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765015

Sigma-Aldrich

2,2′-Dimethyl-N,N′-di-[(1-naphthyl)-N,N′-diphenyl]-1,1′-biphenyl-4,4′-diamine

97% (HPLC)

Synonym(s):

α-NPD, N,N′-Bis(naphthalen-1-yl)-N,N′-bis(phenyl)-2,2′-dimethylbenzidine

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About This Item

Empirical Formula (Hill Notation):
C46H36N2
CAS Number:
495416-60-9
Molecular Weight:
616.79
MDL number:
MFCD22581298
UNSPSC Code:
12352103
PubChem Substance ID:
329767146
NACRES:
NA.23

Assay

97% (HPLC)

form

solid

mp

247-252 °C

λmax

306 nm in THF

SMILES string

Cc1cc(ccc1-c2ccc(cc2C)N(c3ccccc3)c4cccc5ccccc45)N(c6ccccc6)c7cccc8ccccc78

InChI

1S/C46H36N2/c1-33-31-39(47(37-19-5-3-6-20-37)45-25-13-17-35-15-9-11-23-43(35)45)27-29-41(33)42-30-28-40(32-34(42)2)48(38-21-7-4-8-22-38)46-26-14-18-36-16-10-12-24-44(36)46/h3-32H,1-2H3

InChI key

ZJFKMIYGRJGWIB-UHFFFAOYSA-N

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General description

2,2′-Dimethyl-N,N′-di-[(1-naphthyl)-N,N′-diphenyl]-1,1′-biphenyl-4,4′-diamine (α-NPD) is a conducting polymer that can be used as a hole transporting material (HTM) with a transport gap of ~4 eV and an ionization potential of 5.5 eV.

Application

α-NPD can be used as a π-conjugated organic semiconducting material which has good charge transporting properties. It can be used in the fabrication of organic electronic devices such organic light emitting diodes (OLEDs) and organic solar cells (OSCs).
This material is used as a high performance host material for OLED devices showing increased device efficiency (maximum luminance efficiency was 4.4 cd/A at 9 V for the fluorescent device and 24.4 cd/A for phosphorescent device).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Determination of charge-carrier transport in organic devices by admittance spectroscopy: Application to hole mobility in alpha-NPD
Nguyen ND, et al.
Physical Review. B, Condensed Matter and Materials Physics, 75(7), 075307-075307 (2007)
Tsai; Y.- S.; et al.
Thin Solid Films, 517, 5338-5338 (2009)
Optical band gaps of organic semiconductor materials
Costa JCS, et al.
Optical Materials, 58(1), 51-60 (2016)
Band alignment at organic-inorganic semiconductor interfaces: alpha-NPD and CuPc on InP (110)
Chasse T, et al.
Journal of Applied Physics, 85(9), 6589-6592 (1999)
Impact of electrode contamination on the alpha-NPD/Au hole injection barrier
Wan A, et al.
Organic Electronics, 6(1), 47-54 (2005)

Articles

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The conductivity of organic semiconductors can be increased, and the barriers to charge-carrier injection from other materials can be reduced, by the use of highly reducing or oxidizing species to n- or p-dope, respectively, the semiconductor.

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