CA1259628A - Composes nematiques renfermant des groupes cyclohexyle - Google Patents

Composes nematiques renfermant des groupes cyclohexyle

Info

Publication number: CA1259628A
Authority: CA; Canada
Prior art keywords: trans; dielectric; formula; compound; cyano
Prior art date: 1983-08-04
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

Application number

CA000460292A

Other languages

English (en)

Inventor

Stephen M. Kelly

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date 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 date listed.)

1983-08-04

Filing date

1984-08-02

Publication date

1989-09-19

1984-03-23 Priority claimed from DE19843410734 external-priority patent/DE3410734A1/de

1984-08-02 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

1989-09-19 Application granted granted Critical

1989-09-19 Publication of CA1259628A publication Critical patent/CA1259628A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 69
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title description 2
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
239000011737 fluorine Substances 0.000 claims abstract description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
239000000460 chlorine Chemical group 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
239000007788 liquid Substances 0.000 claims description 9
230000006872 improvement Effects 0.000 claims 2
239000000203 mixture Substances 0.000 abstract description 27
239000004973 liquid crystal related substance Substances 0.000 abstract description 13
-1 CYCLOHEXYL Chemical group 0.000 abstract description 9
229940060037 fluorine Drugs 0.000 abstract 2
235000019000 fluorine Nutrition 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
229940076134 benzene Drugs 0.000 description 11
239000012071 phase Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000012043 crude product Substances 0.000 description 4
229940102396 methyl bromide Drugs 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000003989 dielectric material Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
JOLGXBQYTARJLD-UHFFFAOYSA-N 1-ethyl-4-[4-(4-pentylcyclohexyl)phenyl]benzene Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(CC)=CC=2)C=C1 JOLGXBQYTARJLD-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
OXBRRUNAAVNTOZ-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-SHTZXODSSA-N 0.000 description 2
BPVJENLMEMWFBW-QAQDUYKDSA-N CCCCOc1ccc(cc1)[C@H]1CC[C@H](CCC)CC1 Chemical compound CCCCOc1ccc(cc1)[C@H]1CC[C@H](CCC)CC1 BPVJENLMEMWFBW-QAQDUYKDSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000008569 process Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
UISXVYOLBGBYCV-UHFFFAOYSA-N (4-pentylphenyl) 4-methoxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C1=CC=C(OC)C=C1 UISXVYOLBGBYCV-UHFFFAOYSA-N 0.000 description 1
125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
ANXOZOZWHNFHPZ-UHFFFAOYSA-N 1-(2,2-difluoro-1-phenylethenyl)-4-fluorobenzene Chemical compound C=1C=C(F)C=CC=1C(=C(F)F)C1=CC=CC=C1 ANXOZOZWHNFHPZ-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
DOALOUQODWWGEZ-UHFFFAOYSA-N 1-ethyl-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC(CC)=CC=2)C=C1 DOALOUQODWWGEZ-UHFFFAOYSA-N 0.000 description 1
JTNGTRJQFQXTLA-UHFFFAOYSA-N 2-(4-pentylcyclohexyl)acetyl chloride Chemical compound CCCCCC1CCC(CC(Cl)=O)CC1 JTNGTRJQFQXTLA-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
239000005247 4-Ethyl-4'-(trans-4-propylcyclohexyl)biphenyl Substances 0.000 description 1
PPWKQEDYUMJFNK-UHFFFAOYSA-N 4-pentylcyclohexane-1-carbonyl chloride Chemical compound CCCCCC1CCC(C(Cl)=O)CC1 PPWKQEDYUMJFNK-UHFFFAOYSA-N 0.000 description 1
KJYQWFQJHJHTLP-WKILWMFISA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=C(C=C(C=C1)O)F Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=C(C=C(C=C1)O)F KJYQWFQJHJHTLP-WKILWMFISA-N 0.000 description 1
DCCOHKNJQHHEHV-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 DCCOHKNJQHHEHV-SHTZXODSSA-N 0.000 description 1
PJBOOKMLDPERRS-PCYFZWJMSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 PJBOOKMLDPERRS-PCYFZWJMSA-N 0.000 description 1
QVFBANOSNYADEV-MEMLXQNLSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(c(F)c1)-c1ccc(CC)cc1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(c(F)c1)-c1ccc(CC)cc1 QVFBANOSNYADEV-MEMLXQNLSA-N 0.000 description 1
FNUWTRXUMODLEK-MGCOHNPYSA-N CCC[C@H]1CC[C@H](CBr)CC1 Chemical compound CCC[C@H]1CC[C@H](CBr)CC1 FNUWTRXUMODLEK-MGCOHNPYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
101150090209 HCST gene Proteins 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000004988 Nematic liquid crystal Substances 0.000 description 1
JBZRLVKMCLOFLG-UHFFFAOYSA-N O=S=Cl Chemical compound O=S=Cl JBZRLVKMCLOFLG-UHFFFAOYSA-N 0.000 description 1
241000428533 Rhis Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000004990 Smectic liquid crystal Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000008570 general process Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
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 1
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 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012280 lithium aluminium hydride 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
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
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 description 1
230000003287 optical effect Effects 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000005944 trans-halogenation reaction Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal Substances (AREA)

