Theoretical Investigation of Organic Amines as Hole Transporting Materials: Correlation to the Hammett Parameter of the Substituent, Ionization Potential, and Reorganization Energy Level

2009 ◽  
Vol 62 (5) ◽  
pp. 483 ◽  
Author(s):  
Jiunn-Hung Pan ◽  
Yu-Ma Chou ◽  
Houn-Lin Chiu ◽  
Bo-Cheng Wang
Keyword(s):  
Radical Cation ◽  
Density Functional ◽  
Reorganization Energy ◽  
Hole Transport ◽  
Substitution Effects ◽  
Oxidation Potentials ◽  
Hole Transporting ◽  
Organic Amines ◽  
Hammett Parameter ◽  
Hole Transporting Materials

Theoretical calculations on organic amines widely used as hole-transporting materials (HTMs) in multilayer organic light-emitting diodes have been performed. The calculated Ip and the reorganization energy for hole transport (λ+) of triphenylamine (TPA), 9-phenyl-9H-carbazole (PC), and their derivatives, are found to be related to their Hammett parameter (σ). In this study, the density functional theory (DFT) calculation is used to optimize 82 TPA and PC derivatives. Electronic structures of these compounds in the neutral and the radical-cation states are obtained based on calculations on optimized geometrical structures. The Ip and λ+ values are derived from calculated heats of formation (or total energy) of the neutral and the radical-cation states. In particular, the calculated Ips for these derivatives correlate well with the experimental data. The substitution effect for the mono-substituted TPA and PC is displayed in that the Ips of the TPA and PC derivatives with electron-donating and -withdrawing substituents are lower and higher than those of TPA and PC, respectively. For the effect of substitution position, the para-substituted TPA derivatives have higher Ip and –EHOMO than those of meta-substituted TPAs. The substitution effects in di- and tri-substituted TPAs are more pronounced than that of mono-substituted ones. According to the results, the calculated Ips shows an excellent agreement with the experimental oxidation potentials (EP/2) in these TPA derivatives. Furthermore, these calculation results can be employed to predict electro-luminescent properties for new and improved HTMs.

scholarly journals Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions

RSC Advances ◽  
2021 ◽  
Vol 11 (15) ◽  
pp. 8879-8885
Author(s):  
Jui-Heng Chen ◽  
Kun-Mu Lee ◽  
Chang-Chieh Ting ◽  
Ching-Yuan Liu
Keyword(s):  
Solar Cell ◽  
Perovskite Solar Cell ◽  
Hole Transport ◽  
Coupling Reactions ◽  
Hole Transporting ◽  
Shaped Hole ◽  
Hole Transporting Materials

Carbazole or phenothiazine core-based hole-transport materials are facilely accessed by an optimized synthesis-shortcut. Perovskite solar cell devices with 6–13 demonstrate PCEs of up to 17.57%.

Hole transporting materials based on benzodithiophene and dithienopyrrole cores for efficient perovskite solar cells

2018 ◽  
Vol 6 (14) ◽  
pp. 5944-5951 ◽  
Author(s):  
R. Sandoval-Torrientes ◽  
I. Zimmermann ◽  
J. Calbo ◽  
J. Aragó ◽  
J. Santos ◽  
...  
Keyword(s):  
Solar Cells ◽  
High Efficiency ◽  
Perovskite Solar Cells ◽  
Reorganization Energy ◽  
Hole Transporting ◽  
Hole Transporting Material ◽  
Hole Transporting Materials

High efficiency (18.1%) perovskite solar cells are demonstrated by using a hole transporting material with very low reorganization energy (λ).

