Organic compound, crystal dielectric layer and capacitor

• US 10,026,553 B2
• Filed: 10/21/2015
• Issued: 07/17/2018
• Est. Priority Date: 10/21/2015
• Status: Expired due to Fees

• Current Assignee: Capacitor Sciences Incorporated (Bolloré SE)
• Original Assignee: Capacitor Sciences Incorporated (Bolloré SE)
• Inventors: Furuta, Paul, Lazarev, Pavel Ivan
• Primary Examiner(s): Solola, Taofiq A
• Application Number:
  US14/919,337
• Publication Number:
  US 20170117097A1
• Time in Patent Office: 1,000 Days
• Field of Search: 546 27
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C07D 471/22 in which the condensed systems contains four or more hetero rings
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: H01G 4/14 Organic dielectrics
• CPC Class Codes: H01G 4/18 of synthetic material, e.g. derivatives of cellulose H01G4/16 takes precedence
• CPC Class Codes: H10K 10/20 Organic diodes
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: Y02T 10/70 Energy storage systems for electromobility, e.g. batteries

Abstract

The present disclosure provides an organic compound characterized by electronic polarizability and having a following general structural formula:

• • where Core is an aromatic polycyclic conjugated molecule, R₁ is group providing solubility of the organic compound in an organic solvent, n is 1, 2, 3, 4, 5, 6, 7 or 8, R₂ is substitute located in apex positions, R3 and R4 are substitutes located in side (lateral) positions and, the core has flat anisometric form and the R₂ substitutes are selected from hydrogen and electrophilic groups (acceptors) and R₃ substitutes and R₄ substitutes are independently selected from hydrogen and nucleophilic groups (donors) or vice versa R₃ substitutes and R₄ substitutes are independently selected from hydrogen and nucleophilic groups (donors) and R₂ substitutes are selected from hydrogen and electrophilic groups (acceptors), and the substitutes R₂, R₃ and R₄ cannot all be hydrogen.

Claims

1. An organic compound characterized by electronic polarizability and having a following general structural formula:

2. An organic compound according to claim 1, wherein said R₁ groups are isolating groups and are attached to the aromatic polycyclic conjugated core in apex positions and/or side position.

3. An organic compound according to claim 1, wherein the electrophilic groups (acceptors) are selected from —

NO₂, —

NH₃⁺ and —

NR₃⁺ (quaternary nitrogen salts), counterion Cl⁻

or Br⁻

, —

CHO (aldehyde), —

CRO (keto group), —

SO₃H (sulfonic acids), —

SO₃R (sulfonates), SO₂NH₂ (sulfonamides), —

COOH (carboxylic acid), —

COOR (esters, from carboxylic acid side), —

COCl (carboxylic acid chlorides), —

CONH₂ (amides, from carboxylic acid side), —

CF₃, —

CCl₃, —

CN, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl etc.), allyl (—

CH₂—

CH═

CH₂), benzyl (—

CH₂C₆H₅) groups, and phenyl (+substituted phenyl).

4. An organic compound according to claim 1, wherein the nucleophilic groups (donors) are selected from —

O⁻

(phenoxides, like —

ONa or —

OK), —

NH₂, —

NHR, NR₂, —

OH, OR (ethers), —

NHCOR (amides, from amine side), —

OCOR (esters, from alcohol side), alkyls, —

C₆H₅, vinyls, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl etc.), allyl (—

CH₂—

CH═

CH₂), benzyl (—

CH₂C₆H₅) groups, and phenyl (+substituted phenyl).

5. An organic compound according to claim 1, wherein amino groups (—

NH₂) are used as donors and nitro groups are used as acceptors.

6. A crystal dielectric layer comprising the organic compound according to any of claims 1-2, 3-4, 5.

7. A capacitor comprising a first electrode, a second electrode, and a crystal dielectric layer disposed between said first and second electrodes, wherein said crystal dielectric layer comprises the organic compound according to any of claims 1-2, 3-4, 5, and wherein said crystal dielectric layer comprises supramolecules formed with the aromatic polycyclic conjugated cores, and isotropic insulating sublayers formed with the R₁ groups served as the isolating groups.