Electronic switching element

Patent metadata

Field	Value
Publication number	US-11522141-B2
Application number	US-202117340459-A
Country	US
Kind code	B2
Filing date	Jun 7, 2021
Priority date	Jul 7, 2016
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

An electronic switching element is described having, in sequence, a first electrode, a molecular layer bonded to a substrate, and a second electrode. The molecular layer contains compounds of formula I, R1-(A1-Z1)r—B1—(Z2-A2)s-Sp-G, wherein A1, A2, B1, Z1, Z2, Sp, G, r, and s are as defined herein, in which a mesogenic radical is bonded to the substrate via a spacer group, Sp, by means of an anchor group, G. The switching element is suitable for production of components that can operate as a memristive device for digital information storage.

First claim

The invention claimed is:

1. A compound of formula I
R 1 -(A 1 -Z 1 ) r —B 1 —(Z 2 -A 2 ) s -Sp-G  (I)

in which
G denotes —SO 2 OH, —OP(O)(OH) 2 , —P(O)(OH) 2 , —C(OH)(PO(OH) 2 ) 2 , —Si(OR x ) 3 or —SiCl 3 ,
R 1 denotes H, an alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CH═CH—,

—O—, —S—, —CF 2 O—, —OCF 2 —, —CO—O—, or —O—CO—, —SiR 0 R 00 —, —NH—, —NR 0 — or —SO 2 — 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 SF 5 ,
R 0 , R 00 , 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 each be replaced by halogen,
A 1 , A 2 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, SF 5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
B 1
denotes

where the groups may be oriented in both directions,

L 1 to L 5 , independently of one another, denote F, Cl, Br, I, CN, SF 5 , CF 3 or OCF 3 , where L 3 may alternatively also denote H,
Z 1 , Z 2 on each occurrence, identically or differently, denote a single bond, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 O—, —OCH 2 —, —C(O)O—, —OC(O)—, —C(O)S—, —SC(O)—, —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CF 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —C≡C—, —O—, —S—, —C═N—, —N═C—, —N═N—, —N═N(O)—, —N(O)═N— or —N═C—C═N—,
Sp denotes a spacer group or a single bond,
R x denotes straight-chain or branched alkyl having 1 to 6 C atoms, and
r and s, independently of one another, denote 0, 1, 2 or 3,
where r+s≤4; and
wherein the compound of formula I is mesogenic and has negative dielectric anisotropy.

2. The compound according to claim 1 , wherein Y, on each occurrence, is F or Cl.

3. The compound according to claim 1 , wherein L 1 to L 5 , independently of one another, denote Cl or F, and L 3 may alternatively also denote H.

4. The compound according to claim 1 , wherein the compound of formula I is selected from sub-formulae Ia to If:
R 1 —B 1 -Sp-G  Ia

R 1 -(A 1 -Z 1 )—B 1 -Sp-G  Ib

R 1 -(A 1 -Z 1 ) 2 —B 1 -Sp-G  Ic

R 1 —B 1 —(—Z 2 -A 2 )-Sp-G  Id

R 1 —B 1 —(Z 2 -A 2 ) 2 -Sp-G  Ie

R 1 -(A 1 -Z 1 )—B 1 —(Z 2 -A 2 -)-Sp-G  If

wherein
A 1 and
each independently denote

B 1
denotes

where the groups may be oriented in either direction,

R 1 denotes alkyl having 1-15 C atoms,
L 1 and L 2 , independently of one another, denote Cl or F, where at least one of the radicals L 1 and L 2 denotes F,
L 3 denotes F,
Y 1 and Y 2 independently of one another, denote H, Cl or F,
Z 1 and Z 2 independently of one another, denote a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, OCH 2 — or —CH 2 CH 2 —,
Sp denotes unbranched 1, ω-alkylene having 1 to 12 C atoms, and
G denotes —SO 2 OH, —OP(O)(OH) 2 , —PO(OH) 2 , —COH(PO(OH) 2 ) 2 , —Si(OR) 3 or —SiCl 3 .

5. The compound according to claim 4 , wherein Sp denotes unbranched 1,ω-perfluoroalkylene having 1 to 12 C atoms.

6. The compound according to claim 4 , wherein the compound of formula I is selected from sub-formulae Ia, Ib and Id.

7. The compound according to claim 4 , wherein G is —OP(O)(OH) 2 , —P(O)(OH) 2 , or —C(OH)(PO(OH) 2 ) 2 .

8. The compound according to claim 1 , wherein G is —OP(O)(OH) 2 , —P(O)(OH) 2 , or —C(OH)(PO(OH) 2 ) 2 .

9. A compound of formula I
R 1 -(A 1 -Z 1 ) r —B 1 —(Z 2 -A 2 ) s -Sp-G  (I)

in which
Sp denotes —O(CF 2 ) p1 — or —(CF 2 ) p1 —,
p1 denotes an integer from 1 to 12,
R 1 denotes H, an alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in these radicals may each be replaced,

—O—, —S—, —CF 2 O—, —OCF 2 —, —CO—O—, or —O—CO—, —SiR 0 R 00 —, —NH—, —NR 0 — or —SO 2 — 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 SF 5 ,
R 0 , R 00 , 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 each be replaced by halogen,
A 1 , A 2 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, SF 5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
B 1
denotes

where the groups may be oriented in both directions,

L 1 to L 5 , independently of one another, denote F, Cl, Br, I, CN, SF 5 , CF 3 or OCF 3 , where L 3 may alternatively also denote H,
Z 1 , Z 2 on each occurrence, identically or differently, denote a single bond, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 O—, —OCH 2 —, —C(O)O—, —OC(O)—, —C(O)S—, —SC(O)—, —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CF 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —C≡C—, —O—, —S—, —C═N—, —N═C—, —N═N—, —N═N(O)—, —N(O)═N— or —N═C—C═N—,
Sp denotes a spacer group or a single bond,
G denotes —SO 2 OH, —OP(O)(OH) 2 , —PO(OH) 2 , —C(OH)(PO(OH) 2 ) 2 , Si(OR x ) 3 or —SiCl 3 ,
R x denotes straight-chain or branched alkyl having 1 to 6 C atoms, and
r and s, independently of one another, denote 0, 1, 2 or 3,
where r+s≤4; and
wherein the compound of formula I is mesogenic and has negative dielectric anisotropy.

10. The compound according to claim 9 , wherein Y, on each occurrence, is F or Cl.

11. The compound according to claim 9 , wherein L 1 to L 5 , independently of one another, denote Cl or F, and L 3 may alternatively also denote H.

12. The compound according to claim 9 , wherein G is —OP(O)(OH) 2 , —P(O)(OH) 2 , or —C(OH)(PO(OH) 2 ) 2 .

Assignees

• Merck Patent Gmbh

Inventors

• Kirsch Peer
• Ruhl Andreas
• Tornow Marc
• Bora Achyut

Classifications

• C07F9/3839

  Polyphosphonic acids · CPC title

• C09K19/404

  containing boron or phosphorus · CPC title

• C09K19/60 Primary

  Pleochroic dyes · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• G11C2013/009

  Write using potential difference applied between cell electrodes · CPC title