4,4'-Bis(N-carbazolyl)-1,1'-biphenyl
[CAS# 58328-31-7]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl
• Synonyms: 4,4'-Bis(9-carbazolyl)-1,1'-biphenyl; 4,4-N, N'-Dicarbazole-1,1'-biphenyl; DCBP
• Molecular Formula: C₃₆H₂₄N₂
• Molecular Weight: 484.59
• CAS Registry Number: 58328-31-7
• EC Number: 627-757-5
• SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3N2C4=CC=C(C=C4)C5=CC=C(C=C5)N6C7=CC=CC=C7C8=CC=CC=C86

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 281-285 °C (Expl.)
• Index of Refraction: 1.697, Calc.^*
• Boiling Point: 700.8±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 377.6±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

4,4'-Bis(N-carbazolyl)-1,1'-biphenyl, commonly known as biscarbazole biphenyl, is an organic compound that has gained significant attention in the field of material science and organic electronics. The compound consists of two carbazole groups attached to a biphenyl backbone, with each carbazole group playing a key role in the compound's electronic properties. The discovery and application of this substance have been driven by its potential in optoelectronic devices, such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs).

The compound was first synthesized as part of efforts to design materials with improved charge-transporting properties for use in organic electronics. Carbazole is a well-known heterocyclic compound that, when incorporated into larger molecules, can significantly enhance charge mobility and contribute to the stability of organic semiconductors. The biphenyl group, which serves as a bridge between the two carbazole units, provides additional stability and electronic interactions that further improve the performance of the material.

One of the key applications of 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl is in OLED technology. OLEDs are devices that emit light when an electric current is passed through them, and they are used in a variety of applications, including displays for televisions, smartphones, and other electronic devices. The high charge mobility and good stability of biscarbazole biphenyl make it an ideal material for the electron transport layers in OLEDs. It helps improve the efficiency and longevity of OLEDs, which are particularly sensitive to degradation over time. In addition, the material's strong fluorescence properties contribute to the brightness and color purity of OLEDs, making it a valuable component in display technologies.

Another important application of 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl is in organic solar cells. Organic photovoltaics (OPVs) are a type of solar cell that uses organic materials to convert sunlight into electricity. The material's ability to efficiently transport charge and its high degree of stability make it an excellent candidate for use in the active layer or as an electron-transporting material in OPVs. In these applications, biscarbazole biphenyl helps improve the power conversion efficiency of the solar cells, making them more effective at harnessing solar energy. The use of organic materials like 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl in solar cells has the added benefit of potentially reducing production costs compared to traditional silicon-based solar cells.

In the field of organic semiconductors, 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl is also being explored for its use in organic field-effect transistors (OFETs). OFETs are used in various applications, including flexible electronics, sensors, and displays. The material's high charge mobility and stability under different environmental conditions make it an ideal candidate for the active layer in OFETs, where it can improve device performance and reliability. Its excellent charge transport properties enable efficient switching and amplification in these devices, contributing to the development of next-generation electronic devices.

Furthermore, 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl has also been investigated for its potential use in other applications, including light-emitting diodes, photo-detectors, and sensor technologies. The compound's versatile electronic properties, including its high fluorescence quantum yield, make it useful for a range of optoelectronic applications, where efficient light emission or detection is required.

In conclusion, 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl is an important organic compound with significant potential in the field of organic electronics. Its unique chemical structure provides excellent charge transport properties and stability, which are critical for enhancing the performance of OLEDs, organic solar cells, and OFETs. The continued development and application of this material are expected to contribute to advancements in flexible, cost-effective, and high-performance electronic devices.

References

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2024. Efficient blue electroluminescence from reduced-dimensional perovskites. Nature Photonics, 18(3).
DOI: 10.1038/s41566-024-01382-6

2021. Recent Progress in Near-Infrared Organic Electroluminescent Materials. Topics in current chemistry (Cham), 379(6).
DOI: 10.1007/s41061-021-00357-3