TWI387638B - 液晶原化合物，電光顯示器之介質及電光顯示器 - Google Patents
液晶原化合物，電光顯示器之介質及電光顯示器 Download PDFInfo
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- TWI387638B TWI387638B TW093125623A TW93125623A TWI387638B TW I387638 B TWI387638 B TW I387638B TW 093125623 A TW093125623 A TW 093125623A TW 93125623 A TW93125623 A TW 93125623A TW I387638 B TWI387638 B TW I387638B
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- liquid crystal
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 84
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- -1 alkarylalkoxy Chemical group 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000004434 sulfur atom Chemical group 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004416 alkarylalkyl group Chemical group 0.000 claims description 10
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 17
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 239000002131 composite material Substances 0.000 description 8
- 230000003750 conditioning effect Effects 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 230000005684 electric field Effects 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
- 238000005259 measurement Methods 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- LLNDFRUKYOJQJM-UHFFFAOYSA-N 2-[difluoro-(3,4,5-trifluorophenoxy)methyl]-1,3-difluoro-5-(2,4,6-tripropoxyphenyl)benzene Chemical compound CCCOC1=CC(OCCC)=CC(OCCC)=C1C1=CC(F)=C(C(F)(F)OC=2C=C(F)C(F)=C(F)C=2)C(F)=C1 LLNDFRUKYOJQJM-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XXLRRALADNELHD-UHFFFAOYSA-N O1CCCO1.C=C Chemical compound O1CCCO1.C=C XXLRRALADNELHD-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000000407 epitaxy Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
- WWQAGDWTJOKFQB-UHFFFAOYSA-N penta-1,2,3-triene Chemical group CC=C=C=C WWQAGDWTJOKFQB-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
-
- 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
-
- 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
-
- 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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03018707 | 2003-08-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200526763A TW200526763A (en) | 2005-08-16 |
| TWI387638B true TWI387638B (zh) | 2013-03-01 |
Family
ID=34203216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093125623A TWI387638B (zh) | 2003-08-25 | 2004-08-26 | 液晶原化合物，電光顯示器之介質及電光顯示器 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7531106B2 (enExample) |
| EP (1) | EP1658351B1 (enExample) |
| JP (1) | JP2007503487A (enExample) |
| KR (1) | KR101198452B1 (enExample) |
| AT (1) | ATE447001T1 (enExample) |
| DE (1) | DE602004023857D1 (enExample) |
| TW (1) | TWI387638B (enExample) |
| WO (1) | WO2005019378A1 (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8129002B2 (en) * | 2003-08-25 | 2012-03-06 | Merck Patent Gmbh | Compounds for use in liquid crystal media |
| US20050124666A1 (en) | 2003-11-13 | 2005-06-09 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same |
| US7126026B2 (en) | 2003-11-13 | 2006-10-24 | Sanofi-Aventis Deutschland Gmbh | Process for preparing 4-pentafluorosulfanylbenzoylguanidines |
| US7317124B2 (en) | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
| WO2005112540A2 (en) * | 2004-05-21 | 2005-12-01 | Merck Patent Gmbh | Liquid crystal compounds, liquid crystal medium and liquid crystal display |
| JP4776279B2 (ja) * | 2005-06-09 | 2011-09-21 | 株式会社Ａｄｅｋａ | 新規化合物及び液晶組成物 |
