Electronic device including a plurality of cells arranged in a three-dimensional array of cells and method for producing such an electronic device - Patents.com

Abstract

An electronic device (10) is provided that includes a plurality of cells (100) arranged in a three-dimensional array of cells (100), where the cells (100) are located at the intersection between two crossed electrode lines (30, 31). Each cell (100) of the electronic component (100) includes, in that order, a first electrode (102), a portion (104) of a molecular layer (20), and a second electrode (106), where the molecular layer (20) includes a self-assembled monolayer of organic molecules having anchoring groups connected to dipole units by means of conformationally flexible units. Further aspects of the invention relate to methods and compounds for producing such electronic devices (10), and uses of such electronic devices (10).

Description

[Technical field]

[0001] The present invention relates to an electronic device comprising a plurality of cells arranged in a three-dimensional array of cells, where the cells are located at the intersections between two electrode lines. Further aspects of the invention relate to methods for producing such an electronic device, and to uses of such an electronic device. [Background technology]

[0002] Computer technology requires storage media that allow fast writing and reading access to the information stored therein. Solid-state or semiconductor memories make it possible to achieve particularly fast and reliable storage media, since they do not require any moving parts. Currently, dynamic random access memories (DRAMs) are mainly used. DRAMs allow fast access to the stored information, but this information must be updated periodically, which means that the stored information is lost when the power is turned off.

[0003] The prior art also discloses non-volatile semiconductor memories such as flash memory or magnetoresistive random access memory (MRAM), which retain information even after the power is turned off. The disadvantage of flash memory is that write access occurs relatively slowly and flash memory cells cannot be erased indefinitely. The life of flash memory is typically limited to a maximum of one million read / write cycles. MRAM can be used in a similar manner to DRAM and has a long life, but this type of memory has not been able to establish itself due to the difficult production process.

[0004] A further alternative is a memory that works on the basis of memristors. The term "memristor" is a contraction of the words "memory" and "resistor" and describes a component that can reproducibly change its electrical resistance between high and low values. The respective state (high or low resistance) is retained even in the absence of a voltage supply, which means that a non-volatile memory can be achieved with memristors.

[0005] An important alternative application of electrically switchable components comes from the field of neuromorphic or synaptic computing, where computer architectures are pursued in which it is not intended that information is processed sequentially in a classical manner. Instead, the aim is to build circuits in a highly three-dimensionally interconnected manner to make it possible to achieve information processing similar to that of the brain. In this type of artificial neuronal network, the biological connections between nerve cells (synapses) are then represented by memristive electronic switching elements. Under certain circumstances, additional intermediate states (between the digital states "1" and "0") can also be of particular interest here.

[0006] DE 10 2017 005 884 A1 discloses an electronic switching element comprising, in that order, a first electrode, a molecular layer attached to a substrate, and a second electrode. The molecular layer essentially consists of a compound in which rigid polar cyclic or mesogenic radicals are attached to the substrate by means of anchor groups via spacer groups. The resistance of the molecular layer can be switched between a high resistance state and a low resistance state by applying a potential above a certain positive or negative switching voltage.

[0007] WO 2020 / 225270 A1 discloses an electronic switching element for a memristive device comprising a diamondoid compound and a self-assembled monolayer (SAM) comprising the diamondoid compound. The switchable element comprises, in that order, a first electrode, a SAM and a second electrode. WO 2020 / 225398 A1 discloses a similar switchable element having a self-assembled monolayer based on an aryl ether.

[0008] US 6,579,760 describes a memory device that includes a crossbar array of bit lines and word lines, where memory cells are located at the intersections of the bit lines and word lines. The memory cells each include an isolation diode and a phase change layer as a selection device. A memory cell is selected by biasing the word line and bit line that intersect at the selected memory cell such that the isolation diode of the selection device is conductive, while the word line and bit line that are connected to other memory cells are reverse biased such that the isolation diode of the selection device is non-conductive. The phase change layer and isolation diode are formed as a self-aligned stack.

[0009] To further increase the density of electronic devices, especially memory devices, three-dimensional arrangements of memory cells are known in the art using inorganic materials based on phase change materials and other memory materials such as Conductive Bridge Random Access Memory (CB-RAM), Ferroelectric Transistor Random Access Memory (FeTRAM), Magnetoresistive Random Access Memory (MRAM), etc. Such configurations are known as 3D cross-point or 3D X-point memory devices.

[0010] US 2019 / 0043923 A1 discloses a 3D cross-point memory structure having bit lines and word lines, where memory cells are located at the intersections between the bit lines and word lines. To mitigate current spikes, a resistive material is deposited in two or more regions of the array, including at least one region of the memory cells closer to the contact with the conductive bit lines and word lines. Summary of the Invention

[0011] It would be desirable to produce such 3D cross-point structures of cells containing memristive electronic switching elements based on organic self-assembled monolayers, however, the thermal sensitivity of the organic components has prevented the 3D cross-point structures from being fabricated using established processes in microelectronic fabrication.

[0012] It is therefore an object of the present invention to provide such an electronic device having a plurality of cells with a hybrid organic-inorganic structure arranged in a three-dimensional array of cells that can be easily manufactured, and further to provide a method for producing such an electronic device.

[0013] An electronic device is proposed that includes a plurality of cells arranged in a three-dimensional array of cells, where the cells are located at the intersections between two crossed electrode lines, and each cell includes, in that order, a first electrode, a portion of a molecular layer, and a second electrode, where the molecular layer is a self-assembled monolayer of organic molecules having anchoring groups connected to dipole units by means of conformationally flexible units. [Brief description of the drawings]

[0014] [Figure 1] FIG. 1 shows a schematic cross-sectional view of an electronic device having a three-dimensional crossbar arrangement of cells. [Figures 2a-2e] 2a-2l show top and cross-sectional views, respectively, of the electronic device of FIG. 1 at different stages of production. [Fig. 2f-2j] 2a-2l show top and cross-sectional views, respectively, of the electronic device of FIG. 1 at different stages of production. [Figure 2k-2l] 2a-2l show top and cross-sectional views, respectively, of the electronic device of FIG. 1 at different stages of production. [Diagram 3] FIG. 3 shows a schematic diagram of the cell. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] Each of the cells has a switchable unit, where the state of the self-assembled monolayer in the cell can be switched from a first state in which the cell has a high electrical resistance to a second state in which the cell has a low electrical resistance, the electrical resistance of the cell in the high electrical resistance state being preferably 10 to 100,000 times higher than in the low electrical resistance state.

[0016] Such structures for switchable units are known in the art, see, for example, documents WO 2020 / 225270 A1, WO 2020 / 225398 A1 and DE 10 2017 005 884 A1.

[0017] The state of the cell, in particular the state of a part of the molecular layer of the cell, can be switched by applying a switching voltage. Furthermore, the state of the cell can be read by measuring the resistance by applying a read voltage and then measuring the current flowing through the cell, where the read voltage is lower than the switching voltage. The absolute value of the read voltage is preferably at least 10 times lower than the absolute value of the switching voltage. It is especially preferred if the read voltage is between 10 and 300 mV.

[0018] The cell preferably has a first (positive) switching voltage, where the state of the molecular layer switches from a low resistance state to a high resistance state when a positive voltage greater than the first switching voltage is applied, and further, the cell preferably has a second switching voltage having an opposite polarity to the first voltage, where the state of the molecular layer switches from a high resistance state to a low resistance state when a negative voltage greater than the second switching voltage is applied.

[0019] The resistance state can be used to encode a single bit of information, and thus each of the cells can be used as a single-bit storage cell in an electronic element configured as a memory device.

[0020] The plurality of cells are arranged in a three-dimensional array of cells. The array may therefore extend in two directions in a plane that may be defined by the substrate on which the electronic device is formed, and may also extend in a vertical direction perpendicular to this plane. The number of cells arranged in each of the two directions or plane dimensions may be extremely large, ranging from at least a few thousand to thousands, millions or even billions of cells. For example, in a configuration of 1024 cells in the x direction and 1024 cells in the y direction, a single two-dimensional layer of cells contains 1048576 cells. Such a two-dimensional arrangement of cells, where each cell is located at the intersection of two orthogonal electrode lines, is known as a crossbar array.

[0021] The number of levels or layers of cells arranged in a vertical or dimensional manner is typically less and ranges from 2 to at least 64, preferably at least 1024 or even more. Preferably, the array contains at least 16 levels of cells, more preferably at least 32 levels of cells and most preferably at least 64 levels of cells. Such a three dimensional arrangement of cells is known as a 3D crossbar array or a 3D crosspoint device.

[0022] In an array of cells, each individual cell is located at the intersection between two crossed electrode lines that serve as the first and second electrodes of each cell or are connected to the first and second electrodes of each cell. Thus, each cell can be addressed by applying a voltage to the respective electrode lines. However, a portion of the current caused by the applied voltage may flow through adjacent cells due to leakage currents. The effects of such leakage currents may be avoided or at least reduced by including a selector device in each of the cells.

[0023] Two crossed electrode lines may be disposed orthogonally to each other such that the crossed electrode lines enclose an angle of 90°. However, a strict 90° angle is not required, and the angle between the crossed electrode lines may be selected, for example, from the range of 45° to 135°.

[0024] Preferably, each cell further includes a diode, a threshold switch, or a transistor as a selector device.

[0025] The selector device may be configured as an inorganic diode, in particular as a Zener diode or a symmetric Schottky diode. The diode may include, in particular, two layers of a semiconductor material, such as silicon, where the first layer is p-type doped and the second layer is n-type doped. The back-to-back Schottky diode may include a metal-insulator-metal (MIM) layer structure, for example Ni / TiO2 / Ni.

[0026] Due to the bipolar switching characteristics of the molecular layers of the cell, the use of a selector device with nonlinear-like characteristics for both polarities is preferred. For this purpose, a diode may be used, for example in the form of a Zener diode, in which the p-type and n-type doped layers are both highly doped.

