Formation of gap states and enhanced current injection efficiency in organic light emitting diodes incorporated with subphthalocyanine

Chen, Yu-Hung; Chang, Yu-Jen; Lee, Guan-Ru; Chang, Jow‐Ran; Wu, I-Wen; Fang, Jheng-Hao; Hsu, Shu‐Han; Liu, Shun‐Wei; Wu, Chih‐I; Pi, Tun‐Wen

doi:10.1016/j.orgel.2009.11.025

Cited by 17 publications

(5 citation statements)

References 31 publications

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“…This sample was then excited at the wavelength corresponding to its maximum absorbance (λ max,abs ), and the photoluminescence spectrum was collected. This was done in triplicate for each of the three halo-BsubPc compounds as well as for the standard (phenoxy- (1,2,3,4,8,9,10,11,15,16,17,18-dodecafluoro-7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo(c,h,m)(1,6,11)triazacyclopentadecinato)-boron(III), F 12 BsubPc) which was repeated in every distinct session of data collection to control for any use-to-use drift in the fluorimeter. The quantum yield of F 12 BsubPc has been previously reported as 0.40, 23 and this value was used as the reference to calculate quantum yield of each the halo-BsubPcs.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, research targeting organic electronic devices has triggered renewed interest in BsubPcs as functional organic molecules. ,,− As organic electronic materials, BsubPcs have been successfully incorporated into organic photovoltaic cells (OPVs) , where the energy levels of the frontier molecular orbitals of BsubPc are a better match than normal phthalocyanine with commonly used OPV materials such as C 60 resulting in better device performance . They also have applications in other areas of organic electronics, such as organic light emitting diodes (OLEDs) − and field effect transistors . Crucially, BsubPcs are stable under typical process conditions .…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

et al. 2012

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The physical properties, including the solid state arrangement, photophysics, solubility, and electrochemical behavior of a series of halo-BsubPcs (halo = F, Cl, Br) have been measured (IUPAC name halo-(7,12:14,19-diimino-21,5-nitrilo-5H-tribenzo(c,h,m)(1,6,11)triazacyclopentadecinato)-boron(III)). We have found that across the series all are relatively similar in most regards. Exceptions include that F-BsubPc can be 5 to 25 times more soluble than Cl-BsubPc in common organic solvents. F-BsubPc was also found to be hydrolytically stable under the conditions tested, whereas Cl-BsubPc and Br-BsubPc readily hydrolyzed to form HO-BsubPc. The relative rates of reaction for the series of halo-BsubPcs under standard phenoxylation conditions have also been measured. It was found that F-BsubPc does not undergo phenoxylation, whereas Br-BsubPc showed a markedly higher reaction rate relative to Cl-BsubPc. Based on these data some assumptions can be made as to the suitability of either F-BsubPc or Br-BsubPc to be used in place of the more common Cl-BsubPc. The data indicate that F-BsubPc is a potential replacement for Cl-BsubPc in organic electronic materials whereas Br-BsubPc might be more suitable as a chemical intermediate. Comments on the synthetic methods used to produce each halo-BsubPc are also made.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

et al. 2012

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“…Boronsubphthalocyanine ( BsubPc ), the sole contracted member of the well-known phthalocyanine ( Pc ) family of compounds, has recently become of interest as a functional material for organic electronic devices. − Due to its aromatic yet nonplanar π-electron system, BsubPc possesses desirable optical and electronic properties and has been studied for use in organic light-emitting diodes, − organic photovoltaics, − and organic thin film transistors . We have recently highlighted that BsubPc derivatives are relatively insoluble in common organic solvents .…”

Section: Introductionmentioning

confidence: 99%

One Well-Placed Methyl Group Increases the Solubility of Phenoxy Boronsubphthalocyanine Two Orders of Magnitude

Paton

Lough

Bender

2012

Ind. Eng. Chem. Res.

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Boronsubphthalocyanine (BsubPc) derivatives are materials that have recently seen an increase in attention, particularily for application as colorants and functional materials in organic electronic devices. However, the solubilities of most BsubPc derivatives are too low to utilize solution-based processing techniques. Where there are derivatives that are soluble, they rely on the addition of large alkyl chains for solubilization the result of which is an increase in the molecular weight and a decrease of the specific absorptivity of the BsubPc. In this paper we disclose the identity of two mass-efficient, highly soluble BsubPc derivatives: 3-methylphenoxy-BsubPc and 3,4-dimethylphenoxy-BsubPc. We compare their solubilities and crystal packing structures to previously known BsubPc derivatives. We put forward a symmetry-based argument for the reason for their surprisingly high solubility wherein we treat the molecules as two separate fragments: the phenoxy group and the BsubPc group. The symmetry-based argument suggests that by ignoring the BsubPc fragment common to each derivative a better estimate of the relative solubilities can be estimated through previously established empirical formulas.

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“…Heterointerfaces of π-conjugated molecules can exhibit superior photophysical behavior to the pure molecules, − tune the energy-level offsets for desired optoelectronic properties, , and provide opportunities to investigate interfacial covalent reactions. , Because the molecular contact is responsible for these phenomena, the interfacial geometry − and energetics − have been extensively investigated. Multistacking of π-conjugated molecules by either vacuum deposition or solution processing can afford a variety of interface morphologies.…”

Section: Introductionmentioning

confidence: 99%

Structural Disordering upon Formation of Molecular Heterointerfaces

et al. 2019

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The formation of an organic heterointerface is an essential, albeit rather complex, process in the growth of a molecular heterostructure. Sequentially stacking dissimilar molecules occasionally leads to molecular rearrangement, which potentially involves structural perturbation of the first layer. Disorder in the growth process complicates the interface structure and energetic landscape. However, current understanding of this disorder on the molecular scale remains primitive, which hampers the realization of envisioned heterointerface designs. Herein, we used scanning tunneling microscopy to directly observe the disorder upon the formation of sexithiophene (6T, top)/perfluorinated copper phthalocyanine (F 16 CuPc, bottom) interfaces. Vacuum deposition of 6T onto an epitaxially grown F 16 CuPc monolayer completely perturbed the molecular arrangement of F 16 CuPc along the [1−21] direction of the Ag(111) surface. In the disordered structure, the 6T molecules adopted various bent shapes owing to the cis−trans isomerization between the thiophene rings and were randomly mixed with F 16 CuPc. Comparative experiments demonstrated that (i) multiple C−F•••H−C bonds between the F 16 CuPc and bent 6T molecules stabilized the disordered binary structure and (ii) sparse molecular packing of the F 16 CuPc monolayer and the conformational variety of 6T led to substantial disorder. This real-space imaging of the disordered structure facilitates the molecular understanding of the structural perturbation and, furthermore, provides design rules for molecular heterointerfaces.

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Formation of gap states and enhanced current injection efficiency in organic light emitting diodes incorporated with subphthalocyanine

Cited by 17 publications

References 31 publications

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

Crystal Structures, Reaction Rates, and Selected Physical Properties of Halo-Boronsubphthalocyanines (Halo = Fluoride, Chloride, and Bromide)

One Well-Placed Methyl Group Increases the Solubility of Phenoxy Boronsubphthalocyanine Two Orders of Magnitude

Structural Disordering upon Formation of Molecular Heterointerfaces

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