Hexa-Alkoxytriphenylenes As Hole Transporting Materials Inc Stable Oleds Using ALQ3 As Emitting Layer

1999 ◽  
Vol 598 ◽  
Author(s):  
Markus Emerich ◽  
S. Tasch ◽  
R. Resel ◽  
G. Leising ◽  
R. Freudenmann ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hole Transport ◽  
X Ray Diffraction ◽  
X Ray ◽  
Structure Morphology ◽  
Hole Transporting ◽  
Hole Transporting Materials

ABSTRACTDevices consisting of hexa-alkoxythriphenylene derivatives as hole transport materials and 8-hydroxyquinoline aluminium (Alq3) as emitting layer with ITO as anode and magnesium as cathode are presented. Moreover X-ray diffraction studies of evaporated triphenylene films were performed leading to a better understanding of crystal structure, morphology and the alignment of the triphenylene molecules on the surface of the substrate.

scholarly journals Novel Anthracene HTM Containing TIPs for Perovskite Solar Cells

Processes ◽  
2021 ◽  
Vol 9 (12) ◽  
pp. 2249
Author(s):  
Sanghyun Paek
Keyword(s):  
Solar Cells ◽  
High Performance ◽  
Perovskite Solar Cells ◽  
Hole Transport ◽  
Long Term Stability ◽  
Photovoltaic Conversion Efficiency ◽  
Hole Transporting ◽  
Hole Transporting Material ◽  
Hole Transporting Materials

Recently, perovskite solar cells have been in the spotlight due to several of their advantages. Among the components of PSCs, hole transporting materials (HTMs) re the most important factors for achieving high performance and a stable device. Here, we introduce a new D–π–D type hole transporting material incorporating Tips-anthracene as a π–conjugation part and dimethoxy-triphenylamine as a donor part (which can be easily synthesized using commercially available materials). Through the measurement of various optical properties, the new HTM not only has an appropriate energy level but also has excellent hole transport capability. The device with PEH-16 has a photovoltaic conversion efficiency of 17.1% under standard one sun illumination with negligible hysteresis, which can be compared to a device using Spiro_OMeTAD under the same conditions. Ambient stability for 1200 h shown that 98% of PEH-16 device from the initial PCE was retained, indicating that the devices had good long-term stability.

Deciphering the effect of replacing thiophene with selenophene in diketopyrrolopyrrole (DPP)-based low cost hole transport materials on the performance of perovskite solar cells

2021 ◽  
Author(s):  
Gururaj P. Kini ◽  
Mritunjaya Parashar ◽  
Vivek Kumar Shukla ◽  
Ranbir Singh
Keyword(s):  
Solar Cells ◽  
Low Cost ◽  
Perovskite Solar Cells ◽  
Hole Transport ◽  
Hole Transporting ◽  
Hole Transporting Materials

Diketopyrrolopyrrole (DPP)-based low-cost hole-transporting materials are designed via facile approaches for efficient perovskite solar cells, which endowed impressive PCE over 16% along with ambient stability.

Theoretical insights into the effect of a conjugated core on the hole transport properties of hole-transporting materials for perovskite solar cells

2017 ◽  
Vol 19 (36) ◽  
pp. 24574-24582 ◽  
Author(s):  
Zemin Zhang ◽  
Weixia Hu ◽  
Jianyu Cui ◽  
Rongxing He ◽  
Wei Shen ◽  
...  
Keyword(s):  
Solar Cells ◽  
Transport Properties ◽  
Perovskite Solar Cells ◽  
Hole Transport ◽  
Hole Transporting ◽  
Hole Transporting Materials

An improved hole transport ability is obtained by introducing a conjugated core into the structure of HTMs.

