This work reports the first structure-properties relationship study of ortho [2,1-c]-, meta [1,2-a]-, and para [1,2-b]dihydroindenofluorenes, highlighting the influence of bridge rigidification on the electronic properties. This study has made it possible to devise an extended π-conjugated molecule with both a high triplet state energy level and excellent thermal and morphological stability. As a proof of concept, dihydroindenofluorenes were used as the host in sky-blue phosphorescent organic light-emitting diodes (PhOLEDs) with high performance.

This work reports the use of 9,9′-spirobifluorene and 4-phenyl-9,9′-spirobifluorene, pure hydrocarbon small molecules, as hosts for efficient green and blue phosphorescent OLEDs.

No abstract

We report herein new pyridine-substituted spirobifluorene (SBF) dyes, i.e., 4-(9,9′-spirobi[fluoren]-4-yl)pyridine (4-4Py-SBF), 3-(9,9′-spirobi[fluoren]-4-yl)pyridine (4-3Py-SBF), and 2-(9,9′-spirobi[fluoren]-4-yl)pyridine (4-2Py-SBF), built on the association of the 4-substituted spirobifluorenyl core and various regioisomers of pyridine. These organic semiconductors possess high triplet energy levels (E T around 2.7 eV) in accordance with their use as hosts for green and sky-blue phosphorescent organic light-emitting diodes (PhOLEDs). These dyes have been synthesized from the 4-bromo-spirobifluorene (4-Br-SBF) platform, obtained from a new and efficient synthetic approach using the promising building block 4-bromofluorenone as a key intermediate. Synthesis, structural, thermal, electrochemical, and photophysical properties of the three dyes have been investigated in detail and compared to other model compounds, namely, 4-phenyl-SBF (4-Ph-SBF), 2-phenyl-SBF (2-Ph-SBF), and 2,4-pyridyl-SBF (2-4Py-SBF), in order to precisely study the influence of (i) the pyridine unit, (ii) the position of the nitrogen atom within the pyridyl core (in position 4, 3, or 2), and (iii) the substitution at the C4 position of SBF. This rational structure–properties relationship study sheds light on the effect of the substitution in position 4 of the SBF core and may pave the way to the development of such materials in electronics. Finally, the high performance of green PhOLEDs, ca. 63 cd/A, and of sky-blue PhOLED, ca.16 cd/A, clearly evidence the potential of these new SBF derivatives as hosts for phosphorescent dopants.

This work reports the first structure-properties relationship study of ortho [2,1-c]-, meta [1,2-a]-, and para [1,2-b]dihydroindenofluorenes, highlighting the influence of bridge rigidification on the electronic properties. This study has made it possible to devise an extended p-conjugated molecule with both a high triplet state energy level and excellent thermal and morphological stability. As a proof of concept, dihydroindenofluorenes were used as the host in sky-blue phosphorescent organic light-emitting diodes (PhOLEDs) with high performance.