CA000460292A 1983-08-04 1984-08-02 Composes nematiques renfermant des groupes cyclohexyle Expired CA1259628A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH3234/83-5		1983-08-04
CH323483		1983-08-04
DE19843410734 DE3410734A1 (de)	1984-03-23	1984-03-23	Nematische verbindungen
DEP3410734.7		1984-03-23

Publications (1)

Publication Number	Publication Date
CA1259628A true CA1259628A (fr)	1989-09-19

Family

ID=25692529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000460292A Expired CA1259628A (fr)	1983-08-04	1984-08-02	Composes nematiques renfermant des groupes cyclohexyle

Country Status (1)

Country	Link
CA (1)	CA1259628A (fr)

1984
- 1984-08-02 CA CA000460292A patent/CA1259628A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-09-19	MKEX	Expiry

Publication	Publication Date	Title
US4637897A (en)	1987-01-20	Nematic compounds
Gray et al.	1976	Synthesis and liquid crystal properties of chiral alkyl-cyano-biphenyls (and-p-terphenyls) and of some related chiral compounds derived from biphenyl
JP2927542B2 (ja)	1999-07-28	ハロゲン化ベンゼン誘導体および液晶相
JP4734579B2 (ja)	2011-07-27	ジフルオロメチルエーテル誘導体およびその製造方法
US4710315A (en)	1987-12-01	Anisotropic compounds and liquid crystal mixtures therewith
JP5350118B2 (ja)	2013-11-27	電気光学液晶ディスプレイ
JP2722195B2 (ja)	1998-03-04	スメクテイツク液晶相
JP3122426B2 (ja)	2001-01-09	フェニルシクロヘキサン化合物および液晶媒体
US5308542A (en)	1994-05-03	4,4'-disubstituted 2',3-difluorobisphenyls and a liquid-crystalline medium
JPH0217528B2 (fr)	1990-04-20
EP0679707B1 (fr)	1999-06-16	Composé cristalline liquide, composition cristalline liquide et élément d'affichichage à cristaux liquides
JP3142839B2 (ja)	2001-03-07	ベンゼン誘導体および液晶相
JP3982850B2 (ja)	2007-09-26	ビニレン化合物及び液晶媒質
JP2999563B2 (ja)	2000-01-17	ハロフェニルで置換されたジオキサン、その製造方法及び使用
JPH06329573A (ja)	1994-11-29	ベンゼン誘導体および液晶性媒体
EP0440643B1 (fr)	1997-09-03	Terphenyls fluores 4''-cyano substitues
JPH05310605A (ja)	1993-11-22	シクロヘキサン誘導体
CA1259628A (fr)	1989-09-19	Composes nematiques renfermant des groupes cyclohexyle
JP3783248B2 (ja)	2006-06-07	４−（２−シクロヘキシル）プロピル−ｐ−テルフェニル誘導体
KR100251144B1 (ko)	2000-04-15	4개의 고리를 갖는 화합물
JPH08295642A (ja)	1996-11-12	フッ素化ビフェニルシクロヘキサン化合物および液晶媒体
US5312563A (en)	1994-05-17	Fluorinated 4"-cyano substituted terphenyls
JP3429816B2 (ja)	2003-07-28	クロロジフルオロメトキシフェニル誘導体
EP0390329B1 (fr)	1993-12-01	Dérivés pyrimidiques
JPH07145099A (ja)	1995-06-06	ベンゼン誘導体および液晶性媒体