4,4'-Bis(N-carbazolyl)-1,1'-biphenyl Chemical Properties

Melting point:

281-285 °C

Boiling point:

700.8±60.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

slightly sol. in Tetrahydrofuran

form 

powder to crystal

color 

White to Almost white

biological source

mouse

λmax

319nm(CH2Cl2)(lit.)

InChI

InChI=1S/C36H24N2/c1-5-13-33-29(9-1)30-10-2-6-14-34(30)37(33)27-21-17-25(18-22-27)26-19-23-28(24-20-26)38-35-15-7-3-11-31(35)32-12-4-8-16-36(32)38/h1-24H

InChIKey

VFUDMQLBKNMONU-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(N3C4=C(C=CC=C4)C4=C3C=CC=C4)C=C2)=CC=C(N2C3=C(C=CC=C3)C3=C2C=CC=C3)C=C1

CAS DataBase Reference

58328-31-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-36/39

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

4,4'-Bis(N-carbazolyl)-1,1'-biphenyl Usage And Synthesis

Classification

Carbazole derivatives, Hole-injection layer materials, Hole transport layer materials, Hole blocking layer materials, Phosphorescent host materials, Light-emitting fiodes, Organic electronics, Sublimed materials.

Description

As Glasses of a common OLED host material, 4,4′-bis(N-carbazolyl)-1,1′-biphenyl(CBP) were prepared by vapor deposition at various substrate temperatures. It can be doped with molybdenum oxide (MoO3) in the hole transport material.^[1]

Chemical Properties

White to brown powder

Uses

Organic Semiconductor Laser Materials

General Description

TGA/DSC lot specific traces available upon request

Synthesis

Under nitrogen protection, 150 g (369.5 mmol) of 4,4'-diiodobiphenyl, 123.5 g (738.6 mmol) of carbazole, 23 g of copper powder, 100 μL of potassium carbonate, and 500 mL of 1,3-diisopropylbenzene were added to a 2 L triple-necked flask equipped with a stirrer and condensation device. The reaction mixture was heated to reflux and maintained for 30 hours and then naturally cooled to room temperature. Subsequently, an appropriate amount of toluene was added to the reaction mixture and the insoluble material was removed by filtration. The solvent in the filtrate was removed by distillation under reduced pressure to obtain the crude product. To the crude product, 500 mL of methanol was added for recrystallization and a solid was precipitated. The crystals were collected by filtration and dried to give 122.8 g of the target product 4,4'-bis(carbazol-9-yl)biphenyl (CBP) in 68.6% yield.

References

[1] KüHN M, MANKEL E, K?HN A, et al. Doping mechanism of MoO3 in 4,4′‐Bis(N‐carbazolyl)‐1,1′‐biphenyl: A photoelectron spectroscopic study[J]. physica status solidi (b), 2016, 253. DOI:10.1002/pssb.201600144.

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