JP2021503488A - Hein electron-polarizing compounds and their capacitors - Google Patents

Abstract

The electron-polarizing compound has the general formula: (I). In the formula, the aromatic polycyclic conjugated molecular core 1 self-assembles to form a supramolecular structure; m donor groups R1 and m'acceptor groups R1'are attached to core 1; m And m'= 0, 1, 2, 3, 4, 5, or 6, but neither is 0; p = 0, 1, 2, 3, or 4 substituents R2 (1 or Multiple ionic groups) are attached to core 1 either directly or via a binding group. Fragment NLEs have a non-linear polarization effect. The number n of core 2 of the self-assembled electron conductive oligomer can be 0, 2, or 4; s = 0, 1, 2, 3, or 4 ionic groups R3 are attached to core 2. k = 0, 1, 2, 3, 4, 5, 6, 7, or 8 resistant substituents R4 electrically insulate the supramolecular structure.

Description

Priority Claim This application claims priority in US Patent Application No. 15 / 870,504 filed on January 12, 2018, the entire contents of which are incorporated herein by reference. U.S. Patent Application No. 15 / 870,504, in its entirety incorporated herein by reference, U.S. Patent Application No. 15 / 090,509, filed April 4, 2016, May 24, 2016. This is a partial continuation of US Patent Application No. 15 / 163,595 filed and US Patent Application No. 15 / 818,474 filed on November 20, 2017.

The present disclosure generally relates to passive components of electrical circuits, and more particularly to electron-polarizing compounds and capacitors based on this material and intended for energy storage.

A capacitor is a passive electronic component used to store energy in the form of an electrostatic field and contains a pair of electrodes separated by a dielectric layer. If there is a potential difference between the two electrodes, the electric field is in the dielectric layer. An ideal capacitor is characterized by a single constant value of capacitance, which is the ratio of the charge at each electrode to the potential difference between the electrodes. Higher voltage applications require larger capacitors.

One important feature of dielectric materials is their breaking electric field. The breaking electric field corresponds to the value of the electric field strength at which the material suffers a sudden failure and conducts electricity between the electrodes. For most capacitor geometries, the electric field in a dielectric can be approximated by dividing the voltage between the two electrodes by the distance between the electrodes, usually by the thickness of the dielectric layer. Since the thickness is usually constant, it is more common to refer to the breakdown voltage rather than the breakdown electric field. There are many factors that can dramatically reduce the breakdown voltage. In particular, the geometry of the conductive electrode is an important factor influencing the breakdown voltage for capacitor applications. In particular, sharp edges or points can significantly increase the electric field strength locally, resulting in local fracture. If local fracture is initiated at any time, the fracture will quickly "follow" within the dielectric layer until it reaches the counter electrode and causes a short circuit.

Destruction of the dielectric layer usually occurs as follows. The strength of the electric field is high enough to "pull out" electrons from the atoms of the dielectric material, thereby causing current to flow from one electrode to another. The presence of impurities or crystal structure imperfections in the dielectric can result in avalanche fractures as observed in semiconductor devices.

Another important feature of dielectric materials is their permittivity. Different types of dielectric materials are used in capacitors, including different types of ceramics, polymer films, paper, and electrolytic capacitors. The most widely used polymer film materials are polypropylene and polyester. Increasing the permittivity increases the volumetric energy density, so increasing the permittivity is an important technical issue.

The second-order nonlinear optical (NLO) effects of organic molecules have been extensively investigated for their advantages over inorganic crystals. For example, the properties studied include their large optical non-linearity, ultrafast response speed, high damage threshold, low absorption loss and the like. In particular, organic thin films with excellent optical properties have tremendous potential in integrated optics such as optical switching, data manipulation, and information processing. Among the organic NLO molecules, the azo dye chromophore was of particular interest to many researchers due to its relatively large molecular hyperpolarity (b) due to the delocalization of the p-electron cloud. They have almost often been incorporated as guests of polymer base materials (guest-host polymers) or grafted onto polymer base materials (functionalized polymers) over the last decade.

The perelectron polarization of organic compounds is described in Roger D. Hartman and Herbert A. Pohl, "Hyper-electronic Polarization in Macromolecular Solids", Journal of Polymer Science: Part Al Vol. 6, pp. 1135-1152 (1968). There is. Perelectron polarization can be seen as an electrically polarized external field due to the flexible interaction of excitons with charge pairs over the molecularly separated and molecularly restricted domains. In this document, four polyacene quinone radical polymers are investigated. These polymers had a dielectric constant of 1800-2400 at 100 Hz and were reduced to about 58-100 at 100,000 Hz. An essential drawback of the described material production method is the use of high voltage (up to 20 kbar) to form the sample for which the measurement of the dielectric constant is intended.

U.S. Pat. No. 5,739,296 U.S. Pat. No. 6,049,428

Roger D. Hartman and Herbert A. Pohl, "Hyper-electronic Polarization in Macromolecular Solids", Journal of Polymer Science: Part A-l Vol. 6, pp. 1135-1152 (1968) P. Lazarev et al., "X-ray Diffraction by Large Area Organic Crystalline Nano-films", Molecular Materials, 14 (4), pp. 303-311 (2001) Bobrov, "Spectral Properties of Thin Crystal Film Polarizers", Molecular Materials, 14 (3), pp. 191-203 (2001)

The present disclosure is based on the following general formula (I):

To provide an electron-polarizing compound having the above.

Core 1 is an aromatic polycyclic conjugated molecule that has two-dimensional flat morphology and self-assembly to supramolecular structures. R1 is an electron donating group attached to an aromatic polycyclic conjugated molecule (core 1), and R1'is an electron acceptor group (electoron acceptor) attached to an aromatic polycyclic conjugated molecule (core 1). group), m is the number of acceptor groups R1, m'is the number of donor groups R1', and m and m'are 0, 1, 2, 3, 4, 5, or 6 However, m and m'are not equal to 0, and R2 is used in an ionic liquid attached to an aromatic polycyclic conjugated molecule (core 1) either directly or via a linking group. It is a substituent containing one or more ionic groups from the class of ionic compounds to be made, where p is the number of ionic groups R2 equal to 0, 1, 2, 3, or 4. Fragments marked NLE with core 1 with at least one group R1 and / or R1'have a non-linear effect of polarization.