[0027] Suitable threshold switches may be based on Ovonic threshold switching or metal-insulator transitions.

[0028] Suitable switches based on Ovonic threshold switching include chalcogenide-based devices.

[0029] A preferred structure for a metal-insulator transition based threshold switch includes Pt / VO2 / Pt.

[0030] Preferably, the selector device is configured as a self-assembled monolayer of further organic molecules or as a diode arranged between the molecular layer and the first electrode or the second electrode.

[0031] Preferably, the first and / or second electrodes of each cell are made of metals, conductive alloys, conductive ceramics, semiconductors, conductive oxide materials, conductive or semiconductive organic molecules, or layered conductive 2D materials. The first and / or second electrodes may comprise a combination of more than one of said materials, for example in the form of a multilayer system. The materials of the first and second electrodes may be chosen to be the same or different.

[0032] Suitable metals include Ag, Al, Au, Co, Cr, Cu, Mo, Nb, Ni, Pt, Ru, W, Pd, Pt, with Al, Cr and Ti being preferred.

[0033] Suitable conductive ceramic materials include CrN, HfN, MoN, NbN, TiO2, RuO2, VO2, NSTO (niobium doped strontium titanate), TaN and TiN, WN, WCN, VN and ZrN, with TiN being preferred.

[0034] Suitable semiconductor materials include indium tin oxide (ITO), indium gallium oxide (IGO), InGa-α-ZnO (IGZO), aluminum doped zinc oxide (AZO), tin doped zinc oxide (TZO), fluorine doped tin oxide (FTO) and antimony tin oxide.

[0035] Suitable elemental semiconductors include Si, Ge, C (diamond, graphite, graphene, fullerenes), α-Sn, B, Se and Te. Suitable compound semiconductors include III-V semiconductors, especially GaAs, GaP, InP, InSb, InAs, GaSb, GaN, TaN, TiN, MoN, WN, AlN, InN, Alx Ga1-x As and Inx Ga1-x Ni, II-VI semiconductors, especially ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, Hg(1-x) Cd(x) Te, BeSe, BeTex and HgS; and III-VI semiconductors, especially GaS, GaSe, GaTe, InS, InSex and InTe, I-III-VI semiconductors, especially CuInSe2, CuInGaSe2, CuInS2 and CuInGaS2, IV-IV semiconductors, especially SiC and SiGe, IV-VI semiconductors, especially SeTe.

[0036] Suitable highly doped semiconductor materials include p+Si, n+Si. An example of a suitable layered conductive 2D material is graphene.

[0037] Suitable semiconducting organic molecules include polythiophenes, tetracenes, pentacenes, phthalocyanines, PTCDA, MePTCDI, quinacridones, acridones, indanthrones, fulleranthrones, perinones, AlQ3, and mixed systems, especially PEDOT:PSS and polyvinylcarbazole / TLNQ complexes.

[0038] In a preferred embodiment, the first and second electrodes are the same or different and comprise a material selected from the group consisting of Ag, Al, Au, Co, Cr, Cu, Mo, Nb, Ni, Pt, Ru, Si, W, CrN, HfN, MoN, NbN, TiN, TaN, WN, WCN, VN and ZrN.

[0039] More preferably, the first and second electrodes comprise, preferably consist of, a metal nitride, the same or different, selected from CrN, HfN, MoN, NbN, TiN, TaN, WN, tungsten carbonitride (WCN), VN and ZrN.

[0040] In particular, the first electrode is made of a metal nitride selected from CrN, HfN, MoN, NbN, TiN, TaN, WN, WCN, VN and ZrN, and the second electrode is made of TiN. Most specifically, the first and second electrodes are both made of TiN.

[0041] The self-assembled monolayer is disposed between the first and second electrodes and acts as an electrical insulator between the two electrodes, such that a hole-free closed layer is formed within the switchable cell that allows a direct electrical connection between the first and second electrodes.

[0042] The switchable cell, comprising a first electrode, a self-assembled monolayer and a second electrode, forms a tunnel junction, the electrical properties of which can be influenced by switching the state of the self-assembled monolayer. Preferably, the self-assembled monolayer has ferroelectric properties such that a ferroelectric tunnel junction is formed. The ferroelectric tunnel junction allows a high ratio between the electrical resistance of the low and high resistive states of the switchable cell and is therefore preferred.

[0043] Self-assembled monolayers of organic molecules have anchoring groups and dipole units connected by means of conformationally flexible units.

[0044] An anchor group in the sense of the present invention is a functional group that is used to adsorb or bind organic molecules onto a surface, in particular by physical adsorption, chemical adsorption or by chemical reaction.The surface is preferably one of the first and second electrodes.If the first and / or second electrodes are not suitable for binding with anchor groups, an intermediate layer in the form of an anchoring layer may be included in the cell between one of the electrodes and the molecular layer.The anchoring layer is preferably arranged on the surface of the first and / or second electrodes.

[0045] A conformationally flexible unit in the sense of the present invention is a flexible chain between the dipole unit and the anchor group, which creates a separation between these substructures and, due to its flexibility, at the same time improves the mobility of the dipole unit after binding to the substrate.

[0046] The conformationally flexible units allow a change in the shape of the organic molecules when the state of the molecular layer is changed by application of a switching voltage, which in turn affects the electrical properties of the molecular layer, in particular the electrical resistance of the molecular layer.

[0047] Preferably, the organic molecule for the formation of the self-assembled monolayer is represented by the formula I TZ T -(A 1 -Z 1 ) r -B-(Z 2 A 2 ) s -(Z 3 A 3 ) t -(Z 4 A 4 ) u -Sp-G (I) and wherein the compound is selected from one or more compounds represented by Where T is the following group: a) A 3- to 10-membered saturated or partially unsaturated aliphatic ring in which at least one -CH2- group is -O-, -S-, -S(O)-, -SO2-, -NR x-OR- x or at least one -CH= group is replaced by -N=; b) linear or branched alkyl or alkoxy, each having 1 to 20 C atoms, in which one or more CH2 groups in these radicals are each, independently of one another, -C≡C-, -CH=CH-, [ka] -O-, -S-, -CF2O-, -OCF2-, -CO-O-, -O-CO-, -SiR 0 R 00 -, -NH-, -NR 0 - or -SO2- may be substituted in such a manner that the O atoms are not directly linked to each other, and one or more H atoms therein may be substituted by halogen, CN, SCN or SF5; R in the formula 0 , R 00 are identical or different and represent an alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more H atoms may additionally be replaced by halogen, c) diamondoid radicals, preferably those derived from lower diamondoids, very preferably selected from the group consisting of adamantyl, diamantyl and triamantyl, in which one or more H atoms can be replaced by F, alkyl, alkenyl or alkoxy having in each case up to 12 C atoms, which can be optionally fluorinated, especially [ka] is selected from the group of radicals consisting of Z T , Z 1 , Z 2 and Z 4are, for each occurrence, the same or different, a single bond, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2O-, -OCH2-, -C(O)O-, -OC(O)-, -C(O)S, -SC(O)-, -(CH2) n1 -, -(CF2) n2 -, -CF2CH2-, -CH2CF2-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -(CH2) n3 O-, -O(CH2) n4 represents -, -C≡C-, -O-, -S-, -CH=N-, -N=CH-, -N=N-, -N=N(O)-, -N(O)=N- or -N=CC=N-, wherein n1, n2, n3 and n4 are the same or different and each represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; Z 3 -O-, -S-, -CH2-, -C(O)-, -CF2-, -CHF-, -C(R x )2-, -S(O)- or -SO2-; A 1 , A 2 and A 4 represents, for each occurrence, identically or differently, an aromatic, heteroaromatic, alicyclic or heteroaliphatic ring having 4 to 25 ring atoms, which may also contain fused rings, and which may be mono- or polysubstituted by Y; A 3 has 5 to 25 ring atoms and may also contain fused rings, and Y C represents an aromatic or heteroaromatic ring, which may be mono- or polysubstituted by Y for each occurrence is identical or different and represents F, Cl, CN, SCN, SF5 or linear or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, preferably F or Cl, Y Chas one of the meanings of Y or represents cycloalkyl or alkylcycloalkyl, each having 3 to 12 C atoms, preferably methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, methoxy or trifluoromethoxy, B is, [ka] where the groups may be oriented in both directions, L 1 ~L 5 represent, independently of one another, F, Cl, Br, I, CN, SF5, CF3 or OCF3, preferably Cl or F, where L 3 may alternatively represent H, Sp represents a spacer group or a single bond; G is -OH, -SH, -SO2OH, -OP(O)(OH)2, -PO(OH)2, -C(OH)(PO(OH)2)2, -COOH, -Si(OR x )3, -SiCl3, -CH=CH2, -POCl2, -CO(NHOH), -CO(NR 0 OH), -Si(NMe2)3, -OC(O)-OR V , -OC(O)-Si(OR V )3, -PO(OR V )2 or -SO2OR V or a straight-chain or branched alkyl group having 1 to 12 C atoms in which one, two or three non-geminal H atoms are replaced by OH, for example -CH(CHOH) or -C(CHOH), R 0 , R 00 , R x represents a linear or branched alkyl group having 1 to 6 C atoms, R V denotes linear or branched alkyl having 1 to 12 C atoms, preferably secondary or tertiary alkyl, very preferably isopropyl or tert-butyl, especially tert-butyl, and r, s, t, and u are the same or different and each is 0, 1, or 2.

[0048] Suitable compounds of formula I are disclosed in WO 2016 / 110301, WO 2018 / 007337, WO 2019 / 238649, WO2020 / 225270, WO2020 / 225398 and WO2021 / 078699.

