FR2519337A1 - Compose organique du type benzoate de biphenyle triplement substitue, son procede de fabrication et son utilisation comme dopant pour cristal liquide smectique - Google Patents
Compose organique du type benzoate de biphenyle triplement substitue, son procede de fabrication et son utilisation comme dopant pour cristal liquide smectique Download PDFInfo
- Publication number
- FR2519337A1 FR2519337A1 FR8124563A FR8124563A FR2519337A1 FR 2519337 A1 FR2519337 A1 FR 2519337A1 FR 8124563 A FR8124563 A FR 8124563A FR 8124563 A FR8124563 A FR 8124563A FR 2519337 A1 FR2519337 A1 FR 2519337A1
- Authority
- FR
- France
- Prior art keywords
- organic compound
- dopant
- liquid crystal
- compound according
- acid
- 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.)
- Granted
Links
- 239000002019 doping agent Substances 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 8
- 239000004973 liquid crystal related substance Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 BIPHENYL BENZOATE ORGANIC COMPOUND Chemical class 0.000 title 1
- 239000004990 Smectic liquid crystal Substances 0.000 claims abstract description 22
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000012800 visualization Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- OLPCSEIDQQDELO-UHFFFAOYSA-N (2-phenylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1C1=CC=CC=C1 OLPCSEIDQQDELO-UHFFFAOYSA-N 0.000 claims 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 claims 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical group CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RNVFYQUEEMZKLR-UHFFFAOYSA-N methyl 3,5-dihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(O)=C1 RNVFYQUEEMZKLR-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 2
- 238000010587 phase diagram Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- SFIUECPMHKPESB-UHFFFAOYSA-N 1-octyl-4-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCCCCC)(C#N)CC=C1C1=CC=CC=C1 SFIUECPMHKPESB-UHFFFAOYSA-N 0.000 description 1
- ZRMIETZFPZGBEB-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzonitrile Chemical group C1=CC(O)=CC=C1C1=CC=C(C#N)C=C1 ZRMIETZFPZGBEB-UHFFFAOYSA-N 0.000 description 1
- CSQPODPWWMOTIY-UHFFFAOYSA-N 4-(4-octylphenyl)benzonitrile Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 CSQPODPWWMOTIY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8124563A FR2519337A1 (fr) | 1981-12-31 | 1981-12-31 | Compose organique du type benzoate de biphenyle triplement substitue, son procede de fabrication et son utilisation comme dopant pour cristal liquide smectique |
| US06/424,616 US4474679A (en) | 1981-12-31 | 1982-09-27 | Diphenyl benzoates and its use as a dopant for smectic liquid crystals |
| DE8282402345T DE3263794D1 (en) | 1981-12-31 | 1982-12-21 | Organic compound of the triple substituted biphenylyl benzoate type and process for its preparation |
| EP82402345A EP0083886B1 (fr) | 1981-12-31 | 1982-12-21 | Composé organique du type benzoate de biphényle triplement substitué et son procédé de fabrication |
| JP57234972A JPS58118544A (ja) | 1981-12-31 | 1982-12-28 | 三置換ジフエニル安息香酸塩型の有機化合物、該化合物の製造方法ならびにスメクチツク液晶用ド−パントとしての該化合物の使用 |
| KR1019820005889A KR840002767A (ko) | 1981-12-31 | 1982-12-30 | 디페닐 벤조산염의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8124563A FR2519337A1 (fr) | 1981-12-31 | 1981-12-31 | Compose organique du type benzoate de biphenyle triplement substitue, son procede de fabrication et son utilisation comme dopant pour cristal liquide smectique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2519337A1 true FR2519337A1 (fr) | 1983-07-08 |
| FR2519337B1 FR2519337B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-06 |