Core 2 is an electron conductive oligomer, and the number n of electron conductive oligomers is equal to 0, 2, or 4. R3 is a substituent containing one or more ionic groups from the class of ionic compounds used in ionic liquids, which are attached to an electron conductive oligomer (core 2) either directly or via a linking group. And s is the number of ionic groups R3 equal to 0, 1, 2, 3, or 4.

R4 is a resistant substituent attached to an aromatic polycyclic conjugated molecule (core 1) and / or an electron conductive oligomer (core 2), either directly or via a linking group. The resistant substituent R4 provides the solubility of the organic compound in the solvent and electrically insulates the supramolecular structures from each other. The parameter k is the number of substituents R4 equal to 1, 2, 3, 4, 5, 6, 7, or 8.

In one aspect, the disclosure provides a solution comprising an organic solvent and at least one disclosed electron-polarizing compound.

In another aspect, the present disclosure provides a crystalline metadielectric layer comprising a mixture of the above disclosed electron-polarizing compounds. A non-linear polarization fragment containing an aromatic polycyclic supramolecule with at least one group R1 is placed within the resistant dielectric envelope formed by the resistant substituent R4, where the resistant substituent R4 is located. Provides solubility of organic compounds in the solvent and electrically insulates supramolecular structures such as supramolecular columns from each other.

In yet another aspect, the present disclosure comprises two metal electrodes positioned parallel to each other and can be wound or flat and planar with a metadielectric layer between the electrodes, in a meta-capacitor. There is provided a meta-capacitor in which the meta-dielectric layer comprises one or more types of disclosed electron polarization. Non-linear polarization fragments containing aromatic polycyclic conjugated molecules with at least one group R1, electron conductive oligomers, and ionic groups with electronic and / or ionic polarizability are provided by resistant substituents. Arranged within the formed resistant dielectric envelope, where the resistant substituents provide the solubility of the organic compound in the solvent and electrically insulate the supermolecular structures from each other.

Incorporation by Reference All publications, patents, and patent applications described herein are the same as if each of the individual publications, patents, or patent applications is specifically and individually indicated to be incorporated by reference. To a degree, it is incorporated herein by reference.

It is a figure which shows typically the capacitor which has the flat electrode and the flat electrode by the aspect of this disclosure. It is a figure which shows typically the capacitor which has a wound (circular) electrode by another aspect of this disclosure. It is a figure which shows the chemical formula which shows the possible modification with respect to the structure called the riren fragment which can be contained in a Hein electron-polarizing compound by the aspect of this disclosure.

Although various embodiments of the present invention have been shown and described herein, it will be apparent to those skilled in the art that such embodiments are provided by way of example only. A number of modifications, modifications, and substitutions can be imagined by those skilled in the art without departing from the present invention. It should be understood that various alternatives of embodiments of the invention described herein may be used.

The present disclosure provides electron-polarizing compounds. The presence of electrophilic groups (acceptors) and nucleophilic groups (donors, donors) in the aromatic polycyclic conjugated molecule (core 1) promotes a heterogeneous distribution of electron densities in the conjugated molecule: one location (donor). There is a surplus of electrons in the body zone), and there is a shortage of electrons in another place (acceptor zone). The effect of the external electric field on the heterogeneous distribution of electron densities along the conjugated molecule results in inductive polarization _Pind . In general, the induced polarization is a non-linear function of the intensity of the local electric field E _loc . In the assumption of weak nonlinearity, which can be limited to some members of the decomposition of the induced polarization into a series with respect to the degree of intensity of the local electric field, the induced polarization of the (molecular) environment has the form:
_Pind = α ・ E _loc + β ・ E _loc ² + ・ ・ ・
(In the formula, α-linear polarizability, β-square polarizability)
Can be written down. Although the assumption of small electric field is not always correct, the parameters α and β can be used for qualitative analysis of the polarizability of the disclosed compounds. In the present disclosure, the main interest is focused on the method of increasing the induced polarization of the disclosed compounds, and thus the method of increasing the linear polarizability α and the square polarizability β. Such interest is evoked by the constant dipole and quadrupole electric moments being neutralized with each other during self-assembly of such conjugated molecules. Analysis shows that linear polarizability depends on the size of the average electron density in the molecule, and nonlinear polarizability depends on the size of electron density heterogeneity. It is also shown that the non-centrally symmetric arrangement of electron-donating and acceptor groups can result in a strong non-linear response of electron polarization of the compound in the presence of an electric field. The effects of the chemical structure on the linear polarizability α and the square polarizability β are shown in Table 1 below.

An essential feature of the present disclosure is the use of a rigid, non-conjugated limit carbon structure as the resistant substituent. Such structures can bend (curve) and result in a probability distribution of electron densities within the dielectric structure that results in their electrical breakdown, "fat" tails (alkyl, aryl, substituted alkyl). , Substituted aryl, alkyl fluorinated, alkyl chlorinated, branched and composite alkyl, etc.) to distinguish it from the dielectric structure formed. Thus, the resistant substituent R4 is preferably a non-conjugated compound with minimal or no voids / space, with a dense packing of SP3 carbons with H and F substituents. Otherwise, the use of fat tails can result in the formation of brittle dielectric structures (films, layers, and envelopes). Fragile structures may have local regions (“holes”) where the electron density is equal to zero and can be occupied by free electrons (causing electron decay). When a molecule is "extracted" from an ordered structure (from a crystal lattice), it is possible to enter the concept of molecular holes. In this case, a quantum object (quantum hole, quantum point) in which an empty (unoccupied) energy level exists is formed. Such a set of objects creates a state of electron conductivity and electrical breakdown of the dielectric structure.

Resistant substituents preferentially have a single branched chain with carbon-carbon between 5 and 13 unidirectional lengths, and a ring with more than 3 unidirectional lengths. It is selected from non-conjugated condensed carbon ring chains.

The presence of the electron-conducting oligomer results in an increase in the polarizability of the disclosed electron-polarizing compounds due to the electron superconductivity of the electron-conducting oligomer. The ionic group increases the ionic component of the polarization of the disclosed electron-polarizing compounds. A non-linear polarization fragment containing at least one dopant group, an electron conductive oligomer, and an aromatic polycyclic conjugated molecule with an ionic group is placed within a resistant dielectric envelope formed by a resistant substituent. Here, the resistant substituents provide the solubility of the organic compound in the solvent and electrically insulate the supermolecular structures from each other. Resistive substituents increase the electrical strength of these electron-polarizing compounds and the breakdown voltage of the dielectric layer formed on the substrate.

