US 12,193,328 B2
Aromatic compounds and use thereof for formation of molecular layers and fabrication of switching elements for memristive devices
Peer Kirsch, Seeheim-Jugenheim (DE); Sebastian Resch, Mainz (DE); and Henning Seim, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 17/609,456
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed May 8, 2020, PCT No. PCT/EP2020/062799
§ 371(c)(1), (2) Date Nov. 8, 2021,
PCT Pub. No. WO2020/225398, PCT Pub. Date Nov. 12, 2020.
Claims priority of application No. 19173415 (EP), filed on May 9, 2019.
Prior Publication US 2022/0238816 A1, Jul. 28, 2022
Int. Cl. C07F 9/38 (2006.01); C07F 9/655 (2006.01); H10K 10/00 (2023.01); H10K 10/50 (2023.01); H10K 10/82 (2023.01); H10K 71/60 (2023.01); H10K 85/60 (2023.01)
CPC H10K 85/6574 (2023.02) [C07F 9/38 (2013.01); C07F 9/3834 (2013.01); C07F 9/65517 (2013.01); H10K 10/50 (2023.02); H10K 10/701 (2023.02); H10K 10/82 (2023.02); H10K 71/60 (2023.02); H10K 85/60 (2023.02); H10K 85/615 (2023.02)] 15 Claims
 
1. A compound of formula I
R1-(A1-Z1)r—B1—ZL-A2-(Z3-A3)s-G  (I)
in which
R1 denotes H, straight chain or branched alkyl or alkoxy radical having up 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—,

OG Complex Work Unit Chemistry
—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, in addition, one or more H atoms may each be replaced by halogen, CN, SCN or SF5, or alternatively, R1 denotes a group Dia-ZD,
Dia denotes a diamondoid radical,
ZD has one of the meanings of Z1 and Z3 or denotes a straight chain or branched spacer group,
Z1, 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(R)2—, —S(O)—, or —SO2—,
R0, R00, identically or differently, denote an alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more H atoms may each be replaced by halogen,
A1, 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,
A2 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 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 up to 12 C atoms, or cycloalkyl having 3 to 12 C atoms, or alkylcycloalkyl having 4 to 12 C atoms,
B1 denotes

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
where the groups may be oriented in both directions,
L1 to L5, independently of one another, denote F, Cl, Br, I, CN, SF5, CF3 or OCF3, where L3 alternatively denotes H,
G denotes —OP(O)(OH)2, —PO(OH)2, or —C(OH)(PO(OH)2)2,
Rx denotes straight-chain alkyl having 1 to 6 C atoms or branched alkyl having 3 to 6 C atoms, and
r is 0, 1 or 2, and
S is 0, 1 or 2,
where r+s≤4.