ELECTRONIC ELEMENT COMPRISING A PLURALITY OF CELLS ARRANGED IN A THREE DIMENSIONAL ARRAY OF CELLS AND METHOD FOR PRODUCING SUCH AN ELECTRONIC DEVICE

Abstract

An electronic element (10) comprising a plurality of cells (100) arranged in a three dimensional array of cells (100) is provided, wherein the cells (100) are located at crossings between two crossed electrode lines (30, 31). Each cell (100) of the electronic component (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 dipolar unit by means of a conformationally flexible unit.

Further aspects of the invention relate to a method and a compound for producing such an electronic element (10) and the use of such an electronic element (10).

Claims

1. Electronic element (10) comprising a plurality of cells (100) arranged in a three dimensional array of cells (100), wherein the cells (100) are located at crossings between two crossed electrode lines (30, 31), characterized in that 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 dipolar unit by means of a conformationally flexible unit.

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

3. The electronic element (10) according to claim 2, wherein 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 electrode or the second electrode.

4. The electronic element (10) according to claim 1, wherein the first electrodes (102) and/or second electrodes (106) of each cell (100) are made from a metal, a conductive alloy, a conductive ceramic, a semiconductor, a conductive oxidic material, conductive or semiconductive organic molecules or a layered conductive 2D material.

5. The electronic element (10) according to claim 1, wherein the organic molecules for the formation of the self-assembled monolayer are selected from one or more compounds of the formula I
T?Z.sup.T?(A.sup.1?Z.sup.1).sub.r?B?(Z.sup.2A.sup.2).sub.s?(Z.sup.3A.sup.3).sub.t?(Z.sup.4A.sup.4).sub.u?Sp?G(I) in which T is selected from the group of radicals consisting of the following groups: a) a three- to ten-membered saturated or partially unsaturated aliphatic ring, in which at least one CH.sub.2 group is replaced with O, S, S(O), SO.sub.2, NR.sup.X or N(O)R.sup.x, or in which at least one CH? group is replaced with N?, b) straight chain or branched alkyl or alkoxy each having 1 to 20 C atoms, where one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by C?C, CH?CH, ##STR00660## O, S, CF.sub.2O, OCF.sub.2, COO, OCO, SiR.sup.0R.sup.00, NH, NR.sup.0 or SO.sub.2 in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, CN, SCN or SF.sub.5, wherein R.sup.0, R.sup.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 be replaced by halogen, c) a diamondoid radical, preferably derived from a lower diamondoid, very preferably selected from the group consisting of adamantyl, diamantyl, and triamantyl, in which one or more H atoms can be replaced by F, in each case optionally fluorinated alkyl, alkenyl or alkoxy having up to 12 C atoms, in particular ##STR00661## Z.sup.T, Z.sup.1, Z.sup.2 and Z.sup.4, on each occurrence, identically or differently, denote a single bond, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CH.sub.2O, OCH.sub.2, C(O)O, OC(O), C(O)S, SC(O), (CH.sub.2).sub.n1, (CF.sub.2).sub.n2, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, CH?CH, CFCF, CF?CH, CH?CF, (CH.sub.2).sub.n3O, O(CH.sub.2).sub.n4, CC, O, S, CH?N, N?CH, N?N, NN(O), N(O)?N or NCCN, wherein n1, n2, n3, n4, identically or differently, are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, Z.sup.3 denotes O, S, CH.sub.2, C(O), CF.sub.2, CHF, C(R.sup.x).sub.2, S(O) or SO.sub.2, A.sup.1, A.sup.2 and A.sup.4, 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, A.sup.3 denotes an aromatic or heteroaromatic ring having 5 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by Y.sup.C, Y on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain 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.sup.C has one of the meanings of Y or denotes cycloalkyl or alkylcycloalkyl each having 3 to 12 C atoms, preferably methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, methoxy or trifluoromethoxy, B denotes ##STR00662## ##STR00663## where the groups may be oriented in both directions, L.sup.1 to L.sup.5, independently of one another, denote F, Cl, Br, I, CN, SF.sub.5, CF.sub.3 or OCF.sub.3, preferably Cl or F, where L.sup.3 may alternatively also denote H, Sp denotes a spacer group or a single bond, G denotes OH, SH, SO.sub.2OH, OP(O)(OH).sub.2, PO(OH).sub.2, C(OH)(PO(OH).sub.2).sub.2, COOH, Si(OR.sup.x).sub.3, SiCl.sub.3, CH?CH.sub.2, POCl.sub.2, CO(NHOH), CO(NR.sup.0OH), Si(NMe.sub.2).sub.3; OC(O)OR.sup.v, OC(O)Si(OR.sup.V).sub.3, PO(OR.sup.V).sub.2 or SO.sub.2OR.sup.v or straight chain or branched alkyl having 1 to 12 C atoms in which one, two or three not geminal H atoms are substituted by OH; R.sup.0, R.sup.00, R.sup.x identically or differently, denote straight-chain or branched alkyl having 1 to 6 C atoms, R.sup.V denotes straight chain or branched alkyl having 1 to 12 C atoms, and r, s, t, and u, identically or differently, are 0, 1 or 2.

6. The electronic element (10) according to claim 5, wherein the group T in formula I denotes a three- to ten-membered saturated or partially unsaturated aliphatic ring, in which at least one CH.sub.2 group is replaced with O, S, NR.sup.x, S(O), SO.sub.2, NR.sup.x or N(O)R.sup.x, or in which at least one CH? group is replaced with N?.

7. A compound of formula IA
T?(Z.sup.1?A.sup.1).sub.r?B?(Z.sup.2A.sup.2).sub.s?(Z.sup.3A.sup.3).sub.t?(Z.sup.4A.sup.4).sub.u?Sp?G(IA) in which T denotes a three- to ten-membered saturated or partially unsaturated aliphatic ring, in which at least one CH.sub.2 group is replaced with O, S, NR.sup.x, S(O), SO.sub.2, NR.sup.X or N(O)R.sup.x, or in which at least one CH? group is replaced with N?, and the groups Z.sup.1, A.sup.1, B, Z.sup.2, A.sup.2, Z.sup.3, A.sup.3, Z.sup.4, A.sup.4, Sp, G and the parameters r, s, t and u have the meanings defined in claim 5.