In some implementations, among other things, the aromatic polycyclic conjugated molecule (core 1) may contain a lilene fragment, which may be conjugated with a phenylamide, naphthalene amide, and / or anthracene amide. In another embodiment of the disclosed electron-polarizing compounds, the riren fragment is selected from the structures 1 to 17 shown in Table 2.

By way of example and without limitation, the electron donor and acceptor groups (R1) can be selected from nucleophiles (donors, donors) and electrophilic groups (acceptors) and contain m elements. The (various) pairs of groups (R1) _m include donors (R1') and / or acceptors (R1). Electrophilic group (acceptor) is, -NO _2, -NH ₃ +, and -NR ₃ + (quaternary nitrogen salts), counterion Cl ^- or Br ^-, -CHO (aldehyde), - CRO (keto group) , -SO ₃ H (sulfonic acid), -SO ₃ R (sulfonate), -SO ₂ NH ₂ (sulfonamide), -COOH (carboxylic acid), -COOR (ester, from the carboxylic acid side), -COCl (carboxylic acid side) Hydroate), -CONH ₂ (amide, from the carboxylic acid side), -CF ₃ , -CCl ₃ , -CN, -C (CN) ₂ , where R is alkyl (methyl, ethyl, isopropyl, tert). -Butyl, neopentyl, cyclohexyl, etc.), allyl (-CH ₂ -CH = CH ₂ ), benzyl (-CH ₂ C ₆ H ₅ ) groups, phenyl (+ substituted phenyl), and other aryl (aromatic) groups Selected from the groups selected from the containing list. Nucleophile (donor) is, -O ^- (phenoxide, etc. -ONa or _{-OK), - NH 2, -NHR} , -NR 2, -OH, -OR ( ether), - NHCOR (amide, amine side ), -OCOR (ester, from alcohol side), alkyl, -C ₆ H ₅ , vinyl, R is alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl, etc.), allyl (-CH It is selected from a group selected from the list containing ₂ -CH = CH ₂ ), benzyl (-CH ₂ C ₆ H ₅ ) groups, phenyl (+ substituted phenyl), and other aryl (aromatic) groups.

In another embodiment, the polycyclic aromatic core is defined as a lateral dimension [in the present specification, in the plane of compounds 1-17 and perpendicular to the variable length direction in compounds 1-17. The lateral dimension (the longitudinal dimension is defined herein as the vertical dimension). ], It may be extended in the same way. Such an extension is shown in Figure 2. The lateral dimension expansion makes the core more planar, resulting in greater surface area for π-π interactions and enhanced stacking effects. The lateral dimension extension also prevents the molecule from warping due to steric effects from adjacent molecules or substituents. These embodiments may still possess an electron-donating group and an acceptor group, as described for compounds 1-17, and may still possess an intrinsic rigid non-conjugated limit carbon structure as a resistant substituent. Some non-limiting examples of lateral expansion are shown below.

In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independently selected from hydrogen, electrophilic group, nucleophilic group, and resistant group, respectively. In some embodiments, the resistant group is attached via at least one binding group.

In some implementations, the electron-polarizing compound has the following structure:

In the formula, R _a is a nucleophile with or without an alkyl-resistant group, and R _b and R _c are electrophiles. Non-limiting examples of such structures include

In the formula, R and R'are independently selected from hydrogen and alkyl groups in the range C _{1 to} C ₁₈ .

In yet another embodiment of the disclosed electron-polarizing compounds, at least one linking group is selected from the list containing structures 18-35 shown in Table 4, where X is hydrogen. (H) or alkyl group.

In one embodiment of the disclosure, at least one binding group is selected from the group CH ₂ , CF ₂ , SiR ₂ O, CH ₂ CH ₂ O, where R is H, alkyl, and fluorine. Selected from the list that contains.

In yet another embodiment of the disclosure, the resistant substituent R4 is an alkyl, aryl, substituted alkyl, substituted aryl, fluorinated alkyl, chlorinated alkyl, branched and composite alkyl, branched and composite fluorinated alkyl. , Branched and complex chlorinated alkyl groups, and any combination thereof, wherein the alkyl group is selected from methyl, ethyl, propyl, n-butyl, isobutyl, and tert-butyl groups. Aryl groups are selected from phenyl, benzyl and naphthyl groups, or siloxane and / or polyethylene glycol straight or branched chains. In yet another embodiment of the disclosure, the resistant substituent R4 is C _X Q _{2X + 1} , X ≧ 1 in the equation, where Q is hydrogen (H), fluorine (F), or chlorine (Cl). ).

In one embodiment of the electron-polarizing compound, the aromatic polycyclic conjugated molecule (core 1) and group (R1) form a non-centrally symmetric molecular structure. In another embodiment of the electron-polarizing compound, the aromatic polycyclic conjugated molecule (core 1), group (R1), and resistant substituent (R4) form a non-centrally symmetric molecular structure. In one embodiment of the present disclosure, the electron-polarizing compound is represented by the following general formula (II):

Have.

In general formula II, core 1 is the aromatic polycyclic conjugated molecule discussed above and the resistant substituent R4 is the non-conjugated moiety of the disclosed compound, saturated and condensed cyclohydrocarbons, or Rigid spaces of saturated and condensed cyclohalocarbons, including but not limited to structures constructed from tiles of cyclohexane, cyclopentane, polycyclic perfluorohexyls, polycyclic perfluoropentyl, and cyclic carbon molecules. It may have a structure. Tiles of cyclic carbon molecules may have a dense packing of SP3 carbon saturated with H, F, Cl, or Br. In one particular implementation, the parameter n = p = s = 0. In another embodiment of the electron-polarizing compound, the length of the non-conjugated moiety is chosen such that its resistivity is greater than 10 ¹⁵ ohm cm. In yet another embodiment of the electron-polarizing compound, the resistant substituent R4 is a benzyl group, a benzylalkoxy group, a benzylhalo-alkoxy group, an alkoxy group, a benzylalkyl group, a benzylhalo-alkyl group, an alkyl group, a halo-alkoxy group. , A halo-alkyl group, a benzylaryl group, and a benzylhalo-aryl group, where the R4 substituent is attached to the apex of core 1 to which the nucleophilic (donor) R1 is attached. ), Or is attached to the tip of core 1 to which the electrophilic group (acceptor) R1'is attached, but not both. In yet another embodiment of the electron-polarizing compound, the resistant substituent R4 is selected from a list containing long C ₂₅ H ₃₄ and C ₂₅ H ₃₅ or C ₂₅ F ₃₄ and C ₂₅ F ₃₅ and is the tip of core 1. It is positioned on the phenyl ring. In one embodiment of the present disclosure, the electron-polarizing compound is the following general formula (III):

Have.