[0049] Preferably, the organic molecules for the formation of the self-assembled monolayer are selected from one or more compounds of formula IA and its subformulas below.

[0050] A spacer group in the sense of the present invention is a flexible chain between the dipolar moiety and the anchor group, which creates a separation between these substructures and, due to its flexibility, at the same time improves the mobility of the dipolar moiety after binding to the substrate.

[0051] The spacer group can be branched or linear. Chiral spacers are branched and optically active and non-racemic. Halogen is F, Cl, Br or I, preferably F or Cl.

[0052] In this specification, alkyl is linear or branched and has 1 to 15 C atoms, preferably linear and, unless otherwise specified, has 1, 2, 3, 4, 5, 6 or 7 C atoms and is therefore preferably methyl, ethyl, propyl, butyl, pentyl, hexyl or heptyl.

[0053] In this specification, an alkoxy radical is linear or branched and contains 1 to 15 C atoms. It is preferably linear and, unless otherwise specified, has 1, 2, 3, 4, 5, 6 or 7 C atoms and is therefore preferably methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy.

[0054] In the present specification, an alkenyl radical is preferably an alkenyl radical having 2 to 15 C atoms, which is linear or branched and contains at least one CC double bond. It is preferably linear and has 2 to 7 C atoms. It is therefore preferably vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl. If two C atoms of the CC double bond are substituted, the alkenyl radical can be in the form of E and / or Z isomers (trans / cis). Generally, the respective E isomers are preferred. Of the alkenyl radicals, prop-2-enyl, but-2- and -3-enyl, and pent-3- and -4-enyl are especially preferred.

[0055] In the present specification, alkynyl is taken to mean an alkynyl radical having 2 to 15 C atoms, which is linear or branched and contains at least one C-C triple bond. 1- and 2-propynyl and 1-, 2- and 3-butynyl are preferred.

[0056] Preferred aryl groups in formula I are, for example, those derived from the parent structures benzene, naphthalene, tetrahydronaphthalene, 9,10-dihydrophenanthrene, fluorene, indene and indane.

[0057] In formula I, preferred heteroaryl groups are, for example, five-membered rings such as furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole and 1,3,4-thiadiazole, six-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine and 1,2,3-triazine, or condensed rings such as and fused rings such as indole, isoindole, indolizine, indazole, benzimidazole, benzotriazole, purine, naphthoimidazole, benzoxazole, naphthoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazothiophene, 2H-chromene (2H-1-benzopyran), 4H-chromene (4H-1-benzopyran) and coumarin (2H-chromen-2-one), or combinations of these groups.

[0058] In formula I, preferred cycloaliphatic groups are cyclobutane, cyclopentane, cyclohexane, cyclohexene, cycloheptane, decahydronaphthalene, bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, spiro[3.3]heptane, and octahydro-4,7-methanoindane.

[0059] In formula I, preferred heteroaliphatic groups are tetrahydrofuran, dioxolane, tetrahydrothiofuran, pyran, dioxane, dithiane, silinane, piperidine and pyrrolidine.

[0060] A 1 , A 2 and A 4 is for each occurrence identical or different and is particularly preferably selected from the following groups: a) 1,4-phenylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by Y; b) the group consisting of trans-1,4-cyclohexylene and 1,4-cyclohexenylene, in which one or more non-adjacent CH groups may be replaced by -O- and / or -S-, and in which one or more H atoms may be replaced by Y; and c) the group consisting of 1,3-dioxolane-2,4-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, 1,4-bicyclo[2.2.2]octanediyl, piperidine-1,5-diyl and thiophene-2,5-diyl, in which one or more H atoms may be replaced by Y; wherein Y has the meaning given above under formula I and preferably represents F, Cl, CN or CF3.

[0061] A 3 is very preferably selected from the group consisting of 1,4-phenylene, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-2,6-diyl, anthracene-9,10-diyl, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by Y, where Y has the meaning given above under formula I and in which the group Z 3 The position adjacent to is not H.

[0062] In formula I, the group G is preferably -SO2OH, -OP(O)(OH)2, -PO(OH)2, -POCl2, -COH(PO(OH)2), -Si(OR x )3, -SiCl3 or PO(OR V )2, very preferably -OP(O)(OH)2, -PO(OH)2 or -COH(PO(OH)2)2, especially -PO(OH)2, where R Vhas the meaning defined above and is preferably Me, Et, n-Pr, i-Pr or t-Bu.

[0063] Preferred spacer groups Sp are selected from the formula Sp'-X', such that the radical G-Sp- of formula I corresponds to the formula G-Sp'-X'-, So Sp' represents a straight-chain or branched alkylene having 1 to 20, preferably 1 to 12, C atoms, which may be mono- or polysubstituted by F, Cl, Br, I or CN, and in addition one or more non-adjacent CH groups therein are each, independently of one another, -O-, -S-, -NH-, -NR 0 -, -SiR 00 R 000 -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S-, -NR 0 -CO-O-, -O-CO-NR 0 -, -NR 0 -CO-NR 0 the O and / or S atoms may be replaced by -, -CH=CH- or -C≡C- in such a way that they are not directly linked to each other, X' is -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 00 -,-NR 00 -CO-, -NR 00 -CO-NR 00 -, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 00 -, -CY x =CY x‘ represents -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH- or a single bond; R 0 , R 00 and R 000 each independently of one another represents H or alkyl having 1 to 12 C atoms, and Y xand Y x‘ each independently represents H, F, Cl or CN. X' is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 0 - or a single bond.

[0064] A preferred group Sp' is -(CH2) p1 -, -(CF2) p1 -, -(CH2CH2O) q1 -CH2CH2-, -(CF2CF2O) q1 -CF2CF2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 00 R 000 -O) p1 -, wherein p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 00 and R 000 has the meaning indicated above.

[0065] Particularly preferred groups -X'-Sp'- are -(CH2) p1 -, -O-(CH2) p1 -, -(CF2) p1 -, -O(CF2) p1 -, -OCO-(CH2) p1 - and -OC(O)O-(CH2) p1 - in which p1 has the meaning indicated above.

[0066] Very particularly preferred radicals Sp' are, for example, in each case linear, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, perfluoroethylene, perfluoropropylene, perfluorobutylene, perfluoropentylene, perfluorohexylene, perfluoroheptylene, perfluorooctylene, perfluorononylene, perfluorodecylene, perfluoroundecylene, perfluorododecylene, perfluorooctadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.

[0067] An especially preferred group X' is --O-- or a single bond. In a preferred embodiment, the organic molecules for the formation of the self-assembled monolayer are selected from compounds of formula I, as defined above and below, in which the radical T represents a 3-10 membered saturated or partially unsaturated aliphatic ring, in which at least one -CH2- group is -O-, -S-, -S(O)-, -SO2-, -NR x -OR- x or at least one -CH= group is replaced by -N=.

[0068] Represented by formula I and as defined above and below, the group T therein represents a 3-10 membered saturated or partially unsaturated aliphatic ring, at least one -CH2- group of which is -O-, -S-, -NR x -, -S(O)-, -SO2-, -NR x -OR- x The electronic components according to the invention comprising self-assembled monolayers obtained from compounds in which at least one -CH= group is replaced by -N= are distinguished by a particularly strong adhesion of the individual switching layers to the respective upper electrodes, which contributes to improved mechanical stability and structural reliability.

[0069] The present invention therefore further relates to compounds of formula IA, TZ T -(A 1 -Z 1 ) r -B-(Z 2 A 2 ) s -(Z 3 A 3 ) t -(Z 4 A 4 ) u -Sp-G (IA) Among them T represents a 3- to 10-membered saturated or partially unsaturated aliphatic ring, at least one -CH2- group of which is -O-, -S-, -NR x -, -S(O)-, -SO2-, -NR x -OR- x or in which at least one -CH= is replaced by -N=, and the other groups and parameters have the meanings defined above.

[0070] Molecular layers obtained from these compounds are distinguished by significantly improved wettability by typical photoresist formulations and other process chemicals, improved deposition of materials by ALD on top of the SAM, higher quality of films deposited by, for example, physical vapor deposition, and improved adhesion of top electrode films.

[0071] In a preferred embodiment, the compound of formula IA has the subformulae IA-1a to IA-1f TZ T -B-Sp-G IA-1a TZ T -(A 1 -Z 1 )-B-Sp-G IA-1b TZ T -(A 1 -Z 1 )2-B-Sp-G IA-1c TZ T -B-(Z2 -A 2 )-Sp-G IA-1d TZ T -B-(Z 2 -A 2 )2-Sp-G IA-1e TZ T -(A 1 -Z 1 )-B-(Z 2 -A 2 )- Sp-G IA-1f Selected from among T, Z T , A 1 , A 2 , B, Z 1 , Z 2 , Sp and G have the meanings indicated above and preferably T is [ka] R in x represents alkyl having 1 to 6 C atoms, preferably methyl.

[0072] In the compounds of formula I and subformulae thereof, A 1 and A 2 are the same or different, [ka] represents B is, [ka] represents L 1 and L 2 denote, independently of one another, CF3, Cl or F, whereby preferably the radical L 1 and L 2 at least one of represents F; L 3 represents H or F, preferably F, Y 1 and Y 2represent, independently of one another, H, Cl or F, Z 1 , Z 2 , Z T represent, independently of one another, a single bond, -CF2O-, -OCF2-, -CH2O-, -OCH2- or -CH2CH2-, preferably a single bond, Sp represents a branched or unbranched, preferably unbranched, 1,ω-alkylene having 1 to 12 C atoms, G represents -OP(O)(OH)2, -PO(OH)2, or -COH(PO(OH)2).

