JP2001522822A - フェナントレンのフッ素化誘導体、および液晶混合物におけるそれらの使用 - Google Patents
フェナントレンのフッ素化誘導体、および液晶混合物におけるそれらの使用Info
- Publication number
- JP2001522822A JP2001522822A JP2000520400A JP2000520400A JP2001522822A JP 2001522822 A JP2001522822 A JP 2001522822A JP 2000520400 A JP2000520400 A JP 2000520400A JP 2000520400 A JP2000520400 A JP 2000520400A JP 2001522822 A JP2001522822 A JP 2001522822A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- group
- crystal mixture
- formula
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 38
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- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- -1 cyclopropane -1 , 2-diyl Chemical group 0.000 claims description 25
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
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- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 150000001564 phenyl benzoates Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19748819.6 | 1997-11-05 | ||
| DE19748819A DE19748819A1 (de) | 1997-11-05 | 1997-11-05 | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
| PCT/EP1998/007080 WO1999024385A1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001522822A true JP2001522822A (ja) | 2001-11-20 |
| JP2001522822A5 JP2001522822A5 (enExample) | 2006-01-05 |
Family
ID=7847661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000520400A Pending JP2001522822A (ja) | 1997-11-05 | 1998-11-05 | フェナントレンのフッ素化誘導体、および液晶混合物におけるそれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6482478B1 (enExample) |
| EP (1) | EP1028935B1 (enExample) |
| JP (1) | JP2001522822A (enExample) |
| DE (2) | DE19748819A1 (enExample) |
| WO (1) | WO1999024385A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002020330A (ja) * | 2000-06-08 | 2002-01-23 | Merck Patent Gmbh | 水素添加したフェナントレンおよびその液晶混合物中での使用 |
| JP2005325113A (ja) * | 2004-05-07 | 2005-11-24 | Az Electronic Materials (Germany) Gmbh | フッ素化フェナントレンおよびそれらの液晶混合物における使用 |
| JP2008535958A (ja) * | 2005-03-24 | 2008-09-04 | 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 | 液晶媒体 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19825488A1 (de) * | 1998-06-08 | 1999-12-09 | Aventis Res & Tech Gmbh & Co | Monostabiles ferroelektrisches Aktivmatrix-Display |
| 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 |
| 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 |
| DE10002186B4 (de) | 2000-01-19 | 2018-01-18 | Merck Patent Gmbh | Disubstituierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| JP4826005B2 (ja) * | 2000-09-28 | 2011-11-30 | Ｄｉｃ株式会社 | 液晶性化合物の精製方法 |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
| DE10225048B4 (de) * | 2001-06-07 | 2015-03-12 | Merck Patent Gmbh | Fluorierte (Dihydro)phenanthrenderivate und deren Verwendung in flüssigkristallinen Medien |
| US6677479B2 (en) | 2001-11-13 | 2004-01-13 | Clariant Finance Lbvi Limited | Substituted fluoroaromatics, process for preparing them and their use |
| EP1645610A1 (de) * | 2004-10-11 | 2006-04-12 | Covion Organic Semiconductors GmbH | Phenanthren-Derivate |
| DE102005026651A1 (de) * | 2005-06-09 | 2006-12-14 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| TWI507511B (zh) | 2013-11-05 | 2015-11-11 | Ind Tech Res Inst | 負介電異方性液晶化合物、液晶顯示器、與光電裝置 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0853672A (ja) * | 1994-01-17 | 1996-02-27 | Hoechst Ag | フェナントレン誘導体、およびその強誘電性液晶混合物における使用 |
| JPH0931459A (ja) * | 1995-07-17 | 1997-02-04 | Hoechst Ag | 新規な強誘電性液晶組成物 |
| JPH10508890A (ja) * | 1994-11-16 | 1998-09-02 | サイテク・テクノロジー・コーポレーシヨン | １，３，５−トリアジンカルバメート含有水媒介組成物 |
| JPH10236992A (ja) * | 1997-02-25 | 1998-09-08 | Chisso Corp | 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0032362B1 (en) | 1980-01-10 | 1984-08-22 | Noel A. Clark | Chiral smectic liquid crystal electro-optical device and process of making the same |
| DE3920625A1 (de) | 1989-06-23 | 1991-01-03 | Hoechst Ag | Ferroelektrische fluessigkristallelemente mit hoher spontaner polarisation und geringer helixganghoehe |
| DE59009675D1 (de) | 1989-06-29 | 1995-10-26 | Hoffmann La Roche | Bistabile ferroelektrische Flüssigkristallanzeige. |
| DE4222565A1 (de) * | 1992-07-09 | 1994-01-13 | Hoechst Ag | Meta-substituierte Sechsringaromaten zur Verwendung in Flüssigkristallmischungen |
| DE19500768C2 (de) | 1994-01-17 | 2003-11-20 | Aventis Res & Tech Gmbh & Co | Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| DE4432970A1 (de) * | 1994-09-16 | 1996-03-21 | Hoechst Ag | Tetracyclische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| DE19653008A1 (de) * | 1996-12-19 | 1998-06-25 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
-
1997
- 1997-11-05 DE DE19748819A patent/DE19748819A1/de not_active Ceased
-
1998
- 1998-11-05 DE DE59812664T patent/DE59812664D1/de not_active Expired - Lifetime
- 1998-11-05 US US09/530,665 patent/US6482478B1/en not_active Expired - Lifetime
- 1998-11-05 EP EP98961141A patent/EP1028935B1/de not_active Expired - Lifetime
- 1998-11-05 JP JP2000520400A patent/JP2001522822A/ja active Pending
- 1998-11-05 WO PCT/EP1998/007080 patent/WO1999024385A1/de not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0853672A (ja) * | 1994-01-17 | 1996-02-27 | Hoechst Ag | フェナントレン誘導体、およびその強誘電性液晶混合物における使用 |
| JPH10508890A (ja) * | 1994-11-16 | 1998-09-02 | サイテク・テクノロジー・コーポレーシヨン | １，３，５−トリアジンカルバメート含有水媒介組成物 |
| JPH0931459A (ja) * | 1995-07-17 | 1997-02-04 | Hoechst Ag | 新規な強誘電性液晶組成物 |
| JPH10236992A (ja) * | 1997-02-25 | 1998-09-08 | Chisso Corp | 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 |
Non-Patent Citations (1)
| Title |
|---|
| TETRAHEDRON LETTERS, vol. 34, no. 2, JPN6008064040, 1993, pages 281 - 284, ISSN: 0001206920 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002020330A (ja) * | 2000-06-08 | 2002-01-23 | Merck Patent Gmbh | 水素添加したフェナントレンおよびその液晶混合物中での使用 |
| JP2005325113A (ja) * | 2004-05-07 | 2005-11-24 | Az Electronic Materials (Germany) Gmbh | フッ素化フェナントレンおよびそれらの液晶混合物における使用 |
| JP2008535958A (ja) * | 2005-03-24 | 2008-09-04 | 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 | 液晶媒体 |
| JP2012184425A (ja) * | 2005-03-24 | 2012-09-27 | Merck Patent Gmbh | 液晶媒体 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999024385A1 (de) | 1999-05-20 |
| US6482478B1 (en) | 2002-11-19 |
| EP1028935A1 (de) | 2000-08-23 |
| EP1028935B1 (de) | 2005-03-16 |
| DE19748819A1 (de) | 1999-05-06 |
| DE59812664D1 (de) | 2005-04-21 |
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Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100713 |