Family
ID=9265563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8124563A Granted FR2519337A1 (fr) | 1981-12-31 | 1981-12-31 | Compose organique du type benzoate de biphenyle triplement substitue, son procede de fabrication et son utilisation comme dopant pour cristal liquide smectique |
Country Status (6)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670581A (en) * | 1983-01-27 | 1987-06-02 | Sugai Chemical Industry Co., Ltd. | Biphenyl compounds and process for producing the same |
| WO1986002926A1 (en) * | 1984-11-14 | 1986-05-22 | Nauchno-Issledovatelsky Institut Prikladnykh Fizic | LIQUID CRYSTAL 4-(4'-CYANODIPHENYL) ETHERS OF TRANS-4''-n-ALKYLCYCLOHEX-2-ENCARBOXYLIC ACIDS AND LIQUID CRYSTAL COMPOSITION FOR ELECTROOPTICAL INFORMATION PRESENTING DEVICES BASED ON THESE COMPOUNDS |
| KR101138865B1 (ko) * | 2005-03-09 | 2012-05-14 | 삼성전자주식회사 | 나노 와이어 및 그 제조 방법 |
| KR101057546B1 (ko) * | 2007-06-05 | 2011-08-17 | 주식회사 엘지화학 | 광학 이방성 화합물 및 이를 포함하는 수지 조성물 |
| GB0823013D0 (en) | 2008-12-18 | 2009-01-28 | Cambridge Entpr Ltd | Wide temperature-range smectic liquid crystall materials |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2179180A1 (en) * | 1972-04-05 | 1973-11-16 | Matsushita Electric Ind Co Ltd | Liquid crystal compsn - contg added carboxylic acid/ester for spontaneous perpendicular orientation |
| FR2297201A1 (fr) * | 1975-01-10 | 1976-08-06 | Thomson Csf | Produits mesogenes pour cellules a cristal liquide, et procede de fabrication desdits produits |
| US4029594A (en) * | 1976-06-17 | 1977-06-14 | Rca Corporation | Novel liquid crystal compounds and electro-optic devices incorporating them |
| EP0011002A1 (fr) * | 1978-10-27 | 1980-05-14 | Thomson-Csf | Composé organique mésomorphe dont la formule chimique dérive d'un acide alkoxy-4 tétrafluorobenzoique, et dispositif à cristal liquide utilisant un tel composé |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235736A (en) * | 1977-02-11 | 1980-11-25 | Thomson-Csf | Diphenylic esters exhibiting mesomorphic phases |
-
1981
- 1981-12-31 FR FR8124563A patent/FR2519337A1/fr active Granted
-
1982
- 1982-09-27 US US06/424,616 patent/US4474679A/en not_active Expired - Fee Related
- 1982-12-21 DE DE8282402345T patent/DE3263794D1/de not_active Expired
- 1982-12-21 EP EP82402345A patent/EP0083886B1/fr not_active Expired
- 1982-12-28 JP JP57234972A patent/JPS58118544A/ja active Pending
- 1982-12-30 KR KR1019820005889A patent/KR840002767A/ko not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2179180A1 (en) * | 1972-04-05 | 1973-11-16 | Matsushita Electric Ind Co Ltd | Liquid crystal compsn - contg added carboxylic acid/ester for spontaneous perpendicular orientation |
| FR2297201A1 (fr) * | 1975-01-10 | 1976-08-06 | Thomson Csf | Produits mesogenes pour cellules a cristal liquide, et procede de fabrication desdits produits |
| US4029594A (en) * | 1976-06-17 | 1977-06-14 | Rca Corporation | Novel liquid crystal compounds and electro-optic devices incorporating them |
| EP0011002A1 (fr) * | 1978-10-27 | 1980-05-14 | Thomson-Csf | Composé organique mésomorphe dont la formule chimique dérive d'un acide alkoxy-4 tétrafluorobenzoique, et dispositif à cristal liquide utilisant un tel composé |
Also Published As
| Publication number | Publication date |
|---|---|
| US4474679A (en) | 1984-10-02 |
| FR2519337B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-06 |
| JPS58118544A (ja) | 1983-07-14 |
| EP0083886B1 (fr) | 1985-05-22 |
| DE3263794D1 (en) | 1985-06-27 |
| KR840002767A (ko) | 1984-07-16 |
| EP0083886A1 (fr) | 1983-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |