US 12,336,362 B2
Diamondoid compounds
Peer Kirsch, Seeheim-Jugenheim (DE); Sebastian Resch, Mainz (DE); and Henning Seim, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 17/609,441
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed May 6, 2020, PCT No. PCT/EP2020/062491
§ 371(c)(1), (2) Date Nov. 8, 2021,
PCT Pub. No. WO2020/225270, PCT Pub. Date Nov. 12, 2020.
Claims priority of application No. 19173414 (EP), filed on May 9, 2019.
Prior Publication US 2022/0209150 A1, Jun. 30, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 10/50 (2023.01); C07F 9/38 (2006.01); H10K 85/60 (2023.01); H10K 71/00 (2023.01)
CPC H10K 10/50 (2023.02) [C07F 9/3808 (2013.01); H10K 85/624 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 71/00 (2023.02)] 20 Claims
 
1. A compound of formula I
D1-ZD-(A1-Z1)r-B1-(Z2-A2)s-Sp-G  (I)
in which
D1 denotes a diamondoid radical,
A1, A2 on each occurrence, identically or differently, denote an aromatic, heteroaromatic, alicyclic or heteroaliphatic ring having 4 to 25 ring atoms, which optionally contains condensed rings and which may be mono-or polysubstituted by Y,
Y on each occurrence, identically or differently, denotes F, CI, CN, SCN, SF5 or a straight-chain, in each case, optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or a branched, in each case, optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl. alkylcarbonyloxy or alkoxycarbonyloxy having 3 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 may alternatively also denote H,
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, n4identically or differently, are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
Sp denotes Sp′-X′,
Sp′ denotes a straight-chain alkylene having 1 to 20 C atoms or branched alkylene having 3 to 20 C atoms, which is optionally mono- or poly-substituted by F, Cl, Br, I or CN, and in which one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —O—, —S—, —NH—, —NR0, —SiR00R000—, —CO—, —COO-—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —NR0—CO—O—, —O—CO—NR0—NR0—, —CO—NR0, —CH═CH— or —C≡C— in such a way that O and/or S atoms are not linked directly to one another,
X′ denotes —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR00—, —NR00—CO—, —NR—00—CO—NR00—, —OCH2—, —CH2O—, —SCH2—CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═n—, —N═CH—, —N═n—, —CH═CR00—, —CYX═CYX—, C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
R0, R00
and R000 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
Yx and Yx″ each, independently of one another. denote H, F, Cl or CN,
ZD has one of the meanings of Z1 and Z2 or of Sp,
G denotes —CH═CH2, —OH, —CH(CH2OH)2, —C(CH2OH)3, —SH, —SO2OH, —OP(O)(OH)2, —PO(OH)2, —C(OH)(PO(OH)2)2, —COOH, —B(OH)2, —Si(ORx)3 or —SiCl3, —SO2ORV, —OP(O)(ORV)2, —PO(ORV)2, —C(OH)(PO(ORV)2)2, —COORV, or —Si(ORV)3,
RV denotes a straight-chain alkyl having 1 to 20 C atoms, or a branched alkyl having 3 to 20 C atoms
Rx denotes straight-chain alkyl having 1 to 6 C atoms, or branched alkyl having 3 to 6 C atoms, and
r and s independently of one another, denote 0, 1, 2 or 3,
where r+s≤4.