- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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- 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
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- 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
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
- C09K19/3447—Pyridine condensed or bridged with another ring system, e.g. quinoline or acridine
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K2019/181—Ph-C≡C-Ph
-
- 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
- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- C09K2219/11—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used in the High Frequency technical field
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- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ??13004178.3 | 2013-08-23 | ||
| EP13004178 | 2013-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201527494A TW201527494A (zh) | 2015-07-16 |
| TWI633172B true TWI633172B (zh) | 2018-08-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103129089A TWI633172B (zh) | 2013-08-23 | 2014-08-22 | 炔基二苯乙炔化物、含彼之液晶混合物及用於高頻科技之組件 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10099975B2 (enExample) |
| EP (1) | EP3036307B1 (enExample) |
| JP (1) | JP6526666B2 (enExample) |
| KR (1) | KR102237647B1 (enExample) |
| CN (1) | CN105473686B (enExample) |
| TW (1) | TWI633172B (enExample) |
| WO (1) | WO2015024635A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3433337B1 (en) | 2016-03-24 | 2020-04-29 | Merck Patent GmbH | Liquid-crystalline medium |
| WO2017162716A1 (en) * | 2016-03-24 | 2017-09-28 | Merck Patent Gmbh | Liquid-crystalline medium |
| US11069977B2 (en) * | 2016-07-15 | 2021-07-20 | Sharp Kabushiki Kaisha | Liquid crystal alignment agent, liquid crystal panel, and scanning antenna |
| CN109642161B (zh) | 2016-08-25 | 2023-02-10 | 默克专利股份有限公司 | 液晶介质 |
| US11891557B2 (en) * | 2017-09-14 | 2024-02-06 | Merck Patent Gmbh | Isothiocyanato tolane derivatives |
| US11485723B2 (en) | 2017-10-19 | 2022-11-01 | Merck Patent Gmbh | Dibenzofurans and dibenzothiophenes |
| CN108865179B (zh) * | 2018-08-17 | 2021-07-27 | 西安近代化学研究所 | 一种液晶组合物和包含其的高频组件 |
| CN117660019B (zh) * | 2022-08-23 | 2026-05-05 | 西安近代化学研究所 | 高双折射率的液晶化合物、合成方法、液晶组合物及应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5986096A (en) * | 1995-03-28 | 1999-11-16 | The Secretary Of State For Defence In Her Britannic Majesty's A Government Of The U.K. Of Gt. Britain & N. Ireland Of Defence Evaluation & Research Agency | Pyrimidine compounds |
| US20030011725A1 (en) * | 2001-02-19 | 2003-01-16 | Atsuhiro Ohkawa | Optical film comprising support and polarizing layer |
| CN101616883A (zh) * | 2007-01-24 | 2009-12-30 | 智索株式会社 | 液晶性化合物、液晶组成物以及液晶显示元件 |
| TW201247850A (en) * | 2011-03-24 | 2012-12-01 | Merck Patent Gmbh | Mesogenic compounds, liquid-crystalline media and components for high-frequency technology |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2526282B2 (ja) * | 1989-01-06 | 1996-08-21 | チッソ株式会社 | 大きな屈折率異方性を有する新規な液晶化合物 |
| JP3579072B2 (ja) * | 1993-02-19 | 2004-10-20 | 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 | トラン系化合物、その製造法およびそれを有効成分とする液晶組成物 |
| KR100311921B1 (ko) * | 1993-10-13 | 2002-10-31 | 스미또모 가가꾸 고오교오 가부시끼가이샤 | 톨란화합물,그의제조방법,이화합물을유효성분으로하는액정조성물및이액정조성물을사용하여이루어진액정소자 |
| JPH0812599A (ja) * | 1994-06-27 | 1996-01-16 | Sumitomo Chem Co Ltd | トラン化合物の製造法 |
| US5626792A (en) * | 1994-09-06 | 1997-05-06 | Displaytech, Inc. | High birefringence liquid crystal compounds |
| KR100622326B1 (ko) * | 1998-02-25 | 2006-09-12 | 스미또모 가가꾸 가부시끼가이샤 | 페닐아세틸렌 화합물 및 이것을 포함하는 액정 조성물 |
| JP2003207631A (ja) * | 2002-01-11 | 2003-07-25 | Fuji Photo Film Co Ltd | 光学フイルム、偏光板および液晶表示装置 |
| DE602004026006D1 (de) * | 2003-05-21 | 2010-04-29 | Merck Patent Gmbh | Tolan-Derivate und Flüssigkristallmedium |
| CN100558720C (zh) * | 2005-09-06 | 2009-11-11 | 财团法人工业技术研究院 | 具有二苯骈呋喃结构的液晶化合物及其组合物 |
| DE102011112950A1 (de) * | 2010-10-13 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für ein flüssigkristallines Medium und deren Verwendung für Hochfrquenzbauteile |
| TR201903813T4 (tr) * | 2011-09-05 | 2019-04-22 | Merck Patent Gmbh | Sıvı kristal ortam ve bunu içeren yüksek frekanslı komponentler. |
-
2014
- 2014-08-11 EP EP14750445.0A patent/EP3036307B1/de active Active
- 2014-08-11 KR KR1020167007446A patent/KR102237647B1/ko active Active
- 2014-08-11 US US14/913,807 patent/US10099975B2/en active Active
- 2014-08-11 JP JP2016535358A patent/JP6526666B2/ja active Active
- 2014-08-11 WO PCT/EP2014/002194 patent/WO2015024635A1/de not_active Ceased
- 2014-08-11 CN CN201480046608.6A patent/CN105473686B/zh active Active
- 2014-08-22 TW TW103129089A patent/TWI633172B/zh active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5986096A (en) * | 1995-03-28 | 1999-11-16 | The Secretary Of State For Defence In Her Britannic Majesty's A Government Of The U.K. Of Gt. Britain & N. Ireland Of Defence Evaluation & Research Agency | Pyrimidine compounds |
| US20030011725A1 (en) * | 2001-02-19 | 2003-01-16 | Atsuhiro Ohkawa | Optical film comprising support and polarizing layer |
| CN101616883A (zh) * | 2007-01-24 | 2009-12-30 | 智索株式会社 | 液晶性化合物、液晶组成物以及液晶显示元件 |
| TW201247850A (en) * | 2011-03-24 | 2012-12-01 | Merck Patent Gmbh | Mesogenic compounds, liquid-crystalline media and components for high-frequency technology |
Also Published As
| Publication number | Publication date |
|---|---|
| US10099975B2 (en) | 2018-10-16 |
| EP3036307A1 (de) | 2016-06-29 |
| CN105473686B (zh) | 2018-11-16 |
| KR102237647B1 (ko) | 2021-04-09 |
| CN105473686A (zh) | 2016-04-06 |
| WO2015024635A8 (de) | 2016-03-17 |
| TW201527494A (zh) | 2015-07-16 |
| KR20160045847A (ko) | 2016-04-27 |
| EP3036307B1 (de) | 2017-06-21 |
| JP6526666B2 (ja) | 2019-06-05 |
| US20160208167A1 (en) | 2016-07-21 |
| JP2016534108A (ja) | 2016-11-04 |
| WO2015024635A1 (de) | 2015-02-26 |
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