# US 12,016,244 B1 · Asymmetric organic photovoltaic acceptor material in an A-D-D′-A type and use

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- Number: US 12,016,244 B1
- Document ID: US12016244B1
- Status: Granted
- Kind: B1
- Application number: 18/418,330
- Filed: 2024-01-21
- Published: 2024-06-06
- Granted: 2024-06-18
- Earliest claimed: 2021-07-21
- Assignees: Changzhou University
- Applicants: Changzhou University
- Inventors: Weiguo Zhu; Jianing Zhu; Hua Tan; Mengbing Zhu; Rulin Hao
- Web page: https://patentgrep.com/patent/US12016244B1

## CPC

- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07D 495/04: Ortho-condensed systems
- H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/215: {comprising substituents, e.g. PCBM}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An asymmetric organic photovoltaic acceptor material in an A-D-D′-A type is provided. A backbone containing noncovalent conformational lock is co-constructed with alkoxyindenothiophene and cyclopentadithiophene two-electron donor (D-D′) unit, and the ends are modified with fluorine- and chlorine-atom-substituted 3-(dicyanomethylidene)inden-1-one. The acceptor containing only a simple condensed ring has multiple advantages such as a coplanar backbone, low energy disorder, and J-aggregation tendency, and this type of asymmetric small-molecule acceptor has a controllably adjustable optical bandgap in the range of 1.30-1.45 eV, which is capable of combining with most donor materials to construct highly efficient binary bulk heterojunction organic solar cell. When the donor material is polymer PM6, the photoelectric conversion efficiency of the binary organic solar cells (OSCs) device is as high as 13.67%, with an open-circuit voltage (Voc) of 0.85 eV and energy loss (Eloss) is only 0.50 V.

## Claims

### Claim 1

An asymmetric organic photovoltaic acceptor material in an A-D-D′-A type, wherein the asymmetric organic photovoltaic acceptor material has a structure represented by Formula 1:
wherein R1, R2, R3 are linear or branched C1-20 alkyl; and
X is an H, F or Cl atom.

### Claim 2 (depends on 1)

The asymmetric organic photovoltaic acceptor material in the A-D-D′-A type according to claim 1, wherein the asymmetric organic photovoltaic acceptor material has a structure represented by Formula 2:
wherein
when R is —CH3 and X is F, the asymmetric organic photovoltaic acceptor material is named as SM1;
when R is —CH3 and X is Cl, the asymmetric organic photovoltaic acceptor material is named as SM2;
when R is 2-ethylhexyl and X is F, the asymmetric organic photovoltaic acceptor material is named as SM3; or
when R is 2-ethylhexyl and X is Cl, the asymmetric organic photovoltaic acceptor material is named as SM4.

### Claim 3 (depends on 1)

A use of the asymmetric organic photovoltaic acceptor material in the A-D-D′-A type according to claim 1, wherein the asymmetric organic photovoltaic acceptor material is applied to a photoactive layer of an organic solar cell.

### Claim 4 (depends on 3)

The use of the asymmetric organic photovoltaic acceptor material in the A-D-D′-A type according to claim 3, wherein the asymmetric organic photovoltaic acceptor material is blended with a polymer donor material to prepare a photoactive layer of a binary or ternary bulk heterojunction organic solar cell.

### Claim 5 (depends on 4)

The use of the asymmetric organic photovoltaic acceptor material in the A-D-D′-A type according to claim 4, wherein the polymer donor material is PM6, and a mass ratio of the asymmetric organic photovoltaic acceptor material to the PM6 is 1:1.5.

### Claim 6 (depends on 4)

The use of the asymmetric organic photovoltaic acceptor material in the A-D-D′-A type according to claim 4, wherein the photoactive layer of the binary bulk heterojunction organic solar cell is prepared by using 1-chloronaphthalene as a solvent additive.