Synthesis, Electronic Properties and WOLED Devices of Planar Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

Abstract

Abstract:The article deals with the synthesis and the physical properties of polyaromatic hydrocarbons containing P-atom at the edge. In particular, the impact of the successive addition of aromatic rings on the electronic properties was investigated by experimental (UV-vis absorption, fluorescence, cyclic voltammetry) and theoretical studies (DFT). The physical properties recorded in solution and in solid state showed that the P-containing PAHs exhibit the expected properties to be used as emitter in WOLEDs.

A Guide for the Design of Functional Polyaromatic Organophosphorus Materials

“…In turn, the lowest NICS(0) and NICS(1) are obtained by fusing the phosphorus heterocycle with furan (compound 6 , NICS(0)=+3.53 ppm) or benzene (compound 9 , NICS(1)=+0.55 ppm, Table S1). Likewise for phosphole‐based polycyclic compounds, the anti‐aromatic character does not expand to the fused rings, in agreement with Clar's rule, the outer rings have greater aromatic character in all cases.…”

Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

“…Thiss hows the typical hyperfine structure of PAHs. [49] Unlike precursors 7 and 8,d erivative 9 is highly fluorescent in solution (f> 20 %). Interestingly, the picture is rather different in the solid state because compound 9 is not fluorescent as ap owder/thin film, contrary to compound 7.T his phenomenon is rationalised on the basis of aggregation-inducede mission (AIE)/aggregation-caused quenching (ACQ) phenomena.…”

“…As an example of device application, phosphorus-containing PAHs 9 and 17 were inserted as orange dopantso fablueemitting matrix [N,N'-diphenyl-N,N'-bis(1-naphthylphenyl)-1,1'biphenyl-4,4'-diamine (a-NPB)] in white-emitting OLEDs (WOLEDs). [49] The electroluminescence spectrum observed with compound 9 in a-NPB displays both blue emission characteris- Figure 6. UV/Vis absorptionand emission spectra, with time-dependent (TD) DFT simulated spectra(vertical lines) of 7-9, 14-17,and 15M.…”

Organophosphorus Compounds in Organic Electronics

“…The luminescent properties of 30 (Figure ) indicate that this material could be a suitable emitter for OLEDs. Indeed, OLEDs with almost white light (CIE 0.32, 0.35) could be realized by careful optimization of the device architecture in a brightness of 728 cd m −2 (30 mA cm −2 ) at a doping rate of 0.8 % . Baumgartner and co‐workers have achieved a warm white light OLED co‐polymerizing two different phosphole building blocks and styrene ( 31 ; Figure ).…”

“…Indeed, OLEDsw ith almostw hite light (CIE 0.32, 0.35) could be realized by careful optimization of the device architecture in ab rightness of 728 cd m À2 (30 mA cm À2 )a tadoping rateo f0 .8 %. [68] Baumgartner and co-workersh ave achieved aw arm white light OLED co-polymerizing two different phosphole building blocks and styrene (31;F igure6). The resulting polymer of the silyl-(A)a nd amino-(B)s ubstituted dithienophosphole oxides showede mission at around4 60 nm and 600 nm, respectively.…”