TPD - N,N′-Bis(3-methylphenyl)-N,N′-diphenylbenzidine

CAS Number 65181-78-4

MSDS

TPD - N,N′-Bis(3-methylphenyl)-N,N′-diphenylbenzidine CAS 65181-78-4

TPD, HTL material in organic electronic devices

Used as a blue-violet light emitting material or host material on the PhOLEDs

Overview | Specifications | MSDS | Literature and Reviews

N,N′-Bis(3-methylphenyl)-N,N′-diphenylbenzidine, CAS number 65181-78-4, commonly abbreviated as TPD, is widely used as hole transport materials in organic electronic devices.

TPD is also used as a blue-violet light emitting material or host material on the phosphorescence organic light emitting diodes for its wide energy band being about 3.2 eV with highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) being 5.5 eV and 2.3 eV respectively [1, 2].

TPD from Ossila was used in the high-impact paper (IF 14.92), Complete polarization of electronic spins in OLEDs, T. Scharff et al., Nat. Commun., 12, 2071 (2021); DOI: 10.1038/s41467-021-22191-3.

General Information

CAS Number	65181-78-4
Chemical Formula	C₃₈H₃₂N₂
Molecular Weight	516.67 g/mol
Absorption*	λ_max 352 nm in THF
Fluorescence	λ_em 398 nm in THF
HOMO/LUMO	HOMO = 5.5 eV, LUMO = 2.3 eV
Synonyms	TPD, N,N′-Bis(3-methylphenyl)-N,N′-diphenylbenzidine, N,N'-Diphenyl-N,N'-di(m-tolyl)benzidine, 4,4'-Bis[N-phenyl-N-(m-tolyl)amino]biphenyl
Classification / Family	Triphenylamine derivatives, Hole-injection materials, Hole transporting materials, Phosphorescent host materials, Light-emitting diodes, Organic electronics, Sublimed materials

*Measurable with the Ossila USB spectrometer & spectrometer and accessories.

Product Details

Purity	Sublimed* >99%
Melting Point	175 – 177 °C (lit.)
Colour	White powder/crystals

* Sublimation is a technique used to obtain ultra pure-grade chemicals, see sublimed materials.

Chemical Structure

Device Structure(s)

Device Structure	ITO/m-MTDATA/TPD/F-TBB*/Alq3/MgAg [1]
Colour	Blue
Max EQE	1.4%
Maximum luminance	3960 cd m^-2at 15.0 V

Device Structure	ITO/75 wt% TPD:25 wt% PC (50nm) /TCTA (10nm)/6 % PtL³⁰Cl*:94 % [TCTA: TCP] [1:1] (30 nm)/TAZ (30 nm)/LiF/Al [3]
Colour	White
EQE@500 cd/m²	11.3%
Current Efficiency@500 cd/m²	23.5 cd/A
Bias	9.3 V

Device Structure	ITO/m-MTDATA:F4-TCNQ (100 nm)/TPD* (5 nm)/Alq₃ (20 nm)/BPhen (10 nm)/Bphen:Li (30 nm)/LiF (1 nm)/Al (100 nm) [4]
Colour	Green
Max. Luminance	10,000 cd/m² at 5.2 V
Max. Current Efficiency	5.27 cd/A

Device Structure	ITO/CuPc(10 nm)/TPD(50 nm)/Bepp2 (40 nm)/LiF(1.5 nm)/Al(200 nm) [5]
Colour	Blue
Max. Luminance	4,000 cd/m²
Max. Power Efficiency	0.55 lm W⁻¹

Device Structure	ITO/TPD (50 nm)/BePP2 (5 nm)/TPD (4 nm)/BePP2:rubrene (5 nm)/TPD (4 nm)/Alq (10 nm)/Al [6]
Colour	White
Max. Luminance	20,000 cd/m²
Max. Power Efficiency	1.11 lm W⁻¹

Device Structure	ITO/CuPc (18 nm)/TPD (50 nm)/Alq₃ (60 nm)/BCP (10 nm)/LiF (1 nm)/Al (100 nm) [8]
Colour	Green
Max. Luminance	5,993 cd/m²
Max. Current Efficiency	3.82 cd/A
Max. Power Efficiency	2.61 lm W^-1

Device Structure	ITO/PEDOT:PSS/PVK:OXD -7:TPD:(Et-Cvz-PhQ)₂Ir(pic)*/OXD-7 (20 nm)/Ba (3 nm)/Al (100 nm) [9]
Colour	Red
Max. Current Efficiency	17.5 cd/A
Max. EQE	10.6%
Max. Power Efficiency	6.42 lm W⁻¹

Device Structure	ITO/TPD (50 nm)/Zn(BTZ)₂(50 nm)/MgIn (200 nm) [10]
Colour	Greenish-White
Max. Luminance	10,190 cd/m²
Max. Power Efficiency	0.89 lm W⁻¹

*For chemical structure informations please refer to the cited references.

Characterisation

hplc trace of tpd — HPLC trace of N,N′-Bis(3-methylphenyl)-N,N′-diphenylbenzidine (TPD).

MSDS Documentation

TPD MSDS sheet

Literature and Reviews

Development of high-performance blue-violet-emitting organic electroluminescent devices, K. Okumoto et al., Appl. Phys. Lett. 79(9), 1231–1233 (2001).
Efficiency and Aging Comparison Between N,N′-Bis (3-methylphenyl)-N,N′-diphenylbenzidine (TPD) and N,N′-Di-[(1-naphthalenyl)-N,N′-diphenyl]-1,1′-biphenyl-4,4′-diamine (NPD) Based OLED Devices, M. Maglione et al., Macromol. Symp., 247, 311–317 (2007).
Blue-shifting the monomer and excimer phosphorescence of tridentate cyclometallated platinum(II) complexes for optimal white-light OLEDs, L. Murphy et al., Chem. Commun., 48, 5817-5819 (2012), DOI: 10.1039/C2CC31330H.

Low-voltage organic electroluminescent devices using pin structures, J. Huang et al., Appl. Phys. Lett. 80, 139 (2002); http://dx.doi.org/10.1063/1.143211.
Hydroxyphenyl-pyridine Beryllium Complex (Bepp2) as a Blue Electroluminescent Material, Y. Li et al., Chem. Mater., 12, 2672–2675 (2000); DOI: 10.1021/cm000237u.
Organic white light electroluminescent devices, S. Liu et al., Thin Solid Films, 363, 294-297 (2000); doi:10.1016/S0040-6090(99)01017-2.
Highly efficient bilayer green phosphorescent organic light emitting devices, W-S. Jeon et al., Appl. Phys. Lett., 92, 113311 (2008); http://dx.doi.org/10.1063/1.2898527.
High-Efficiency Organic Electroluminescent Device with Multiple Emitting Units, C-C. Chang et al., Jpn. J. Appl. Phys., 43, 6418–6422 (2004); [DOI: 10.1143/JJAP.43.6418.
High efficiency, solution-processed, red phosphorescent organic light-emitting diodes from a polymer doped with iridium complexes, M. Song et al., Org. Electronics, 10 (7), 1412–1415 (2009), doi:10.1016/j.orgel.2009.07.012.
White-Light-Emitting Material for Organic Electroluminescent Devices, Y. Hamada et al., Jpn. J. Appl. Phys. 35 L1339-L1341 (1996); http://iopscience.iop.org/1347-4065/35/10B/L1339.
A Novel Yellow Fluorescent Dopant for High-Performance Organic Electroluminescent Devices, X. Q. Lin et al, Chem. Mater., 13 (2), 456–458 (2001), DOI: 10.1021/cm0004679.
Organic plasmon-emitting diode, D. M. Koller et al., Nature Photonics 2, 684 - 687 (2008)
Enhancing the electroluminescent properties of organic light-emitting devices using a thin NaCl layer, et al., S. J. Kang, Appl. Phys. Lett. 81, 2581 (2002); http://dx.doi.org/10.1063/1.1511817.
White light emission from blends of blue-emitting organic molecules: A general route to the white organic light-emitting diode?, J. Thompson et al., Appl. Phys. Lett. 79, 560 (2001); http://dx.doi.org/10.1063/1.1388875.
Investigation of ultra-thin titania films as hole-blocking contacts for organic photovoltaics, H. Kim et al., J. Mater. Chem. A, 3, 17332-17343 (2015).