Browse
Submit Data
Databases
API
Help

Dataset Information

19 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Acridine Based Small Molecular Hole Transport Type Materials for Phosphorescent OLED Application.

ABSTRACT: Two small molecular hole-transporting type materials, namely 4-(9,9-dimethylacridin-10(9H)-yl)-N-(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-N-phenylaniline (TPA-2ACR) and 10,10'-(9-phenyl-9H-carbazole-3,6-diyl)bis(9,9-dimethyl-9,10-dihydroacridine) (PhCAR-2ACR), were designed and synthesized using a single-step Buchwald-Hartwig amination between the dimethyl acridine and triphenylamine or carbazole moieties. Both materials showed high thermal decomposition temperatures of 402 and 422 °C at 5% weight reduction for PhCAR-2ACR and TPA-2ACR, respectively. TPA-2ACR as hole-transporting material exhibited excellent current, power, and external quantum efficiencies of 55.74 cd/A, 29.28 lm/W and 21.59%, respectively. The achieved device efficiencies are much better than that of the referenced similar, 1,1-Bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC)-based device (32.53 cd/A, 18.58 lm/W and 10.6%). Moreover, phenyl carbazole-based PhCAR-2ACR showed good device characteristics when applied for host material in phosphorescent OLEDs.

SUBMITTER: Braveenth R

PROVIDER: S-EPMC8703516 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Bithieno Thiophene-Based Small Molecules for Application as Donor Materials for Organic Solar Cells and Hole Transport Materials for Perovskite Solar Cells.

Project description:This quantum mechanical study focuses on the designing of twelve (MPAM1-MPAM12) bithieno thiophene (BTTI) central core-based small molecules to explore optoelectronic properties as donor candidates for organic solar cells (OSCs) and hole transport materials (HTMs) accompanied by enhanced charge mobility for perovskite solar cells (PSCs). MPAM1-MPAM6 have been designed by the substitution of thiophene-bridged end-capped acceptors on both side terminals of reference (MPAR). MPAM7-MPAM12 are tailored by adopting the same tactic on one side terminal only. MPW1PW91/6-311G (d,p) has been employed for all computational simulations. MPAM12 revealed the highest λmax at 639 nm in dichloromethane (DCM) solvent with the lowest E g of 1.78 eV and dipole moment (20.74 D) in the solvent phase, showing excellent miscibility as compared to the reference. All designed chromophores (MPAM1-MPAM12) demonstrated higher estimated V OC and power conversion efficiency (PCE) when compared to MPAR, suggesting their prominent operational efficiency. Among all, MPAM4 manifested the highest PCE (47.86%). MPAM2 portrayed the highest electron mobility (0.0041573 eV) and MPAM3 exhibited the highest hole mobility (0.0047178 eV). The outcomes highlight the adequacy of the planned strategies, paving a new route for the development of small-molecule HTMs for PSCs and donor contributors for OSCs.

| S-EPMC8757340 | biostudies-literature

Facile tailoring of the electrical transport in representative hole transport materials by molecular doping.

Project description:N,N'-Diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) and 4,4',4''-tris (N-3-methylphenyl-N-phenylamine) triphenylamine (m-MTDATA) are widely used as hole transport materials in organic optoelectronic devices. In the present article, the hole transport properties of blends of NPB and m-MTDATA compared with the pristine materials are investigated using admittance spectroscopy and considering temperature dependent current-voltage characteristics and electroluminescent characteristics. It has been found that m-MTDATA dramatically lowers the carrier mobility in the NPB matrix to a large extent by enhancing the total density of traps and results in more dispersive transport. However, by introducing NPB into m-MTDATA the hole mobility is nearly unchanged in comparison with pristine m-MTDATA film. These differences are attributed to two different charge transport mechanisms, trapping and scattering. Obtained quantitative information regarding the charge transport parameters could help to extend optimization strategies for the fabrication of new organic optoelectronic devices by enabling the facile tailoring of the charge transport process.

| S-EPMC9082722 | biostudies-literature

Dirhodium C-H Functionalization of Hole-Transport Materials.

Project description:Hole-transport materials (HTMs) based on triarylamine derivatives play important roles in organic electronics applications including organic light-emitting diodes and perovskite solar cells. For some applications, triarylamine derivatives bearing appropriate binding groups have been used to functionalize surfaces, while others have been incorporated as side chains into polymers to manipulate the processibility of HTMs for device applications. However, only a few approaches have been used to incorporate a single surface-binding group or polymerizable group into triarylamine materials. Here, we report that Rh-carbenoid chemistry can be used to insert carboxylic esters and norbornene functional groups into sp2 C-H bonds of a simple triarylamine and a 4,4'-bis(diarylamino)biphenyl, respectively. The norbenene-functionalized monomer was polymerized by ring-opening metathesis; the electrochemical, optical, and charge-transport properties of these materials were similar to those of related materials synthesized by conventional means. This method potentially offers straightforward access to a diverse range of HTMs with different functional groups.

| S-EPMC10088024 | biostudies-literature

High-efficiency, solution-processed, multilayer phosphorescent organic light-emitting diodes with a copper thiocyanate hole-injection/hole-transport layer.