[0073] Very particularly preferred subformulae of formula IA-1 are the subformulae IA-1a-1 to IA-1d-18: [ka] [ka] [ka] [ka] [ka] [ka] [ka] Among them, T and Z T and G have the meaning given above, v is an integer from 1 to 12, preferably from 2 to 7, and preferably T is [ka] represents Z T represents -CHO-, -C≡C- or a single bond, very preferably a single bond, G represents -PO(OH)2 or -COH(PO(OH)2)2, and v is an integer from 2 to 7.

[0074] In a preferred embodiment, the compound of formula I is represented by formula IA-2 TZ T -(A 1 -Z 1 ) r -BZ 3 -A 3 -(Z 4 -A 4 ) u -G IA-2 in which the occurring radicals and parameters have the meanings given above for formula I, and preferably T is [ka] Represents.

[0075] In the compounds A-2 of formula I and its subformulae, preferably A 1 and A 4 are the same or different, [ka] represents A 3 -Z 3 teeth, [ka] represents B is, [ka] represents Z T represents a single bond, -CH2O-, -OCH2- or -CH2CH2-; L 1 and L 2 are the same or different and represent F, CF3 or Cl, Y 1 and Y 2 is identical or different and has one of the meanings given above for Y and preferably represents H, F or Cl, Y 3 and Y 4 are the same or different, Y 1 and Y 2 and preferably denotes methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, very preferably methyl, Z 3 represents CH2 or -O-, preferably O, Z 1 , Z 2 denote, independently of one another, a single bond, -C(O)O-, -OC(O)-, -CF2O-, -OCF2-, -CH2O-, OCH2- or -CH2CH2-, in particular a single bond, and G represents -PO(OH)2 or -COH(PO(OH)2)2, preferably -PO(OH)2; r and u are independently 0, 1 or 2, preferably 0 or 1.

[0076] Highly preferred subformulae of formula IA-2 are the subformulae IA-2-1 to IA-2-7: [ka] [ka] in which the occurring radicals have the meanings given above for formula IA-2.

[0077] According to another aspect of the invention, the molecular layer comprises one or more chiral, non-racemic compounds selected from the compounds of formula I.

[0078] Molecular layers derived from chiral compounds of formula I enable memristic devices with significantly reduced stochastic noise and faster switching, reducing the read and write error rate, which has a positive effect on energy efficiency. In addition, increased tunneling currents are observed, which allows integration into smaller junction sizes.

[0079] Preferably, the chiral compounds have an enantiomeric excess (ee) of greater than 50%, preferably greater than 80%, 90% or 95%, more preferably greater than 97%, especially greater than 98%.

[0080] Chirality is achieved by means of a branched chiral group Sp of formula I above, which has one or more, preferably one or two, very preferably one, asymmetrically substituted carbon atoms, hereinafter referred to as Sp* (or: asymmetric carbon atom, C*).

[0081] In Sp*, the asymmetric carbon atom is preferably linked to two differently substituted carbon atoms, a hydrogen atom and a substituent selected from the group of halogen (preferably F, Cl or Br), alkyl or alkoxy having in each case 1 to 5 carbon atoms, and CN.

[0082] The chiral organic radical Sp* preferably has the formula in which X' has the meaning defined above for formula I and preferably represents -CO-O-, -O-CO-, -O-CO-O-, -CO-, -O-, -S-, -CH=CH-, -CH=CH-COO- or a single bond, more preferably -CO-O-, -O-CO-, -O- or a single bond, very preferably -O- or a single bond, Q and Q' are the same or different and each represents a single bond or an optionally fluorinated alkylene having 1 to 10 carbon atoms, in which the CH2 group not connected to X can also be replaced by -O-, -CO-O-CO-, -CO-O- or -CH=CH-, preferably an alkylene having 1 to 5 carbon atoms or a single bond, particularly preferably -(CH2) n5 - or a single bond, n5 is 1, 2, 3, 4, 5, or 6; Y represents optionally fluorinated alkyl having 1 to 15 carbon atoms, in which one or two non-adjacent CH2 groups can also be replaced by -O-, -CO-, -O-CO-, -CO-O- and / or -CH=CH-, furthermore CN or halogen, preferably optionally fluorinated alkyl or alkoxy having 1 to 7 C atoms, -CN or Cl, particularly preferably -CH3, -C2H5, -CF3 or Cl.

[0083] The compounds of general formula IA according to the invention are prepared by methods known per se, precisely as described in the literature (for example standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), under reaction conditions which are known and suitable for the reaction, whereby variants known per se, but not mentioned here in more detail, can be used.

[0084] The preferred synthetic route for the compound of formula IA according to the present invention is illustrated in the following scheme and further explained with examples.Suitable synthesis is also published for example in CN 103319444A, or in P. Kirsch, M. Bremer, Angew. Chem. Int. Ed. 2000, 39, 4216-4235; M. Bremer, P. Kirsch, M. Klasen-Memmer, K. Tarumi, Angew. Chem. Int. Ed. 2013, 52, 8880-8896; and the references cited therein, and can be adapted to the specific desired compound of general formula IA by selecting suitable starting materials.

[0085] The synthesis is illustrated by Scheme 1 below. Scheme 1: [ka]

[0086] The synthesis of S- and N-heterocyclic analogs works similarly, starting from the corresponding thianones and N-alkylpiperidones instead of tetrahydropyran-4-ones (Scheme 1). The S- and N-oxides are obtained from the corresponding thioethers or amines using known procedures, such as by treatment with ozone (Scheme 2). Scheme 2: [ka]

[0087] The electronic device is preferably disposed on a base substrate. Furthermore, the electronic device preferably includes a dielectric material disposed for electrical insulation of the electrode lines and / or the first / second electrodes.

[0088] The suitable materials for the base substrate and the dielectric are electrical insulators, where materials with good thermal conductivity are preferred.For example, large band gap semiconductors such as GaN or SiC are suitable.Further particularly suitable materials include SiO2, ZrO2, diamond and Al2O3.The materials for the dielectric material and the base substrate may be selected independently of each other, so that they may be the same or different materials.

[0089] In the case of a base substrate, the base substrate may be provided in the form of a further substrate coated with a layer forming the base substrate. For example, a wafer of highly doped p++ Si may be coated with a layer of SiO2, where the SiO2 layer forms the base substrate. Other suitable examples for materials suitable as further substrates are Si, Ge, diamond, graphite, graphene, fullerene, α-Sn, B, Se, Te; GaAs, GaP, InP, InSb, InAs, GaSb, CrN, HfN, GaN, TaN, TiN, MoN, NbN, WCN, WN, AlN, InN, VN, ZrN, AlxGa1-xAs and InxGa1-xNi, ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, Hg(1- x )Cd( x ) Te, BeSe, BeTe x and HgS; GaS, GaSe, GaTe, InS, InSe x and InTe, CuInSe2, CuInGaSe2, CuInS2 and CuInGaS2, SiC and SiGe, SeTe; Polythiophene, tetracene, pentacene, phthalocyanine, PTCDA, MePTCDI, quinacridone, indanthrone, flamenthrone, perinone, AlQ3, PEDOT:PSS and polyvinylcarbazole / TLNQ complex; Ta, Ti, Co, Cr, Mo, Nb, Ni, Pt, Ru, Au, Ag, Cu, Al, W and Mg; indium tin oxide, indium gallium oxide, InGa-α-ZnO, aluminum doped zinc oxide, tin doped zinc oxide, fluorine doped tin oxide and antimony tin oxide.

[0090] Preferably, the anchoring layer, if present, comprises a material selected from the group consisting of Ag, Al, Au, Co, Cr, Cu, Mo, Nb, Ni, Pt, Ru, Si, W, CrN, HfN, MoN, NbN, TiN, TaN, WN, WCN, VN and ZrN, Al2O3, HfO2, RuO2, SiO2, TiO2, and ZrO2.

[0091] A further aspect of the present invention is to provide a method for producing the electronic devices described herein.

[0092] A method for producing an electronic device including a plurality of cells as described herein comprises the steps of: A) providing a base substrate; B) forming a first electrode layer including electrode lines separated by a dielectric material on a base substrate; C) forming a molecular layer comprising a monolayer of organic molecules having anchoring groups connected to dipole units by means of conformationally flexible units; and D) Deposition of a further electrode layer (22) comprising electrode lines (30) separated by dielectric material (18).

[0093] Steps C) and D) are repeated until a desired number of layers of cells are formed, where the electrode lines of two adjacent electrode layers are rotated relative to each other such that the electrode lines of the two adjacent electrode layers cross each other. For example, the two adjacent electrode layers may be rotated 90° such that the two adjacent electrode layers are perpendicular to each other.

[0094] Preferably, step A) of providing a base substrate comprises a step of cleaning the substrate. The cleaning step may involve the use of one or more solvents and the use of an ultrasonic bath.

[0095] Preferably, a selector device in the form of a diode layer structure or a threshold switch structure is deposited after the formation of the first electrode layer according to step B) or the formation of the further electrode layer according to step D) and before the formation of the molecular monolayer according to step C). The diode layer structure preferably comprises at least a p-type doped semiconducting layer and an n-type doped semiconducting layer.

[0096] Preferably, the formation of the first electrode layer and / or the further electrode layer of electrode lines separated by a dielectric material comprises: - Deposition of electrode materials, - Removal of electrode material from non-electrode areas, - Deposition of dielectric materials, and - Planarization of the resulting layer structure down to the level of the electrode material. or, in the case of forming a first electrode layer, - Deposition of dielectric materials, - Removal of dielectric material from the electrode area, - Deposition of electrode materials, and - Planarization of the resulting layer structure down to the level of the dielectric material. The steps include:

[0097] Planarization is preferably accomplished using chemical mechanical polishing.

[0098] Preferably, the removal of electrode material in the non-electrode areas or the removal of dielectric material in the electrode areas is performed by photolithography to define the areas to be removed, and etching.