In General Formula III, the parameters m and m'are equal to 1, R1'is the acceptor group, R1 is the donor group, and k and k'are the R4 resistant groups at both ends of the molecule. In another embodiment of the electron-polarizing compound, core 1 has the following structural formula:

In the equation, the repeat parameter t is a variety of integers from 0 to 5, and the set of electron donor and acceptor groups is at the position of the ribene phenyl ring and / or the tip phenyl ring of core 1. Fragments containing one positioned donor group-NEt ₂ and one acceptor group-NO ₂ (m and m'both equal to 1) and therefore have a non-linear effect of polarization (NLE) are listed below. Represented by the chemical structure of (if t = 0):

Here, the resistant substituent (R4) is a benzylalkoxy group, and in some cases:

Etc. are attached via a benzyl group, where n and n'are in the range of 4-25. This is the following structural formula (IV):

Bring.

In some embodiments, the resistant substituent (R4) is an alkyne-binding group, eg:

It is a branched alkyl or alkoxy group bonded via, and in the formula, n and n'are in the range of 4 to 25. This is the following structural formula (V):

Bring.

In another embodiment of the present disclosure, the electron-polarizing compound is represented by the following general formula (VI):

Have.

In the general formula VI, core 1 is the aromatic polycyclic conjugated molecule described above, m is equal to 6, R1'is the donor group, R1 is the acceptor group, and k is equal to 2. In yet another embodiment of the electron-polarizing compound, the core 1 has the following structural formula:

The repeat parameter t varies from 1 to 5 in the formula, and the set of electron donor and acceptor groups contains 3 donor groups-NH ₂ and 3 acceptor groups. -NO ₂ (m equals 6) is located at the ribene phenyl ring and / or the tip phenyl ring position of core 1, so fragments with a non-linear effect of polarization (NLE) have the following chemical structure (t = 1): When):

The resistant substituent (R4) is represented by the following type of amine structure:

And the following structural formula (VII):

The resistant substituents are attached via a binding group.

Non-limiting examples of electronically polar cores include the following structures:

It contains at least two positional isomers selected from, and in the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independently hydrogen, electrophilic, and nucleophilic groups, respectively. , And a resistant group; n is an integer greater than or equal to 1. Non-limiting examples of such combinations of substituents are listed in Table 5.

R and R'can be selected from alkyl, alkene, and substituted alkyl groups, either equally or independently; DB is 3,5-dimethoxyphenyl. The electron-polarizing compound may be further modified to include a resistant substituent attached to the core via a DB group or a binding group listed in Table 4.

In some embodiments, the dielectric layer of the electron-polarizing compound comprises a plurality of positional isomers. In some embodiments, the dielectric layer containing the electron-polarizing compound comprises a mixture of the electron-polarizing compounds.

In one embodiment of the present disclosure, a form of decomposition of the induced polarization _Pind of an electron-polarizing compound into a series with respect to the degree of intensity of the local electric field E _loc :
_Pind = α ・ E _loc + β ・ E _loc ² + ・ ・ ・
In the equation, α represents the linear polarizability and β represents the square polarizability.

In some embodiments, the present disclosure provides an organic solvent comprising the disclosed electron-polarizing compounds. In one embodiment, the solution comprises a mixture of various electron-polarizing compounds. In another embodiment of the disclosed organic solvent, the mixture of electron-polarizing compounds comprises ribene fragments of different lengths. In yet another embodiment, the organic solvent is selected from a list comprising ketones, carboxylic acids, hydrocarbons, cyclic hydrocarbons, chlorohydrocarbons, alcohols, ethers, esters, and any combination thereof. In yet another case, the organic solvent is acetone, xylene, toluene, ethanol, methylcyclohexane, ethyl acetate, diethyl ether, octane, chloroform, methylene chloride, dichloroethane, trichloroethane, tetrachloroethane, carbon tetrachloride, 1,4-. It is selected from a list containing dioxane, tetrahydrofuran, pyridine, triethylamine, nitromethane, acetonitrile, dimethylformamide, dimethylsulfoxide, and any combination thereof. In yet another embodiment of the disclosure, the solution is a lyotropic liquid crystal solution.

In another aspect, aspects of the present disclosure provide a crystalline metadielectric layer comprising at least one type of disclosed electron-polarizing compound. The crystalline meta-dielectric layer is produced from organic compounds disclosed by cascade crystallization; a method of producing crystalline thin films (or crystalline thin layers) known as the Optiva-process. U.S. Pat. Nos. 5,739,296 and 6,049,428 and P. Lazarev et al., "X-ray Diffraction by Large Area Organic Crystalline Nano-films," Molecular Materials, 14 (4), pp. 303-311 (2001), and Bobrov, See "Spectral Properties of Thin Crystal Film Polarizers", Molecular Materials, 14 (3), pp. 191-203 (2001).

In the cascade crystallization process, four steps are performed: a chemical modification step and an ordering step during the formation of the crystal metadielectric layer. The chemical modification step introduces a hydrophilic group around the molecule of the disclosed organic compound in order to impart amphipathicity to the molecule. The amphipathic molecules are laminated together to form a supramolecular structure as the first step in ordering. At a particular concentration, the supramolecular structure is transformed into a liquid crystal state to form a lyotropic liquid crystal as a second step in ordering. The lyotropic liquid crystal is deposited under the action of a shear force (or meniscus force) on the substrate based on the Mayer Rod shearing technique, so that the direction of the shear force (or meniscus) is the crystal axis direction in the obtained solid crystal layer. To determine. External alignment on supramolecular liquid crystals uses any other means, such as an external electric field at normal temperature or high temperature, with additional illumination, magnetic field, or optical field (eg, coherent photovoltaic effect). It can be produced by application with or without; the degree of external alignment provides a structure that serves as the supramolecular structure of the lyotropic liquid crystal and as the base of the crystal lattice of the dielectric layer. It should be enough to form. This directional deposition is the third step of ordering and represents the overall ordering of crystalline or polycrystalline structures on the surface of the substrate. The final fourth step of the cascade crystallization process is drying / crystallization, which transforms the lyotropic liquid crystal into a solid crystal dielectric layer. The term cascade crystallization process is used to refer to chemical modification and four ordering processes as a combinatorial process.

