JPH0533943B2 - - Google Patents
Info
- Publication number
- JPH0533943B2 JPH0533943B2 JP28773086A JP28773086A JPH0533943B2 JP H0533943 B2 JPH0533943 B2 JP H0533943B2 JP 28773086 A JP28773086 A JP 28773086A JP 28773086 A JP28773086 A JP 28773086A JP H0533943 B2 JPH0533943 B2 JP H0533943B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- group
- acid
- benzene
- 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.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000013329 compounding Methods 0.000 claims description 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 23
- 230000003287 optical effect Effects 0.000 description 19
- -1 Sm3: SmA Substances 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
- 230000010287 polarization Effects 0.000 description 9
- 230000002269 spontaneous effect Effects 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 7
- 238000004566 IR spectroscopy Methods 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- PXUHUAWWMDRECM-UHFFFAOYSA-N 2-fluorooctan-1-ol Chemical compound CCCCCCC(F)CO PXUHUAWWMDRECM-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- AZNXVEGNSSSWHX-UHFFFAOYSA-N 2-fluorooctyl 5-octoxy-2-phenylbenzoate Chemical compound CCCCCCC(F)COC(=O)C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1 AZNXVEGNSSSWHX-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YFCQBVBHKCQDON-UHFFFAOYSA-N FC(COCC(CCCCCCCC)F)CCCCCCCC Chemical compound FC(COCC(CCCCCCCC)F)CCCCCCCC YFCQBVBHKCQDON-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SJZQQJOIMGMRKP-UHFFFAOYSA-N 2-fluorodecan-1-ol Chemical compound CCCCCCCCC(F)CO SJZQQJOIMGMRKP-UHFFFAOYSA-N 0.000 description 2
- UEBHTEIKXIPNGN-UHFFFAOYSA-N 2-fluoroheptan-1-ol Chemical compound CCCCCC(F)CO UEBHTEIKXIPNGN-UHFFFAOYSA-N 0.000 description 2
- JVFMBLCEZICHGT-UHFFFAOYSA-N 2-fluorooctyl 4-acetyloxybenzoate Chemical compound CCCCCCC(F)COC(=O)C1=CC=C(OC(C)=O)C=C1 JVFMBLCEZICHGT-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IALWCYFULVHLEC-UHFFFAOYSA-N 4-(octyloxy)benzoic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=C1 IALWCYFULVHLEC-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- OXMNXNYRYIMGCP-UHFFFAOYSA-N 2-[4-(2-fluoroheptoxy)phenyl]-5-octylpyrimidine Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(OCC(F)CCCCC)C=C1 OXMNXNYRYIMGCP-UHFFFAOYSA-N 0.000 description 1
- BGSOIHDNGJTTCV-UHFFFAOYSA-N 2-fluorooctyl 4-hydroxybenzoate Chemical compound CCCCCCC(F)COC(=O)C1=CC=C(O)C=C1 BGSOIHDNGJTTCV-UHFFFAOYSA-N 0.000 description 1
- JTFWIFQALWOEGT-UHFFFAOYSA-N 4-(2-methylbutyl)benzoyl chloride Chemical compound CCC(C)CC1=CC=C(C(Cl)=O)C=C1 JTFWIFQALWOEGT-UHFFFAOYSA-N 0.000 description 1
- QKHJFAHFTKYIEP-UHFFFAOYSA-N 4-(5-octylpyrimidin-2-yl)phenol Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(O)C=C1 QKHJFAHFTKYIEP-UHFFFAOYSA-N 0.000 description 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 1
- FMRRBUROSXDNJP-UHFFFAOYSA-N 5-hydroxy-2-phenylbenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1C1=CC=CC=C1 FMRRBUROSXDNJP-UHFFFAOYSA-N 0.000 description 1
- IEKOCLQHTNIIGH-UHFFFAOYSA-N 5-octoxy-2-phenylbenzoic acid Chemical compound OC(=O)C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1 IEKOCLQHTNIIGH-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003862 amino acid derivatives Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N methyl propyl carbinol Natural products CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/022,928 US4867903A (en) | 1986-03-10 | 1987-03-06 | Fluoroalkane derivative |
