Back to results
US 11,236,063 B2Granted
Dibenzofuran derivatives and dibenzothiophene derivatives
AssigneeMerck Patent GmbH
InventorsLars Lietzau, Achim Goetz, Harald Hirschmann, Martin Engel
Life of this patent
Estimating the term…
Abstract
Compounds of the formula I in which groups and parameters that occur have the definitions given in the disclosure. Preparation methods for these compounds. Uses of the compounds as components in liquid-crystalline media. Electrooptical display elements comprising the liquid-crystalline media.
Claims11
Compound of the formula I
- in which
- W is —S—,
- Y1 and Y2 are independently H, F, Cl, CN or CF3,
- R11 and R12 are independently H, an unsubstituted, mono-CN— or —CF3-substituted or at least mono-halogen-substituted 1 to 15 carbon atom alkyl radical or 2 to 15 carbon atom alkenyl radical, where one or more CH2 groups in these radicals may also be replaced by —O—, —S—, —C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— such that oxygen atoms are not bonded directly to one another,
- R2 is an unsubstituted, mono-CN— or —CF3-substituted or at least mono-halogen-substituted 1 to 15 carbon atom alkyl radial or 2 to 15 carbon atom alkenyl radical, where one or more CH2 groups in these radicals may also be replaced by —O—, —S—, —C≡C—, —CF2O—, —OCF2—, —OC— O— or —O—CO— such that oxygen atoms are not bonded directly to one another, and also H, halogen, CN, SCN or SF5,
- A1 with the R11 and R12 groups, is
- B1 is the same or different at each instance and is
- a) a 1,4-phenylene radical in which one or two CH groups may be replaced by N,
- b) a 1,4-cyclohexenylene or 1,4-cyclohexylene radical in which one or two nonadjacent CH2 groups may be replaced by —O— or —S—, a cyclobutane-1,3-diyl radical,
- c) a radical from the group of 1,4-bicyclo[2,2,2]-octylene, spiro[3.3]heptane-2,6-diyl, naphthalene-2,6-diyl,
- decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or thiophene-2,5-diyl,
- where the groups a), b) and c) may be mono- or polysubstituted by an L group,
- L at each instance is independently F, Cl, CN, SCN, SF5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 carbon atoms or 3 to 12 carbon atoms if branched,
- Z1 and Z2 are each independently a single bond, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF— CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CH2S—, —SCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
- n is 0, 1 or 2.
12 more elements
Compound of the formula II
- in which
- R11 and R12 are independently H, an unsubstituted, mono-CN— or —CF3-substituted or at least mono-halogen-substituted 1 to 15 carbon atom alkyl radical or 2 to 15 carbon atom alkenyl radical, where one or more CH2 groups in these radicals may also be replaced by —O—, —S—, —C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— such that oxygen atoms are not bonded directly to one another,
- Y1 and Y2 are independently H, F, Cl, CN or CF3,
- W is —O— or —S—,
- Z2 are each independently a single bond, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CH2S—, —SCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
- B1 is the same or different at each instance and is
- a) a 1,4-phenylene radical in which one or two CH groups may be replaced by N,
- R2 is an unsubstituted, mono-CN— or —CF3-substituted or at least mono-halogen-substituted 1 to 15 carbon atom alkyl radical or 2 to 15 carbon atom alkenyl radical, where one or more CH2 groups in these radicals may also be replaced by —O—, —S—, —C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— such that oxygen atoms are not bonded directly to one another, and also H, halogen, CN, SCN or SF5,
- n is 0, 1 or 2.
6 more elements
Dependencies are inferred from the claim text.