The cascade crystallization process is used to produce a thin crystalline metadielectric layer. The dielectric layer produced by the cascade crystallization process has an overall order, which means that the orientation of the crystal axis of the layer on the surface of the entire substrate is controlled by the deposition process. The molecules of the deposited material fill the supramolecular structure with limited diffusion or motion freedom. The thin crystalline dielectric layer is characterized by a distance between planes of 3.4 ± 0.3 angstroms (Å) in one direction of the optic axis.

In one embodiment of the disclosure, the crystalline metadielectric layer comprises a supramolecular structure such as a column, needle, etc. formed by an electron-polarizing compound containing relen fragments of different lengths. The length of the various Riren fragments increases the randomness of the laminate. In one embodiment according to aspects of the present disclosure, the relative permittivity of the layer is greater than or equal to 1000. In one embodiment, the real part of the relative permittivity (ε') of the crystalline meta-dielectric layer is:

Including the primary (ε ⁽¹⁾ ) and secondary (ε ⁽²⁾ ) permittivity according to, in the equation V ₀ is the DC-voltage applied to the crystalline meta-dielectric layer and d is the layer thickness. That's right. In another embodiment of the present invention, the resistivity of the layer is equal to greater or 10 ¹³ ohm / cm than 10 ¹³ ohm / cm.

The present disclosure provides a meta-capacitor that includes two metal electrodes positioned parallel to each other and can be wound or flat and planar with a metadielectric layer between the electrodes. The layer comprises the above disclosed electron-polarizing compounds.

The metacapacitor includes a first electrode 1, a second electrode 2, and a metadielectric layer 3 disposed between the first and second electrodes, as shown in FIG. 1A. Electrodes 1 and 2 may be made of a metal such as copper, zinc or aluminum, or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape.

The electrodes 1 and 2 may be flat or flat, or may be positioned parallel to each other. Alternatively, the electrodes may be planar and parallel, but not necessarily flat, and are coiled, wound, bent, and folded to reduce the overall Scherrer equation of the capacitor. , Or other shapes. The electrodes can be non-flat, non-planar, or non-parallel, or can be any combination of two or more of these. By way of example, but not limited to, the spacing between electrodes 1 and 2 can range from about 100 nm to about 10,000 μm. The maximum voltage V _bd between electrodes 1 and 2 is approximately the product of the breaking electric field E _bd and the electrode spacing d. If E _bd = 0.1 V / nm and the spacing d between electrodes 1 and 2 is 10,000 microns (100,000 nm), the maximum voltage V _bd can be 100,000 volts.

Electrodes 1 and 2 may have the same shape, the same dimensions, and the same area A as each other. As an example, but not limited to, the area A of each electrode 1 and 2 can range from about 0.01 m ² to about 1000 m ² . By way of example, but not limited to, in the case of wound capacitors, the electrodes can be up to, for example, 1000 m long and 1 m wide.

These ranges are non-limiting. Other ranges of electrode spacing d and area A are within the scope of aspects of the present disclosure.

If the spacing d is small compared to the characteristic linear dimensions of the electrodes (eg, length and / or width), then the capacitance C of the capacitor is:
C = εε _o A / d, (V)
In the equation, ε ₀ is the permittivity of free space (8.85 × 10 ^-12 Coulomb ² / (Newton meter ² )) and ε is the dielectric constant of the dielectric layer. The energy storage capacity U of the capacitor is:
U = _1/2 εε _o AE _bd ² d (VI)
May be approximated as.

The energy storage capacity U is determined by the dielectric constant ε, the area A, and the breaking electric field E _bd . With proper design and fabrication, the capacitor or capacitor bank may be designed to have any desired energy storage capacity U. By way of example, given, but not limited to, the dielectric constant ε, the electrode area A, and the electric field E _bd , the capacitors according to aspects of the present disclosure are from about 500 joules to about 2.10 ¹⁶ joules. It may have an energy storage capacity U in the range of.

For example, for a dielectric constant ε in the range of about 100 to about 1,000,000, and for example a constant _decay electric field E _bd between about 0.1 and 0.5 V / nm, the types of capacitors described herein are about 10 W · h /. It may have a specific energy capacity per unit mass in the range of kg to a maximum of about 100,000 W · h / kg, but the implementation examples are not limited to this.

The present disclosure includes a coiled metacapacitor, eg, as shown in FIG. 1B. In this embodiment, the metacapacitor 20 includes a first electrode 21, a second electrode 22, and a metadielectric material layer 23 of the type described above arranged between the first and second electrodes. The electrodes 21 and 22 may be made of a metal such as copper, zinc or aluminum, or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape. In one embodiment, the electrode and metadielectric material layer 23 are sandwiched and coiled together with an insulating material, such as a plastic film such as polypropylene or polyester, to prevent short circuits between the electrodes 21 and 22. It takes the form of long strips of rolled material.

In order to make the present invention easier to understand, reference is made to the following examples, which are intended to illustrate the invention but not limit its scope.

[Example 1]

Synthesis of 3,5-dihydroxybromobenzene: In a reaction flask dried overnight at 90 ° C., 3,5-dimethoxybromobenzene (1 eq) was dissolved in anhydrous CH ₂ Cl ₂ and placed in an ice-water bath. Allowed to cool for 10 minutes. BBr ₃ (2.2 eq in 1 M, CH ₂ Cl ₂ ) was slowly added to this chilled solution over 5 minutes. After this addition was complete, the reactants were removed from the ice water bath, warmed to room temperature in air and stirred overnight. After 18 hours, it was confirmed that the reaction was completed by SiO ₂ TLC using 1: 1 hexane: EtOAc. The reaction was placed in the original ice-water bath and cooled for 10 minutes, after which 1 mL of methanol was added to quench all unreacted BBr ₃ that was still present. The reaction mixture was washed with aqueous HC1 (2M) and extracted with EtOAc (3x). Organic fractions were collected, dried in Na ₂ SO ₃ and then filtered. The crude reaction mixture was concentrated in vacuo and precipitated in hexanes to give 3,5-dihydroxy-bromobenzene.

