4CzIPN

CAS Number 1416881-52-1

Dopant Materials, High Purity Sublimed Materials, Semiconducting Molecules, TADF Materials

4CzIPN, highest PLQY compared to its isomers

Available online in sensible quantities for priority dispatch

4CzIPN (CAS number 1416881-52-1), namely 1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene, has a fully substituted benzene ring with two cyano groups as electron accepting units at meta-positions to each other and four carbazolyl groups as electron donating units. It is a powerful metal-free organophotocatalyst and also a typical donor–acceptor fluorophore.

4CzIPN from Ossila was used in the high-impact paper (IF 15.72), A comprehensive picture of roughness evolution in organic crystalline growth: the role of molecular aspect ratio, J. Dull et al., Mater. Horiz., 9, 2752 (2022); DOI: 10.1039/d2mh00854h.

Out of its three isomers, 4CzIPN has the highest photo-luminescence quantum efficiency (PLQY) of above 90%. This is due to the wide dispersion the highest-occupied molecular orbital (HOMO) over the donor moieties. Relatively short excited-state lifetime of delayed emission was reported. Additionally, higher external quantum efficiency (EQE) was observed by using 4CzIPN as an emitter in TADF-OLED devices.

Despite its low solubility in most of the aromatic solvents, 4CzIPN is also solution-processable in solvents such as dichloromethane or chloroform. This is due to the structure distortion of the carbazole units caused by steric hindrance.

General Information

CAS Number	1416881-52-1
Full Name	1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene
Chemical Formula	C₅₆H₃₂N₆
Molecular Weight	788.89 g/mol
Absorption*	λ_max 365 nm in acetonitrile
Fluorescence	λ_em 551 nm in acetonitrile
HOMO/LUMO	HOMO = 5.8 eV, LUMO = 3.4 eV [1]
Synonyms	2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile
Classification / Family	Carbazole, TADF green emitter materials, Phosphorescent organic light-emitting devices (PHOLEDs), Photocatalyst, Sublimed materials

* Measurable with the Ossila Optical Spectrometer, see our Spectrometers and Spectroscopy Accessories for more information.

Product Details

Purity	Unsublimed >98% (1H NMR); Sublimed >99.0% (HPLC)
Melting Point	TGA: >300 °C (0.5% weight loss)
Appearance	Orange-yellow powder/crystals

Sublimation is a technique used to obtain ultra pure-grade chemicals, see sublimed materials.

Chemical Structure

Device Structure(s)

Device structure	ITO (70 nm)/(4 wt% ReO 3 ):mCP (50 nm)/mCP (15 nm)/mCP:B3PyMPM:(5 wt% 4CzIPN) (30 nm)/B3PYMPM (20 nm)/(4 wt% Rb₂CO₃):B3PYMPM (35 nm)/Al (100 nm) [3]
Colour	Green
Max. Current Efficiency	94.5 cd/A
Max. EQE	29.6%
Max. Power Efficiency	88.6 Im/W

Device structure	ITO (50 nm)/PEDOT:PSS (60 nm)/poly(9-vinylcarbazole) (15 nm)/SiCz:4CzIPN (30 nm)/TSPO1 (35 nm)/LiF (1 nm)/Al (200 nm) [4]
Colour	Green
Max. EQE	26%
Max. Power Efficiency	63.4 Im/W

Device structure	ITO(130 nm)/TAPC (35 nm)/CBP (5 nm)/5 wt% 4CzIPN doped CBP (5 nm)/B4PyPPM (65 nm)/LiF (0.8 nm)/Al (100 nm) [5]
Colour	Green
Max. Current Efficiency	83.2 cd/A
Max. EQE	25.7%
Max. Power Efficiency	106.9 Im/W

MSDS Documentation

4CzIPN MSDS Sheet

Pricing Table

Grade	Order Code	Quantity	Price
Sublimed (>99.0% purity)	M2100A1	100 mg	£240
Sublimed (>99.0% purity)	M2100A1	250 mg	£480
Sublimed (>99.0% purity)	M2100A1	500 mg	£760
Sublimed (>99.0% purity)	M2100A1	1 g	£1200
Unsublimed (>98.0% purity)	M2100B1	250 mg	£230
Unsublimed (>98.0% purity)	M2100B1	500 mg	£370
Unsublimed (>98.0% purity)	M2100B1	1 g	£580

Literature and Reviews

A comprehensive picture of roughness evolution in organic crystalline growth: the role of molecular aspect ratio, J. Dull et al., Mater. Horiz., 9, 2752 (2022); DOI: 10.1039/d2mh00854h.
Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations, T. Shang et al., Chem. Commun., 55, 5408-5419 (2019); DOI: 10.1039/C9CC01047E.
Promising operational stability of high-efficiency organic light-emitting diodes based on thermally activated delayed fluorescence, H. Nakanotani et al., Sci Rep., 3: 2127 (2013); doi: 10.1038/srep02127.

Solvent Effect on Thermally Activated Delayed Fluorescence by 1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene, R. Ishimatsu et al., J. Phys. Chem. A, 117, 5607−5612 (2013); DOI: 10.1021/jp404120s.
A Fluorescent Organic Light-Emitting Diode with 30% External Quantum Efficiency, J-W. Sun et al., Adv. Mater., 26, 5684–5688 (2014); DOI: 10.1002/adma.201401407.
High Efficiency in a Solution-Processed Thermally Activated Delayed-Fluorescence Device Using a Delayed-Fluorescence Emitting Material with Improved Solubility, Y-J. Cho et al., Adv. Mater., 26, 6642–6646 (2014); DOI: 10.1002/adma.201402188.
High-Performance Green OLEDs Using Thermally Activated Delayed Fluorescence with a Power Efﬁ ciency of over 100 lmW⁻¹, Y. Seino et al; Adv. Mater., 28, 2638–2643 (2016); DOI: 10.1002/adma.201503782.