Rubrene
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| Names | |
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| IUPAC name
5,6,11,12-Tetraphenyltetracene
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| Other names
5,6,11,12-Tetraphenylnaphthacene, rubrene
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.494 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C42H28 | |
| Molar mass | 532.7 g/mol |
| Melting point | 315 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rubrene (5,6,11,12-tetraphenylnaphthacene) is a red colored polycyclic aromatic hydrocarbon. Rubrene is used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.
As an organic semiconductor, the major application of rubrene is in organic light-emitting diodes (OLEDs) and organic field-effect transistors, which are the core elements of flexible displays. Single-crystal transistors can be prepared using crystalline rubrene, which is grown in a modified zone furnace on a temperature gradient. This technique, known as physical vapor transport, was introduced in 1998.[1][2]
Rubrene holds the distinction of being the organic semiconductor with the highest carrier mobility, which reaches 40 cm2/(V·s) for holes. This value was measured in OFETs prepared by peeling a thin layer of single-crystalline rubrene and transferring to a Si/SiO2 substrate.[3]
Crystal structure
Rubrene crystals are formed through competition between rather weak intermolecular interactions, namely π-stacking and quadrupolar interactions. Owing to these weak interactions, different growth conditions can lead to different crystalline structures – a phenomenon common to many organic crystals. Therefore, several polymorphs of rubrene are known for crystals grown from vapor in vacuum using sealed ampoules, including a monoclinic,[4] triclinic[5] and orthorhombic (space group Aba2) forms.[6] Another orthorhombic form (space group Bbam) is known in crystals obtained in a closed system, in a two-zone furnace, at ambient pressure.[7]
References
- ^ A. Laudise, C. Kloc, P. Simpkins, and T. Siegrist "Physical vapor growth of organic semiconductors" J. Cryst. Growth 187, 449 (1998) doi:10.1016/S0022-0248(98)00034-7
- ^ Oana Diana Jurchescu "Molecular organic semiconductors for electronic devices" chapter Low Temperature Crystal Structure of Rubrene Single Crystals Grown by Vapor Transport, PhD thesis (2006) Rijksuniversiteit Groningen
- ^ Tatsuo Hasegawa and Jun Takeya (2009). "Organic field-effect transistors using single crystals". Sci. Technol. Adv. Mater. 10: 024314. doi:10.1088/1468-6996/10/2/024314.
{{cite journal}}:|format=requires|url=(help) - ^ W. H. Taylor, Z. Kristallogr. 93, 151 (1936)
- ^ S. A. Akopyan, R. L. Avoyan, and Yu. T. Struchkov, Z. Strukt. Khim. 3, 602 (1962)
- ^ D. E. Henn, and W. G. Williams, J. Appl. Cryst. 4, 256 (1971)
- ^ I. Bulgarovskaya, V. Vozzhennikov, S. Aleksandrov, and V. Belsky, Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4, 53 (1983) 115