Electronic switching device

A compound of the formula IA

• R1A-(A1-Z1)r—B1—(Z2-A2)s-SpA-G (IA)
• in which
• R1A denotes straight chain or branched alkyl or alkoxy each having 1 to 20 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CH═CH—,
• —O—, —S—, —CF2O—, —OCF2—, —CO—O—, —O—CO—, —SiR0R00—, —NH—, —NR0— or —SO2— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, CN, SCN or SF5,
• Z1, Z2 on each occurrence, identically or differently, denote a single bond, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2O—, —OCH2—, —C(O)O—, —OC(O)—, —C(O)S—, —SC(O)—, —(CH2)n1—, —(CF2)n2—, —CF2—CH2—, —CH2—CF2—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CH2)n3O—, —O(CH2)n4—, —C≡C—, —O—, —S—, —CH═N—, —N═CH—, —N═N—, —N═N(O)—, —N(O)═N— or —N═C—C═N—,
• n1, n2, n3, n4 identically or differently, are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
• R0, R00, identically or differently, denote an alkyl or alkoxy radical having 1 to 15 C atoms, in which, in addition, one or more H atoms may be replaced by halogen,
• A1, A2 on each occurrence, identically or differently, denote an aromatic, heteroaromatic, alicyclic or heteroaliphatic ring having 4 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by Y,
• Y on each occurrence, identically or differently, denotes 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 C atoms,
• B1 denotes
• in which R0 and R00 denote F or alkyl having 1 to 6 C atoms,
• where the groups may be oriented in both directions,
• L1 to L3, independently of one another, denote F, Cl, Br, I, CN, SF5, CF3 or OCF3, where L3 may alternatively also denote H,
• SpA denotes a spacer group or a single bond,
• G denotes —OH, —CH(CH2OH)2, —C(CH2OH)3, —SH, —SO2OH, —OP(O)(OH)2, —PO(OH)2, —C(OH)(PO(OH)2)2, —COOH, —Si(ORx)3, —SiCl3, SO2ORV, —OP(O)(ORV)2, —PO(ORV)2, —C(OH)(PO(ORV)2)2, —COORV or —Si(ORV)3,
• RV denotes secondary or tertiary alkyl having 1 to 20 C atoms,
• Rx denotes straight-chain or branched alkyl having 1 to 6 C atoms, and
• r, s on each occurrence, identically or differently, are 0, 1 or 2,
• wherein at least one of the groups SpA and R1A is chiral.

An electronic switching device (100) comprising, in this sequence,

• a first electrode (102),
• a molecular layer (103) bonded to the first electrode, and
• a second electrode (104),
• where the first and second electrodes comprise a metal nitride, and
• where the molecular layer is formed from one or more compounds selected from formulae IBa to IBf and IC-1 to IC-6:
• D1-ZD—B1-Sp-G IBa
• D1-ZD-(A1-Z1)—B1-Sp-G IBb
• D1-ZD-(A1-Z1)2—B1-Sp-G IBc
• D1-ZD—B1—(Z2-A2)-Sp-G IBd
• D1-ZD—B1—(Z2-A2)2-Sp-G IBe
• D1-ZD-(A1-Z1)—B1—(Z2-A2)-Sp-G IBf
• wherein, in formulae IBa to IBf
• A1 and A2 identically or differently, denote
• B1 denotes
• D1 denotes adamantyl or diamantyl,
• L1 and L2, independently of one another, denote CF3, Cl or F, where at least one of L1 and L2 denotes F,
• L3 denotes F,
• Y1 and Y2, independently of one another, denote CF3, Cl or F,
• ZD denotes a single bond, —C≡C—, —C(O)O—, —OC(O)—, —OCH2—, —CH2O—, —CH2CH2—, —CH2CH2CH2—, or —CH2CH2CH2CH2—,
• Z1, Z2, independently of one another, denote a single bond, —C(O)O—, —OC(O)—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, or —CH2CH2—,
• Sp denotes unbranched 1,ω-alkylene having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 C atoms,
• G denotes —OP(O)(OH)2, —PO(OH)2, or —COH(PO(OH)2)2;
• and
• wherein formulae IC-1 to IC-6
• R1C denotes H, straight chain or branched alkyl, alkenyl, alkynyl, alkoxy each having up to 12 C atoms, adamantly, or adamantylmethyloxy,
• L1 and L2 identically or differently, denote F, CF3, or Cl,
• Y3 and Y4, identically or differently, methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methoxy, trifluoromethyl, trifluoromethoxy, or trifluoromethylthio, and
• G denotes —PO(OH)2, or —COH(PO(OH)2)2.