[0099] Suitable etching methods include dry etching methods, wet etching methods, or a combination thereof. Suitable dry etching methods include reactive ion etching and dry (plasma) etching techniques, including, for example, high pressure chemical etching, ion milling, or reactive ion etching.

[0100] Preferably, deposition of the dielectric and / or electrode materials is carried out using physical vapor deposition, chemical vapor deposition, chemical solution deposition, atomic layer deposition, microcontact printing or transfer printing, or sol-gel processes. Physical vapor deposition techniques include evaporation, sputtering, and epitaxy, among others.

[0101] Preferably, the coating with a molecular monolayer comprises - Pretreatment of the substrate to be coated for cleaning and activation, - dipping the substrate into a solution containing organic molecules to form a self-assembled monolayer of said molecules; - rinsing with an organic solvent; and - Annealing of the formed molecular monolayer wherein the substrate to be coated is the first electrode layer, the further electrode layer, or the surface of a selector device.

[0102] As an alternative to dip coating, spin coating may be used to form the self-assembled monolayer.

[0103] The solution used for dipping is preferably a mixture of molecular phosphonic acid and a solvent for forming a self-assembled monolayer. The concentration of molecular phosphonic acid is preferably 0.01 mM to 100 mM (millimolar concentration, 10 -3 mol / L), and preferably in the range of 0.1 mM to 10 mM.

[0104] Suitable solvents for preparing the solution and for rinsing include alcohols, ketones, nitriles, esters, ethers and dipolar aprotic solvents.

[0105] Preferred alcohols include ethanol, isopropanol. Suitable ketones include acetone, ethyl methyl ketone (EMK) and cyclohexanone. Suitable nitriles are, for example, acetonitrile. Suitable esters include propylene glycol methyl ether (PGME), propylene glycol methyl ether acetate (PGMEA), gamma-butyrolactone (GBL). Suitable ethers include tetrahydrofuran (THF), dioxane, diglyme, anisole. Suitable dipolar aprotic solvents include N-methyl-2-pyrrolidone (NMP), dimethylformamide (DMF), 1,3-dimethyl-2-imidazolidinone (DMEU), N,N'-dimethylpropyleneurea (DMPU), dimethylsulfoxide (DMSO).

[0106] In the case of preparing a solution for dipping, further suitable solvents include chlorobenzene, 1,2-dichlorobenzene, 1,2,4-trichlorobenzene, 1,2-difluorobenzene, chloroform and dichloromethane.

[0107] Preferably, the annealing is carried out at a temperature in the range of 50° C. to 250° C. for a time period of 1 min to 60 min.

[0108] Preferably, prior to dipping the substrate into the solution, a pretreatment is performed using a UV-ozone treatment. The pretreatment is preferably performed using UV light having a wavelength in the range of 150 nm to 350 nm, where the substrate has a temperature in the range of 50° C. to 300° C. The intensity of the UV light is preferably less than 10 μW / cm 2 ~200μW / cm 2 The ozone used in pretreatment is obtained by reacting oxygen present in the environment with UV light.

[0109] Preferably, after dipping and / or rinsing, the substrate is blown dry, for example by using a stream of nitrogen.

[0110] A further aspect of the invention is the use of one of the described electronic elements or an electronic element obtained using one of the described methods as a memory device, in which the cells of the electronic element serve as memory cells, and / or as a neural network device, in which the cells of the electronic element serve as synapses.

[0111] When the electronic element is used as a memory device, each of the cells serves as a memory cell, which can be individually addressed, inter alia, for reading / writing, by applying appropriate signals to two orthogonal electrode lines associated with each cell, which serve as bit and word lines.

[0112] Preferably, the cells have memristive properties, where the cells can have a high resistance state where current flow is essentially blocked, and a low resistance state where current flow is permitted. By exploiting these properties, a path for an electronic signal through the electronic element can be configured by selectively adjusting the state of certain cells of the electronic element. This is particularly useful for electronic elements configured as neural network devices. For example, the signal / current path can evolve in a percolation-like manner depending on the excitation history, patterns and parameters, such as bias voltage, pulse time / off pulse time, compliance current, etc. In such configurations, the electronic element is preferably contacted only by a small number of comprehensive external electrical probes, in contrast to the conventional individual addresses of memory devices with word and bit lines.

[0113] Preferably, an electronic device is formed having one of the proposed electronic elements interfaced to a general CMOS circuitry for processing input / weight / output information data.

[0114] Such electronic devices configured as neural network devices are particularly useful for neuromorphic sensing to process image / video data.

[0115] The drawings show: FIG. 1 is a schematic cross-sectional view of an electronic device having a three-dimensional crossbar arrangement of cells; 2a-2l show top and cross-sectional views, respectively, of the electronic device of FIG. 1 at different stages of production; and Figure 3. Schematic of the cell.

[0116] Figure 1 illustrates in schematic cross-section one embodiment of an electronic device 10 having a plurality of cells 100. The schematic in Figure 1 shows only a portion of an overall three-dimensional crossbar arrangement of cells 100. The electronic device 10 may be further extended toward each of the three dimensions and may encompass many more than the six cells 100 depicted.

[0117] The electronic device 10 of Figure 1 comprises a multi-level layer structure, where a first level comprises, in that order, a base substrate 12, a first electrode layer 14, a molecular layer 20, and a further electrode layer 22. The base substrate 12 is preferably electrically insulating while having good thermal conductivity.

[0118] The first electrode layer 14 includes electrode wires 30 separated by a dielectric material 18. The electrode wires 30 are made from an electrically conductive electrode material 16. Two electrode wires 30 are visible in Figure 1; however, the electronic component 10 may include multiple electrode wires 30.

[0119] The molecular layer 20, in the embodiment shown in FIG. 1, is in direct contact with the first electrode layer 14, and in particular with the electrode lines 30. The molecular layer 20 is a self-assembled monolayer of organic molecules. The organic molecules have anchoring groups connected to dipole units by means of conformationally flexible units. The anchoring groups are in contact with the first electrode layer 14, and in particular with the conductive material 16 forming the electrode lines 30, and thus anchor the molecules to the surface of the first electrode layer 14. In further embodiments, the electronic device 10 may include an anchoring layer located between the first electrode layer 14 and the molecular layer 20.

[0120] The further electrode layer 20 has a similar setup to that of the first electrode layer 14, but rotated by 90°. Thus, rotated electrode lines 31 are formed in the further electrode layer 20 which are electrically insulated by the dielectric material 18 and perpendicular to the electrode lines 30. In other embodiments, the angle of rotation may be selected in the range of 45° to 135° to form crossed electrode lines 31, 30.

[0121] The cells 100 are located at the intersection between two orthogonal electrode wires 30, 31, specifically, at the intersection between the electrode wire 30 and the rotated electrode wire 31. Each cell 100 includes a first electrode 102, a portion 104 of the molecular layer 20, and a second electrode 106. In the embodiment of Figure 1, a portion of the electrode wire 30 serves as the first electrode 102 and a portion of the rotated electrode wire 31 serves as the second electrode 106.

[0122] This structure may be extended to further levels, where the second level of the structure of FIG. 1 further comprises another molecular layer 20' and another further electrode layer 22', in that order. The third level of the structure comprises another molecular layer 20'' and another further electrode layer 22''. In FIG. 1, the second level cells 100' and the third layer cells 100'' are marked.

[0123] With each addition of a molecular layer 20 and further electrode layer 22 , the structure is expanded to further levels, and thus further layers, of the cell 100 .

[0124] An example embodiment of the production of an electronic device is further described with respect to Figures 2a-2l, in which the lower part shows a top view and the upper part shows a cross-sectional view along dashed line A as viewed from the side.

[0125] Figure 2a shows a provided base substrate 12. In a first step i), an insulating layer in the form of a dielectric material 18 is coated onto the substrate 12. FIG. 2 b shows the base substrate 12 coated with a dielectric material 18 .

[0126] In a subsequent step ii), trenches are formed in the layer of dielectric material 18. The trenches define electrode areas 34 in which electrodes will be formed in a subsequent third step iii), as shown in Fig. 2c. The trenches depicted in Fig. 2c are arranged in a first direction and parallel to one another.

[0127] Figure 2d shows that electrode lines 30 have been formed by deposition of electrode material 16 in electrode areas 34 defined by the trenches prepared in step ii) and subsequent planarization down to the level of dielectric material 18. The formed electrode lines 30 are aligned in a first direction and parallel to each other.

[0128] In a further step iv), a molecular layer 20 comprising a monolayer of organic molecules is coated onto the surface of the dielectric material 18 and the electrode material 16. Prior to coating, the surface is preferably cleaned and activated by UV-ozone treatment. Coating may for example be performed by dipping the formed structure into a solution containing the organic molecules. Figure 2e) shows the molecular layer 20 formed on the previously formed structure.

[0129] In a subsequent step v), a further layer of conductive material 16 is deposited onto the structure to form a base for a further layer of conductive electrodes. After deposition, the conductive material 16 is selectively removed to form rotated electrode lines 31 arranged in a second direction orthogonal to the first direction of the electrode lines 30, depicted in FIG. 2f.

[0130] The portion of molecular layer 20 located between the intersection of electrode wire 30 and rotated electrode wire 31 , and the electrode wires 30 , 31 acting as first and second electrodes, form a cell 100 .

[0131] Figure 2g shows the structure after a further step vi), in which a further layer of dielectric material 18 is deposited and subsequently planarised down to the level of the rotated electrode lines 31 formed in the previous step.

[0132] In step vii), a further molecular layer 20 is coated onto the structure as shown in figure 2h.

[0133] Figure 2i shows the structure after a subsequent step viii), in which a further layer of conductive material 16 is deposited and selectively removed in the non-electrode areas 32. After removal of the conductive material 16 in the non-electrode areas 32, further electrode lines 30 are formed, arranged along the first direction.