Project description:Copper thiocyanate (CuSCN) is introduced as a hole-injection/hole-transport layer (HIL/HTL) for solution-processed organic light-emitting diodes (OLEDs). The OLED devices reported here with CuSCN as HIL/HTL perform significantly better than equivalent devices fabricated with a PEDOT:PSS HIL/HTL, and solution-processed, phosphorescent, small-molecule, green OLEDs with maximum luminance ≥10 000 cd m(-2) , maximum luminous efficiency ≤50 cd A(-1) , and maximum luminous power efficiency ≤55 lm W(-1) are demonstrated.

| S-EPMC4315901 | biostudies-literature

3D hole-transporting materials based on coplanar quinolizino acridine for highly efficient perovskite solar cells.

Project description:Over the past five years, perovskite solar cells (PSCs) have gained intense worldwide attention in the photovoltaic community due to their low cost and high power conversion efficiencies (PCEs). One of the most significant issues in achieving high PCEs of PSCs is the development of suitable low-cost hole-transporting materials (HTMs). Here, we put forward a new concept of HTMs for PSCs: a 3D structure with a core of coplanar quinolizino acridine, derived from the conventional concept of 2D triphenylamine HTMs. A cheaper Ag nanolayer was utilized to replace Au as the counter electrodes, and the title HTM TDT-OMeTAD was synthesized via an easy four-step synthesis (total yield: 61%) to achieve the low cost and convenient manufacture of PSCs. Compared with the conventional 2D triphenylamine HTM, TTPA-OMeTPA, PSC devices based on the 3D HTM TDT-OMeTPA showed a significant improvement in PCE from 10.8% to 16.4%, even outperforming Spiro-OMeTAD (14.8%). TDT-OMeTAD's highest PCE mainly results from it having the highest open-circuit voltage (Voc) of 1.01 V in this work, which is proven to be due to the higher hole mobility, matching energy levels, higher hydrophobicity and the smaller dark current. Moreover, an incident photon-current conversion efficiency (IPCE) test and time-resolved photoluminescence (TRPL) have been carried out to observe the better hole injecting efficiency and photoelectric conversion capability of TDT-OMeTPA based PSCs than Spiro-OMeTAD. The TDT-OMeTPA based PSCs exhibited >75% reproducibility (PCE > 15%) and retained 93.2% of the initial PCE after >500 hours.

| S-EPMC5674323 | biostudies-literature

Theoretical modeling of charge transport in triphenylamine-benzimidazole based organic solids for their application as host-materials in phosphorescent OLEDs.

Project description:The dynamic disorder and electric field effects on charge transport in triphenylamine-benzimidazole based molecular solids have been investigated using electronic structure calculations, molecular dynamics and Monte-Carlo simulations. During the charge propagation, the energy loss of the carrier in each hopping step is monitored by Monte-Carlo simulation. We derive a survival probability correlated momentum-energy distribution for drift-diffusion analysis and we demonstrate the dispersion initiated charge trapping mechanism which is indeed ideal for light emission efficiency via recombination. In the present model, the proposed carrier drift energy-current density expression and Shockley diode current density equation are used to study the current density-voltage characteristics; accordingly the ideality factor (∼1.8-2.0) dictates the deviation of Einstein's classical diffusion-mobility relation (where the ideality factor is unity). The dual mechanism of electric field assisted site energy gap on coherent-like transport and the electric field stretched dispersion on recombination are observed in tris(3'-(1-phenyl-1H-benzimidazole-2-yl)biphenyl-4-yl)amine (TBBI) and tris(4'-(1-phenyl-1H-benzimidazole-2-yl)biphenyl-4-yl)amine (TIBN) molecular systems, which can be used as host materials in organic light emitting diodes (OLEDs). We find the transport going from coherent to incoherent, due to the conversion mechanism of dynamic to static disorder. This can also be a controlled by applied electric field. By adjusting the applied electric field, film thickness and changing the π-stacked molecular aggregation via substitutions, one can fix the dispersive parameter and accordingly calculate the charge transport properties to design efficient host-materials for photovoltaic and light emitting diode devices.

| S-EPMC9085285 | biostudies-literature

Design rules for high mobility xanthene-based hole transport materials.

Project description:Tunable and highly conductive hole transport materials are crucial for the performance of organic electronics applications such as organic light emitting diodes and perovskite solar cells. For commercial applications, these materials' requirements include easy synthesis, high hole mobility, and highly tuned and compatible electronic energy levels. Here, we present a systematic study of a recently discovered, easy-to-synthesize class of spiro[fluorene-9,9'-xanthene]-based organic hole transport materials. Systematic side group functionalization allows us to control the HOMO energy and charge carrier mobility. Analysis of the bulk simulations enables us to derive design rules for mobility enhancement. We show that larger functional groups (e.g. methyl) decrease the conformational disorder due to steric effects and thus increase the hole mobility. Highly asymmetric or polar side groups (e.g. fluorine), however, increase the electrostatic disorder and thus reduce the hole mobility. These generally applicable design rules will help in the future to further optimize organic hole transport materials.

| S-EPMC6839588 | biostudies-literature

Effects of heteroatom substitution in spiro-bifluorene hole transport materials.

Project description:Three new spirofluorene-based hole transport materials, Spiro-S, Spiro-N, and Spiro-E, are synthesized by replacing the para-methoxy substituent in 2,2',7,7'-tetrakis(N,N-di-p-methoxyphenylamine)-9,9'-spirobifluorene (Spiro-MeOTAD) with methylsulfanyl, N,N-dimethylamino and ethyl groups. Their properties as hole transport materials in perovskite solar cells are investigated. The impact of replacing the para-methoxy substituent on bulk properties, such as the photophysical properties, HOMO/LUMO energy level, hole extraction properties and morphologies of perovskite thin films are investigated. Their optoelectronic and charge-transport properties and performance in perovskite solar cells are compared with the current benchmarked and structurally-related hole transport material (HTM) Spiro-MeOTAD. Surprisingly, the methylsulfanyl substituted spirofluorene shows the highest power conversion efficiency of 15.92% among the investigated spirofluorenes, which is an over 38% increase in PCE compared with that of Spiro-MeOTAD under similar device fabrication conditions.

| S-EPMC6018644 | biostudies-literature

Phosphorescent [3 + 2 + 1] coordinated Ir(iii) cyano complexes for achieving efficient phosphors and their application in OLED devices.

Project description:A series of neutral [3 + 2 + 1] coordinated iridium complexes bearing tridentate bis-NHC carbene chelates (2,6-bisimidazolylidene benzene), bidentate chelates (C^N ligands, e.g. derivatives of 2-phenylpridine), and monodentate ions (halides and pseudo-halides, such as Br, I, OCN and CN ions) have been systematically designed and synthesized. X-ray single crystal structure characterization revealed that the nitrogen atom in C^N ligands is located trans to the carbon atom in the benzene ring in tridentate chelates, while the coordinating carbon atom in C^N ligands is located trans to the monodentate ligands. Photophysical studies reveal that the C^N ligands play a vital role in tuning the UV absorption and emission properties, while the tridentate bis-NHC carbene chelates influence the lowest absorption band and emission energy when compared to heteroleptic Ir(ppy)2(acac) [i.e. molar absorptivities at ∼450 nm for ppy-OCN and Ir(ppy)2(acac) are 350 M-1 cm-1 and 1520 M-1 cm-1 and emission maximum peaks are at 465 nm and 515 nm respectively]. Among monodentate ligands that the complexes bear, the group containing the cyanide ligand displays higher emission energy, higher photophysical quantum yields, longer triplet lifetimes and better electrochemical and thermal stabilities than those of cyanate and bromide. Particularly, a blue organic light-emitting diode (OLED) based on dfppy-CN exhibited a maximum external quantum efficiency of 22.94% with CIE coordinates of (0.14, 0.24). Furthermore, a small efficiency roll-off of 5.7% was observed for this device at 1000 cd m-2.

| S-EPMC8336439 | biostudies-literature

Novel Triarylamine-Based Hole Transport Materials: Synthesis, Characterization and Computational Investigation.

Project description:Three novel triarylamine-based electron-rich chromophores were synthesized and fully characterized. Compounds 1 and 2 were designed with electron-rich triphenylamine skeleton bearing two and four decyloxy groups namely, 3,4-bis(decyloxy)-N,N-diphenylaniline and N-(3,4-bis(decyloxy)phenyl)-3,4-bis(decyloxy)-N-phenylaniline, respectively. The well-known electron-rich phenothiazine was introduced to diphenylamine moiety through a thiazole ring to form N,N-bis(3,4-bis(decyloxy)phenyl)-5-(10H-phenothiazin-2-yl)thiazol-2-amine (Compound 3). These three novel compounds were fully characterized and their UV-vis absorption indicated their transparency as a favorable property for hole transport materials (HTMs) suitable for perovskite solar cells. Cyclic voltammetry measurements revealed that the HOMO energy levels were in the range 5.00-5.16 eV for all compounds, indicating their suitability with the HOMO energy level of the perovskite photosensitizer. Density functional theory (DFT) and time-dependent DFT (TD-DFT) have been used to investigate the possibility of the synthesized compounds to be utilized as HTMs for perovskite solar cells (PSCs). The computational investigation revealed that the hole mobility of Compound 1 was 1.08 × 10-2 cm2 V-1 s-1, and the substitution with two additional dialkoxy groups on the second phenyl ring as represented by Compound 2 significantly boosted the hole mobility to reach the value 4.21 × 10-2 cm2 V-1 s-1. On the other hand, Compound 3, in which the third phenyl group was replaced by a thiazole-based phenothiazine, the value of hole mobility decreased to reach 5.93 × 10-5 cm2 V-1 s-1. The overall results indicate that these three novel compounds could be promising HTMs for perovskite solar cells.

| S-EPMC8200960 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data