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Fluorene (Fl) is a polycyclic aromatic compound, which received its name due to strong violet fluorescence which arise from high conjugated planar -electron system.
Poly(9,9-dihexylfluorene) (PDHF, comp 187) is generally considered amorphous. Some PFs with larger alkyl side chains dioctyl (PFO, comp 188) or bis(2-ethylhexyl) (PEHF, Comp 189) show liquid crystal behavior, opening a possibility to fabricate polarized LEDs.
PFO is clearly crystalline with a melting point around 150 C. Nanoscale crystallinity of PFO was demonstrated by X-ray diffraction (XRD) experiments
This result in polymers with relatively low molecular weight (Mn up to 5,000) A serious drawback of this synthesis method was also a significant amount of residual metal impurities, which dramatically affected the PLED performance
The next step towards soluble PF as material for PLEDs, was an application of Yamamoto
- Polymer has high molecular weight (Mn = 94,000; PDI = 2.3) - Although Ni catalyzed reaction allowed improvement of the regiospecificity and minimization of cross-linking and miss-linking reaction as compared to FeCl3 oxidation method, it employs large amount of metals (Ni, Zn) during the synthesis and resulting polymer should be carefully purified from the metal impurities. - Thus, whereas relatively high MW Mn 94,000 can be achieved for PF comp.190, containing hydrophilic 3,6-dioxaheptyl substituents, in the cases of various alkyl substituents the MW are limited 14,000 60,000
2.4 The problem of pure blue emission in PFs: excimer/aggregate formation or fluorenone defects?
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