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930997

Sigma-Aldrich

VNPB

Synonym(s):

N-(4-Ethenylphenyl)-N-[4-[4-[(4-ethenylphenyl)-naphthalen-1-ylamino]phenyl]phenyl]naphthalen-1-amine, N4,N4′-Di(naphthalen-1-yl)-N4,N4′-bis(4-vinylphenyl)-[1,1′-biphenyl]-4,4′-diamine, N4,N4′-Di(naphthalen-1-yl)-N4,N4′-bis(4-vinylphenyl)biphenyl-4,4′-diamine, N4,N4′-di(Naphthalen-1-yl)-N4,N4′-bis(4- vinylphenyl)biphenyl-4,4′-diamine, VNPB, [1,1′-Biphenyl]-4,4′-diamine, N4,N4′-bis(4-ethenylphenyl)-N4,N4′-di-1-naphthalenyl, N4,N4′-di(Naphthalen-1-yl)-N4,N4′-bis(4- vinylphenyl)biphenyl-4,4′-diamine

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About This Item

Empirical Formula (Hill Notation):
C48H36N2
CAS Number:
Molecular Weight:
640.81
MDL number:
UNSPSC Code:
12352103
NACRES:
NA.23

Assay

≥97% (HPLC)

Quality Level

solubility

THF: soluble
chloroform: soluble
toluene: soluble

λmax

350 nm±5 nm in THF (UV)

fluorescence

λem 450 nm in THF (PL)

Orbital energy

HOMO 5.3 eV 
LUMO 2.4 eV 

SMILES string

C=CC(C=C1)=CC=C1N(C2=CC=CC3=C2C=CC=C3)C(C=C4)=CC=C4C5=CC=C(N(C6=CC=C(C=C)C=C6)C7=CC=CC8=C7C=CC=C8)C=C5

InChI

1S/C48H36N2/c1-3-35-19-27-41(28-20-35)49(47-17-9-13-39-11-5-7-15-45(39)47)43-31-23-37(24-32-43)38-25-33-44(34-26-38)50(42-29-21-36(4-2)22-30-42)48-18-10-14-40-12-6-8-16-46(40)48/h3-34H,1-2H2

InChI key

WTEWXIOJLNVYBZ-UHFFFAOYSA-N

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Application

N4,N4′-Di(naphthalen-1-yl)-N4,N4′-bis(4-vinylphenyl)biphenyl-4,4′-diamine, also known as VNPB, is a solution-processable Hole Transport / Electron Blocking Layer (HTL / EBL) material popularly used in organic electronics, such as OLEDs and perovskite solar cells .
In OLED devices, the use of VNPB enabled the maximum current efficiency of 22.2 Cd/A, compared to 9.7 Cd/A in the reference device without VNPB, and the device lifetime was extended by up to 74.8% . VNPB allowed a simple and additive-free strategy to prevent the formation of defects in solution processed thin-film stacks made of small-molecular materials.
In solar cells, VNPB increased open-circuit voltage (VOC) and power conversion efficiency (PCE) of wide-bandgap perovskite solar cells by changing the hole transport layer (HTL) from commonly used poly(bis(4-phenyl)(2,4,6-trimethylphenyl)amine) (PTAA) to in-situ cross-linked small mol. VNPB . PCEs of 24.9% and 25.4% have been achieved in perovskite/perovskite and perovskite/silicon tandem solar cells, resp.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Solution-processed multilayer OLEDs with wide bandgap host
Hamidabadi, Vahid Fallah, et al.
Applied Physics. A, Materials Science & Processing, 126, 79-79 (2020)
Semi-transparent perovskite solar cells with a cross-linked hole transport layer
Yu, Jae Choul et al.
Nano Energy, 71, 104635-104635 (2020)
Cross-linked hole transport layers for high-efficiency perovskite tandem solar cells
Wang, Yurui, et al.
Science China: Chemistry, 64, 2025-2034 (2021)
Binary Solvent Effects on Thermally Crosslinked Small Molecular Thin Films for Solution Processed Organic Light-Emitting Diodes
Bail Robert, et al.
Electronic Materials Letters, 17, 74?86-74?86 (2021)
Steric Engineering Enables Efficient and Photostable Wide-Bandgap Perovskites for All-Perovskite Tandem Solar Cells
Wen, Jin, et al.
Advanced Materials, 34, 2110356-2110356 (2022)

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