Covalently bound hole-injecting nanostructures. Systematics of molecular architecture, thickness, saturation, and electron-blocking characteristics on organic light-emitting diode luminance, turn-on voltage, and quantum efficiency

Qinglan Huang, Guennadi A. Evmenenko, Pulak Dutta, Paul Lee, Neal R. Armstrong, Tobin J. Marks

Research output: Contribution to journalArticle

141 Citations (Scopus)


Hole transporting materials are widely used in multilayer organic and polymer light-emitting diodes (OLEDs, PLEDs, respectively) and are indispensable if device electroluminescent response and durability are to be truly optimized. This contribution analyzes the relative effects of tin-doped indium oxide (ITO) anode-hole transporting layer (HTL) contact versus the intrinsic HTL materials properties on OLED performance. Two siloxane-based HTL materials, N,N-bis(p-trichlorosilylpropyl)-naphthalen-1-yl)-N,N-diphenyl-biphenyl-4, 4′-diamine (NPB-Si2) and 4,4′-bis[(p- trichlorosilylpropylphenyl)phenylamino]biphenyl (TPD-Si2), are designed and synthesized. They have the same hole transporting triarylamine cores as conventional HTL materials such as 1,4-bis(1-naphthylphenylamino) biphenyl (NPB) and N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl)-4,4- diamine (TPD), respectively. However, they covalently bind to the ITO anode, forming anode-HTL contacts that are intrinsically different from those of the anode to TPD and NPB. Applied to archetypical tris(8-hydroxyquinolato) aluminum(III) (Alq)-based OLEDs as (1) the sole HTLs or (2) anode-NPB HTL interlayers, NPB-Si2 and TPD-Si2 enhance device electroluminescent response significantly versus comparable devices based on NPB alone. In the first case, OLEDs with 36 000 cd/m2 luminance, 1.6% forward external quantum efficiency (ηext), and 5 V turn-on voltages are achieved, affording a 250% increase in luminance and ∼50% reduction in turn-on voltage, as compared to NPB-based devices. In the second case, even more dramatic enhancement is observed (64 000 cd/m2 luminance; 2.3% ηext; turn-on voltages as low as 3.5 V). The importance of the anode-HTL material contact is further explored by replacing NPB with saturated hydrocarbon siloxane monolayers that covalently bind to the anode, without sacrificing device performance (30 000 cd/m2 luminance; 2.0% ηext; 4.0 V turn-on voltage). These results suggest new strategies for developing OLED hole transporting structures.

Original languageEnglish
Pages (from-to)10227-10242
Number of pages16
JournalJournal of the American Chemical Society
Issue number29
Publication statusPublished - Jul 27 2005


ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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