| WO2007147516A1 (en) * | 2006-06-23 | 2007-12-27 | Merck Patent Gmbh | Mesogenic compounds, liquid crystal medium and liquid crystal display |
| WO2008105286A1 (ja) | 2007-02-28 | 2008-09-04 | Chisso Corporation | Ｃｆ２ｏ結合基を有する５環液晶化合物、液晶組成物および液晶表示素子 |
| JP5371954B2 (ja) * | 2007-04-24 | 2013-12-18 | 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 | 液晶混合物のためのピリジン化合物 |
| JP2009067780A (ja) * | 2007-08-22 | 2009-04-02 | Chisso Corp | クロロナフタレン部位を有する液晶化合物、液晶組成物および光素子 |
| CN101778924B (zh) * | 2007-08-27 | 2013-04-10 | Jnc株式会社 | 液晶组成物以及液晶显示元件 |
| US7879413B2 (en) * | 2007-08-29 | 2011-02-01 | Chisso Corporation | Optically isotropic liquid crystal medium and optical device |
| WO2009028446A1 (ja) * | 2007-08-29 | 2009-03-05 | Chisso Corporation | 液晶組成物および液晶表示素子 |
| US8182885B2 (en) | 2007-08-30 | 2012-05-22 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| US8153021B2 (en) * | 2007-08-31 | 2012-04-10 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| JP5577566B2 (ja) | 2007-08-31 | 2014-08-27 | Ｊｎｃ株式会社 | 液晶組成物および液晶素子 |
| EP2284148B1 (en) * | 2008-06-09 | 2016-03-02 | JNC Corporation | Pentacyclic liquid crystal compound having cyclohexane ring, liquid crystal composition and liquid crystal display element |
| JP5359053B2 (ja) * | 2008-06-24 | 2013-12-04 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| JP5359055B2 (ja) * | 2008-06-25 | 2013-12-04 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| WO2010042652A2 (en) | 2008-10-08 | 2010-04-15 | Amira Pharmaceuticals, Inc. | Heteroalkyl biphenyl antagonists of prostaglandin d2 receptors |
| US8475888B2 (en) * | 2008-10-21 | 2013-07-02 | Jnc Corporation | Five-ring liquid crystal compound having a nitrogen-containing heterocyclic ring, liquid crystal composition and liquid crystal display device |
| TWI458811B (zh) * | 2009-01-16 | 2014-11-01 | Jnc Corp | 液晶性化合物、液晶組成物以及液晶顯示元件 |
| CN102326286B (zh) | 2009-02-18 | 2014-04-02 | 旭化成电子材料株式会社 | 锂离子二次电池用电解液和锂离子二次电池 |
| WO2010143658A1 (ja) | 2009-06-10 | 2010-12-16 | 旭化成イーマテリアルズ株式会社 | 電解液及びそれを用いたリチウムイオン二次電池 |
| KR101770004B1 (ko) * | 2009-09-25 | 2017-08-21 | 메르크 파텐트 게엠베하 | 액정 매질용 화합물, 및 이를 포함하는 고주파 부품 |
| US8168084B2 (en) * | 2009-12-18 | 2012-05-01 | Vanderbilt University | Polar nematic compounds |
| WO2011099572A1 (ja) * | 2010-02-12 | 2011-08-18 | 旭化成イーマテリアルズ株式会社 | フルオロアルカン誘導体、ゲル化剤及びゲル状組成物 |
| KR20120058901A (ko) * | 2010-11-30 | 2012-06-08 | 주식회사 동진쎄미켐 | 양쪽 메소제닉기의 유전율 이방성이 조절된 고속응답특성 발현 바이메소제닉 화합물 |
| JP6058644B2 (ja) * | 2011-06-01 | 2017-01-11 | 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Ｍｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体および液晶ディスプレイ |
| EP2568032B1 (en) * | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| JPWO2013114772A1 (ja) * | 2012-01-31 | 2015-05-11 | Dic株式会社 | 化合物の製造方法 |
| EP2811003B1 (en) | 2012-02-03 | 2016-08-10 | JNC Corporation | Liquid crystal compound, liquid crystal composition, and liquid crystal display device |
| TWI570221B (zh) * | 2012-03-19 | 2017-02-11 | Dainippon Ink & Chemicals | Nematic liquid crystal composition |
| KR101555596B1 (ko) | 2012-08-22 | 2015-09-24 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 |
| KR101590149B1 (ko) * | 2012-09-03 | 2016-02-01 | 디아이씨 가부시끼가이샤 | 네마틱 액정 조성물 |
| JP6419713B2 (ja) * | 2012-12-10 | 2018-11-07 | 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Ｍｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン媒体 |
