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925764

Sigma-Aldrich

Tris(4-carbazoyl-9-ylphenyl)amine

≥97%

Synonym(s):

TCTA

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About This Item

Empirical Formula (Hill Notation):
C54H36N4
CAS Number:
Molecular Weight:
740.89
MDL number:
UNSPSC Code:
12352103
NACRES:
NA.23

Quality Level

Assay

≥97%

form

(Solid/Powder)

color

light yellow, transparent

mp

179-183 °C

λmax

385 nm (in THF)

Orbital energy

HOMO 5.83 eV 
LUMO 2.43 eV 

UV absorption

λ: 293 nm Amax: in THF
λ: 326 nm Amax: in THF

storage temp.

2-8°C

SMILES string

c1ccc2c(c1)n(-c3ccc(cc3)N(c4ccc(cc4)-n5c6ccccc6c7ccccc57)c8ccc(cc8)-n9c%10ccccc%10c%11ccccc9%11)c%12ccccc2%12

InChI

1S/C54H36N4/c1-7-19-49-43(13-1)44-14-2-8-20-50(44)56(49)40-31-25-37(26-32-40)55(38-27-33-41(34-28-38)57-51-21-9-3-15-45(51)46-16-4-10-22-52(46)57)39-29-35-42(36-30-39)58-53-23-11-5-17-47(53)48-18-6-12-24-54(48)58/h1-36H

InChI key

AWXGSYPUMWKTBR-UHFFFAOYSA-N

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Application

Having three carbazole units as the pendants and triarylamine at the core, tris(4-carbazoyl-9-ylphenyl)amine (TCTA) is electron-rich. With low electron mobility, TCTA has also been used as exciton/electron blocking layer materials because of its high lying LUMO energy level (LUMO = 2.4 eV).

TCTA is widely used as a hole-transport and hole-injection material in light-emitting diodes and perovskite solar cells.

TCTA is a very popular phosphorescent host material due to its large band gap (Eg = 3.4 eV) for green, red and white phosphorescent organic light-emitting diodes (PhOLEDs).

Examples of OLED device performance:

1. ITO/NPD/TCTA/BCPO:Ir(piq)3 (7-8%)/BCP/Alq3/LiF/Al
Color: red
Max. Luminance: 24529 Cd/m2
Max. EQE: 17 %
Turn-On Voltage: 2.7 V

2. ITO/NPD/TCTA/BCPO:Ir(ppy)3 (7-8%)/BCP/Alq3/LiF/Al
Color: green
Max. Luminance: 207839 Cd/m2
Max. EQE: 21.6 %
Turn-On Voltage: 2.1 V

3. ITO/PEDOT:PSS/NPD/TCTA/m-CBTZ:FIrpic (10 wt%)/DPPS/TAZ/LiF/Al
Color: blue
Max. Luminance: 29500 Cd/m2
Max. EQE: 8.8 %
Turn-On Voltage: 3.5 V

4. ITO/PEDOT:PSS/NPD/TCTA/m-CBTZ:Ir(Bt)2(acac) (10%)/TPBI/LiF/Al
Color: yellow
Max. Luminance: 106000 Cd/m2
Max. EQE: 17.5 %
Turn-On Voltage: 3 V
TCTA is widely used as a hole transport material in OLED and organic photovoltaic (OPV) devices. It possesses excellent hole injection and transport properties, helping to efficiently transport positive charges (holes) from the anode to the emitting layer, enabling improved device efficiency and stability.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Xinxin Ban et al.
ACS applied materials & interfaces, 8(3), 2010-2016 (2016-01-05)
A benzimidazole/phosphine oxide hybrid 1,3,5-tris(1-(4-(diphenylphosphoryl)phenyl)-1H-benzo[d]imidazol-2-yl)benzene (TPOB) was newly designed and synthesized as the electron-transporting component to form an exciplex-type host with the conventional hole-transporting material tris(4-carbazoyl-9-ylphenyl)amine (TCTA). Because of the enhanced triplet energy and electron affinity of TPOB, the energy

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