Difluoro-substituted heterocyclic compounds (e.g. chromanes or chromenes) are prepared by fluorination of novel intermediates and are useful in liquid crystal media e.g. in vertical alignment (VA) displays are new

摘要

A difluoro-substituted heterocyclic compound in which both fluorine substituents are bonded to the same carbon atom of a benzene ring-fused, oxygen-containing heterocyclic ring is new. A difluoro-substituted heterocyclic compound of formula (I) in which both fluorine substituents are bonded to the same carbon atom of a benzene ring-fused, oxygen-containing heterocyclic ring is new. a, b, c, d and e : 0 or 1; R 1and R 2H, Cl, F, Br, I, CN, SCN, NCS, SF 5or an up to 15C alkyl, alkoxy, alkenyl or alkynyl group (optionally substituted once by CN or CF 3or once or more by F, Cl, Br or I), these groups (i) optionally having one or more -CH 2- groups replaced by -O-, -S-, -SO 2-, -CO-, -COO-, -OCO- or -OCO-O-without heteroatoms being directly coupled or (ii) being polymerizable groups; Y 1- Y 3H, halogen or 1-8C halo-alkyl or -alkoxy; A 1- A 41,4-phenylene (optionally 1-4 times substituted by CN, F, Cl, Br, I, 1-6C alkyl and/or 1-6C alkoxy, these latter 2 themselves optionally being substituted one or more times with F and/or Cl), 1,4-cyclohex(en)ylene or 1,4-cyclohexadienylene, each of these latter 3 groups being optionally substituted 1-4 times by F, Cl, Br and/or I and/or optionally having 1 or 2 -CH 2- groups replaced by -O- or -S- without heteroatoms being directly coupled; Z 1- Z 4a single bond, -CF 2O-, -OCF 2-, -CH 2CH 2-, -CF 2CF 2-, -CF 2CH 2-, -CH 2CF 2-, -CHF-CHF-, -C(O)-O-, -OC(O)-, -CH 2O-, -OCH 2-, -CF:CH-, -CH:CF-, -CF=CF-, CH=CH- or -Ctriple boundC-; and the bond beginning at [ ] ein the oxygen heterocycle is a C-C single bond and, when e : 1, is optionally also a -C=C- double bond; and there also being the proviso that Y 2is not H or F and simultaneously R 2is not H, F or Cl when simultaneously a, b, c and d : 0, e = 1, R 1= H, Y 1and Y 3both = H and the bond beginning at [ ] ein the oxygen heterocycle = a C-C single bond. Independent claims are also included for (1) the preparation of (I); and (2) a compound of formula (I) but in which the 2 fluorine atoms bonded to a common carbon atom in the oxygen heterocyclic group are replaced respectively by groups W 1and W 2such that W 1= SR 3; W 2= SR 4; or W 1and W 2together = :S or -S-W 3-S- with R 3and R 4= 1-8C alkyl and W 3= =2C divalent organic group, exclusion being made of such compounds in which a, b, c and d all = 0, e = 1, R 1and R 2both = H, Y 1- Y 3all = H, the bond beginning at [ ] ein the oxygen heterocycle = a C-C single bond and W 1and W 2= -S-CH 2CH 2-S-. [Image].