| CA000531404A CA1341038C (en) | 1986-03-10 | 1987-03-06 | Fluoroalkaned derivative |
| DE3789151T DE3789151T2 (de) | 1986-03-10 | 1987-03-09 | Fluoralkanderivat und Flüssigkristallmischung. |
| EP87103332A EP0237007B1 (de) | 1986-03-10 | 1987-03-09 | Fluoralkanderivat und Flüssigkristallmischung |
| ES87103332T ES2051699T3 (es) | 1986-03-10 | 1987-03-09 | Derivado fluoroalcano y composicion de cristal liquido. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5058386 | 1986-03-10 | ||
| JP61-50583 | 1986-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6322042A JPS6322042A (ja) | 1988-01-29 |
| JPH0533943B2 true JPH0533943B2 (de) | 1993-05-20 |
Family
ID=12862999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28773086A Granted JPS6322042A (ja) | 1986-03-10 | 1986-12-04 | フルオロアルカン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6322042A (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2538578B2 (ja) * | 1987-02-02 | 1996-09-25 | チッソ株式会社 | ２−置換アルキルエ−テル類および液晶組成物 |
| US6146547A (en) * | 1987-02-02 | 2000-11-14 | Chisso Corporation | 2-substituted-alkyl ether and liquid crystal composition |
| JPH0624683B2 (ja) * | 1987-03-10 | 1994-04-06 | 株式会社菊川鉄工所 | ワイドベルトサンダ |
| EP0289270B1 (de) * | 1987-04-27 | 1994-12-14 | Chisso Corporation | Optisch aktive 2-Biphenylpyrimidinderivate und diese enthaltende Flüssigkristallmischungen |
| US4917821A (en) * | 1987-11-09 | 1990-04-17 | Canon Kabushiki Kaisha | Optically active mesomorphic compound and liquid crystal composition containing same |
| JP2566807B2 (ja) * | 1987-11-11 | 1996-12-25 | キヤノン株式会社 | 光学活性物質、その製造方法およびそれを含む液晶組成物 |
| JP2610467B2 (ja) * | 1987-11-12 | 1997-05-14 | キヤノン株式会社 | 液晶性化合物、それを含有する液晶組成物およびそれを使用した液晶素子 |
| JP2627918B2 (ja) * | 1988-03-28 | 1997-07-09 | チッソ株式会社 | フルオロアルコキシジフェニルピリミジン、液晶組成物および電気光学素子 |
| JPH0289020A (ja) * | 1988-09-26 | 1990-03-29 | Semiconductor Energy Lab Co Ltd | 強誘電性液晶素子 |
| JP2547857B2 (ja) * | 1989-04-10 | 1996-10-23 | シャープ株式会社 | 強誘電性液晶組成物 |
| US5250219A (en) * | 1989-05-08 | 1993-10-05 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same |
| US5413735A (en) * | 1990-05-24 | 1995-05-09 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the liquid crystal composition, and display method and apparatus using the liquid crystal composition and device |
| JP2984322B2 (ja) * | 1990-06-06 | 1999-11-29 | キヤノン株式会社 | 液晶組成物およびこれを含む液晶素子 |
| JP2941971B2 (ja) * | 1991-02-13 | 1999-08-30 | キヤノン株式会社 | 液晶組成物、それを有する液晶素子、それ等を用いた表示方法及び表示装置 |
| JP3005063B2 (ja) * | 1991-02-20 | 2000-01-31 | キヤノン株式会社 | 液晶組成物、それを有する液晶素子、それ等を用いた表示方法及び表示装置 |
| EP0640676B1 (de) * | 1993-08-31 | 1999-01-20 | Canon Kabushiki Kaisha | Mesomorphe Verbindung, eine diese enthaltene Flüssigkristallzusammensetzung, eine diese Zusammensetzung verwendende Flüssigkristallvorrichtung, Flüssigkristallapparat und Anzeigeverfahren |
| DE69521458T2 (de) * | 1994-07-26 | 2001-11-08 | Canon Kk | Flüssigkristallzusammensetzung, -vorrichtung, -apparat und Anzeigeverfahren, die sie verwenden |
| EP0768360B1 (de) * | 1995-10-12 | 2002-01-09 | Canon Kabushiki Kaisha | Flüssigkristallzusammensetzung, Flüssigkristallvorrichtung und Flüssigkristallanzeigeapparat |
-
1986
- 1986-12-04 JP JP28773086A patent/JPS6322042A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6322042A (ja) | 1988-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |