HATCN

Order Code: M791
MSDS sheet

Price

(excluding Taxes)

£89.00


General Information

CAS number 105598-27-4
Chemical formula C18N12
Molecular weight 384.27 g/mol
Absorption λmax 282, 321 nm (in CH2Cl2)
Fluorescence λem 422 nm (in CH2Cl2)
HOMO/LUMO HOMO 7.5 eV, LUMO 4.4 eV [1]
Synonyms 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, HAT-CN6, HATCN, Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile
Classification / Family Charge generation layer (CGL) materials, Hole injection layer materials (HIL), OLED and PLED materials, Organic electronics, Perovskite solar cells.

 

Product Details

Purity 99.06%
Thermal Gravimetric Analysis (TGA) 430 °C (0.5% weight loss)
Colour Dark yellow powder/crystals

 

Chemical Structure

chemical structure of HATCNChemical Structure of 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN); CAS No. 105598-27-4; Chemical Formula C18N12.

 

Applications

1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, also known as HAT-CN, is one of the members of the 1,4,5,8,9,12-hexaazatriphenylene (HAT) family, which have an electron deficient, rigid, planar, aromatic discotic system with an excellent π–π stacking ability. For this reason, HAT-CN finds applications in organic light-emitting diodes (OLEDs) serving either as the hole-injection layer (HIL) or charge generation layer (CGL) material.

It has been proven that utilisation of HAT-CN as hole injection layer (HIL) materail can result in a dramatic enhancement of the performance of solution-processed organic light-emitting diodes [2]. Lin et al further demonstrated that the external quantum efficiency, current efficiency, and power efficiency of the HAT-CN based devices were higher than or almost similar to those of optimised PEDOT:PSS-based devices. Solution-processed HAT-CN is promising as a novel alternative to conventional PEDOT:PSS HILs, due to its efficient carrier-injection capability and the capacity to prevent interfacial mixing and erosion during fabrication. 

The following are all PEDOT:PSS free devices.

Device structure ITO/HAT-CN(10 nm)/HAT-CN:TAPc(2:1, 60 nm)/TAPc(20 nm)/TcTa:Be(pp)2:Ir(mppy)3(1:1:8 wt% 10 nm)/Be(pp)2:Liq (1:10%, 35 nm)/Liq(1 nm)/Al(1 nm)/HAT-CN(20 nm)/HAT-CN:TAPC(2:1, 10 nm)/TAPC(40 nm)/ TcTa:Be(pp)2:Ir(mppy)3(1:1:8 wt% 10 nm)/Be(pp)2(15 nm)/Be(pp)2:Liq (1:10%, 35 nm)/Liq(1 nm)/Al(100 nm) [1]
Colour Green  green
Max. Current Efficiency 241 cd/A
Max. Power Efficiency 143 lm W1  
Device structure ITO/HAT-CN (10 nm)/TAPC (45 nm)/BCzSCN*:FIrpic:PO-01 (8 wt%, 0.5 wt%, 20 nm)/TmPyPB (50 nm)/Liq (2 nm)/Al (120 nm) [3]
Colour Blue blue
Max. EQE  22%
Max. Current Efficiency 66.0 cd/A
Max. Power Efficiency 64.0 lm W1  
Device structure ITO/HAT-CN (10 nm)/TAPC (45 nm)/mCP:Ir(dbi)10 wt% (20 nm)/TmPyPB (40 nm)/Liq (2 nm)/Al (120 nm) [4]
Colour Sky Blue  blue
Max. EQE  23.1%
Max. Current Efficiency 61.5 cd/A
Max. Power Efficiency 43.7 lm W1  
Device structure    ITO (150 nm)/HAT-CN (4 nm)/VB-FNPD* (35 nm)/TCTA:Ir(mppy)3 10 wt% (20 nm)/TPBi (60 nm)/ CsF (1 nm)/Al (120 nm) [5]
Colour Green   green
Max. EQE  14.7%
Max. Current Efficiency 50.9 cd/A
Max. Power Efficiency 55.0 lm W1  
Device structure Graphene (2–3 nm)/TAPC(30 nm)/HAT-CN(10 nm)/TAPC(30 nm)/HAT-CN(10 nm)/TAPC(30 nm)/ TCTA:FIrpic (5 nm)/DCzPPy: FIrpic (5 nm)/BmPyPB (40 nm)/LiF (1 nm)/Al (100 nm) [6]
Colour Blue   blue
Max. EQE  15.1%
Max. Power Efficiency 14.5 lm W1  
Device structure ITO/HATCN (5 nm)/NPB (40 nm)/TCTA (10 nm)/mCP:6 wt%2CzPN (11 nm)/TAZ:4 wt% PO-01 (4 nm)/TAZ (40 nm)/LiF (0.5 nm)/Al (150 nm) [7]
Colour White  white
Max. EQE 38.4%
Max. Power Efficiency 80.1 lm W1
Device structure Ag (100 nm)/ITO (10 nm)/DNTPD* (30 nm)/NPB (44 nm)/Bebq2:3 wt% Ir(mphmq)2(acac) (20 nm)/Bphen (31 nm)/Bphen: 5 wt% Li (10 nm)/HATCN (7 nm)/NPB (63 nm)/Bebq2: 3 wt% Ir(mphmq)2(acac) (20 nm)/Bphen (40 nm)/Liq (1 nm)/Mg:Ag (10:1; 18 nm)/NPB (60 nm) [8]
Colour Red  red
Max. EQE 26.5%
Max. Current Efficiency 95.8 cd/A                  
Device structure ITO/HATCN (5 nm)/NPB (30 nm)/TCTA (10 nm)/mCP (10 nm)/DMAC-DPS:PO-01* (0.8 wt% 30 nm)/DPEPO (10 nm)/Bphen (30 nm)/LiF (0.5 nm)/Al(150 nm) [9]
Colour White  white
Max. EQE 20.8%
Max. Power Efficiency 51.2 lm W1

