Organic light-emitting diodes (OLEDs) have attracted much attention given their advantages to self-emission of light, wide angle, and applications in flat-panel displays. Red, green, and blue OLEDs with high efficiencies and low device driving voltages are necessary for full color displays.
1In red fluorescent OLEDs, donor-acceptor type materials such as 4-(dicyanomethylene)-2-methyl-6-[p-(dimethylamino)styryl]-4H-pyran (DCM) derivatives have been widely used as red fluorescent emitters.
2-8In this paper, a series of donor-acceptor-donor red fluorescent emitters (1-4) were synthesized and their electroluminescent properties were investigated. In compounds 1-4, the bulky adamantane groups were incorporated in donor moieties in order to prevent molecular aggregation between emitters, thus reducing concentration quenching. Compared to the simple donor-acceptor type materials such as DCM derivatives, these donor-acceptor-donor type materials (1)(2)(3)(4) are expected to show improved color chromaticity due to the extended π-conjugation length. In addition, to study the structural effects of emitters on EL performance, various acceptor moieties containing -CN groups were introduced into red fluorescent materials 1-4.Usually, doping is used to obtain red emissions, in which the emitting layer is compose of a host and red dopant in order to prevent concentration quenching in the emitting layer.9-12 Recently, a co-host system was reported to overcome the incomplete energy transfer between host and dopant. [13][14][15][16] In this study, rubrene is employed as an assistant host in order to enhance energy transfer from host to dopants and thus improve the EL efficiencies.Scheme 1 shows the synthetic route of the designed donoracceptor-donor type red fluorescent emitters. 5-(3-Adamantyl-7,7-dimethyljulolidyl)carbaldehyde was prepared through Vilsmeier reaction. Compounds 1, 2, and 4 were prepared by the Knoevenagel condensation of aldehyde with the corresponding active methylene compounds (1a, 2a, and 4a). The reaction of aldehyde with phosphonate intermediates (3a) gave 3 by the Horner-Emmons reaction.The UV-vis absorption and PL spectra of red materials 1-4 are shown in Figure 1. The photophysical properties of 1-4 are summarized in Table 1. Compound 2, having phenylenediacetonitrile moiety as a acceptor, shows the longest maximum absorption and emission peak of 587 and 648 nm, respectively, while compound 1, having diaminomaleonitrile