New pyran compounds are useful as components in liquid crystalline media, preferably in optoelectronic displays

摘要

Pyran compounds are new. Pyran compounds of formula (I) are new. [Image] a-e : 0 or 1; W : -CH 2- or -C(=O)-; R 11>H, 1-15 C alkyl optionally substituted by halo or CN and optionally having at least one CH 2group replaced by -Ctriple boundC-, -CH=CH-, -O-, -S-, or -C(O)O- such that heteroatoms are not directly bonded to each other; R 12>H, halo, -CN, -NCS, -O-aralkyl or 1-15 C alkyl optionally substituted by halo or CN and optionally having at least one CH 2group replaced by -CC-, -CH=CH-, -O-, -S-, or -C(O)-O- such that heteroatoms are not directly bonded to each other; Z 1>1>single bond, -CH 2-, -CH 2CH 2, -CF 2CH 2, -CF 2CF 2-, -CH=CH- or -Ctriple boundC-; Z 1>2>-CH 2-, -CH 2CH 2-, -CF 2CH 2- or -CF 2CF 2-; Z 1>3>-Z 1>5>a single bond, -CH 2CH 2-, -CF 2CH 2-, -CH 2CF 2-, -CF 2CF 2-, -CH=CH-, -Ctriple boundC-, -CH 2O-, -CF 2O- or -C(O)- or -C(O)-O-; A 11>, A 12>1,4-cyclohexylene or 1,3-dioxane-5,2-diyl; A 13>, A 14>1,3-cyclobutylene, spiro[cyclobutane-1,1'-cyclobutane)-3,3'-diyl, 1,4-cyclohexylene, 1,4-phenylene (optionally substituted by 1-4 fluoro atoms), tetralin-2,6-diyl (optionally fluoro-substituted on the aromatic ring) or naphthalene-2,6-diyl (optionally fluoro-substituted); A 15>as A 13>; or A 15>-R 12>4-hydroxyphenyl (optionally fluoro-substituted), cyclobutanone-3-yl, cyclohexanone-4-yl or a substituted cyclohexyl group of formula (i); or [Image] Z 13>-[A 13>-Z 14>] c-[A 14>-Z 15>] d-[A 15>] e-R 12>a group of formula (ii) or (iii); [Image] L 1>7>-L 1>9>H or F; R 13>,R 1>4>1-7C alkyl or together form a 2-7C alkylene bridge. With the provisos that: when Z 13>and R 1>2>are directly bonded R 1>2>is aralkyl, alkyl or alkenyl, if Z 1>3>is -C(=O)-O- or -C(=O)- and Z 1>3>is not -CH 2O or -CF 2O-, when Z 1>4>is -C(=O)-O- or -C(=O)- and Z 1>4>is not -CH 2O or -CF 2O-, when Z 1>5>and R 1>2>are directly bonded, R 1>2>= is aralkyl, alkyl or alkenyl when Z 1>5>is -C(=O)-O- or -C(=O)- and Z 1>5>is not -CH 2O- or -CF 2O-, R 1>1>is not H when a and b are both 0 and Z 1>2>is a single bond, R 1>1>is not CH 3when a and b are both O, Z 1>2>and Z 1>3>are a single bond, W is -CH 2- and -[A 1>3>-Z 1>4>] c-[A 1>4>-Z 1>5>] d-[A 1>5>] c-R 1>2>is phenyl. Independent claims are included for: (1) a process for the preparation of the pyran compounds (I); and (2) allyl compounds of formula (II). R 11>-[A 11>] a[Z 11>-A 12>] b-Z 12>-C(CH 2>X 11a>)=CH2 (II) a, b : 0 or 1; X 11a>Cl, Br, I, sulfonic acid, -OH, alkoxy or O-aralkyl or =O.