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4CzIPN

chemical structure of 4czipn
Product Code M2100A1-250mg
Price $363.00 ex. VAT
$ USD

4CzIPN, highest PLQY compared to its isomers

Available online in sensible quantities for priority dispatch

4CzIPN, 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.

Ossila's 4CzIPN used in a high-impact paper

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* λmax 365 nm in acetonitrile
Fluorescence λem 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 an Optical Spectrometer, see our spectrometer application notes.

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 for OLED devices.

Chemical Structure

chemical structure of 4CzIPN
Chemical Structure of 2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)

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 green light emitting device
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 green light emitting device
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 green light emitting device
Max. Current Efficiency 83.2 cd/A
Max. EQE 25.7%
Max. Power Efficiency 106.9 Im/W

Pricing

Grade Order Code Quantity Price
Sublimed (>99.0% purity) M2100A1 250 mg £290
Sublimed (>99.0% purity) M2100A1 500 mg £500
Sublimed (>99.0% purity) M2100A1 1 g £850
Unsublimed (>98.0% purity) M2100B1 250 mg £207
Unsublimed (>98.0% purity) M2100B1 500 mg £332
Unsublimed (>98.0% purity) M2100B1 1 g £531

MSDS Documentation

4CzIPN MSDS4CzIPN MSDS sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.

To the best of our knowledge the information provided here is accurate. However, Ossila assume no liability for the accuracy of this page. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. All products are for laboratory and research and development use only, and may not be used for any other purpose including health care, pharmaceuticals, cosmetics, food or commercial applications.

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