[0134] In a subsequent step ix), the trenches formed by the removal of the conductive material 16 and the molecular layer 20 in the non-electrode areas 32 are filled with a dielectric material 18. The deposition of the dielectric material 18 is followed by planarization down to the level of the conductive material 16, as shown in figure 2j.

[0135] FIG. 2k shows the structure after deposition of a further molecular layer 20 in step x). FIG. 2l shows the structure after deposition and selective removal of a further layer of conductive material 16 in step xi) to form further rotated electrode lines 31.

[0136] By repeating steps vi) to xi), further levels can be obtained with further cells 100 located at the intersections between the electrode line 30 and the rotated electrode line 31.

[0137] 3 shows the layer structure of the cell 100 according to the second embodiment. The cell 100 of the first embodiment as shown in FIG. 1 includes three layers, namely, a first electrode 102, a portion 104 of the molecular layer 20, and a second electrode 106, while the cell 100 of the second embodiment as depicted in FIG. 3 includes an additional selector device 108.

[0138] Thus, the cell 100 of the second embodiment includes, in order, a first electrode 102, a selector device 108, a portion 104 of the molecular layer 20, and a second electrode 106. The selector device 108 may itself be configured as a layered structure including one or more layers. For example, the selector device 108 may be configured as a diode including an n-type doped semiconducting layer and a p-type doped semiconducting layer.

[0139] Synthesis Example Synthesis Example 1 Step 1: 4-Bromo-2,3-difluorophenyl benzyl ether [ka]

[0140] A mixture of 4-bromo-2,3-difluorophenol (78.6 g, 0.376 mol), acetone (786 ml), benzyl chloride (50 g, 0.395 mol) and potassium carbonate 325 mesh (207.9 g, 1.50 mol) was heated to reflux for 16 h, the reaction was allowed to cool to room temperature and then filtered. The filtrate was evaporated to dryness in vacuo leaving an off-white solid (121.6 g). The solid was dissolved in isopropanol (500 ml) at 65° C. then allowed to cool and stirred overnight to give a white suspension. The solid was collected by vacuum filtration, washed with isopropanol (2×50 ml) and dried to give 4-bromo-2,3-difluorophenyl benzyl ether as a crystalline white solid, mp 70-73° C. 1 H NMR (400 MHz, CDCl3) δ ppm 5.16 (2H, s), 6.71 (1H, ddd, J=9.2, 7.5, 2.1 Hz), 7.19 (1H, ddd, J=9.2, 7.0, 2.5 Hz), 7.31 - 7.48 (5H, m). 13C NMR (101 MHz, CDCl3) δ ppm 71.68, 101.04 (d, J=18.3 Hz), 111.08 (d, J=2.9 Hz), 126.28 (d, J=4.4 Hz), 127.34, 128.34, 128.64, 135.60, 142.14 (dd, J=254.0, 14.8 Hz), 147.57 (dd, J=8.1, 2.9 Hz), 148.65 (dd, J=249.7, 11.8 Hz). 19 F NMR (376 MHz, CDCl3) δ ppm -128.7 (d, J=20.5 Hz), -135.8 (d, J=20.5 Hz).

[0141] Step 2: 4-(4-benzyloxy-2,3-difluoro-phenyl)-3,6-dihydro-2H-pyran [ka]

[0142] 4-Bromo-2,3-difluorophenylbenzyl ether (20.0 g, 66.9 mmol) was dissolved in dry THF (200 ml) under nitrogen and cooled to -85°C. n-BuLi (2.5 M in hexanes, 17.0 ml, 73.6 mmol) was added dropwise over 30 min. After 1 h at -70°C, the reaction was cooled to -85°C and 4-oxotetrahydropyran (8.0 g, 80.2 mmol) was added dropwise over 10 min. The cooling bath was removed and the reaction was allowed to warm to room temperature and stirred overnight. The reaction was cooled to 10°C and then water (30 ml) was added slowly. After stirring for 30 min, the mixture was partitioned between ethyl acetate (200 ml) and water (100 ml). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (2 x 100 ml). The combined organic phases were dried (MgSO4) and concentrated to dryness in vacuo to leave a pale yellow solid. The solid was dissolved in dichloromethane and applied to a pad of silica (40-63μ, 70 g) packed in dichloromethane.

[0143] The pad was eluted with dichloromethane until all the faster running 1-(benzyloxy)-2,3-difluorobenzene reduction products had been removed. The pad was then eluted with ethyl acetate which removed the major reaction product of the tertiary alcohol. The ethyl acetate eluate was evaporated in vacuo to leave a pale yellow solid. The solid was dissolved in toluene (225 ml) at 40° C. and then p-toluenesulfonic acid monohydrate (0.93 g, 4.9 mmol) was added. The solution was heated to 70° C. for 1 h and cooled to room temperature. The reaction mixture was washed with water (3×30 ml), then dried (MgSO4) and evaporated to an off-white solid which was recrystallized from methanol (195 ml) to give 4-(4-benzyloxy-2,3-difluoro-phenyl)-3,6-dihydro-2H-pyran as colorless crystals, mp 103-107° C. 1 H NMR (400 MHz, CDCl3) δ ppm 2.40 - 2.55 (2 H, m), 3.92 (2 H, t, J=5.4 Hz), 4.32 (2 H, m), 5.16 (2 H, s), 5.95 - 6.07 (1 H, m), 6.75 (1 H, ddd, J=9.0, 7.4, 1.9 Hz), 6.90 (1 H, td, J=8.4, 2.3 Hz), 7.30 - 7.53 (5 H, m). 13 C NMR (100.6 MHz, CDCl3) δ ppm 28.23 (d, J=2.2 Hz), 64.21, 65.53, 71.50, 109.87 (d, J=3.7 Hz), 121.45 (t, J=4.5 Hz), 123.37 (d, J=10.4 Hz), 126.23 (d, J=5.9 Hz), 127.30, 128.17, 128.58, 129.64 (t, J=2.2 Hz), 136.05, 141.79 (dd, J=249.7, 15.6 Hz), 146.89 (dd, J=8.5, 3.5 Hz), 149.10 (dd, J=250.6, 13.2 Hz). 19 F NMR (376 MHz, CDCl3) δ ppm -158.23 (d, J=19 Hz), -139.63 (d, J=19 Hz).

[0144] Step 3: 2,3-Difluoro-4-tetrahydropyran-4-yl-phenol [ka]

[0145] 4-(4-benzyloxy-2,3-difluoro-phenyl)-3,6-dihydro-2H-pyran (105 g, 34.7 mmol) was dissolved in a mixture of isopropanol (210 ml) and THF (31.5 ml) by sonication and then hydrogenated over 5% Pd / C (0.53 g, 50% wet) at 5 bar pressure for 18 h, at which point no further hydrogen was picked up. After releasing excess hydrogen, degassing and backfilling with nitrogen, the solution was filtered through a GF / F 0.7μ filter to remove the catalyst and the filtrate was concentrated in vacuo to give 2,3-difluoro-4-tetrahydropyran-4-yl-phenol as an off-white product and used directly without further purification, mp 143-147° C. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.53 - 1.77 (4 H, m), 2.85 - 3.03 (1 H, m), 3.43 (2 H, td, J=11.5, 2.6 Hz), 3.83 - 4.01 (2 H, m), 6.73 (1 H, td, J=8.4, 2.0 Hz), 6.90 (1 H, td, J=8.4, 2.2 Hz), 10.14 (1 H, br. s.). 13C NMR (100.6 MHz, DMSO-d6) δ ppm 32.46, 33.77, 67.37, 112.75 (m), 121.31 (dd, J=5.9, 4.5 Hz), 123.98 (dd, J=11.7, 1.5 Hz), 139.81 (d, J=242, 14.7 Hz), 144.76 (dd, J=8.8, 2.9 Hz), 148.90 (dd, J=243, 10.5 Hz). 19 F NMR (376 MHz, DMSO-d6) δ ppm -161.89 (d, J=20.5 Hz), -144.54 (d, J=20.5 Hz).

[0146] Step 4: 4-[4-(11-diethoxyphosphorylundecaoxy)-2,3-difluoro-phenyl]tetrahydropyran [ka]

[0147] 2,3-Difluoro-4-tetrahydropyran-4-yl-phenol (5.0 g, 23.3 mmol) was dissolved in butanone (65 ml) under nitrogen with stirring, then diethyl (11-bromoundecyl)-phosphonate (11.3 g, 30.3 mmol) and anhydrous potassium carbonate 325 mesh (12.9 g, 93.4 mmol) were added. The mixture was heated under reflux for 18 hours. The reaction was cooled to 30° C. and filtered. The combined filtrates were evaporated in vacuo, and the resulting orange oil (14.3 g) was applied to a silica column prepared with 40-63μ silica gel (140 g) packed in dichloromethane. The column was eluted with an increasing gradient of 0-40% ethyl acetate in dichloromethane and the product rich fractions (10-30% ethyl acetate) were combined and evaporated to a colorless oil (9.6 g) that was used directly without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.21 - 1.52 (20 H, m), 1.52 - 1.66 (2 H, m), 1.66 - 1.89 (8 H, m), 2.94 - 3.14 (1 H, m), 3.55 (2 H, td, J=11.7, 2.3 Hz), 3.95 - 4.21 (8 H, m), 6.63 - 6.75 (1 H, m), 6.85 (1 H, td, J=8.2, 2.3 Hz). 13 C NMR (101 MHz, CDCl3) δ ppm 16.39, 16.45, 22.34 (d, J=5.1 Hz), 25.62 (d, J=140 Hz), 25.81, 29.02, 29.11, 29.24, 29.27, 29.42, 30.45, 30.62, 32.64, 34.12, 61.31 (d, J=5.9 Hz), 68.20, 69.78, 109.47 (d, J=2.9 Hz), 120.41 (t, J=5.1 Hz), 126.12 (d, J=11.7 Hz), 141.40 (dd, J=247, 14.7 Hz), 146.74 (dd, J=8.1, 2.9 Hz), 149.35 (dd, J=246, 10.3 Hz). 19 F NMR (376 MHz, CDCl3) δ ppm -159.28 (d, J=20.5 Hz), -143.542 (d, J=20.5 Hz). 31 P NMR (162 MHz, CDCl3) δ ppm 32.64.