 *For chemical structure informations please refer to the cited references

 

Characterisation

hplc of hat-cn
HPLC trace of Hexaazatriphenylenehexacabonitrile (HATCN).

 

Literature and Reviews

  1. Highly efficient and stable tandem organic light-emitting devices based on HAT-CN/HAT-CN:TAPC/TAPC as a charge generation layer, Y. Dai et al., J. Mater. Chem. C, 3, 6809-6814 (2015);DOI: 10.1039/C4TC02875A.
  2. Solution-processed hexaazatriphenylene hexacarbonitrile as a universal hole-injection layer for organic light-emitting diodes, H. Lin et al., Org. Electronics 14, 1204–1210 (2013); http://dx.doi.org/10.1016/j.orgel.2013.02.011.
  3. Bipolar host materials for high efficiency phosphorescent organic light emitting diodes: tuning the HOMO/LUMO levels without reducing the triplet energy in a linear system, L. Cui et al., J. Mater. Chem. C, 1, 8177-8185 (2013); DOI: 10.1039/C3TC31675K.
  4. Highly efficient phosphorescent organic light-emitting diodes using a homoleptic iridium(III) complex as a sky-blue dopant, J. Zhuang et al., Org. Electronics 14, 2596–2601 (2013); http://dx.doi.org/10.1016/j.orgel.2013.06.029.
  5. High-Performance Hybrid Buffer Layer Using 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile/Molybdenum Oxide in Inverted Top-Emitting Organic Light-Emitting Diodes, C-H. Park et al., ACS Appl. Mater. Interfaces, 7 (11), 6047–6053 (2015); DOI: 10.1021/am5091066.
  6. Multilayered graphene anode for blue phosphorescent organic light emitting diodes, J. Hwang et al., Appl. Phys. Lett. 100, 133304 (2012); http://dx.doi.org/10.1063/1.3697639.
  7. Highly efficient and color-stable hybrid warm white organic light-emitting diodes using a blue material with thermally activated delayed fluorescence, D. Zhang et al., J. Mater. Chem. C, 2, 8191-8197 (2014); DOI: 10.1039/c4tc01289e.
  8. High efficiency red top-emitting micro-cavity organic light emitting diodes, M. Park et al., 22, (17), Optics Express, 19919 (2014), DOI:10.1364/OE.22.019919.
  9. Highly Efficient Simplified Single-Emitting-Layer Hybrid WOLEDs with Low Roll-off and Good Color Stability through Enhanced Förster Energy Transfer, D. Zhang et al., ACS Appl. Mater. Interfaces, 7 (51), 28693–28700 (2015); DOI: 10.1021/acsami.5b10783