| JP6471500B2 (ja) | 2012-12-17 | 2019-02-20 | Jnc株式会社 | オクタヒドロ−ビナフチル系キラル化合物を含有する液晶組成物および光素子 |
| JP6102423B2 (ja) * | 2013-03-29 | 2017-03-29 | Dic株式会社 | 重合性化合物及び光学素子 |
| JP5776864B1 (ja) | 2013-08-30 | 2015-09-09 | Dic株式会社 | ネマチック液晶組成物 |
| WO2016017615A1 (ja) | 2014-07-31 | 2016-02-04 | Dic株式会社 | ネマチック液晶組成物 |
| CN104513665A (zh) * | 2014-12-31 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | 一种含三联苯类化合物的液晶介质及其应用 |
| JP6578690B2 (ja) * | 2015-03-23 | 2019-09-25 | Jnc株式会社 | ハロゲン化されたアルキルを有する液晶化合物、液晶組成物および液晶表示素子 |
| KR20170000052A (ko) * | 2015-06-22 | 2017-01-02 | 삼성디스플레이 주식회사 | 화합물, 이를 포함하는 액정 조성물 및 이를 포함하는 액정 표시 장치 |
| DK3405047T3 (da) * | 2016-01-22 | 2020-03-09 | Tetra Laval Holdings & Finance | Fremgangsmåde og indretning til hydrolyse af modermælkserstatning |
| WO2019089638A1 (en) * | 2017-10-31 | 2019-05-09 | The Regents Of The University Of California | Organic ligands for templatable mesoscale nanocapsules |
| CN110655926B (zh) * | 2018-06-28 | 2023-06-13 | 江苏和成显示科技有限公司 | 液晶组合物及其液晶显示器件 |
| FR3090317B1 (fr) | 2018-12-19 | 2021-05-07 | Cvasthera | Utilisation d’un antagoniste de par-1 pour le traitement d’une maladie inflammatoire chronique intestinale |
| JP6863406B2 (ja) * | 2019-05-27 | 2021-04-21 | Jnc株式会社 | ハロゲン化されたアルキルを有する液晶化合物、液晶組成物および液晶表示素子 |
| KR20230114276A (ko) * | 2020-12-02 | 2023-08-01 | 메르크 파텐트 게엠베하 | 액정 화합물 |
| CN113897202A (zh) * | 2021-11-17 | 2022-01-07 | 浙江工业大学 | 一种二氟亚甲氧基类液晶化合物及其合成方法 |
| CN115960074A (zh) * | 2022-05-27 | 2023-04-14 | 华南理工大学 | 一类含杂原子六元脂环的含氟铁电液晶分子及其合成方法 |
| CN115627175B (zh) * | 2022-09-30 | 2024-12-27 | 南昌虚拟现实研究院股份有限公司 | 液晶组合物以及液晶光学元件 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5958290A (en) * | 1989-10-02 | 1999-09-28 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Electrooptical liquid crystal system |
| EP0452460B2 (de) * | 1989-10-02 | 1999-08-11 | MERCK PATENT GmbH | Elektrooptisches flüssigkristallsystem |
| JP3797435B2 (ja) * | 1994-11-17 | 2006-07-19 | 大日本インキ化学工業株式会社 | ５−置換アルコキシベンゼン誘導体 |
| JPH1087543A (ja) * | 1996-09-17 | 1998-04-07 | Chisso Corp | アルコキシベンゼン誘導体、液晶組成物および液晶表示素子 |
| DE60137810D1 (de) * | 2000-02-14 | 2009-04-16 | Merck Patent Gmbh | Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige |
| US8129002B2 (en) * | 2003-08-25 | 2012-03-06 | Merck Patent Gmbh | Compounds for use in liquid crystal media |
-
2004
- 2004-08-10 WO PCT/EP2004/008942 patent/WO2005019378A1/en not_active Ceased
- 2004-08-10 AT AT04763959T patent/ATE447001T1/de not_active IP Right Cessation
- 2004-08-10 JP JP2006524270A patent/JP2007503487A/ja active Pending
- 2004-08-10 KR KR1020067003696A patent/KR101198452B1/ko not_active Expired - Fee Related
- 2004-08-10 EP EP04763959A patent/EP1658351B1/en not_active Expired - Lifetime
- 2004-08-10 DE DE602004023857T patent/DE602004023857D1/de not_active Expired - Lifetime
- 2004-08-10 US US10/569,459 patent/US7531106B2/en not_active Expired - Fee Related
- 2004-08-26 TW TW093125623A patent/TWI387638B/zh not_active IP Right Cessation
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|---|---|
| US20060286308A1 (en) | 2006-12-21 |
| TW200526763A (en) | 2005-08-16 |
| KR20060119877A (ko) | 2006-11-24 |
| WO2005019378A1 (en) | 2005-03-03 |
| EP1658351B1 (en) | 2009-10-28 |
| ATE447001T1 (de) | 2009-11-15 |
| EP1658351A1 (en) | 2006-05-24 |
| KR101198452B1 (ko) | 2012-11-06 |
| DE602004023857D1 (de) | 2009-12-10 |
| US7531106B2 (en) | 2009-05-12 |
| JP2007503487A (ja) | 2007-02-22 |
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