8. The compound according to claim 7, wherein the compound is selected from the group consisting of the formulae IA-la to IA-If
T?Z.sup.T?B?Sp?GIA-1a
T?Z.sup.T?(A.sup.1?Z.sup.1)?B?Sp?GIA-1b
T?Z.sup.T?(A.sup.1?Z.sup.1).sub.2?B?Sp?GIA-1c
T?Z.sup.T?B?(Z.sup.2?A.sup.2)?Sp?GIA-1d
T?Z.sup.T?B?(Z.sup.2?A.sup.2).sub.2?Sp?GIA-1e
T?Z.sup.T?(A.sup.1?Z.sup.1)?B?(Z.sup.2?A.sup.2)?Sp?GIA-1f in which T, Z.sup.T, A.sup.1, A.sup.2, B, Z.sup.1, Z.sup.2, Sp and G have the meanings given in claim 7.

9. The compound according to claim 7, wherein T denotes ##STR00664## in which R.sup.x denotes alkyl having 1 to 6 C atoms, A.sup.1 and A.sup.2, identically or differently, denote ##STR00665## B denotes ##STR00666## L.sup.1 and L.sup.2, independently of one another, denote CF.sub.3, Cl or F, L.sup.3 denotes H or F, Y.sup.1 and Y.sup.2, independently of one another, denote H, Cl or F, Z.sup.1, z.sup.2, Z.sup.T independently of one another, denote a single bond, CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2 or CH.sub.2CH.sub.2, Sp denotes branched or unbranched 1,?-alkylene having 1 to 12 C atoms, and G denotes OP(O)(OH).sub.2, PO(OH).sub.2, or COH(PO(OH).sub.2).sub.2.

10. The compounds according to claim 7, wherein the compound is selected from the compounds of the formula IA-2
T?Z.sup.T?(A.sup.1?Z.sup.1).sub.r?B?Z.sup.3?A.sup.3?(Z.sup.4?A.sup.4).sub.u?GIA-2 in which the occurring groups and parameters have the meanings given in claim 7.

11. The compound according to claim 10, wherein T denotes ##STR00667## in which R.sup.x denotes alkyl having 1 to 6 C atoms, A.sup.1 and A.sup.4, identically or differently, denote ##STR00668## A.sup.3-Z.sup.3 denotes ##STR00669## B denotes ##STR00670## Z.sup.T denote a single bond, CH.sub.2O, OCH.sub.2 or CH.sub.2CH.sub.2, L.sup.1 and L.sup.2 identically or differently, denote F, CF.sub.3 or Cl, Y.sup.1 and Y.sup.2 identically or differently, have one of the meanings given above for Y and preferably denote H, F or Cl, Y.sup.3 and Y.sup.4, identically or differently, have one of the meanings given above for Y.sup.1 and Y.sup.2 and preferably denote methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, methoxy, trifluoromethyl, trifluoromethoxy, or trifluoromethylthio, Z.sup.3 denotes CH.sub.2 or O, z.sup.1, Z.sup.2, independently of one another, denote a single bond, C(O)O, OC(O), CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2 or CH.sub.2CH.sub.2, G denotes PO(OH).sub.2, or COH(PO(OH).sub.2).sub.2, and r and u independently are 0, 1 or 2.

12. Method for producing of an electronic element (10) comprising a plurality of cells (100) according to claim 1, wherein the method comprises: A) providing a base substrate (12), B) formation of 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 dipolar unit by means of a conformationally flexible unit, and D) deposition of a further electrode layer (22) comprising electrode lines (30, 31) separated by a dielectric material (18), wherein C) and D) are repeated until the desired number of layers of cells (100) is formed and wherein the electrode lines (30, 31) of two adjacent electrode layers (14, 22) are rotated with respect to each other so that the electrode lines (30, 31) of the two adjacent electrode layers (14, 22) cross each other.

13. The method according to claim 12, wherein a selector device (108) in the form of a diode layer structure or a threshold switch structure is deposited after formation of the first electrode layer (14) according to step B) or a further electrode layer (22) according to step D) and before forming of the molecular monolayer (20) according to step C).

14. The method according to claim 12, wherein formation of the first electrode layer (14) and/or the further electrode layers (22) of electrode lines (30, 31) separated by a dielectric material (18) comprises deposition of an electrode material (16), removing of the electrode material (16) from non-electrode areas (32), deposition of a dielectric material (18), and planarization of the obtained layer structure down to the level of the electrode material (16), or, in case of formation of the first electrode layer (14) comprises deposition of a dielectric material (18), removing of the dielectric material (18) from electrode areas (34), deposition of an electrode material (16), and planarization of the obtained layer structure down to the level of the dielectric material (18).

15. The method according to claim 14, wherein removal of electrode material (16) in the non-electrode (32) areas or removal of dielectric material (18) in the electrode areas (34) is performed by a photolithographic method defining areas to be removed and etching.

16. The method according to claim 12, wherein the dielectric material (18) and/or the material of the base substrate (12) is selected from SiO2, ZrO2, diamond, Al2O3 or GaN.

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

18. The method according to claim 12, wherein the coating with a molecular monolayer (20) comprises the steps of pretreating of the substrate to be coated for cleaning and activation, dipping the substrate into a solution comprising organic molecules for forming a self-assembled monolayer of said molecules, rinsing with an organic solvent, and annealing of the formed molecular monolayer (20), wherein the substrate to be coated is the first electrode layer (14), a further electrode layer (22) or a surface of the selector device (108).