[0148] Step 5: 11-(2,3-difluoro-4-tetrahydropyran-4-yl-phenoxy)undecylphosphonic acid [ka]

[0149] 4-[4-(11-diethoxyphosphorylundecaoxy)-2,3-difluoro-phenyl]tetrahydropyran (9.2 g, 93.5% w / w, 17.0 mmol) was dissolved in dichloromethane (138 ml) with stirring and bromotrimethylsilane (28.1 g, 182.3 mmol) was added over 10 min at ambient temperature, then stirred overnight. The mixture was evaporated in vacuum and the resulting oil was redissolved in dichloromethane (125 ml) and methanol (125 ml) and then reevaporated in vacuum to an oil. The oil was redissolved in dichloromethane (75 ml) and methanol (75 ml) and then slowly concentrated in vacuum to a final volume of approximately 40 ml to remove dichloromethane. The solution was then cooled to -15°C in an ice / acetone bath for 1 h, leading to the formation of a white precipitate. The solid was filtered off and dried under vacuum at 50° C. overnight to give an off-white solid. The solid was dissolved in THF (50 ml) and heptane (50 ml) was added.

[0150] The solution was concentrated in vacuo at 400 mbar at 45° C. to slowly remove THF until a solid began to precipitate. Distillation was stopped and the mixture was allowed to stir at ambient temperature for 90 min, then the solid was collected by vacuum filtration and washed with heptane (3×10 ml). Drying under vacuum at 50° C. overnight gave 11-(2,3-difluoro-4-tetrahydropyran-4-yl-phenoxy)undecylphosphonic acid as a colorless solid, mp 94-98° C. 1H NMR (400 MHz, THF-d8) δ ppm 1.27 - 1.43 (12 H, m), 1.43 - 1.52 (2 H, m), 1.53 - 1.69 (6 H, m), 1.69 - 1.83 (4 H, m), 3.02 (1 H, tt, J=11.9, 3.8 Hz), 3.46 (2 H, td, J=11.6, 2.1 Hz), 3.95 (2 H, dd, J=11.0, 3.9 Hz), 4.02 (2 H, t, J=6.5 Hz), 6.77 - 6.87 (1 H, m), 6.94 (1 H, td, J=8.3, 2.2 Hz). 13 C NMR (101 MHz, THF-d8) δ ppm 23.76, 23.80, 26.92, 27.90 (d, J=142 Hz), 30.19, 30.28, 30.37, 30.50, 30.60 (br.), 31.60, 31.77, 33.84, 35.41, 68.77, 70.39, 110.46 (d, J=2.2 Hz), 121.71 (t, J=5.1 Hz), 127.23 (d, J=13.2 Hz), 142.21 (dd, J=247, 14.7 Hz), 147.93 (dd, J=8.1, 2.9 Hz), 150.31 (dd, J=244, 10.3 Hz). 19 F NMR (376 MHz, THF-d8) δ ppm -162.90 (d, J=20.5 Hz), -147.28 (d, J=20.5 Hz). 31 P NMR (162 MHz, THF-d8) δ ppm 30.71. MS (ES negative): Found m / z [MH]- 447.2108 (28%); Requires C22H34F2O5P- m / z 447.21

[0151] Application Test Test chips were prepared from compound A according to the invention (Synthesis Example 1) and, for comparison, from compounds B and C from the prior art: [ka]

[0152] Preparation of test chips: Silicon chips (Siegert wafer substrate lot 19335; 8 × 8 × 0.5 mm; p-Si / SiO2 (~0.5 mm) / SiAlOx (1-2 nm) / Al2O3 (2 nm); conditioned by oxygen plasma treatment (<0.2 mbar O2, 1 min, 200 W) were immersed in a 1 mM solution of the corresponding phosphonic acid (A, B or C) in THF for 24 h. The chips were removed from the bath, blown dry under nitrogen, and then heated on a hotplate at 120 °C under nitrogen for 1 h. The chips were then washed three times with ethanol and dried on a hotplate at 120 °C under nitrogen for 5 min.

[0153] Water contact angle (WCA) measurement The water contact angle of the test chips with A, B or C is determined by known methods. It is found that the tetrahydropyran derivative A induces a much smaller contact angle than B or C, which suggests a strongly increased surface energy. In fact, the WCA resembles that of typical oxide materials, making it well compatible with standard photoresist formulations. As the comparison of compounds B and C shows, the mere omission of the terminal alkyl chain results in only a very modest decrease in the WCA. [Table 1]

[0154] Adhesion Test Onto the SAM modified chips 1 and 2, chromium (30 nm) was first sputtered, followed by gold (200 nm). The samples were then subjected to a "scotch tape adhesion test" according to DIN EN ISO 2409 (ASTM D 3002, ASTM D 3359), available at https: / / www.astm.org / Standards / D4541.htm: The metal-sputtered samples are scratched with a grid cutter (BYK-Gardner Multi-Cut tool; cutting distance 1 mm). Permacel tape is then applied and removed again. Test chip 1 treated with compound 7 remains >90% intact, whereas chip 2 is only 30% intact.

[0155] The following compounds can be obtained in the same manner as in Synthesis Example 1. Compounds of formula IA-1a [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6] [Table 2-7] [Table 2-8] [Table 2-9]

Table 2-10

Table 2-11

Table 2-12

[0156] Compounds of formula IA-1b

Table 3-1

Table 3-2

Table 3-3

Table 3-4

Table 3-5

Table 3-6

Table 3-7

Table 3-8

Table 3-9

Table 3-10

[0157] Compounds represented by formulae IA-2-1 to IA-2-7 [Table 4]

[0158] Compounds with alternative anchoring groups can be obtained analogously by procedures known from the prior art, for example as follows: [ka]

[0159] List of Reference Numbers 10 Electronic elements 12 Base board 14 First electrode layer 16 Electrode materials 18 Dielectric Materials 20 molecular layers 22 Further electrode layers 30 electrode wire 31 Rotated electrode wire 32 Non-electrode area 34 Electrode Area 100 cells 102 First electrode 104 (part of molecular layer) 106 Second electrode 108 Selector Device

Claims

1. An electronic device (10) comprising a plurality of cells (100) arranged in a three-dimensional array of cells (100), wherein the cells (100) are located at the intersection between two intersecting electrode lines (30, 31), Each cell (100) comprises, in this order, a first electrode (102), a part (104) of a molecular layer (20), and a second electrode (106), wherein the molecular layer (20) is a self-assembled monolayer of organic molecules having an anchoring group connected to a dipole unit using a conformationally flexible unit, characterized in that said electronic device (10).

2. The electronic device (10) according to claim 1, characterized in that each cell (100) further comprises a diode, threshold switch or transistor as a selector device (108).

3. The electronic device (10) according to claim 2, characterized in that the selector device (108) is configured as a further self-assembled monolayer of organic molecules or as an inorganic diode arranged between the molecular layer and the first or second electrode.

4. The electronic device (10) according to any one of claims 1 to 3, characterized in that the first electrode (102) and / or the second electrode (106) of each cell (100) is made of metal, conductive alloy, conductive ceramic, semiconductor, conductive oxide material, conductive or semiconductive organic molecule, or layered conductive 2D material.

5. The organic molecule for forming the self-assembled monolayer has the formula I T-Z T -(A 1 -Z 1 ) r -B-(Z 2 A 2 ) s -(Z 3 A 3 ) t -(Z 4 A 4 ) u -Sp-G (I) selected from one or more compounds represented by wherein T is the following group: a) a saturated or partially unsaturated aliphatic ring having 3 to 10 members, wherein at least one -CH 2 - group is replaced by -O-, -S-, -S(O)-, -SO 2 -, -NR x - or -N(O)R x -, or at least one -CH= group therein is replaced by -N=, b) a straight-chain or branched alkyl or alkoxy each having 1 to 20 C atoms, wherein one or more CH 2 groups in these radicals are each, independently of one another, -C≡C-, -CH=CH-, 【Chemical Formula 1】 -O-, -S-, -CF 2 O-, -OCF 2 -, -CO-O-, -O-CO-, -SiR 0 R 00 -, -NH-, -NR 0 - or -SO 2 - such that O atoms are not directly linked to each other, may be replaced, and one or more H atoms therein may be replaced by halogen, CN, SCN or SF 5 (wherein R , R 0 , R 00 are the same or different and represent an alkyl or alkoxy radical having 1 to 15 C atoms, and in addition one or more H atoms therein may be replaced by halogen), c) a diamondoid radical, preferably derived from a lower diamondoid, most preferably selected from the group consisting of adamantyl, diamantyl, and triamantyl, wherein one or more H atoms therein can be replaced by F, alkyl, alkenyl or alkoxy having up to 12 C atoms which may optionally be fluorinated in each case, especially 【Chemical Formula 2】 selected from the group of radicals consisting of, Z T , Z 1 , Z 2 and Z 4 is, for each occurrence, the same or different and is 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 ) n1 -, -(CF 2 ) n2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CH=CH-,-CF=CF-, -CF=CH-, -CH=CF-, -(CH 2 ) n3 O-, -O(CH 2 ) n4 -, -C≡C-, -O-, -S-, -CH=N-, -N=CH-, -N=N-, -N=N(O)-, -N(O)=N- or -N=C-C=N-, where n1, n2, n3, n4 are the same or different and are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, Z 3 is -O-, -S-, -CH 2 (-), -C(O)-, -CF 2 (-), -CHF-, -C(R x ) 2 -, -S(O)- or -SO 2 (-), A 1 , A 2 and A 4 is, for each occurrence, the same or different and represents an aromatic ring, heteroaromatic ring, alicyclic ring or heteroaliphatic ring having 4 to 25 ring atoms, which may also contain a fused ring and may be mono- or polysubstituted by Y, A 3has 5 to 25 ring atoms, may also contain fused rings, and Y C represents an aromatic or heteroaromatic ring which may be mono- or polysubstituted by Y Y, each occurrence being the same or different, is F, Cl, CN, SCN, SF 5 , or a linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, optionally fluorinated in each case, preferably F or Cl Y C has one of the meanings of Y or represents a cycloalkyl or alkylcycloalkyl having 3 to 12 C atoms each, preferably methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, methoxy or trifluoromethoxy B is 【Chemical Formula 3】 and the groups may be directed in both directions L 1 to L 5 are, independently of one another, F, Cl, Br, I, CN, SF 5 , CF 3 or OCF 3 , preferably Cl or F, where L 3 may alternatively also represent H Sp represents a spacer group or a single bond G is -OH, -SH, -SO 2 OH, -OP(O)(OH) 2 , -PO(OH) 2 , -C(OH)(PO(OH) 2 ) 2 , -COOH, -Si(OR x ) 3 , -SiCl 3 , -CH=CH 2 , -POCl 2 , -CO(NHOH), -CO(NR 0 OH), -Si(NMe 2 ) 3 ; -O-C(O)-OR V 、-O-C(O)-Si(OR V ) 3 、-PO(OR V ) 2 または-SO 2 OR V 、 or a straight-chain or branched alkyl having 1 to 12 carbon atoms, wherein one, two or three non-geminal H atoms therein are replaced by OH; R 0 、R 00 、R x are the same or different and represent a straight-chain or branched alkyl having 1 to 6 carbon atoms, R V represents a straight-chain or branched alkyl having 1 to 12 carbon atoms, and r, s, t and u are the same or different and are 0, 1 or 2 The electronic element (10) according to any one of claims 1 to 3, characterized in that.

