Synthesis and Photovoltaic Properties of a Solution-Processable Organic Molecule Containing Triphenylamine and DCM Moieties

Abstract

A solution processible organic conjugated molecule 2-[2,6-bis-(2-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}vinyl)pyran-4-ylidene]malononitrile (TPA−DCM−TPA) was designed and synthesized for application in organic solar cells (OSCs). The molecule consists of two electron-rich triphenylamine moieties and one electron-deficient 2-pyran-4-ylidenemalononitrile unit linked with conjugated bridges. The optical and electrochemical properties, the light-induced electron spin resonance (LESR), and the electronic ground state configuration of the compound were characterized. TPA−DCM−TPA film showed a broad absorption band covering from 350 to 650 nm. The bulk-heterojunction OSCs with the device structure of ITO/PEDOT:PSS/TPA−DCM−TPA:PCBM/LiF/Al or Ba/Al were fabricated, in which TPA−DCM−TPA was used as donor and PCBM as acceptor material. The open-circuit voltage, short-circuit current, and power-conversion efficiency of the optimized OSC with Ba/Al as cathode, TPA−DCM−TPA:PCBM = 1:3 (w/w), and ca. 85 nm thickness of the active layer reached 0.9 V, 2.14 mA/cm2, and 0.79%, respectively, under the illumination of AM1.5, 100 mW/cm2. The results indicate that TPA−DCM−TPA is a promising photovoltaic organic molecule.

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

“…Alkene including vinylene, styrene and phenylacrylonitrile is a kind of common π-bridges [58][59][60][61][62][63][64][65][66][67][68]. Introducing the alkene into D-A typed molecular architecture not only enhance the conjugation degree but also strengthen the coplanarity of the molecule.…”

Synthesis and photovoltaic properties of a star-shaped molecule with triphenylamine as core and benzo[1,2,5]thiadiazol vinylene as arms

“…In contrast with polymers, organic conjugated molecules possess exact molecular weight and can be highly purified by sublimation and column chromatography. Therefore, amorphous conjugated organic molecules with good solution-processability have received growing attention in recent years for the application in OSCs [19][20][21][22][23][24][25][26][27][28].…”

“…Organic molecules containing triphenylamine (TPA) units are of significant importance in the solution-processable amorphous organic molecules, and have been intensively investigated for the applications in optoelectronic devices [24][25][26][27][28][29][30]. TPA unit is in 3D propeller structure, which benefits the amorphous structure and solution-processability of the molecules containing it.…”

“…Moreover, TPAs have good optical properties and hole transporting ability. Some TPA containing molecules have been synthesized and used as photovoltaic materials in solution-processable OSCs [24][25][26][27][28]31].…”

New discotic-shaped azomethines with triphenylamine moieties: Thermal, structural behaviors and opto-electrical properties

“…Many TPA derivatives were tested as hole-transporting materials in light emitting diodes construction [10][11][12][13][14]. Among the huge group of molecules and macromolecules with TPA units also poly(azomethine)s were investigated by few research groups [15][16][17][18][19][20][21] for OLEDS applications.…”