Carbo- and heterocyclic spiro compounds as donor materials for organic photovoltaics and their preparation

Patent metadata

Field	Value
Publication number	US-9691989-B2
Application number	US-201514823520-A
Country	US
Kind code	B2
Filing date	Aug 11, 2015
Priority date	Aug 11, 2014
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

The subject invention provides compositions of and methods of using carbo- and heterocyclic spiro compounds as donor materials for organic photovoltaic (OPV) devices. In preferred embodiments, spiro compounds comprising triarylamine and derivatives thereof demonstrate effective hole-transporting properties in OPV devices, achieving up to 5.46% of power conversion efficiency. Advantageously, preferred compounds provided herein are thermally stable and volatile enough to form thin films for the photoactive layer of an OPV device by vacuum deposition or by spin-coating.

First claim

We claim:

1. A heterocyclic spiro compound of the following Formula:

wherein A, B, C, and D are benzenes;
wherein X is a heteroatom or an oxidized heteroatom, each being optionally substituted with at least one functional group R, wherein the heteroatom is sulfur and R is selected from alkyl, aryl, heteroaryl, and alkoxy groups; and
wherein D 1 and D 3 are absent, and wherein D 2 and D 4 are present and independently selected from optionally substituted functional groups of alkylaminos, arylamines, thiophenes, oligo-thiophenes, fused-thiophenes, fluorenes, dibenzothiophenes, dibenzofurans, and dibenzophospholes.

2. An organic photovoltaic (OPV) device, comprising in sequence an anode, an anodic buffer layer, a photoactive layer, an exciton-blocking layer, and a cathode, the photoactive layer comprising a fullerene compound, or a derivative thereof, and the heterocyclic spiro-compound according to claim 1 .

3. The device according to claim 2 , wherein the spiro compound is thermally evaporated or spin-coated onto the anodic buffer layer.

4. The device according to claim 2 , wherein the heterocyclic Spiro compound is thermally co-evaporated with the fullerene compound, or a derivative thereof, onto the anodic buffered layer.

Assignees

• Univ Hong Kong

Inventors

• Yam Vivian Wing-Wah
• Chan Chin-Yiu
• Chan Mei-Yee

Classifications

• C07D335/04

  condensed with carbocyclic rings or ring systems · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D333/78

  condensed with rings other than six-membered or with ring systems containing such rings · CPC title

• C07D221/20

  Spiro-condensed ring systems · CPC title

• Y02E10/549

  Organic PV cells · CPC title