Disilanyl Double‐Pillared Bisanthracene: A Bipolar Carrier Transport Material for Organic Light‐Emitting Diode Devices

Abstract

Vorsicht Stufe! Ein stufenartiges Molekül (siehe Bild) wurde als Material für den Ladungstransport in schichtförmigen organischen Leuchtdioden hergestellt. Dieses Molekül mit zweisäuligem Gerüst vereint π‐Systeme aromatischer Kohlenwasserstoffe mit Silicium‐σ‐Bindungen und transportiert Löcher wie auch Elektronen in einer Baueinheit.

[n]Cyclo‐2,7‐naphthylenes: Synthesis and Isolation of Macrocyclic Aromatic Hydrocarbons having Bipolar Carrier Transport Ability

“…We envisaged that the macrocyclization of naphthalene molecules through single-bond linkages would be attractive for the design of organic electronic materials without perturbing transparency, chemical stability, or intrinsic mobility. [4] Herein, we report the concise synthesis of the cyclic aromatic hydrocarbons, [n]cyclo-2,7-naphthylenes ([n]CNAP), and their performance as bipolar carrier transport materials in organic light-emitting diode (OLED) devices. Pure hydrocarbon macrocycles without appended functionalities such as heteroatoms and side chains have been found to enhance thermal stability and bipolar carrier transport ability.…”

“…Theoretical calculations showed that the large rigid macrocyclic structures, albeit nonplanar, allow effective distribution of charge and spin of radical ions. [4,15] The reorganization energies through the carrier transport for [5]-, [6]-, and [7]CNAP were thus estimated as 88, 66, and 53 meV, respectively, for the hole transport and 132, 134, and 113 meV, respectively, for the electron transport (Table S5). The results show that the CNAPs have a reorganization energy that is much smaller than that of the parent naphthalene (186 meV for hole and 261 meV for electron) and an even smaller energy for the hole transport than that of pentacene (100 meV for hole and 125 meV for electron).…”

“…Finally, the carrier transport performance of CNAP was evaluated with the abundant compounds, [6]-and [7]CNAP, in standard phosphorescent OLED devices with the following configurations: [4,17] Figure S8 and S9). The macrocycles are both thermally stable and discrete molecular entity; thus they can be deposited in HTL and/or ETL by vacuum deposition.…”

Illusory Molecular Expression of “Penrose Stairs” by an Aromatic Hydrocarbon

“…Although the peculiar topology of molecular entities has been explored by using dynamic noncovalent chemical bonds, [23] the everincreasing variety of chemical reactions for covalent bond formations may further add to this intriguing repertoire with severe structural constraints and could stimulate intellectual amusement. The convergent synthesis of rigid aromatic hydrocarbons with mobile p electrons may also be beneficial for the molecular design of organic materials, [24] and the combination of unique covalent topologies with noncovalent assembly should be explored in the near future. [25,26] Received: March 30, 2011 Published online: May 23, 2011 .…”

Illusory Molecular Expression of “Penrose Stairs” by an Aromatic Hydrocarbon

“…Although the peculiar topology of molecular entities has been explored by using dynamic noncovalent chemical bonds,23 the ever‐increasing variety of chemical reactions for covalent bond formations may further add to this intriguing repertoire with severe structural constraints and could stimulate intellectual amusement. The convergent synthesis of rigid aromatic hydrocarbons with mobile π electrons may also be beneficial for the molecular design of organic materials,24 and the combination of unique covalent topologies with noncovalent assembly should be explored in the near future 25. 26…”