19. The method according to claim 18, wherein pretreatment is performed by means of a UV-ozone treatment.

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

21. The method according to claim 18, wherein the organic molecules for forming the self-assembled monolayer are selected from one or more compounds of the formula I
T?Z.sup.T?(A.sup.1?Z.sup.1).sub.r?B?(Z.sup.2A.sup.3).sub.s?(Z.sup.3A.sup.3).sub.t?(Z.sup.4A.sup.4).sub.u?Sp?G(I) in which T is selected from the group of radicals consisting of the following groups: a) a three- to ten-membered saturated or partially unsaturated aliphatic ring, in which at least one CH.sub.2 group is replaced with O, ?S, S(O), SO.sub.2, NR.sup.X or N(O)R.sup.x, or in which at least one CH? group is replaced with N?, b) straight chain or branched alkyl or alkoxy each having 1 to 20 C atoms, where one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by C?C, CH?CH, ##STR00671## O, S, CF.sub.2O, OCF.sub.2, COO, OCO, SiR.sup.0R.sup.00, NH, NR.sup.0 or SO.sub.2 in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, CN, SCN or SF.sub.5, wherein R.sup.0, R.sup.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 be replaced by halogen, c) a diamondoid radical, preferably derived from a lower diamondoid, very preferably selected from the group consisting of adamantyl, diamantyl, and triamantyl, in which one or more H atoms can be replaced by F, in each case optionally fluorinated alkyl, alkenyl or alkoxy having up to 12 C atoms, in particular ##STR00672## z.sup.T, z.sup.1, Z.sup.2 and Z.sup.4, on each occurrence, identically or differently, denote a single bond, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CH.sub.2O, OCH.sub.2, C(O)O, OC(O), C(O)S, SC(O), (CH.sub.2).sub.n1, (CF.sub.2).sub.n2, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, CH?CH, CF?CF, CFCH, CHCF, (CH.sub.2).sub.n3O, O(CH.sub.2).sub.n4, C.sup.0C, O, S, CH?N, N?CH, NN, N?N(O), N(O)?N or N?CC?N, wherein n1, n2, n3, n4, identically or differently, are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, Z.sup.3 denotes O, S, CH.sub.2, C(O), CF.sub.2, CHF, C(R.sup.x).sub.2, S(O) or SO.sub.2, A.sup.1, A.sup.2 and A.sup.4, 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, A.sup.3 denotes an aromatic or heteroaromatic ring having 5 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by Y.sup.C Y on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain 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.sup.C has one of the meanings of Y or denotes cycloalkyl or alkylcycloalkyl each having 3 to 12 C atoms, preferably methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, methoxy or trifluoromethoxy, B denotes ##STR00673## ##STR00674## where the groups may be oriented in both directions, L.sup.1 to L.sup.5, independently of one another, denote F, Cl, Br, I, CN, SF.sub.5, CF.sub.3 or OCF.sub.3, preferably Cl or F, where L.sup.3 may alternatively also denote H, Sp denotes a spacer group or a single bond, G denotes OH, SH, SO.sub.2OH, OP(O)(OH).sub.2, PO(OH).sub.2, C(OH)(PO(OH).sub.2).sub.2, COOH, Si(OR.sup.x).sub.3, SiCl.sub.3, CH?CH.sub.2, POCI.sub.2, CO(NHOH), CO(NR.sup.0OH), Si(NMe.sub.2).sub.3; OC(O)OR.sup.V, OC(O)Si(OR.sup.V).sub.3, PO(OR.sup.V).sub.2 or SO.sub.2OR.sup.v or straight chain or branched alkyl having 1 to 12 C atoms in which one, two or three not geminal H atoms are substituted by OH; R.sup.0, R.sup.00R.sup.X identically or differently, denote straight-chain or branched alkyl having 1 to 6 C atoms, R.sup.V denotes straight chain or branched alkyl having 1 to 12 C atoms, and r, s, t, and u, identically or differently, are 0, 1 or 2.

22. The method according to claim 18, wherein annealing is performed at a temperature in the range of from 50? C. to 250? C. for a time of from 1 minutes to 60 minutes.

23. A memory device comprising an electronic element (10) according to claim 1, wherein cells (100) of the electronic element (10) serve as memory cells, and/or as neural network device, wherein cells (100) of the electronic element (10) serve as synapses.

Description

[0198] FIG. 1 a schematic cross section of an electronic element having a three dimensional cross-bar arrangement of cells,

[0199] FIGS. 2a to 2l each show a top view and a cross section of the electronic element of FIG. 1 in different stages of production, and

[0200] FIG. 3 a schematic view of a cell.

[0201] FIG. 1 shows an example embodiment of an electronic element 10 having a plurality of cells 100 in a schematic cross section view. The schematic view of FIG. 1 shows only a part of the entire three-dimensional cross-bar arrangement of cells 100. The electronic element 10 may extend further in each of the three dimensions and may include much more than the six depicted cells 100.

[0202] The electronic element 10 of FIG. 1 comprises a layer structure having multiple levels, wherein a first level comprises in this 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 a good heat conductivity.

[0203] The first electrode layer 14 comprises electrode lines 30 separated by a dielectric material 18. The electrode lines 30 are made from an electrode material 16, which is electrically conductive. In FIG. 1, two electrode lines 30 are visible. However, the electronic component 10 may comprise a large number of electrode lines 30.

[0204] The molecular layer 20 is in the embodiment shown in FIG. 1 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 an anchoring group connected to a dipolar unit by means of a conformationally flexible unit. The anchoring group is in contact with the first electrode layer 14, in particular with the conductive material 16 forming the electrode lines 30 and thus anchors the molecules to a surface of the first electrode layer 14. In further embodiments, the electronic element 10 may include an anchoring layer located between the first electrode layer 14 and the molecular layer 20.

[0205] The further electrode layer 20 has a setup similar to the setup of the first electrode layer 14, but is rotated by 90?. Thus, rotated electrode lines 31 are formed in the further electrode layer 20 which are electrically insulated by dielectric material 18 and are orthogonal 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.

[0206] Cells 100 are located at crossings between two orthogonal electrode lines 30, 31, in particular at a crossing between an electrode line 30 and a rotated electrode line 31. Each cell 100 has a first electrode 102, a part 104 of the molecular layer 20 and a second electrode 106. In the embodiment of FIG. 1, a part of the electrode line 30 serves as first electrode 102 and a part of the rotated electrode line 31 serves as second electrode 106.

[0207] This structure may be extended by further levels, wherein a second level of the structure of FIG. 1 further comprises in this order another molecular layer 20 and another further electrode layer 22. A third level of the structure comprises yet another molecular layer 20 and yet another further electrode layer 22. In FIG. 1, a cell 100 of the second level and a cell 100 of the third layer are marked.

[0208] With each addition of a molecular layer 20 and a further electrode layer 22, the structure is extended by a further level and thus a further layer of cells 100.

[0209] An example embodiment of the production of the electronic element is further described with respect to FIGS. 2a to 2l. In each of the FIGS. 2a to 2l, the lower part shows a top view and the upper part shows a cross section along the dashed line A viewed from the side.

[0210] FIG. 2a shows a provided base substrate 12. In a first step i), an insulating layer in form of a dielectric material 18 is coated onto the substrate 12.

[0211] FIG. 2b shows the base substrate 12 coated with the dielectric material 18.

[0212] In a subsequent step ii), trenches are formed in the layer of dielectric material 18. The trenches define electrode areas 34 as shown in FIG. 2c, in which an electrode will be formed in the following third step iii). The trenches depicted in FIG. 2c are aligned in a first direction and are parallel to each other.

[0213] FIG. 2d shows that electrode lines 30 have been formed by deposition of electrode material 16 in the electrode areas 34 defined by the trenches prepared in step ii) and subsequent planarization down to the level of the dielectric material 18. The formed electrode lines 30 are aligned in a first direction and are parallel to each other.

[0214] 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 the coating, the surface is preferably cleaned and activated by an UV-ozone treatment. Coating may, for example, be performed by dipping the formed structure into a solution comprising the organic molecules. FIG. 2e) shows the formed molecular layer 20 on the previously formed structure.

[0215] In a subsequent step v) a further layer of conductive material 16 is deposited onto the structure to form the basis for a further layer of conductive electrodes. After deposition, the conductive material 16 is selectively removed to form rotated electrode lines 31 depicted in FIG. 2f which are aligned in a second direction which is orthogonal to the first direction of the electrode lines 30.

[0216] The part of the molecular layer 20 located between a crossing of an electrode line 30 with a rotated electrode line 31 and the electrode lines 30, 31 serving as first and second electrode form a cell 100.

[0217] FIG. 2g shows the structure after a further step vi). In step vi) a further layer of dielectric material 18 is deposited and subsequently planarized down to the level of the rotated electrode lines 31 formed in the previous step.

[0218] In step vii) a further molecular layer 20 is coated onto the structure as shown in FIG. 2h.

[0219] FIG. 2i shows the structure after performing a subsequent step viii) in which a further layer of conductive material 16 is deposited and selectively removed in non-electrode areas 32. After removal of the conductive material 16 in the non-electrode areas 32, further electrode lines 30 arranged along the first direction are formed.

[0220] In a subsequent step ix) the trenches formed by removal of the conductive material 16 and of the molecular layer 20 in the non-electrode areas 32 are filled with dielectric material 18. After deposition of the dielectric material 18, planarization is performed down to the level of the conductive material 16 as shown in FIG. 2j.

[0221] FIG. 2k shows the structure after deposition of a further molecular layer 20 in a step x).

[0222] FIG. 21 shows the structure after forming further rotated electrode lines 31 by deposition and selective removal of a further layer of conductive material 16 in a step xi).

[0223] By repeating the steps vi) to xi), further levels with further cells 100 located at crossings between an electrode line 30 and a rotated electrode line 31 can be obtained.

[0224] FIG. 3 shows a layer structure of a cell 100 according to a second embodiment. While the cell 100 of the first embodiment, as shown in FIG. 1, comprises three layers, namely the first electrode 102, a part 104 of the molecular layer 20 and a second electrode 106, the cell 100 of the second embodiment as depicted in FIG. 3 comprises an additional selector device 108.

[0225] Accordingly, the cell 100 of the second embodiment comprises in this order the first electrode 102, the selector device 108, a part 104 of the molecular layer 20 and the second electrode 106. The selector device 108 itself may be configured as a layer structure comprising one or more layers. For example, the selector device 108 may be configured as a diode comprising an n-doped semiconducting layer and a p-doped semiconducting layer.

SYNTHESIS EXAMPLES

Synthesis Example 1

Step 1: 4-Bromo-2,3-Difluorophenylbenzylether

[0226] ##STR00027##

[0227] 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) is heated at reflux for 16 h, The reaction is allowed to cool to room temp, and then filtered. The filtrates are evaporated to dryness in vacuo to leave an off-white solid (121.6 g). The solid is dissolved in isopropanol (500 ml) at 65? C. then allowed to cool and stir overnight to give a white suspension. The solid is collected by vacuum filtration, washed with isopropanol (2?50 ml) and dried, to give 4-bromo-2,3-difluorophenylbenzylether as a crystalline white solid, m.p. 70-73? C.

[0228] .sup.1H NMR (400 MHZ, CDCl.sub.3) ? 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). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 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). .sup.19F NMR (376 MHZ, CDCl.sub.3) ? ppm ?128.7 (d, J=20.5 Hz), ?135.8 (d, J=20.5 Hz).

Step 2: 4-(4-Benzyloxy-2,3-Difluoro-Phenyl)-3,6-Dihydro-2H-Pyran

[0229] ##STR00028##

[0230] 4-bromo-2,3-difluorophenylbenzylether (20.0 g, 66.9 mmol) is dissolved in dry THF (200 ml) under nitrogen and cooled to ?85? C. n-BuLi (2.5M in hexanes, 17.0 ml, 73.6 mmol) is added dropwise over 30 min. After 1 h at ?70? C., the reaction is cooled to ?85? C. and 4-oxotetrahydropyran (8.0 g, 80.2 mmol) is added dropwise over 10 min. The cooling bath is removed and the reaction allowed to warm to room temp, and stir overnight. The reaction is cooled to 10? C., then water (30 ml) is slowly added. After stirring for 30 min the mixture is partitioned between ethyl acetate (200 ml) and water (100 ml). The organic layer is collected and the aqueous layer extracted with ethyl acetate (2?100 ml). The combined organic phases are dried (MgSO.sub.4) and concentrated to dryness in vacuo to leave a pale yellow solid. The solid is dissolved in dichloromethane and applied to a pad of silica (40-63 u, 70 g) packed in dichloromethane. The pad is eluted with dichloromethane until all faster running 1-(benzyloxy)-2,3-difluorobenzene reduction product is removed. The pad is then eluted with ethyl acetate to remove the tertiary alcohol major reaction product. The ethyl acetate eluent is evaporated in vacuo to leave a pale yellow solid. The solid is dissolved in toluene (225 ml) at 40? C., then p-toluenesulfonic acid monohydrate (0.93 g, 4.9 mmol) is added. The solution is heated to 70? C. for 1 h, cooled to room temp. The reaction mixture is washed with water (3?30 ml) then dried (MgSO.sub.4) and evaporated to an off-white solid, which is recrystallised from methanol (195 ml) to give 4-(4-benzyloxy-2,3-difluoro-phenyl)-3,6-dihydro-2H-pyran as colourless crystals, m.p. 103-107? C.

[0231] .sup.1H NMR (400 MHZ, CDCl.sub.3) ? ppm 2.40-2.55 (2H, m), 3.92 (2H, t, J=5.4 Hz), 4.32 (2 H, m), 5.16 (2 H, s), 5.95-6.07 (1H, m), 6.75 (1H, ddd, J=9.0, 7.4, 1.9 Hz), 6.90 (1 H, td, J=8.4, 2.3 Hz), 7.30-7.53 (5H, m).

[0232] .sup.13C NMR (100.6 MHZ, CDCl.sub.3) ? 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). .sup.19F NMR (376 MHZ, CDCl.sub.3) ? ppm ?158.23 (d, J=19 Hz), ?139.63 (d, J=19 Hz).

Step 3: 2,3-Difluoro-4-Tetrahydropyran-4-Yl-Phenol

[0233] ##STR00029##

[0234] 4-(4-benzyloxy-2,3-difluoro-phenyl)-3,6-dihydro-2H-pyran (10.5 g, 34.7 mmol) is dissolved in a mixture of isopropanol (210 ml) and THF (31.5 ml) by sonication then hydrogenated over 5% Pd/C (0.53 g, 50% wetted) at 5 bar pressure for 18 h, at which point, no further hydrogen is taken up. After release of excess hydrogen, degassing and back-filling with nitrogen, the solution is filtered through a GF/F 0.7 u filter to remove the catalyst and the filtrates concentrated in vacuo to give 2,3-difluoro-4-tetrahydropyran-4-yl-phenol as an off-white and used directly without further purification, m.p. 143-147? C.

[0235] .sup.1H NMR (400 MHZ, DMSO-d6) ? ppm 1.53-1.77 (4H, m), 2.85-3.03 (1H, m), 3.43 (2 H, td, J=11.5, 2.6 Hz), 3.83-4.01 (2H, 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.).

[0236] .sup.13C NMR (100.6 MHZ, DMSO-d6) ? 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). .sup.19F NMR (376 MHZ, DMSO-d6) ? ppm ?161.89 (d, J=20.5 Hz), ?144.54 (d, J=20.5 Hz).

Step 4: 4-[4-(11-Diethoxyphosphorylundecoxy)-2,3-Difluoro-Phenyl]Tetrahydropyran

[0237] ##STR00030##

[0238] 2,3-difluoro-4-tetrahydropyran-4-yl-phenol (5.0 g, 23.3 mmol) is dissolved in butanone (65 ml) with stirring under nitrogen then diethyl (11-bromoundecyl)-phosphonate (11.3 g, 30.3 mmol) and anhydrous potassium carbonate 325 mesh (12.9 g, 93.4 mmol) are added. The mixture is heated under reflux for 18 hour. The reaction is allowed to cool to 30? C. and filtered. The combined filtrates are evaporated in vacuo and the obtained orange oil (14.3 g) applied to a silica column prepared with 40-63 u silica gel (140 g) packed in dichloromethane. The column is eluted with an increasing gradient of ethyl acetate from 0-40% in dichloromethane and the product enriched fractions (10-30% ethyl acetate) are combined and evaporated to a colourless oil (9.6 g), which is used directly without further purification.

[0239] .sup.1H NMR (400 MHZ, CDCl.sub.3) ? ppm 1.21-1.52 (20H, m), 1.52-1.66 (2H, m), 1.66?1.89 (8H, m), 2.94-3.14 (1H, m), 3.55 (2 H, td, J=11.7, 2.3 Hz), 3.95-4.21 (8H, m), 6.63-6.75 (1H, m), 6.85 (1 H, td, J=8.2, 2.3 Hz).

[0240] .sup.13C NMR (101 MHZ, CDCl.sub.3) ? 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).

[0241] .sup.19F NMR (376 MHZ, CDCl.sub.3) ? ppm ?159.28 (d, J=20.5 Hz), ?143.542 (d, J=20.5 Hz). .sup.31P NMR (162 MHZ, CDCl.sub.3) ? ppm 32.64.

