TWI338034B - Benzochromene derivatives - Google Patents
Benzochromene derivatives Download PDFInfo
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- TWI338034B TWI338034B TW093104656A TW93104656A TWI338034B TW I338034 B TWI338034 B TW I338034B TW 093104656 A TW093104656 A TW 093104656A TW 93104656 A TW93104656 A TW 93104656A TW I338034 B TWI338034 B TW I338034B
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- VCDAWCBLCCVSKE-UHFFFAOYSA-N 2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=CCO2 VCDAWCBLCCVSKE-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 128
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 74
- 239000004973 liquid crystal related substance Substances 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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 1
- 201000010099 disease Diseases 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 250
- -1 cyclic lactone Chemical class 0.000 description 76
- 239000000203 mixture Substances 0.000 description 60
- 238000000819 phase cycle Methods 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000013213 extrapolation Methods 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 229910052740 iodine Inorganic materials 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 10
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- 239000012043 crude product Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002309 gasification Methods 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
- 150000002596 lactones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LUCHFKBTWHPREI-UHFFFAOYSA-N 1-(4-propylcyclohexyl)-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical compound C1CC(CCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C2CCC(CCC)CC2)C=C1 LUCHFKBTWHPREI-UHFFFAOYSA-N 0.000 description 2
- OXBRRUNAAVNTOZ-UHFFFAOYSA-N 1-ethoxy-4-(4-propylcyclohexyl)benzene Chemical compound C1CC(CCC)CCC1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-UHFFFAOYSA-N 0.000 description 2
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 2
- DNZASWNTGKYDSP-UHFFFAOYSA-N 4-(4-butylcyclohexyl)-1-heptylcyclohexane-1-carbonitrile Chemical compound C1CC(CCCCCCC)(C#N)CCC1C1CCC(CCCC)CC1 DNZASWNTGKYDSP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- BEUDCHGZCTUAOG-UHFFFAOYSA-N 6h-benzo[c]chromene Chemical compound C1=CC=C2COC3=CC=CC=C3C2=C1 BEUDCHGZCTUAOG-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000006411 Negishi coupling reaction Methods 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
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- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
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- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
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- TVDGCJHEEOTNED-UHFFFAOYSA-N (6-bromo-2-fluoro-3-phenylmethoxyphenyl) 6-bromo-3-ethoxy-2-fluorobenzoate Chemical compound CCOC1=CC=C(Br)C(C(=O)OC=2C(=C(OCC=3C=CC=CC=3)C=CC=2Br)F)=C1F TVDGCJHEEOTNED-UHFFFAOYSA-N 0.000 description 1
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- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
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- ZMTIHOQUIPYSQK-UHFFFAOYSA-N 4-bromo-1-ethoxy-2-fluorobenzene Chemical compound CCOC1=CC=C(Br)C=C1F ZMTIHOQUIPYSQK-UHFFFAOYSA-N 0.000 description 1
- KWDPNPVCQGEUKZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(4-pentylcyclohexen-1-yl)benzene Chemical compound C1C(CCCCC)CCC(C=2C(=CC(Br)=CC=2)F)=C1 KWDPNPVCQGEUKZ-UHFFFAOYSA-N 0.000 description 1
- YZFVUQSAJMLFOZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(Br)C=C1F YZFVUQSAJMLFOZ-UHFFFAOYSA-N 0.000 description 1
- KXFJNXXTTNGXTQ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C=C1F KXFJNXXTTNGXTQ-UHFFFAOYSA-N 0.000 description 1
- HTRNHWBOBYFTQF-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylbenzene Chemical group FC1=CC(Br)=CC=C1C1=CC=CC=C1 HTRNHWBOBYFTQF-UHFFFAOYSA-N 0.000 description 1
- IIPFNVDIFYPRQW-UHFFFAOYSA-N 4-bromo-2-fluoro-1H-indole Chemical compound BrC1=C2C=C(NC2=CC=C1)F IIPFNVDIFYPRQW-UHFFFAOYSA-N 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- C09K19/34—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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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)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10308266 | 2003-02-25 |
Publications (2)
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|---|---|
| TW200418958A TW200418958A (en) | 2004-10-01 |
| TWI338034B true TWI338034B (en) | 2011-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093104656A TWI338034B (en) | 2003-02-25 | 2004-02-24 | Benzochromene derivatives |
Country Status (7)
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| US (1) | US7326447B2 (https=) |
| EP (1) | EP1618101B1 (https=) |
| JP (1) | JP4860464B2 (https=) |
| KR (1) | KR101133905B1 (https=) |
| DE (1) | DE102004004228A1 (https=) |
| TW (1) | TWI338034B (https=) |
| WO (1) | WO2004076438A2 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4403307B2 (ja) * | 2003-03-28 | 2010-01-27 | Ｄｉｃ株式会社 | ６員環ラクトン骨格を有する化合物を含有する液晶組成物 |
