Cyclopenta[b]naphthalene derivatives

Cyclopenta[b]naphthalene derivatives of formula (VII) to (XI)

• wherein
• Z is in each case, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
• A is in each case, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—, and which may be monosubstituted to tetrasubstituted, independently of one another, by halogen (—F, —Cl, —Br, —I), —CN, —CH3,—CH2F, —CHF2, —CF3, —OCH3, —OCH2F, —OCHF2 or —OCF3, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that heteroatoms are not directly adjacent, and which may be monosubstituted or polysubstituted by halogen, or is 1,3-cyclobutylene or bicyclo[2.2.2]octane,
• R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted, monosubstituted by —CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2 or —OCH2F,
• n is 0, 1, 2 or 3, and
• L1-L6 and L8 are each, independently of one another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2, —OCH2F or -(Z-A-)n—R,
• and L7's are F.

Cyclopental[b]naphthalene derivatives of formula (VII) to (XI)

• wherein
• Z is in each case, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —c≡C—,
• A is in each case, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—, and which may be monosubstituted to tetrasubstituted, independently of one another, by halogen (—F, —Cl —Br, —I), —CN, —CH3, —CH2F, —CHF2, —CF3, —OCH3, —OCH2F, —OCHF2 or —OCF3, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that heteroatoms are not directly adjacent, and which may be monosubstituted or polysubstituted by halogen, or is 1,3-cyclobutylene or bicyclo[2.2.2]octane,
• R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted, monosubstituted by —CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2 or —OCH2F,
• n is 0, 1, 2 or 3, and
• L1-L8 are each, independently of one another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2, —OCH2F or -(Z-A-)n—R
• wherein at least L8 is F.