Step 5: 11-(2,3-Difluoro-4-Tetrahydropyran-4-Yl-Phenoxy)Undecylphosphonic Acid

[0242] ##STR00031##

[0243] 4-[4-(11-diethoxyphosphorylundecoxy)-2,3-difluoro-phenyl]tetrahydropyran (9.2 g, 93.5% w/w, 17.0 mmol) is dissolved in dichloromethane (138 ml) with stirring and bromotrimethylsilane (28.1 g, 182.3 mmol) is added over 10 min at ambient temperature, then stirred overnight. The mixture is evaporated in vacuo and the resultant oil is re-dissolved in dichloromethane (125 ml) and methanol (125 ml) then re-evaporated in vacuo to an oil. The oil is re-dissolved in dichloromethane (75 ml) and methanol (75 ml) and then slowly concentrated in vacuo to ca. 40 ml final volume to remove the dichloromethane. The solution is then cooled in an ice/acetone bath to ?15? C. for 1 hour, which led to the formation of a white precipitate. The solid is filtered-off and dried overnight at 50? C. under vacuum to give an off-white solid. The solid is dissolved in THF (50 ml) and heptane (50 ml) is added. The solution is concentrated in vacuo at 45? C., 400 mbar, slowly removing the THF, until a solid began to precipitate. The distillation is stopped and the mixture is allowed to stir at ambient temperature for 90 min before the solid is collected by vacuum filtration and washed with heptane (3?10 ml). Drying overnight at 50? C. under vacuum gives 11-(2,3-difluoro-4-tetrahydropyran-4-yl-phenoxy)undecylphosphonic acid as a cloourless solid, m.p. 94-98? C.

[0244] .sup.1H NMR (400 MHZ, THF-d8) ? ppm 1.27-1.43 (12H, m), 1.43-1.52 (2H, m), 1.53?1.69 (6H, m), 1.69-1.83 (4H, 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 (2H, dd, J=11.0, 3.9 Hz), 4.02 (2H, t, J=6.5 Hz), 6.77-6.87 (1H, m), 6.94 (1 H, td, J=8.3, 2.2 Hz).

[0245] .sup.13C NMR (101 MHZ, THF-d8) ? 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).

[0246] .sup.19F NMR (376 MHZ, THF-d8) ? ppm-162.90 (d, J=20.5 Hz), ?147.28 (d, J=20.5 Hz). .sup.31P NMR (162 MHZ, THF-d8) ? ppm 30.71.

[0247] MS (ES negative): Found m/z [M-H]-447.2108 (28%); C22H34F205P-requires m/z 447.21.

Application Tests

[0248] Test chips are prepared from Compound A (Synthesis Example 1) according to the invention and for comparison from compounds B and C from prior art:

##STR00032## ##STR00033##

Preparation of Test Chips:

[0249] A silicon chip (Siegert wafer substrate lot 19335; 8?8?0.5 mm; p-Si/SiO.sub.2 (?0.5 mm)/SiAIOx (1-2 nm)/Al2O3 (2 nm); conditioned by oxygen plasma treatment (<0.2 mbar 02, 1 min, 200 W) is immersed for 24 h into a 1 mM solution of the corresponding phosphonic acid (A, B or C) in THF. The chip is removed from the bath, blown dry under nitrogen, then heated on a hotplate at 120? C. for 1 h under nitrogen. Afterwards the chip is washed with ethanol three times and dried on a hotplate at 120? C. for 5 min under nitrogen.

Measurement of Water Contact Angle (WCA)

[0250] The water contact angle of the test chips with A, B or C is determined by known methods. It is found that the tetrahydropyrane derivative A induces a much lower contact angle than B or C, indicating a strongly increased surface energy. Actually the WCA is similar to that of typical oxidic materials, making it well compatible with standard photoresist formulations. Just omitting the terminal alkyl chain results only in a very moderate reduction of the WCA, as the comparison of the compounds B and C shows.

TABLE-US-00001 Test chip compound WCA 1 A 64.0? 2 B 99.5? 3 C 107.6?

Adhesion Test

[0251] Onto the SAM-modified chips 1 and 2 first chromium (30 nm), then gold (200 nm) is sputtered.

[0252] Then, the samples are subjected to a scotch tape adhesion test according to DIN EN ISO 2409 (ASTM D 3002, ASTM D 3359), analogous to ASTM D 3359; available at https://www.astm.org/Standards/D4541.htm: The metal-sputtered sample is scratched with a lattice cutter (BYK-Gardner Multi-Cut tool; 1 mm cut distance). Then Permacel tape is applied and removed again. The test chip 1 treated with compound 7 remains >90% intact, whereas chip 2 is only 30% intact.

[0253] In analogy to Synthesis Example 1 the following compounds are obtained.

TABLE-US-00002 Compounds of formula IA-1a No. T Z.sup.T B Sp G 2 [00034] [00035] OCH.sub.2CH.sub.2 PO(OH).sub.2 3 [00036] [00037] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 4 [00038] [00039] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 5 [00040] [00041] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 6 [00042] [00043] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 7 [00044] [00045] O(CH2).sub.8CH.sub.2 PO(OH).sub.2 8 [00046] [00047] [00048] PO(OH).sub.2 9 [00049] CH.sub.2CH.sub.2 [00050] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 10 [00051] [00052] OCH.sub.2CH.sub.2 PO(OH).sub.2 11 [00053] [00054] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 12 [00055] [00056] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 13 [00057] [00058] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 14 [00059] [00060] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 15 [00061] [00062] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 16 [00063] [00064] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 17 [00065] [00066] [00067] PO(OH).sub.2 18 [00068] CH.sub.2CH.sub.2 [00069] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 19 [00070] [00071] OCH.sub.2CH.sub.2 PO(OH).sub.2 20 [00072] [00073] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 21 [00074] [00075] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 22 [00076] [00077] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 23 [00078] [00079] O(CH.sub.2).sub.5CH.sub.2 OH 24 [00080] [00081] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 25 [00082] [00083] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 26 [00084] [00085] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 27 [00086] [00087] [00088] PO(OH).sub.2 28 [00089] CH.sub.2CH.sub.2 [00090] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 29 [00091] [00092] OCH.sub.2CH.sub.2 PO(OH).sub.2 30 [00093] [00094] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 31 [00095] [00096] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 32 [00097] [00098] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 33 [00099] [00100] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 34 [00101] [00102] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 35 [00103] [00104] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 36 [00105] [00106] [00107] PO(OH).sub.2 37 [00108] CH.sub.2CH.sub.2 [00109] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 38 [00110] [00111] OCH.sub.2CH.sub.2 PO(OH).sub.2 39 [00112] [00113] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 40 [00114] [00115] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 41 [00116] [00117] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 42 [00118] [00119] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 43 [00120] [00121] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 44 [00122] [00123] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 45 [00124] [00125] [00126] PO(OH).sub.2 46 [00127] CH.sub.2CH.sub.2 [00128] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 47 [00129] [00130] OCH.sub.2CH.sub.2 PO(OH).sub.2 48 [00131] [00132] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 49 [00133] [00134] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 50 [00135] [00136] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 51 [00137] [00138] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 52 [00139] [00140] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 53 [00141] [00142] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 54 [00143] [00144] [00145] PO(OH).sub.2 55 [00146] CH.sub.2CH.sub.2 [00147] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 56 [00148] [00149] OCH.sub.2CH.sub.2 PO(OH).sub.2 57 [00150] [00151] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 58 [00152] [00153] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 59 [00154] [00155] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 60 [00156] [00157] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 61 [00158] [00159] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 62 [00160] [00161] O(CH2).sub.10CH.sub.2 PO(OH).sub.2 63 [00162] [00163] [00164] PO(OH).sub.2 64 [00165] CH.sub.2CH.sub.2 [00166] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 65 [00167] [00168] OCH.sub.2CH.sub.2 PO(OH).sub.2 66 [00169] [00170] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 67 [00171] [00172] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 68 [00173] [00174] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 69 [00175] [00176] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 70 [00177] [00178] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 71 [00179] [00180] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 72 [00181] [00182] [00183] PO(OH).sub.2 73 [00184] CH.sub.2CH.sub.2 [00185] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 74 [00186] [00187] OCH.sub.2CH.sub.2 PO(OH).sub.2 75 [00188] [00189] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 76 [00190] [00191] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 77 [00192] [00193] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 78 [00194] [00195] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 79 [00196] [00197] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 80 [00198] [00199] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 81 [00200] [00201] [00202] PO(OH).sub.2 82 [00203] CH.sub.2CH.sub.2 [00204] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 83 [00205] [00206] OCH.sub.2CH.sub.2 PO(OH).sub.2 84 [00207] [00208] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 85 [00209] [00210] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 86 [00211] [00212] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 87 [00213] [00214] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 88 [00215] [00216] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 89 [00217] [00218] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 90 [00219] [00220] [00221] PO(OH).sub.2 91 [00222] CH.sub.2CH.sub.2 [00223] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 92 [00224] [00225] OCH.sub.2CH.sub.2 PO(OH).sub.2 93 [00226] [00227] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 94 [00228] [00229] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 95 [00230] [00231] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 96 [00232] [00233] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 97 [00234] [00235] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 98 [00236] [00237] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 99 [00238] [00239] [00240] PO(OH).sub.2 100 [00241] CH.sub.2CH.sub.2 [00242] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 101 [00243] [00244] OCH.sub.2CH.sub.2 PO(OH).sub.2 102 [00245] [00246] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 103 [00247] [00248] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 104 [00249] [00250] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 105 [00251] [00252] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 106 [00253] [00254] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 107 [00255] [00256] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 108 [00257] [00258] [00259] PO(OH).sub.2 109 [00260] CH.sub.2CH.sub.2 [00261] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2