Synthesis of A: In a reaction flask dried overnight at 90 ° C., 3,5-dihydroxybromobenzene (1 eq) and K ₂ CO ₃ (3 eq) were dissolved in anhydrous DMF and stirred at room temperature for 10 minutes. .. Bromododecane (3 eq) was added to the mixture and the reaction was placed in a preheated 100 ° C. oil bath and stirred overnight. After 18 hours, it was confirmed that the reaction was completed by SiO ₂ TLC using 1: 1 hexane: EtOAc. The reaction was removed from the oil bath and cooled to room temperature in air. Excess K ₂ CO ₃ was quenched with aqueous HC1 (2M) and the reaction was extracted with EtOAc. Organic fractions were collected, washed with deionized water, dried over Na ₂ SO ₃ and then filtered. The solvent was removed by vacuum and the product was purified by silica gel chromatography (100% hexane to 10% EtOAc: 90% hexane) and isolated as a colorless oil, which was slowly solidified to a white solid.

Synthesis of B: A (1 eq), bis (pinacolato) diboron (1.6 eq), potassium acetate (3 eq), Pd (dppf) Cl ₂ (0.03 eq) are drained into a 100 mL round bottom flask. N ₂ was refilled. In another flask, dioxane was sparged under N ₂ stream for 15 minutes and then added to the reaction flask via syringe. The reaction solution was placed in a preheated oil bath set at 90 ° C. and monitored with TLC (9: 1 hexane: EtOAc). When the reaction was complete, the reaction mixture was washed with 2M HCl and extracted with ethyl acetate. The organic fraction was collected, dried over Na ₂ SO ₄ and filtered before removing the solvent under reduced pressure. The crude material was redissolved in hexane and filtered using a silica plug using hexane as the eluent. Hexane was removed under reduced pressure to isolate the viscous oil. The crude mixture was stirred in methanol for 1 hour to give a white solid precipitate, which was collected by vacuum filtration. B was isolated as a white solid.

Synthesis of C: 2,6-dinitroaniline (1 eq), Ag ₂ SO ₄ (1.4 eq), and I ₂ (1.4 eq) were added to a 50 mL round bottom flask at room temperature. Ethanol was added to this mixture and the reaction was stirred for 18 hours at room temperature. The next morning, a yellow precipitate was formed and TLC analysis (1: 1 EtOAc: Hexanes) showed that the starting material was completely consumed. The reaction mixture was filtered and the solid residue was washed with EtOAc until the filtrate was clear. The solvent was then evacuated from the filtrate and the crude solid was redissolved in a minimum amount of CH ₂ Cl ₂ and then precipitated in hexane. The mixture was left for 30 minutes until the solid no longer settled and the solid was isolated via vacuum filtration. C was isolated as an orange solid.

Synthesis of D: C (1 eq), B (1.1 eq), Pd (PPh ₃ ) ₂ Cl ₂ (0.03 eq), and K ₂ CO ₃ (2 eq) were added to a 25 mL round bottom flask, followed by , Drained and refilled with N ₂ 3 times. In another flask, N ₂ was bubbled in a solution of toluene and H ₂ O for 30 minutes, after which the solution was added to the reaction flask. The solution was then placed in an oil bath preheated to 100 ° C. and stirred overnight. The reaction was monitored with TLC (7: 3 hexane: EtOAc). When the reaction was complete, it was removed from the oil bath and cooled in air at room temperature for 30 minutes. The mixture was washed with distilled water and the excess base was carefully acidified with the addition of 2M HCl and then extracted with EtOAc. Organic fractions were collected, dried over NaSO ₄ , filtered and the solvent removed under vacuum distillation. The crude product was dissolved in a minimal amount of CH ₂ Cl ₂ and precipitated in MeOH. The solid was filtered to give D as a yellow solid.

Synthesis of E: D (1 eq) was added to a round bottom flask and dissolved in n-butanol at 80 ° C. To this solution was added a 20 wt% aqueous solution of (NH ₄ ) ₂ S (2 eq). The reaction was stirred for 1 hour and monitored with TLC (7: 3 hexane / EtOAc). When the reaction was complete, the reaction mixture was washed with 2M HCl and extracted with ethyl acetate. The organic fractions were collected, dried over Na ₂ SO ₄ , filtered and then the solvent removed under reduced pressure. The crude material was redissolved in hexane purified using SiO ₂ column chromatography (7: 3 hexane / EtOAc) to give E as a viscous red oil.

Synthesis of F: E (1 eq), 4-bromophthalic anhydride (1.2 eq), and Zn (OAc) ₂ 2H ₂ O (0.4 eq) were added to the round bottom flask, then drained and N ₂ was refilled. In a separate flask, quinoline was purged under a stream of N ₂ for 15 minutes and added to the reaction mixture. The suspension was heated to 170 ° C. and stirred overnight. When the reaction was complete, the hot solution was poured into MeOH and the resulting solid was washed with 20 mL additional MeOH and then collected. Residual MeOH was removed under reduced pressure to give F.

Synthesis of G: F (1 eq) was added to the round bottom flask with butanol (0.3 M). The suspension was heated to 80 ° C. and the reducing agent (SnCl ₂ , (NH ₄ ) ₂ S, or HNaS; 1 eq) was transferred to the high temperature reaction mixture. The reaction was monitored by TLC analysis and stirred overnight. When the reaction was complete, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic fraction was collected, dried over Na ₂ SO ₄ and filtered before removing the solvent under reduced pressure. The crude material was redissolved in hexane (hexane / EtOAc, then EtOAc) purified using SiO ₂ column chromatography to give G.

Synthesis of H: F (1 eq), Pd (dppf) Cl ₂ (0.05 eq), AcOK (2 eq), and B ₂ Pin ₂ (1.5 eq) were added to a 25 mL round bottom flask. The mixture was then drained and refilled with N ₂ three times. In another flask, dioxane (0.3 M) was bubbled with N ₂ for 30 minutes. The degassed solvent was then added to the reaction flask in an N ₂ atmosphere, placed in a preheated oil bath at 100 ° C. and stirred overnight. When the reaction was complete, it was removed from the oil bath, cooled to room temperature, washed with 2M HCl and extracted with EtOAc. The organic layer was collected, dried over Na ₂ SO ₄ , filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography (100% hexane-8: 2 hexane / EtOAc). The solvent was removed to give H.

Synthesis of I: H (1 eq), Pd (PPh ₃ ) ₄ (0.05 eq), K ₂ CO ₃ (2 eq), and G (1 eq) were added to the reaction flask. The mixture was then drained and refilled with N ₂ three times. In another flask, N ₂ was bubbled into a mixture of toluene, H ₂ O (2: 1) for 10 minutes. This degassing solvent was then added to the reaction flask via a syringe under an N ₂ atmosphere, placed in a preheated oil bath at 100 ° C. and stirred overnight. When finished, the reactants were removed from the oil bath, cooled to room temperature, washed with 2M HCl and extracted with EtOAc. The organic layer was collected, dried over Na ₂ SO ₄ , filtered and the solvent removed under reduced pressure. The crude solid was dissolved in a minimal amount of CH ₂ Cl ₂ and precipitated in MeOH. H was isolated by filtration.

I (1 eq) was dispersed in triethanolamine (0.02M) and K ₂ CO ₃ (25 eq) was added. The mixture was stirred at 130 ° C. for 24 hours under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and washed with water. The organic layer was purified by drying over anhydrous sodium sulfate and precipitating in methanol, resulting in J as a deep purple solid.

[Example 2]
This example describes the synthesis of organic compounds disclosed by the structural scheme below:

procedure:

Bromo-amine 4 (1 eq), naphthalene 14 (1 eq), Pd (PPh ₃ ) ₄ (10 mol%) and K ₂ CO ₃ (1.5 eq) were stirred in toluene at 70 ° C. for 18 hours. The mixture was filtered through diatomaceous earth and the filtrate was washed with LVDS ₃ and brine. The organic was dried over DDL ₄ and the solvent was removed under reduced pressure to give 15.

Naphthalene anhydride 16 (1 eq) and naphthalene 15 (1 eq) were stirred in imidazole overnight at 130 ° C. The mixture was dissolved in THF and washed 3 times with water. The organics were combined and dried on DDL ₄ . The solvent was removed under reduced pressure to give 17.

Amidine 17 (1 eq) and Pd / C (20% wt / wt) were stirred in a three-necked flask fitted with an H ₂ balloon for 18 hours. The mixture was filtered through diatomaceous earth and the solvent was removed under reduced pressure to give 18.

Amidine 17 (1 eq) was dissolved in THF and stirred at -80 ° C. N-Butyllithium (1.2 eq, 2.5 M, in hexane) was added drop by drop. After 1 hour, triisopropylborane was added drop by drop and warmed to room temperature overnight. The mixture was washed with LVDS ₃ and brine and dried over DDL ₄ . The solvent was removed under reduced pressure to give 19.

Bromoamidine 18 (1 eq), amidine boronic acid ester 19 (1 eq), Pd (PPh ₃ ) ₄ (10 mol%) and K ₂ CO ₃ (1.5 eq) were stirred in toluene at 70 ° C. for 18 hours. The mixture was filtered through diatomaceous earth and the filtrate was washed with LVDS ₃ and brine. The organic was dried over DDL ₄ and the solvent was removed under reduced pressure to give 20.

A mixture of potassium tert-butoxide (1 eq), diazabicyclo [5.4.0] undeca-7-ene (DBU) (1.2 eq), ethanolamine (2.8 eq), and 20 (1 eq) at 140 ° C. for 11 hours. It was heated. The same amount of potassium tert-butoxide, DBU, and ethanolamine were then added and the mixture was kept at 140 ° C. for 18 hours. The reaction mixture was cooled to room temperature, poured into 1M HCl, filtered, washed to neutral pH and then dried to give the final product 21.

Aspects of the present disclosure provide compounds characterized by a high degree of non-linear electric polarizability. Such compounds are useful as high dielectric constant metadielectrics for metacapacitors with extremely high capacitance and extremely high energy storage capacity.

The above content is a complete description of preferred embodiments of the invention, but various alternatives, modifications, and equivalents can be used. Therefore, the scope of the present invention should not be determined with reference to the above description, but rather with reference to the appended claims, along with the full scope of its equivalents. .. Any feature described herein may or may not be combined with any other feature described herein, preferably or otherwise. In the claims below, the indefinite article "A" or "An" refers to one or more quantities of items following an article, unless otherwise stated. In the enumeration of the elements of the alternative example, the word "or" is used in a logically comprehensive sense, for example, "X or Y" is X alone, Y alone, or X unless otherwise specified. And Y are included together. Two or more elements listed as alternatives may be combined together. The appended claims are given by the limitation of means-plus-function, such limitation using the phrase "means for". It is not construed to include unless explicitly listed in the claims.

1 1st electrode
2 Second electrode
3 Metadielectric layer
20 Metacapacitor
21 First electrode
22 Second electrode
23 Metadielectric material layer

Claims (20)

The following general formula (I):

It is an electron-polarizing compound having
In the formula, core 1 is an aromatic polycyclic conjugated molecule having a two-dimensional flat morphological supermolecular structure, and R1 is an electron donating group bonded to the aromatic polycyclic conjugated molecule (core 1). Yes, R1'is the electron acceptor group attached to the aromatic polycyclic conjugated molecule (core 1), m is the number of acceptor groups R1, and m'is the number of donor groups R'. M and m'are equal to 0, 1, 2, 3, 4, 5, or 6, but neither m and m'are equal to 0, and R2 is aromatic, either directly or through a linking group. A substituent containing one or more ionic groups from the class of ionic compounds used in ionic liquids attached to a group polycyclic conjugated molecule (core 1), where p is 0, The number of ionic groups R2 equal to 1, 2, 3, or 4
Fragments marked NLE with core 1 with at least one group R1 and / or R1'have a non-linear effect of polarization.
Core 2 is an electron conductive oligomer, n is the number of electron conductive oligomers equal to an integer from 0 to 4, and R3 is attached to the electron conductive oligomer (core 2) either directly or via a binding group. Also, a substituent containing one or more ionic groups from the class of ionic compounds used in ionic liquids, where s is an ionic group equal to 0, 1, 2, 3, or 4. The number of R3,
R4 is a resistant substituent attached directly or via a linking group to an aromatic polycyclic conjugated molecule (core 1) and / or an electron conductive oligomer (core 2), where k is 1, 2 , 3, 4, 5, 6, 7, or an electron-polarizing compound that is the number of substituents R4 equal to 8. The electron-polarizing compound according to claim 1, wherein the aromatic polycyclic conjugated molecule (core 1) contains one or more rylene fragments. The second aspect of claim 2, wherein the one or more ribene fragments are conjugated to one or more phenyl groups and / or one or more naphthyl groups and / or one or more anthryl groups. Electropolarizing compound. Riren fragments, structures 1-17:

The electron-polarizing compound according to claim 2, wherein n is an integer of 0 to 3, selected from. Acceptor group (R1 ') is, -NO _2, -NH ₃ ⁺ and -NR ₃ ⁺ (quaternary nitrogen salts), counterion Cl ^- or Br ^-, -CHO (aldehyde), - CRO (keto group), -SO ₃ H (sulfonic acid), - SO ₃ R _{(sulfonate), - SO 2 NH 2,} -SO 2 NHR, -SO 2 NR 2 ( sulfonamide), - COOH (carboxylic acid), - COOR (ester, (From the carboxylic acid side), -CONH ₂ , -CONHR, -CONR ₂ (from the amide, carboxylic acid side), -CF ₃ , -CCl ₃ , -CN, -C (CN) ₂ selected from the formula, R Are alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl, etc.), allyl (-CH ₂ -CH = CH ₂ ), benzyl (-CH ₂ C ₆ H ₅ ) groups, phenyl (+ substituted phenyl). The electron-polarizing compound according to claim 1, which is a group selected from the list containing, and other aryl (aromatic) groups, SO ₂ CN, and COCF ₃ . Donating group (R1) is, -O ^- (phenoxide, -ONa or -OK, _{etc.), - NH 2, -NHR,} -NR 2, -NRR '( amine), - OH, -OR (ether), - Selected from NHCOR (from the amide, amine side), -OCOR (from the ester, alcohol side), alkyl, -C ₆ H ₅ , vinyl, R and R'in the formula are independently alkyl (methyl, ethyl, Isopropyl, tert-butyl, neopentyl, cyclohexyl, etc.), allyl (-CH ₂ -CH = CH ₂ ), benzyl (-CH ₂ C ₆ H ₅ ) groups, phenyl (+ substituted phenyl), and other aryls (aromatics) The electron-polarizing compound according to claim 1, which is selected from a list containing a group. Bonding groups are CH ₂ , CF ₂ , SiR ₂ O, CH ₂ CH ₂ O, and structures 18-35:

The electron-polarizing compound according to claim 1, wherein R is H, alkyl, and fluorine, and X is hydrogen (H) or an alkyl group, selected from a list comprising. Resistant substituent R4 is alkyl, aryl, substituted alkyl, substituted aryl, halo-alkyl, branched and composite alkyl, branched and composite halo-alkyl, benzyl group, benzyl alkoxy group, benzyl halo-alkoxy group, alkoxy. The electron-polarizing compound according to claim 1, which is selected from the group of a group, a benzylalkyl group, a benzylhalo-alkyl group, a halo-alkoxy group, a benzylaryl group, and a benzylhalo-aryl group, and any combination thereof. The resistant substituent R4 is C _X Q _{2X + 1} , in the equation X ≧ 1, where Q is selected from the list containing hydrogen (H), fluorine (F), and chlorine (Cl). , The electron-polarizing compound according to claim 1. The electron-polarizing compound according to claim 1, wherein the aromatic polycyclic conjugated molecule (core 1) and the groups R1 and R1'form a non-centrally symmetric molecular structure. The electron-polarizing compound according to claim 1, wherein the aromatic polycyclic conjugated molecule (core 1), the groups R1 and R1', and the resistant substituent (R4) form a non-centrally symmetric molecular structure. .. The following general formula (II):

In the formula, core 1 is an aromatic polycyclic conjugated molecule, and the resistant substituent R4 is a non-conjugated moiety of compound II.
The electronic polarization according to claim 1, wherein k is the number of substituents R4 equal to 1, 2, 3, 4, 5, 6, 7, or 8 and the parameter n = p = s = 0. Compound. The length of the non-conjugated portions, the resistivity of the electronic polarization compound is selected to be equal to 10 ¹⁵ greater than ohm · cm or 10 ¹⁵ ohm · cm, electronic polarization compound of claim 12. The resistant substituent R4 contains a polycyclic alkyl group and a polycyclic halo-alkyl group, and the polycyclic halo-alkyl group is attached to the tip of the core 1 to which the electrophilic group (acceptor) R1 is attached. Alternatively, the electron-polarizing compound according to claim 12, which is attached to the tip of core 1 to which the nucleophilic group (donor) R1'is attached. Resistant substituent R4 is alkyl, aryl, substituted alkyl, substituted aryl, halo-alkyl, branched and composite alkyl, branched and composite halo-alkyl, benzyl group, benzyl alkoxy group, benzyl halo-alkoxy group, alkoxy. The electron-polarizing compound according to claim 12, which is selected from the group of a group, a benzylalkyl group, a benzylhalo-alkyl group, a halo-alkoxy group, a benzylaryl group, and a benzylhalo-aryl group, and any combination thereof. A metadielectric layer comprising a layer of a material containing one or more of the electron-polarizing compounds according to claim 1. The non-linear polarization fragment comprises an aromatic polycyclic conjugated molecule having at least one R4 group, said at least one R4 group forming a resistant envelope that electrically insulates the supramolecular structure from each other. A metadielectric layer containing the electron-polarizing compound according to claim 1. A meta-dielectric layer comprising one or more supramolecular structures, wherein the supramolecular structure is formed by an electron-polarizing compound containing lilene fragments of different lengths. The relative dielectric constant of meta dielectric layer is equal to larger or 1000 than 1000, the resistivity of the layer is equal to the greater or 10 ¹⁵ ohm · cm than 10 ¹⁵ ohm · cm, according to claim 16 Meta Dielectric layer. A meta-condenser that includes two metal electrodes positioned parallel to each other and can be wound or flat and planar with a metadielectric layer between the metal electrodes. Aromatic polycyclic conjugated molecules, electron conductive oligomers, and electronic types in which the layer comprises one or more types of the electron-polarizing compound according to claim 1 and has at least one group R1 or R1'. Non-linear polarization fragments containing ionic groups with and / or ionic polarizabilities are located within a resistant dielectric envelope formed by the resistant substituent R4 that electrically insulates the supermolecules from each other. , Meta-condenser.

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