| CPC G11C 13/0014 (2013.01) [C07F 9/3808 (2013.01); G11C 13/02 (2013.01); H10K 10/50 (2023.02); H10K 10/701 (2023.02); H10K 10/82 (2023.02); H10K 19/202 (2023.02); H10K 85/60 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] | 20 Claims |
|
1. 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 IA, IB and IC:
R1A-(A1-Z1)r—B1—(Z2-A2)s-SpA-G (IA)
D1-ZD-(A1-Z1)r—B1—(Z2-A2)s-Sp-G (IB)
R1C-(A1-Z1)r—B1—ZL-A2C-(Z3-A3)s-G (IC)
in which
R1A, R1C denote 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, where R1C alternatively denotes a group D1-ZD,
ZD has one of the meanings of Z1, Z2 and Z3 or denotes a spacer group,
Z1, Z2, Z3 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,
ZL denotes —O—, —S—, —CH2—, —C(O)—, —CF2—, —CHF—, —C(Rx)2—, —S(O)— or —SO2—,
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,
D1 denotes a diamondoid radical,
A1, A2, A3 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,
A2C denotes an aromatic or heteroaromatic ring having 5 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by YC,
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,
YC 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, or cycloalkyl or alkylcycloalkyl each having 3 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,
Sp denotes a spacer group,
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 of the compounds of formula IA, or at least one of the groups ZD and Sp of the compounds of formula IB, or the group R1C of the compounds of formula IC, respectively, is chiral.
|