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105598-27-4

105598-27-4 Structure

105598-27-4 Structure
IdentificationBack Directory
[Name]

Hexaazatriphenylenehexacabonitrile
[CAS]

105598-27-4
[Synonyms]

Hexaazatriphenylenehexacabonitrile
hexaazatriphenylenehexacarbonitrile
2,3,6,7,10,11-hexacyanohexaazatriphenylene
1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile
2,3,6,7,10,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene
HAT-CN , Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hex
Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C18N12
[MDL Number]

MFCD19689401
[MOL File]

105598-27-4.mol
[Molecular Weight]

384.27
Chemical PropertiesBack Directory
[Melting point ]

>500°C
[Boiling point ]

988.7±65.0 °C(Predicted)
[density ]

1.86
[refractive index ]

n/550 1.81
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

acetone: soluble
acetonitrile: soluble
methylene chloride: soluble
[form ]

powder or crystals
[pka]

-22.82±0.50(Predicted)
[color ]

Dark yellow
[semiconductor properties]

(mobility=0.1-1cm2/V·s) (electron mobility)
[λmax]

282-321 nm in methylene chloride (PL: 422 nm)
[InChI]

InChI=1S/C18N12/c19-1-7-8(2-20)26-14-13(25-7)15-17(29-10(4-22)9(3-21)27-15)18-16(14)28-11(5-23)12(6-24)30-18
[InChIKey]

DKHNGUNXLDCATP-UHFFFAOYSA-N
[SMILES]

N1C2C(=C3N=C(C#N)C(C#N)=NC3=C3N=C(C#N)C(C#N)=NC3=2)N=C(C#N)C=1C#N
[Absorption]

λmax?282, 321 nm (in?CH2Cl2)
[Description]

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.
[Odor]

Dark yellow powder/crystals
Hazard InformationBack Directory
[Uses]

Hole transport layer materials for low voltage top-emitting organic green light emitting devices; a templating material that forces the copper phthalocyanine (CuPc) donor molecule to assume a vertical-standing morphology.
[Chemical Properties]

2,3,6,7,10,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene is a heteroatom-substituted triphenylene derivative. It is a dark yellow solid powder at room temperature and pressure. It has a certain alkalinity and a large conjugated structure. It is insoluble in water and poorly soluble in common organic solvents such as ether and n-hexane.

Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H332-H315-H319-H335
[Precautionary statements ]

P501-P261-P270-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405
[WGK Germany ]

3
[HS Code ]

2933998090
[Storage Class]

11 - Combustible Solids
Questions And AnswerBack Directory
[Classification]

Charge-generation layer (CGL) materials, Hole-injection layer materials (HIL), OLED and PLED materials, Organic electronics, Perovskite solar cells.
[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 using HAT-CN as a hole injection layer (HIL) material can dramatically enhance 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.
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