1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, also known as HAT-CN (CAS number 105598-27-4), 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.
General Information
CAS Number
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105598-27-4
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Chemical Formula
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C18N12
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Molecular Weight
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384.27 g/mol
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Absorption
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λmax 282, 321 nm (in CH2Cl2)
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Fluorescence
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λem 422 nm (in CH2Cl2)
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HOMO/LUMO
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HOMO 7.5 eV, LUMO 4.4 eV [1]
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Synonyms
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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
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Classification / Family
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Charge-generation layer (CGL) materials, Hole-injection layer materials (HIL), OLED and PLED materials, Organic electronics, Perovskite solar cells
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Product Details
Purity
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Sublimed M791 >99.0%
Unsublimed M792 >98.0%
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Thermal Gravimetric Analysis (TGA)
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430 °C (0.5% weight loss)
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Appearance
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Dark yellow powder/crystals
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Chemical Structure
Chemical Structure of 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN)
Device Structure(s)
The following are all PEDOT:PSS free devices.
Device Structure
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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]
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Colour
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Green
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Max. Current Efficiency
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241 cd/A
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Max. Power Efficiency
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143 lm W−1
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Device Structure
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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]
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Colour
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Blue
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Max. EQE
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22%
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Max. Current Efficiency
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66.0 cd/A
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Max. Power Efficiency
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64.0 lm W−1
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Device Structure
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ITO/HAT-CN (10 nm)/TAPC (45 nm)/mCP:Ir(dbi)3 10 wt% (20 nm)/TmPyPB (40 nm)/Liq (2 nm)/Al (120 nm) [4]
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Colour
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Sky Blue
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Max. EQE
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23.1%
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Max. Current Efficiency
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61.5 cd/A
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Max. Power Efficiency
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43.7 lm W−1
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Device Structure
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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]
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Colour
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Green
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Max. EQE
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14.7%
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Max. Current Efficiency
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50.9 cd/A
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Max. Power Efficiency
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55.0 lm W−1
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Device Structure
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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]
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Colour
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Blue
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Max. EQE
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15.1%
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Max. Power Efficiency
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14.5 lm W−1
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Device Structure
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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]
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Colour
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White
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Max. EQE
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38.4%
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Max. Power Efficiency
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80.1 lm W−1
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Device Structure
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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]
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Colour
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Red
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Max. EQE
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26.5%
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Max. Current Efficiency
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95.8 cd/A
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Device Structure
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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]
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Colour
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White
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Max. EQE
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20.8%
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Max. Power Efficiency
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51.2 lm W−1
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*For chemical structure information please refer to the cited references.