Synthesis, thermal, electrochemical, and photophysical characterization of 1,5-bis(diarylamino)naphthalene derivatives as potential hole transport OLED materials

2005 ◽  
Vol 83 (6-7) ◽  
pp. 958-968 ◽  
Author(s):  
Jingning Shan ◽  
Glenn PA Yap ◽  
Darrin S Richeson
Keyword(s):  
Photophysical Properties ◽  
Energy Levels ◽  
Hole Transport ◽  
Similar Degree ◽  
Naphthalene Derivatives ◽  
Emission Data ◽  
Oxidation Potentials ◽  
Hole Transporting ◽  
Palladium Catalyzed ◽  
The Difference

Novel 1,5-bis(diarylamino)naphthalene derivatives (1–9), which have potential as hole-transporting materials for electroluminescent devices, were obtained through palladium-catalyzed coupling of diarylamines and 1,5-dibromonaphthalene. The thermal, electrochemical, and photophysical properties of these compounds were examined and the effects of the N-aryl substituents on these properties were investigated. These materials possess glass transition temperatures (Tg) that range from 70–131 °C and these values are related to the identity of the aryl substituents. Cyclic voltammetric measurements demonstrated that these compounds possess two reversible oxidation processes and were further used to estimate the HOMO energy levels of these materials by comparison with the ferrocene/ferrocenium couple. The intramolecular charge mobility, as gauged by the difference between the two oxidation potentials, indicates that compounds 1–8 have a similar degree of delocalization as meta-diaminobenzene derivatives while that of 9 is similar to TPD. Compounds 1–9 emit in the blue-green region and optical absorption and emission data for these materials can be rationalized in terms of the electronic donating properties of the aryl substituents. This data when combined with the electrochemically determined HOMO energies allowed estimation of the LUMO energy levels.Key words: hole transport materials, diaminonaphthalene, thermal analysis, palladium-catalyzed arylation.

The theoretical investigation on the 4-(4-phenyl-4-α-naphthylbutadieny)-triphenylamine derivatives as hole transporting materials for perovskite-type solar cells

2015 ◽  
Vol 17 (8) ◽  
pp. 5991-5998 ◽  
Author(s):  
Wei-Jie Chi ◽  
Ze-Sheng Li
Keyword(s):  
Solar Cells ◽  
Theoretical Investigation ◽  
Hole Mobility ◽  
Hole Transport ◽  
Face To Face ◽  
Substituent Group ◽  
Hole Transporting ◽  
The Face ◽  
Perovskite Type ◽  
Hole Transporting Materials

The hole mobility of hole transport materials is improved by the face-to-face packing mode, and phenyl is an outstanding substituent group for improving hole mobility.

Investigation of Organic-Organic Interfaces by Time-Resolved Photocurrent, Electrochemical, And Photoemission Techniques

1997 ◽  
Vol 488 ◽  
Author(s):  
Liang-Bih Lin ◽  
M. Gary Mason ◽  
Ralph H. Young ◽  
Deniz E. Schildkraut ◽  
Paul M. Borsenberger ◽  
...  
Keyword(s):  
Hole Transport ◽  
Hole Injection ◽  
Photoemission Spectroscopy ◽  
Energy Barriers ◽  
Time Resolved ◽  
Transient Photocurrent ◽  
Oxidation Potentials ◽  
Organic Interfaces ◽  
Hole Transporting ◽  
Organic Electroluminescent

AbstractHole transporting properties and energy barriers at organic-organic interfaces relevant to electrophotographic and organic electroluminescent (EL) devices are described. Three wellknown hole transporting molecules, 1,1-bis(di-4-tolylaminophenyl)cyclohexane (TAPC), N,N′- diphenyl-N,N′-bis(1 -naphthyl)-(1,1 ′-biphenyl)-4,4′-diamine (NPB), and N,N,N′,N′-tetrakis(4- tolyl)-(1,1 ′-biphenyl)-4,4′-diamine (TTB) are used in this study. The ionization potentials (IP) and oxidation potentials (Eox) of these materials are determined by photoemission spectroscopy and electrochemical measurements, from which a conversion formula is obtained (IP ∼ 4.5 eV + eEox). Hole transport across organic-organic interfaces is investigated by time-of-flight transient photocurrent techniques. The efficiencies of hole injection are consistent with the energy barriers, when present, at these interfaces.

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