| DE10337346A1 (de) * | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
| CN1989225B (zh) | 2004-07-02 | 2012-07-11 | 默克专利股份有限公司 | 液晶介质和包含该液晶介质的电光学显示器 |
| JP5015774B2 (ja) * | 2004-07-29 | 2012-08-29 | 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 | ジフルオロ置換複素環化合物および液晶媒体における構成要素としてのその使用 |
| JP2008522958A (ja) * | 2004-10-07 | 2008-07-03 | 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 ハフトング | クロマン誘導体類、それらの調製方法、およびそれらの使用 |
| USRE46558E1 (en) | 2005-04-28 | 2017-09-26 | Paloma Pharmaceuticals, Inc. | Compositions and methods to treat diseases characterized by cellular proliferation and angiogenesis |
| EP1958945B1 (en) * | 2005-12-08 | 2014-11-12 | JNC Corporation | Compound having hydrocoumarin skeleton, liquid crystal composition and liquid crystal display element |
| WO2007079840A2 (de) * | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Benzochromenderivate |
| DE102005062098A1 (de) | 2005-12-22 | 2007-06-28 | Merck Patent Gmbh | Oxaphenanthren-Derivate |
| DE102006057027B4 (de) | 2005-12-22 | 2023-07-06 | Merck Patent Gmbh | Benzochromenderivate |
| US7998541B2 (en) * | 2005-12-22 | 2011-08-16 | Merck Patent Gmbh | Benzochromene derivatives for use in liquid crystal media and as therapeutic active substances |
| BRPI0708318A2 (pt) * | 2006-02-28 | 2011-05-24 | Paloma Pharmaceuticals, Inc. | composições e uso de compostos para tratar doenças caracterizadas por proliferação celular e angiogênese |
| US8303844B2 (en) * | 2007-11-27 | 2012-11-06 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Benzo[f]chrome any pyrano[3,2-f]chrome derivatives for use in liquid crystal media |
| US20110021618A1 (en) * | 2008-03-25 | 2011-01-27 | Paloma Pharmaceuticals, Inc. | Methods of treating fibrotic disorders |
| DE102009022309A1 (de) | 2009-05-22 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| EP2669263B1 (en) | 2010-12-21 | 2017-11-22 | JNC Corporation | Compound containing dihydrophenanthrene, liquid crystal composition and liquid crystal display device |
| WO2012112791A1 (en) | 2011-02-16 | 2012-08-23 | Paloma Pharmaceuticals, Inc. | Radiation countermeasure agents |
| EP2514800B2 (de) * | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| JP5983393B2 (ja) | 2012-01-27 | 2016-08-31 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| TWI452122B (zh) | 2012-02-24 | 2014-09-11 | Dainippon Ink & Chemicals | 液晶組成物 |
| CN104610217A (zh) * | 2015-02-09 | 2015-05-13 | 石家庄诚志永华显示材料有限公司 | 含有环戊基的二苯并吡喃酮衍生物的液晶化合物及其应用 |
| CN105647543A (zh) * | 2016-01-13 | 2016-06-08 | 石家庄诚志永华显示材料有限公司 | 液晶组合物 |
| JP6738044B2 (ja) | 2016-07-22 | 2020-08-12 | Jnc株式会社 | ベンゾピラン骨格を有する液晶性化合物、液晶組成物、および液晶表示素子 |
| CN107253942B (zh) * | 2017-06-19 | 2019-07-12 | 清华大学 | 侧向二氟亚甲基醚桥键双末端烷基环己基联苯衍生物及其制备方法与应用 |
| CN108018048B (zh) * | 2017-12-15 | 2021-11-05 | 石家庄诚志永华显示材料有限公司 | 一种负介电各项异性液晶组合物 |
| CN111484475B (zh) * | 2019-01-28 | 2022-11-04 | 北京八亿时空液晶科技股份有限公司 | 一种液晶化合物及其制备方法与应用 |
| CA3206062A1 (en) * | 2021-01-27 | 2022-08-04 | Said Oumouch | Urolithin derivatives and methods of use thereof |
| CN116179214B (zh) * | 2021-11-29 | 2025-04-25 | 石家庄诚志永华显示材料有限公司 | 一种含有苯并色烯化合物的液晶组合物及其应用 |
| WO2024119140A1 (en) | 2022-12-01 | 2024-06-06 | Massachusetts Institute Of Technology | Cleavable comonomer strategy for accelerating removal of gel nail polish |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR95364E (fr) * | 1967-08-11 | 1970-09-11 | Ugine Kuhlmann | Nouveaux colorants méthiniques et leurs procédés de préparation. |
| US5648021A (en) * | 1994-01-17 | 1997-07-15 | Hoechst Aktiengesellschaft | Phenanthrene derivatives and their use in liquid-crystalline mixtures |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| JP4048570B2 (ja) * | 1997-02-25 | 2008-02-20 | チッソ株式会社 | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| JP4449105B2 (ja) * | 1999-07-12 | 2010-04-14 | チッソ株式会社 | ジベンゾピラン−６−オン誘導体およびそれを含む液晶組成物 |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
-
2004
- 2004-01-28 EP EP04705793.0A patent/EP1618101B1/de not_active Expired - Lifetime
- 2004-01-28 JP JP2006501636A patent/JP4860464B2/ja not_active Expired - Fee Related
- 2004-01-28 KR KR1020057015682A patent/KR101133905B1/ko not_active Expired - Fee Related
- 2004-01-28 DE DE200410004228 patent/DE102004004228A1/de not_active Withdrawn
- 2004-01-28 WO PCT/EP2004/000731 patent/WO2004076438A2/de not_active Ceased
- 2004-01-28 US US10/546,801 patent/US7326447B2/en not_active Expired - Lifetime
- 2004-02-24 TW TW093104656A patent/TWI338034B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004004228A1 (de) | 2004-09-02 |
| JP2006520327A (ja) | 2006-09-07 |
| WO2004076438A3 (de) | 2005-02-24 |
| WO2004076438A2 (de) | 2004-09-10 |
| TW200418958A (en) | 2004-10-01 |
| EP1618101B1 (de) | 2017-12-20 |
| US20060177603A1 (en) | 2006-08-10 |
| KR20050115872A (ko) | 2005-12-08 |
| US7326447B2 (en) | 2008-02-05 |
| JP4860464B2 (ja) | 2012-01-25 |
| EP1618101A2 (de) | 2006-01-25 |
| KR101133905B1 (ko) | 2012-04-10 |
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