6. The group T in formula I represents a saturated or partially unsaturated aliphatic ring having 3 to 10 members, wherein at least one -CH 2 - group is replaced by -O-, -S-, -NR x -, -S(O)-, -SO 2 -, -NR x - or -N(O)R x -, or at least one -CH= group therein is replaced by -N=, the electronic element (10) according to claim 5.

7. Represented by formula IA, T-(Z 1 -A 1 ) r -B-(Z 2 A 2 ) s -(Z 3 A 3 ) t -(Z 4 A 4 ) u-Sp-G (IA) Among them T represents a 3- to 10-membered saturated or partially unsaturated aliphatic ring, and at least one -CH 2 - group therein is replaced by -O-, -S-, -NR x -, -S(O)-, -SO 2 -, -NR x - or -N(O)R x -, or at least one -CH= group therein is replaced by -N=, and the group Z 1 , A 1 , B, Z 2 , A 2 , Z 3 , A 3 , Z 4 , A 4 , Sp, G and the parameters r, s, t and u have the meanings defined in claim 5, a compound.

8. The compound is selected from the group consisting of formulas IA-1a to IA-1f, T-Z T -B-Sp-G IA-1a T-Z T -(A 1 -Z 1 )-B-Sp-G IA-1b T-Z T -(A 1 -Z 1 ) 2 -B-Sp-G IA-1c T-Z T -B-(Z 2 -A 2 )-Sp-G IA-1d T-Z T -B-(Z 2 -A 2 ) 2 -Sp-G IA-1e T-Z T -(A 1 -Z 1 )-B-(Z 2 -A 2 )-Sp-G IA-1f Among them, T, Z T , A 1, A 2 , B, Z 1 , Z 2 , Sp and G have the meanings given in claim 7, the compound according to claim 7.

9. T is 【Chemical Formula 4】 represents, in which R x represents alkyl having 1 to 6 C atoms, A 1 and A 2 are the same or different, 【Chemical Formula 5】 represents, B is 【Chemical Formula 6】 represents, L 1 and L 2 are, independently of one another, CF 3 , Cl or F, L 3 represents H or F, Y 1 and Y 2 are, independently of one another, H, Cl or F, Z 1 , Z 2 , Z T are, independently of one another, a single bond, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 - or -CH 2 CH 2 -, Sp represents a branched or unbranched 1,ω-alkylene having 1 to 12 C atoms, and G is -OP(O)(OH) 2 , -PO(OH) 2 , or -COH(PO(OH) 2 ) 2 represents, the compound according to claim 7.

10. The compound is a compound represented by formula IA-2 T-Z T -(A 1 -Z 1 ) r -B-Z 3 -A 3 -(Z 4 -A 4 ) u -G IA-2 selected from, wherein the groups and parameters occurring therein have the meanings given in claim 7, the compound according to claim 7.

11. T is 【Chemical Formula 7】 represents, wherein R x represents alkyl having 1 to 6 carbon atoms, A 1 and A 4 are the same or different and 【Chemical Formula 8】 represents, A 3 -Z 3 is 【Chemical Formula 9】 represents, B is 【Chemical Formula 10】 represents, Z T represents a single bond, -CH 2 O-, -OCH 2 - or -CH 2 CH 2 -, L 1 and L 2 are the same or different and represent F, CF 3 or Cl, Y 1 and Y 2 are the same or different and have one of the meanings given above for Y and preferably represent H, F or Cl, Y 3 and Y 4is the same or different and is Y 1 and Y 2 has one of the meanings given above for Y, and preferably represents methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methoxy, trifluoromethyl, trifluoromethoxy, or trifluoromethylthio, Z 3 represents CH 2 or O, Z 1 Z, 2 independently of one another, represents a single bond, -C(O)O-, -OC(O)-, -CF 2 O-, -OCF 2 -, -CH 2 O-, OCH 2 -, or -CH 2 CH 2 -, G represents -PO(OH) 2 , or -COH(PO(OH) 2 ) 2 and r and u are independently 0, 1, or 2, A compound represented by formula IA-2 according to claim 10.

12. A method for the production of an electronic device (10) comprising a plurality of cells (100) according to claim 1, comprising the following: A) providing a base substrate (12), B) forming a first electrode layer (14) comprising electrode lines (30, 31) separated by a dielectric material (18), C) forming a molecular layer (20) comprising a monolayer of organic molecules having an anchoring group connected to a dipole unit using a conformationally flexible unit, and D) depositing a further electrode layer (22) comprising electrode lines (30, 31) separated by a dielectric material (18) including, where steps C) and D) are repeated until a desired number of layers of the cell (100) are formed, and where the electrode lines (30, 31) of two adjacent electrode layers (14, 22) are rotated relative to each other such that the electrode lines (30, 31) of the two adjacent electrode layers (14, 22) cross each other, said method. Claim 13 A selector device (108) in the form of a diode layer structure or a threshold switch structure is deposited after the formation of the first electrode layer (14) according to step B) or after the formation of a further electrode layer (22) according to step D) and before the formation of the molecular monolayer (20) according to step C), the method according to claim 12. Claim 14 The formation of the first electrode layer (14) and / or a further electrode layer (22) with electrode lines (30, 31) separated by a dielectric material (18) comprises - deposition of an electrode material (16), - removal of the electrode material (16) from the non-electrode area (32), - deposition of a dielectric material (18), - flattening of the resulting layer structure to a level of the electrode material (16), or, in the case of the formation of the first electrode layer (14), - deposition of a dielectric material (18), - removal of the dielectric material (18) from the electrode area (34), - deposition of an electrode material (16), - flattening of the resulting layer structure to a level of the dielectric material (18), characterized in that it comprises the steps of, the method according to claim 12 or 13. Claim 15 The removal of the electrode material (16) in the non-electrode (32) area or the removal of the dielectric material (18) in the electrode area (34) is carried out by a photolithography method defining the area to be removed and by etching, the method according to claim 14. Claim 16 The material of the dielectric material (18) and / or the base substrate (12) is SiO 2 , ZrO 2 , diamond, Al 2 O 3 or GaN, and the method according to claim 12 is characterized in that.

17. The deposition of the dielectric material (18) and / or the electrode material (16) is carried out by physical vapor deposition, chemical vapor deposition, chemical solution deposition, atomic layer deposition, microcontact printing or transfer printing, or the sol-gel method, and the method according to claim 14 is characterized in that.

18. Coating with the molecular monolayer (20) - Pretreatment of the substrate to be coated for cleaning and activation, - Dipping the substrate into a solution containing organic molecules for forming a self-assembled monolayer of the molecules, - Rinsing with an organic solvent, and - Annealing of the formed molecular monolayer (20) including the steps, where the substrate to be coated is the surface of the first electrode layer (14), the further electrode layer (22), or the selector device (108), and the method according to claim 12 is characterized in that.

19.

20. The pretreatment is carried out using UV-ozone treatment, and the method according to claim 18 is characterized in that.

21. The solution is a mixture of a phosphonic acid of the molecules for forming a self-assembled monolayer and a solvent, and the method according to claim 18 is characterized in that.

22. The organic molecules for forming a self-assembled monolayer are selected from one or more compounds represented by formula I as defined in claim 5, and the method according to claim 18 is characterized in that.

23. The method according to claim 18, characterized in that annealing is carried out at a temperature in the range of 50 °C to 250 °C for a time between 1 minute and 60 minutes.

23. Use of the electronic device (10) according to claim 1, as a memory device, wherein the cell (100) of the electronic device (10) serves as a memory cell, and / or as a neural network device, wherein the cell (100) of the electronic device (10) serves as a synapse, or use of the electronic device (10) obtained by using the method according to claim 12.

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