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M-MTDATA

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4,4',4"-Tris(N-3-methylphenyl-N-phenylamino)triphenylamine
Names
Other names
  • m-MTDATA
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C57H48N4/c1-43-16-13-25-55(40-43)59(46-19-7-4-8-20-46)52-34-28-49(29-35-52)58(50-30-36-53(37-31-50)60(47-21-9-5-10-22-47)56-26-14-17-44(2)41-56)51-32-38-54(39-33-51)61(48-23-11-6-12-24-48)57-27-15-18-45(3)42-57/h4-42H,1-3H3
    Key: DIVZFUBWFAOMCW-UHFFFAOYSA-N
  • CC1=CC(=CC=C1)N(C2=CC=CC=C2)C3=CC=C(C=C3)N(C4=CC=C(C=C4)N(C5=CC=CC=C5)C6=CC=CC(=C6)C)C7=CC=C(C=C7)N(C8=CC=CC=C8)C9=CC=CC(=C9)C
Properties
C57H48N4
Molar mass 789.02
Appearance White or yellow powder, crystals
Melting point 194-203°C[1] 210°C[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

m-MTDATA - whose full name is 4,4',4"-Tris(N-3-methylphenyl-N-phenyl-amino) triphenylamine - is an organic molecule belonging to the class of starburst molecules,[3] often used as a material for the production of organic electronic devices. It is particularly appreciated for its hole-transporting ability and is widely used in OLED and other optoelectronic technologies.

Electronic properties

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In terms of electronic properties, m-MTDATA has a HOMO (Highest Occupied Molecular Orbital) level of 5.1 eV and a LUMO (Lowest Unoccupied Molecular Orbital) level of 2.0 eV.[4][5] Its relatively high HOMO level favors efficient hole transport, making it a material with an affinity for efficient acceptance and transport of positive charges. The molecule is also characterized by a conjugated structure that facilitates electron delocalization.[6]

Applications

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Being a material that exhibits good thermal stability as well as low ionization energy, m-MTDATA is an organic electronic material widely used in various optoelectronic devices.[7] Its main application is in OLEDs, where it is employed as a hole transporting layer.

The efficiency of m-MTDATA in optoelectronic devices can be improved by combining it with other electron transport molecules or by optimizing its chemical properties through structural modifications. An example of this is the combined use with a strong electron acceptor such as F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), which is able to optimize hole injection.[8] m-MTDATA is also often used in combination with PPT (2,8-Bis(diphenylphosphoryl)-dibenzo[b,d]thiophene), another compound employed to optimize its electronic performance.[9]

From a new materials research perspective, the typical structure of a device including m-MTDATA sees the material deposited on electrodes such as indium tin oxide (ITO),[10] but it can also be applied on noble metal substrates, such as gold, for advanced charge transport studies. m-MTDATA is widely tested in laboratories for its ability to form active films in organic devices, including thin-film solar cells and organic field-effect transistors (OTFTs).

Security and stability

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m-MTDATA is stable under normal conditions of temperature and pressure.[11] However, it can degrade under prolonged exposure to elevated temperatures or intense UV radiation. Studies of degradation due to use (simulated with prolonged filler injection) have found a decrease in the performance of m-MTDATA, although to a lesser extent than other polymer semiconductors.[12]

History

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Developed in the late 1980s for the production of amorphous molecular materials for use in organic electronic applications,[13] its importance has grown in parallel with the development of organic semiconductor technologies, particularly for the organic LED display industry.

