Phenylacetylene compound and liquid crystal composition comprising the same

A process for producing the phenyl acetylene compound shown by the following general formula (1);

• ##STR64## wherein A.sup.1 to A.sup.12 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group (provided that, in A.sup.1 to A.sup.12, the cases are excluded where both of A.sup.1 and A.sup.2 are methyl groups at the same time, while the others are hydrogen atoms, and where both of A.sup.7 and A.sup.12 are methyl groups at the same time, while the others are hydrogen atoms);
• R.sup.1 and R.sup.2 each independently represent a fluorine atom, a cyano group, a 4-R.sup.3 -(cycloalkyl) group, a 4-R.sup.3 -(cycloalkenyl) group, or a R.sup.4 --(O).sub.q group (where R.sup.3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by fluorine, or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, and R.sup.4 represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom;
• and q represents 0 or 1, wherein derivatives represented by the general formula (IM-1), ##STR65## wherein A.sup.1, A.sup.3, A.sup.4, A.sup.5, A.sup.9, A.sup.10, A.sup.11, A.sup.12 and R.sup.1 represent the same meaning as defined in the general formula (1) provided that at least one of A.sup.1, A.sup.3, A.sup.4, A.sup.5, A.sup.9, A.sup.10, A.sup.11, or A.sup.12 is an alkyl group
• and the general formula (IM-2) are reacted in the presence of a palladium catalyst and a basic substance, with or without further addition of copper iodide, ##STR66## in the formula, X represents I, Br or OSO.sub.2 CF.sub.3, and R.sup.2, A.sup.2, A.sup.6, A.sup.7, and A.sup.8 represent the same meaning as defined in the general formula (1).

A compound represented by the general formula (IM-3), ##STR67## in the formula, X represents I, Br or OSO.sub.2 CF.sub.3 ;

• and A.sup.1, A.sup.3, A.sup.4, A.sup.5, A.sup.9, A.sup.10, A.sup.11, and A.sup.12 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group;
• and R.sup.1 represents a fluorine atom, a cyano group, a 4-R.sup.3 -(cycloalkyl) group, a 4-R.sup.3 -(cycloalkenyl) group, or a R.sup.4 --(O).sub.q group (where R.sup.3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by fluorine, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by fluorine, or a linear or branched alkynyl group having a 2 to 12 carbon atoms which may be substituted by a fluorine atom, and R.sup.4 represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom;
• and q represents 0 or 1;
• provided that at least one of them is an alkyl group, and that the compound is not:
• ##STR68##

A process for producing the phenyl acetylene compound shown by the following general formula (1);

• wherein A.sup.1 to A.sup.12 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group (provided that, in A.sup.1 to A.sup.12, the cases are excluded where both of A.sup.1 and A.sup.2 are methyl groups at the same time, while the others are hydrogen atoms, and where both of A.sup.7 and A.sup.12 are methyl groups at the same time, while the others are hydrogen atoms);
• R.sup.1 and R.sup.2 each independently represent a fluorine atom, a cyano group, a 4-R.sup.3 -(cycloalkyl) group, a 4-R.sup.3 -(cycloalkenyl) group, or a R.sup.4 --(O).sub.q group (where R.sup.3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by fluorine, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by fluorine, or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, and R.sup.4 represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, and q represents 0 or 1, wherein a compound represented by the general formula (IM-3), ##STR69## in the formula, X represents I, Br or OSO.sub.2 CF.sub.3 ;
• and A.sup.1, A.sup.3, A.sup.4, A.sup.5, A.sup.9, A.sup.10, A.sup.11, A.sup.12 and R.sup.1 represent the same meaning as defined in the general formula (1), provided that at least one of them is an alkyl group;
• and ethynylbenzene derivative represented by the general formula (IM-4) are reacted in the presence of a palladium catalyst and a basic substance, with or without further addition of copper iodide ##STR70## in the formula, A.sup.2, A.sup.6, A.sup.7 and A.sup.8 represent the same meaning as defined in the general formula (1).

A liquid crystal composition, comprising at least one phenylacetylene compound represented by the following formula (2);

• ##STR73## wherein A.sup.1 to A.sup.12 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group;
• R.sup.1 and R.sup.2 each independently represent a fluorine atom, a cyano group, a 4-R.sup.3 -(cycloalkyl) group, a 4-R.sup.3 -(cycloalkenyl) group, or a R.sup.4 --(O).sub.q group (where R.sup.3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by fluorine, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, and R.sup.4 represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, a linear or branched alkenyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom, or a linear or branched alkynyl group having 2 to 12 carbon atoms which may be substituted by a fluorine atom;
• and q represents 0 to 1) and at least one compound represented by the following formula (3), and/or a compound represented by the following formula (4), ##STR74## in the formula (3), rings A, B, C, and D each independently represent 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, 4,1-cyclohexenylene, 2,5-cyclohexenylene, 5,2-cyclohexenylene, 3,6-cyclohexenylene, 6,3-cyclohexenylene, 2,5-pyrimedinediyl, 5,2-pyrimedinediyl, 2,5-pyridinediyl, 5,2-pyridinediyl, 2,5-dioxanediyl or 5,2-dioxanediyl (provided that each hydrogen atom on the rings A, B, C, and D may be substituted by a fluorine atom);
• R.sup.5 to R.sup.6 represent a hydrogen atom, a fluorine atom, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a cyano group, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, a linear or branched alkenyloxy group having 2 to 12 carbon atoms, a linear or branched alkynyloxy group having 3 to 12 carbon atoms, a linear or branched alkoxyalkyl group having 2 to 16 carbon atoms, or a linear or branched alkoxyalkenyl group having 3 to 16 carbon atoms, and methylene groups or alkyl, alkenyl, or alkynyl group thereof may be replaced with oxygen, sulfur or silicon atom;
• Z.sup.1, Z.sup.2 and Z.sup.3 each independently represent --COO--, --OCO--, --OCH.sub.2 --, --CH.sub.2 O--, an alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms, an alkynylene group having 2 to 5 carbon atoms, or a single bond;
• b, c and d each independently represent 0 or 1, and satisfy b+c+d.gtoreq.1;
• in the bond of R.sup.5 with ring A, ring B or ring C, each ring does not bond directly to an alkenyl group, and in the bond of R.sup.6 with the ring D, the ring does not bond directly to an alkenyl group;
• and ##STR75## in the formula (4), J.sup.1 represents a hydrogen atom, and fluorine atom, a cyano group, or a J.sup.3 (O)m.sup.1 (where J.sup.3 represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms, which may be substituted by fluorine, and m.sup.1 represents 0 or 1) J.sup.2 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 16 carbon atoms;
• A represents ##STR76## k, m, and n represent 0 or 1, but m.noteq.n, X.sup.1 to X.sup.8 each independently represent CH or CF;
• G.sup.1 to G.sup.4 each independently represent a hydrogen atom or a fluorine atoms;
• and Z.sup.4 represents --C.tbd.C-- or --C.tbd.C--C.tbd.C-- (provided that when n=0, Z.sup.4 is --C.tbd.C--).