TABLE-US-00003 Compounds of formula IA-1b No. T Z.sup.T A.sup.1Z.sup.1 B Sp G 119 [00262] [00263] [00264] OCH.sub.2CH.sub.2 PO(OH).sub.2 120 [00265] [00266] [00267] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 121 [00268] [00269] [00270] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 122 [00271] [00272] [00273] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 123 [00274] [00275] [00276] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 124 [00277] [00278] [00279] O(CH2).sub.8CH.sub.2 PO(OH).sub.2 125 [00280] [00281] [00282] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 126 [00283] [00284] [00285] [00286] PO(OH).sub.2 127 [00287] [00288] [00289] OCH.sub.2CH.sub.2 PO(OH).sub.2 128 [00290] [00291] [00292] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 129 [00293] [00294] [00295] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 130 [00296] [00297] [00298] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 131 [00299] [00300] [00301] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 132 [00302] [00303] [00304] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 133 [00305] [00306] [00307] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 134 [00308] [00309] [00310] [00311] PO(OH).sub.2 135 [00312] [00313] [00314] OCH.sub.2CH.sub.2 PO(OH).sub.2 136 [00315] [00316] [00317] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 137 [00318] [00319] [00320] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 138 [00321] [00322] [00323] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 139 [00324] [00325] [00326] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 140 [00327] [00328] [00329] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 141 [00330] [00331] [00332] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 142 [00333] [00334] [00335] [00336] PO(OH).sub.2 143 [00337] [00338] [00339] OCH.sub.2CH.sub.2 PO(OH).sub.2 144 [00340] [00341] [00342] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 145 [00343] [00344] [00345] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 146 [00346] [00347] [00348] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 147 [00349] [00350] [00351] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 148 [00352] [00353] [00354] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 149 [00355] [00356] [00357] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 150 [00358] [00359] [00360] [00361] PO(OH).sub.2 151 [00362] [00363] [00364] OCH.sub.2CH.sub.2 PO(OH).sub.2 152 [00365] [00366] [00367] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 153 [00368] [00369] [00370] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 154 [00371] [00372] [00373] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 155 [00374] [00375] [00376] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 156 [00377] [00378] [00379] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 157 [00380] [00381] [00382] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 158 [00383] [00384] [00385] [00386] PO(OH).sub.2 159 [00387] [00388] [00389] OCH.sub.2CH.sub.2 PO(OH).sub.2 160 [00390] [00391] [00392] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 161 [00393] [00394] [00395] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 162 [00396] [00397] [00398] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 163 [00399] [00400] [00401] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 164 [00402] [00403] [00404] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 165 [00405] [00406] [00407] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 166 [00408] [00409] [00410] [00411] PO(OH).sub.2 167 [00412] CH.sub.2CH.sub.2 [00413] [00414] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 168 [00415] [00416] [00417] OCH.sub.2CH.sub.2 PO(OH).sub.2 169 [00418] [00419] [00420] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 170 [00421] [00422] [00423] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 171 [00424] [00425] [00426] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 172 [00427] [00428] [00429] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 173 [00430] [00431] [00432] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 174 [00433] [00434] [00435] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 175 [00436] [00437] [00438] [00439] PO(OH).sub.2 176 [00440] [00441] [00442] OCH.sub.2CH.sub.2 PO(OH).sub.2 177 [00443] [00444] [00445] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 178 [00446] [00447] [00448] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 179 [00449] [00450] [00451] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 180 [00452] [00453] [00454] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 181 [00455] [00456] [00457] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 182 [00458] [00459] [00460] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 183 [00461] [00462] [00463] [00464] PO(OH).sub.2 184 [00465] [00466] [00467] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 185 [00468] [00469] [00470] OCH.sub.2CH.sub.2 PO(OH).sub.2 186 [00471] [00472] [00473] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 187 [00474] [00475] [00476] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 188 [00477] [00478] [00479] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 189 [00480] [00481] [00482] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 190 [00483] [00484] [00485] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 191 [00486] [00487] [00488] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 192 [00489] [00490] [00491] [00492] PO(OH).sub.2 193 [00493] [00494] [00495] OCH.sub.2CH.sub.2 PO(OH).sub.2 194 [00496] [00497] [00498] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 195 [00499] [00500] [00501] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 196 [00502] [00503] [00504] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 197 [00505] [00506] [00507] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 198 [00508] [00509] [00510] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 199 [00511] [00512] [00513] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 200 [00514] [00515] [00516] [00517] PO(OH).sub.2 2010 [00518] [00519] [00520] OCH.sub.2CH.sub.2 PO(OH).sub.2 202 [00521] [00522] [00523] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 203 [00524] [00525] [00526] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 204 [00527] [00528] [00529] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 205 [00530] [00531] [00532] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 206 [00533] [00534] [00535] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 207 [00536] [00537] [00538] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 208 [00539] [00540] [00541] [00542] PO(OH).sub.2 209 [00543] [00544] [00545] OCH.sub.2CH.sub.2 PO(OH).sub.2 210 [00546] [00547] [00548] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 211 [00549] [00550] [00551] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 212 [00552] [00553] [00554] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 213 [00555] [00556] [00557] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 214 [00558] [00559] [00560] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 215 [00561] [00562] [00563] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 216 [00564] [00565] [00566] [00567] PO(OH).sub.2 217 [00568] [00569] [00570] OCH.sub.2CH.sub.2 PO(OH).sub.2 218 [00571] [00572] [00573] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 219 [00574] [00575] [00576] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 220 [00577] [00578] [00579] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 221 [00580] [00581] [00582] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 222 [00583] [00584] [00585] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 223 [00586] [00587] [00588] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 224 [00589] [00590] [00591] [00592] PO(OH).sub.2 225 [00593] [00594] [00595] OCH.sub.2CH.sub.2 PO(OH).sub.2 226 [00596] [00597] [00598] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 227 [00599] [00600] [00601] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 228 [00602] [00603] [00604] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 229 [00605] [00606] [00607] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 230 [00608] [00609] [00610] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 231 [00611] [00612] [00613] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 232 [00614] [00615] [00616] [00617] PO(OH).sub.2 233 [00618] CH.sub.2CH.sub.2 [00619] [00620] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 234 [00621] [00622] [00623] OCH.sub.2CH.sub.2 PO(OH).sub.2 235 [00624] [00625] [00626] O(CH.sub.2).sub.3CH.sub.2 PO(OH).sub.2 236 [00627] [00628] [00629] O(CH.sub.2).sub.4CH.sub.2 PO(OH).sub.2 237 [00630] [00631] [00632] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2 238 [00633] [00634] [00635] O(CH.sub.2).sub.6CH.sub.2 PO(OH).sub.2 239 [00636] [00637] [00638] O(CH.sub.2).sub.8CH.sub.2 PO(OH).sub.2 240 [00639] [00640] [00641] O(CH.sub.2).sub.10CH.sub.2 PO(OH).sub.2 241 [00642] [00643] [00644] O(CH.sub.2).sub.5CH.sub.2 PO(OH).sub.2

TABLE-US-00004 Compounds of formula IA-2-1 to IA-2-7 No. T Z.sup.T L.sup.1 L.sup.2 Y.sup.3 Y.sup.4 G 242 [00645] F F CH.sub.3 CH.sub.3 PO(OH).sub.2 243 [00646] F F CH.sub.3 CH.sub.3 PO(OH).sub.2 244 [00647] F F CH.sub.3 CH.sub.3 PO(OH).sub.2 245 [00648] F F CH.sub.3 CH.sub.3 PO(OH).sub.2 246 [00649] F F CH.sub.3 CH.sub.3 PO(OH).sub.2 247 [00650] CH.sub.2 F F CH.sub.3 CH.sub.3 PO(OH).sub.2 248 [00651] CH.sub.2CH.sub.2 F F CH.sub.3 CH.sub.3 PO(OH).sub.2 249 [00652] CH.sub.2CH.sub.2 F F CH.sub.3 CH.sub.3 PO(OH).sub.2 250 [00653] Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2 251 [00654] Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2 252 [00655] Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2 253 [00656] Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2 254 [00657] CH.sub.2CH.sub.2 Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2 255 [00658] CH.sub.2CH.sub.2 Cl F CH.sub.3 CH.sub.3 PO(OH).sub.2

[0254] Compounds with alternative anchoring groups are obtained analogusly by procedures known from prior art, as for example the following:

##STR00659##

LIST OF REFERENCE NUMERALS

[0255] 10 electronic element [0256] 12 base substrate [0257] 14 first electrode layer [0258] 16 electrode material [0259] 18 dielectric material [0260] 20 molecular layer [0261] 22 further electrode layer [0262] 30 electrode line [0263] 31 rotated electrode line [0264] 32 non-electrode area [0265] 34 electrode area [0266] 100 cell [0267] 102 first electrode [0268] 104 part (of molecular layer) [0269] 106 second electrode [0270] 108 selector device