US5204019A Expired / Lapsed US ⏱️ 0.0 years remaining

2,3-difluorobiphenyls

Assignee: Merck Patent GmbH

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Filing: 1989-02-27

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Granted: 1993-04-20

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Expires: 2009-02-27

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Abstract

Abstract 4-Q 1 -4'-Q 2 -2,3-Difluorobiphenyls wherein Q 1 and Q 2 independently of one another are each R or R-A 1 -A 2 -Z in which R (sic) alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms each of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH 2 groups can also be replaced by --O--, --CO--, --O--CO, --CO--O-- or --O--COO--, (sic) --COO--, --O--CO--, --CH 2 O, --O--CH 2 --, --CH 2 CH 2 -- or a single bond, and A 1 and A 2 independently of one another . . (sic) each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups can also be replaced by --O--, and one of the two groups A 1 and A 2 can also be a single bond, subject to the proviso that Z is --CO--O, --O--CO--, --CH 2 O--, --OCH 2 -- or --CH 2 CH 2 --, if one of the groups Q 1 or Q 2 is alkyl or alkoxy and the other group Q 1 or Q 2 is R-A 1 -A 2 -Z wherein one of the two groups A 1 and A 2 is a single bond, are suitable for use as components of liquid-crystal media.

Inventors

👤 Volker Reiffenrath
👤 Joachim Krause
👤 Andreas Wachtler
👤 Georg Weber
👤 Ulrich Finkenzeller
👤 David Coates
👤 Ian C. Sage
👤 Simon Greenfield
👤 George W. Gray
👤 Michael Hird
👤 David Lacey
👤 Kenneth J. Toyne

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-11-01 15:41

CPC Classifications

C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/20; C09K19/14; C09K19/12; C09K19/126; C09K19/2007; C09K19/2021; C09K19/30; C09K19/3001; C09K19/34; C09K19/3441

Claims Analysis

Total Claims: 13

Claim 1

Independent Claim 169 words

A 4--Q 1 --4'--Q 2 --2,3-difluorobiphenyl compound wherein Q 1 and Q 2 independently of one another are each R or R--A 1 --A 2 --Z in which R is alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms each of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH 2 groups can also be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --O--COO--; Z is --COO--, --O--CO--, --CH 2 O--, --O--CH 2 --, or --CH 2 CH 2 --; and A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups can also be replaced by --O--, and one of the two groups A 1 and A 2 can also be a single bond.

Claim 2

Dependent Claim 169 words

Claim 3

Dependent Claim 31 words

A difluorobiphenyl compound according to claim 1, wherein said compound is of formula ##STR6## wherein R 1 and R 2 independently of one another are each alkyl having 1-15 C atoms.

Claim 4

Dependent Claim 24 words

In a liquid-crystalline medium comprising at least two liquid-crystal components, the improvement wherein at least one component is a compound according to claim 1.

Claim 5

Dependent Claim 20 words

In an electrooptical display element containing a dielectric, the improvement wherein said dielectric is a medium according to claim 3.

Claim 6

Dependent Claim 16 words

A compound according to claim 1, wherein said compound is of formula Ih or Ii: ##STR7##

Claim 7

Dependent Claim 16 words

A compound according to claim 5, wherein said compound is of formula Ih1 or Ih2. ##STR8##

Claim 8

Dependent Claim 13 words

A compound according to claim 5, wherein said compound is: 1-(trans-4-propyl-cyclohexyl)-2-(4'-pentyloxy-2,3-difluorobiphenyl-4-yl)-ethane, or 1-(trans-4-pentyl-cyclohexyl)-2-(4'-pentyl-2,3-difluorophenyl-4-yl)-ethane.

Claim 9

Dependent Claim 24 words

A compound according to claim 6, wherein said compound is: 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-ethylphenyl)-ethane, 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-butylphenyl)-ethane, 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-pentylphenyl)-ethane, 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-hexylphenyl)-ethane, 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-heptylphenyl)-ethane, 1-(4'-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-octylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-ethylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-propylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-butylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-pentylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-hexylphenyl)-ethane, 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-heptylphenyl)-ethane, or 1-(4'-propyl-2,3-difluorobiphenyl-4-yl)-2-(4-octylphenyl)-ethane.

Claim 10

Dependent Claim 24 words

A 2,3-difluorobiphenyl compound according to claim 6, wherein said compound is: 1-(4-propylphenyl)-2-(4'pentyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-ethyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-propyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-butyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-hexyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-heptyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-propylphenyl)-2-(4'-octyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-pentylphenyl)-2-(4'-ethoxy-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-pentylphenyl)-2-(4'-propyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-pentylphenyl)-2-(4'-hexyl-2',3'-difluorobiphenyl-4-yl)-ethane, 1-(4-pentylphenyl)-2-(4'-heptyl-2',3'-difluorobiphenyl-4-yl)-ethane, or 1-(4-pentylphenyl)-2-(4'-octyl-2',3'-difluorobiphenyl-4-yl)-ethane.

Claim 11

Dependent Claim 75 words

A 2,3-difluorobiphenyl of the formula, ##STR9## wherein the two R groups are each independently alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH 2 groups can also be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --O--COO--, and BPF 2 is a group of the formula ##STR10##

Claim 12

Dependent Claim 75 words

Claim 13

Dependent Claim 29 words

A difluorophenyl compound according to claim 10, wherein said compound is of the formula: ##STR11## wherein R 1 and R 2 are each independently alkyl having 1-15 C atoms.

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USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1996-04-19	1996-10-19	1997-04-20	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2000-04-19	2000-10-19	2001-04-20	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2004-04-19	2004-10-19	2005-04-20	$7700.00	Window Closed / Lapsed

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