References

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  1. ^ https://www.sigmaaldrich.com/IT/it/product/aldrich/776327
  2. ^ https://www.tcichemicals.com/GB/en/p/T2251
  3. ^ Shirota, Yasuhiko; Kuwabara, Yoshiyuki; Okuda, Daisuke; Okuda, Ryoji; Ogawa, Hiromitsu; Inada, Hiroshi; Wakimoto, Takeo; Nakada, Hiroshi; Yonemoto, Yoshinobu; Kawami, Shin; Imai, Kunio (1997-06-01). "Starburst molecules based on π-electron systems as materials for organic electroluminescent devices". Journal of Luminescence. Luminescence and Optical Spectroscopy of Condensed Matter. 72–74: 985–991. Bibcode:1997JLum...72..985S. doi:10.1016/S0022-2313(96)00396-1. ISSN 0022-2313.
  4. ^ Goushi, Kenichi; Yoshida, Kou; Sato, Keigo; Adachi, Chihaya (April 2012). "Organic light-emitting diodes employing efficient reverse intersystem crossing for triplet-to-singlet state conversion". Nature Photonics. 6 (4): 253–258. Bibcode:2012NaPho...6..253G. doi:10.1038/nphoton.2012.31. ISSN 1749-4893.
  5. ^ Deotare, P. B.; Chang, W.; Hontz, E.; Congreve, D. N.; Shi, L.; Reusswig, P. D.; Modtland, B.; Bahlke, M. E.; Lee, C. K.; Willard, A. P.; Bulović, V.; Van Voorhis, T.; Baldo, M. A. (November 2015). "Nanoscale transport of charge-transfer states in organic donor–acceptor blends". Nature Materials. 14 (11): 1130–1134. Bibcode:2015NatMa..14.1130D. doi:10.1038/nmat4424. ISSN 1476-4660. PMID 26413986.
  6. ^ Zhang, T.; Brumboiu, I. E.; Lanzilotto, V.; Grazioli, C.; Guarnaccio, A.; Johansson, F. O. L.; Coreno, M.; Simone, M. de; Santagata, A.; Brena, B.; Puglia, C. (2019-08-15). "Electronic structure modifications induced by increased molecular complexity: from triphenylamine to m-MTDATA". Physical Chemistry Chemical Physics. 21 (32): 17959–17970. Bibcode:2019PCCP...2117959Z. doi:10.1039/C9CP02423A. ISSN 1463-9084. PMID 31384854.
  7. ^ US5374489A, Imai, Kunio; Wakimoto, Takeo & Shirota, Yasuhiko et al., "Organic electroluminescent device", issued 1994-12-20 
  8. ^ Huang, Jingsong; Pfeiffer, Martin; Werner, Ansgar; Blochwitz, Jan; Leo, Karl; Liu, Shiyong (2002-01-07). "Low-voltage organic electroluminescent devices using pin structures". Applied Physics Letters. 80 (1): 139–141. Bibcode:2002ApPhL..80..139H. doi:10.1063/1.1432110. ISSN 0003-6951.
  9. ^ Goushi, Kenichi; Adachi, Chihaya (July 2012). "Efficient organic light-emitting diodes through up-conversion from triplet to singlet excited states of exciplexes". Applied Physics Letters. 101 (2): 023306. Bibcode:2012ApPhL.101b3306G. doi:10.1063/1.4737006.
  10. ^ US6573651B2, Adachi, Chihaya; Baldo, Marc A. & Forrest, Stephen R., "Highly efficient OLEDs using doped ambipolar conductive molecular organic thin films", issued 2003-06-03 
  11. ^ Kuwabara, Yoshiyuki; Ogawa, Hiromitsu; Inada, Hiroshi; Noma, Naoki; Shirota, Yasuhiko (15 September 2004). "Thermally stable multilared organic electroluminescent devices using novel starburst molecules, 4,4′,4″-Tri( N -carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenylamino)triphenylamine ( m -MTDATA), as hole-transport materials". Advanced Materials. 6 (9): 677–679. doi:10.1002/adma.19940060913. ISSN 0935-9648.
  12. ^ Rao, K. Sudheendra; Kataria, Devika; Tripathi, Durgesh C. (2021-01-01). "Electrical defects in m-MTDATA studied using charge transient spectroscopy". Materials Today: Proceedings. International Conference on Innovation in Technology & Management for Achieving Sustainable Development Goals (SDGs): Materials Science. 38: 1245–1249. doi:10.1016/j.matpr.2020.07.559. ISSN 2214-7853.
  13. ^ Shirota, Yasuhiko; Kobata, Tomokazu; Noma, Naoki (1989-07-01). "Starburst Molecules for Amorphous Molecular Materials. 4,4′,4″-Tris(N,N-diphenylamino)triphenylamine and 4,4′,4″-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine". Chemistry Letters. 18 (7): 1145–1148. doi:10.1246/cl.1989.1145. ISSN 0366-7022.
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