Bathocuproine Property

Melting point:

279-283 °C(lit.)

Boiling point:

482.47°C (rough estimate)

Density 

1.2408 (rough estimate)

refractive index 

1.7620 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Benzene (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly, Heated)

form 

Powder

pka

5.88±0.30(Predicted)

color 

Yellow

Water Solubility 

Soluble in methanol (36mg/100ml), ethanol, 2-propanol, bezene, and acetone. Partly miscible in water.

BRN 

306714

InChI

InChI=1S/C26H20N2/c1-17-15-23(19-9-5-3-6-10-19)21-13-14-22-24(20-11-7-4-8-12-20)16-18(2)28-26(22)25(21)27-17/h3-16H,1-2H3

InChIKey

STTGYIUESPWXOW-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C3C=2N=C(C)C=C3C2=CC=CC=C2)C(C2=CC=CC=C2)=CC=1C

CAS DataBase Reference

4733-39-5(CAS DataBase Reference)

EPA Substance Registry System

1,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl- (4733-39-5)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

24/25-36-26-37/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29339990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

Bathocuproine Chemical Properties,Usage,Production

Classification

Electron-transport layer materials, Electron-injection layer materials, Hole-blocking layer materials, OFET, OLED, Organic Photovoltaics, Perovskite solar cells, Sublimed materials.

Applications

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, also known as Bathocuproine (BCP), is a wide-band-gap material and has a high electron affinity. When it is embedded into organic electronic devices, bathocuproine acts as an exciton-blocking barrier which prohibits exciton diffusion process towards the Al electrode otherwise being quenched. One of the most commonly used buffer layer between acceptor and cathode layers is bathocuproine. The introduction of the buffer layer can greatly improve the PCE of polymer organic solar cells. BCP is one of the most popular hole-blocking layer materials that is used in organic electronics, including perovskite solar cells.
It was demonstrated that a BCP buffer layer reduces nonradiative recombination of excitons at the C60 –Al interface. Its most important function is to establish an Ohmic contact between the C60 film and the Al electrode in photovoltaic devices.

Description

Organic photovoltaic cells (OPVCs) are considered to be promising devices because of their mechanical flexibility, ease of fabrication and potential for low-cost production. For small-molecule OPVCs the most-common material to use between the acceptor, here C60, and the top electrode, Al, is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, also known as bathocuproine. Indeed, the insertion of BCP results in an enhanced power-conversion efficiency (PCE). The improved power-conversion efficiency has been attributed to an increased exciton harvesting in the active layer. As BCP is a wide-band-gap material it acts as an exciton-blocking barrier (EBL) that prohibits excitons diffusing towards the Al electrode where they would otherwise be quenched.

Chemical Properties

Yellow powder

Uses

Bathocuproine is used as a reagent for the determination of copper. It acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched. It is the most commonly used buffer layer between acceptor and cathode layer.

Uses

Bathocuproine can be used as an electron-modifying layer or as an interlayer between ETLs (electron transport layers) in calcite solar cells, and it can be prepared by spin-coating deposition or vacuum thermal evaporation. The addition of Bathocuproine enhances the energy conversion efficiency of organic photovoltaic cells.

General Description

TGA/DSC Lot specific scans available upon request

Purification Methods

Purify it by recrystallisation from *benzene. [Smith & Wilkins Anal Chem 25 510 1953, Beilstein 23 III/IV 2160.]

References

[1] Mao, Lingling et al. “Role of Organic Counterion in Lead- and Tin-Based Two-Dimensional Semiconducting Iodide Perovskites and Application in Planar Solar Cells.” Chemistry of Materials 28 (2016): 7781–7792.