TW572997B - Hydrogenated phenanthrenes and their use in liquid-crystal mixtures - Google Patents
Hydrogenated phenanthrenes and their use in liquid-crystal mixtures Download PDFInfo
- Publication number
- TW572997B TW572997B TW90113497A TW90113497A TW572997B TW 572997 B TW572997 B TW 572997B TW 90113497 A TW90113497 A TW 90113497A TW 90113497 A TW90113497 A TW 90113497A TW 572997 B TW572997 B TW 572997B
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- patent application
- liquid crystal
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- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 20
- 150000002987 phenanthrenes Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
- 230000002079 cooperative effect Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 230000003098 cholesteric effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- -1 acryl Chemical group 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- SWRNHMXIOFDOLQ-UHFFFAOYSA-N 1-(2-bromoethyl)-2,3-difluorobenzene Chemical compound FC1=CC=CC(CCBr)=C1F SWRNHMXIOFDOLQ-UHFFFAOYSA-N 0.000 description 1
- FQGDFWIQBCQXPS-UHFFFAOYSA-N 1-(2-bromoethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCBr FQGDFWIQBCQXPS-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- AAYWIXGLVAEPTP-UHFFFAOYSA-N 2,3-dimethylbutan-2-ylboron Chemical compound [B]C(C)(C)C(C)C AAYWIXGLVAEPTP-UHFFFAOYSA-N 0.000 description 1
- YPWLZGITFNGGKW-UHFFFAOYSA-N 2-phenanthrol Chemical class C1=CC=C2C3=CC=C(O)C=C3C=CC2=C1 YPWLZGITFNGGKW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OAVNBVAYHQPKDH-UHFFFAOYSA-N 6,8-difluoro-4-prop-2-enyl-1,2-dihydronaphthalene Chemical compound C1CC=C(CC=C)C2=CC(F)=CC(F)=C21 OAVNBVAYHQPKDH-UHFFFAOYSA-N 0.000 description 1
- KVWCIBGTMQQCFX-UHFFFAOYSA-N BC(C)(C)C(C)C.BC(C)(C)C(C)C Chemical compound BC(C)(C)C(C)C.BC(C)(C)C(C)C KVWCIBGTMQQCFX-UHFFFAOYSA-N 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
-
- 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
-
- 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
- C09K2323/04—Charge transferring layer characterised by chemical composition, i.e. conductive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10028451 | 2000-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW572997B true TW572997B (en) | 2004-01-21 |
Family
ID=7645160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW90113497A TW572997B (en) | 2000-06-08 | 2001-06-04 | Hydrogenated phenanthrenes and their use in liquid-crystal mixtures |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6515163B2 (enExample) |
| EP (1) | EP1162185B1 (enExample) |
| JP (1) | JP4841755B2 (enExample) |
| KR (1) | KR20010111019A (enExample) |
| AT (1) | ATE251100T1 (enExample) |
| DE (2) | DE10123088A1 (enExample) |
| TW (1) | TW572997B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI418549B (zh) * | 2006-01-28 | 2013-12-11 | Merck Patent Gmbh | 三環芳香族化合物及液晶介質 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10341154B4 (de) * | 2003-09-06 | 2012-05-16 | Nematel Gmbh & Co. Kg | Tricyclische Fluorverbindungen, flüssigkristallines Medium sowie dessen Verwendung |
| US7998541B2 (en) | 2005-12-22 | 2011-08-16 | Merck Patent Gmbh | Benzochromene derivatives for use in liquid crystal media and as therapeutic active substances |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0365962B1 (de) * | 1988-10-20 | 1994-09-21 | MERCK PATENT GmbH | Matrix-Flüssigkristallanzeige |
| DE19748819A1 (de) * | 1997-11-05 | 1999-05-06 | Hoechst Ag | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
| JP5050293B2 (ja) * | 1999-08-03 | 2012-10-17 | Ｄｉｃ株式会社 | 縮合環化合物 |
| JP4586246B2 (ja) * | 1999-08-03 | 2010-11-24 | Ｄｉｃ株式会社 | ヒドロフェナントレン誘導体 |
| JP4644888B2 (ja) * | 1999-08-03 | 2011-03-09 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
| US7067179B1 (en) * | 1999-08-03 | 2006-06-27 | Dainippon Ink And Chemicals, Inc. | Fused ring compound |
| JP4605412B2 (ja) * | 1999-08-27 | 2011-01-05 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
-
2001
- 2001-05-12 DE DE10123088A patent/DE10123088A1/de not_active Withdrawn
- 2001-05-30 AT AT01113142T patent/ATE251100T1/de not_active IP Right Cessation
- 2001-05-30 EP EP01113142A patent/EP1162185B1/de not_active Expired - Lifetime
- 2001-05-30 DE DE50100697T patent/DE50100697D1/de not_active Expired - Lifetime
- 2001-06-04 TW TW90113497A patent/TW572997B/zh active
- 2001-06-07 KR KR1020010031719A patent/KR20010111019A/ko not_active Withdrawn
- 2001-06-08 US US09/876,222 patent/US6515163B2/en not_active Expired - Lifetime
- 2001-06-08 JP JP2001173627A patent/JP4841755B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI418549B (zh) * | 2006-01-28 | 2013-12-11 | Merck Patent Gmbh | 三環芳香族化合物及液晶介質 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20020049348A1 (en) | 2002-04-25 |
| JP2002020330A (ja) | 2002-01-23 |
| DE50100697D1 (de) | 2003-11-06 |
| EP1162185A1 (de) | 2001-12-12 |
| US6515163B2 (en) | 2003-02-04 |
| JP4841755B2 (ja) | 2011-12-21 |
| KR20010111019A (ko) | 2001-12-15 |
| DE10123088A1 (de) | 2001-12-13 |
| ATE251100T1 (de) | 2003-10-15 |
| EP1162185B1 (de) | 2003-10-01 |
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