A Review of Benzophenone-Based Derivatives for Organic Light-Emitting Diodes

Organic light-emitting diodes (OLEDs) have garnered considerable attention in academic and industrial circles due to their potential applications in flat-panel displays and solid-state lighting technologies, leveraging the advantages offered by organic electroactive derivatives over their inorganic counterparts. The thin and flexible design of OLEDs enables the development of innovative lighting solutions, facilitating the creation of customizable and contoured lighting panels. Among the diverse electroactive components employed in the molecular design of OLED materials, the benzophenone core has attracted much attention as a fragment for the synthesis of organic semiconductors. On the other hand, benzophenone also functions as a classical phosphor with high intersystem crossing efficiency. This characteristic makes it a compelling candidate for effective reverse intersystem crossing, with potential in leading to the development of thermally activated delayed fluorescent (TADF) emitters. These emitting materials witnessed a pronounced interest in recent years due to their incorporation in metal-free electroactive frameworks and the capability to convert triplet excitons into emissive singlet excitons through reverse intersystem crossing (RISC), consequently achieving exceptionally high external quantum efficiencies (EQEs). This review article comprehensively overviews the synthetic pathways, thermal characteristics, electrochemical behaviour, and photophysical properties of derivatives based on benzophenone. Furthermore, we explore their applications in OLED devices, both as host materials and emitters, shedding light on the promising opportunities that benzophenone-based compounds present in advancing OLED technology

New Electroactive Polymers with Electronically Isolated 4,7-Diarylfluorene Chromophores as Positive Charge Transporting Layer Materials for OLEDs

The OLED materials were developed in the frame of project funded by the Research Council of Lithuania (grant No. S-LLT-19-2). B.Z. is thankful to the National Natural Science Foundation of China (No. 51773195), and the Research & Development Projects in Key Areas of Guangdong Province, China (No. 2019B010933001). We are also obliged to D. Volyniuk for measurements of the ionization potentials.A group of polyethers containing electroactive pendent 4,7-diarylfluorene chromophores have been prepared by the multi-step synthetic route. Full characterization of their structures has been presented. The polymeric materials represent derivatives of high thermal stability with initial thermal degradation temperatures in a range of 392–397 °C. Glass transition temperatures of the amorphous polymers range from 28 °C to 63 °C and depend on structures of the 4,7-diarylfluorene chromophores. Electron photoemission spectra of thin layers of the electroactive derivatives showed ionization potentials in the range of 5.8–6.0 eV. Hole injecting/transporting properties of the prepared polymeric materials were confirmed during formation of organic light-emitting diodes with tris(quinolin-8-olato)aluminium (Alq3) as a green emitter, which also serves as an electron transporting layer. The device using hole-transporting polymer with electronically isolated 2,7-di(4-biphenyl) fluorene chromophores demonstrated the best overall performance with low turn on voltage of 3 V, high current efficiency exceeding 1.7 cd/A, and with maximum brightness over 200 cd/m2. The organic light-emitting diode (OLED) characteristics were measured in non-optimized test devices. The efficiencies could be further improved by an optimization of device structure, formation conditions, and encapsulation of the devices..---//---This work is licensed under a CC BY 4.0 license.Research Council of Lithuania (grant No. S-LLT-19-2); National Natural Science Foundation of China (No. 51773195); Research & Development Projects in Key Areas of Guangdong Province, China (No. 2019B010933001); Institute of Solid State Physics, University of Latvia as the Center of Excellence has received funding from the European Union’s Horizon 2020 Framework Programme H2020-WIDESPREAD-01-2016-2017-TeamingPhase2 under grant agreement No. 739508, project CAMART

Bifunctional Bicarbazole-Benzophenone-Based Twisted Donor–Acceptor–Donor Derivatives for Deep-Blue and Green OLEDs

Organic light-emitting diodes (OLEDs) have played a vital role in showing tremendous technological advancements for a better lifestyle, due to their display and lighting technologies in smartphones, tablets, television, and automotive industries. Undoubtedly, OLED is a mainstream technology and, inspired by its advancements, we have designed and synthesized the bicarbazole-benzophenone-based twisted donor–acceptor–donor (D-A-D) derivatives, namely DB13, DB24, DB34, and DB43, as bi-functional materials. These materials possess high decomposition temperatures (>360 °C) and glass transition temperatures (~125 °C), a high photoluminescence quantum yield (>60%), wide bandgap (>3.2 eV), and short decay time. Owing to their properties, the materials were utilized as blue emitters as well as host materials for deep-blue and green OLEDs, respectively. In terms of the blue OLEDs, the emitter DB13-based device outperformed others by showing a maximum EQE of 4.0%, which is close to the theoretical limit of fluorescent materials for a deep-blue emission (CIEy = 0.09). The same material also displayed a maximum power efficacy of 45 lm/W as a host material doped with a phosphorescent emitter Ir(ppy)3. Furthermore, the materials were also utilized as hosts with a TADF green emitter (4CzIPN) and the device based on DB34 displayed a maximum EQE of 11%, which may be attributed to the high quantum yield (69%) of the host DB34. Therefore, the bi-functional materials that are easily synthesized, economical, and possess excellent characteristics are expected to be useful in various cost-effective and high-performance OLED applications, especially in displays

3-(N,N-Diphenylamino)carbazole Donor Containing Bipolar Derivatives with Very High Glass Transition Temperatures as Potential TADF Emitters for OLEDs

Well-defined electroactive bipolar derivatives of new structure have been synthesized from 3-(N,N-diphenylamino)-9H-carbazole and bis(4-fluorophenyl)sulfone, 4-fluorophenylsulfone or 4,4′-difluorobenzophenone, respectively. The full characterization of their structure is described. The amorphous materials with very high glass transition temperatures of 111–173 °C also possess high thermal stability, with onset decomposition temperatures of 351–398 °C. Some of the compounds having the best solubility were tested as the emitters dispersed in 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP) host for preparation of organic light emitting diodes (OLEDs). A device containing 15 wt% of the guest bis[4-{3-(N,N-diphenylamino)carbazol-9-yl}phenyl] sulfone demonstrated the best overall characteristics with maximum brightness exceeding 2630 cd/m2, current efficiency of 3.2 cd/A, power efficiency of 2.2 lm/W, and external quantum efficiency exceeding 1.7% at 100 cd/m2

Highly Efficient Candlelight Organic Light-Emitting Diode with a Very Low Color Temperature

Low color temperature candlelight organic light-emitting diodes (LEDs) are human and environmentally friendly because of the absence of blue emission that might suppress at night the secretion of melatonin and damage retina upon long exposure. Herein, we demonstrated a lighting device incorporating a phenoxazine-based host material, 3,3-bis(phenoxazin-10-ylmethyl)oxetane (BPMO), with the use of orange-red and yellow phosphorescent dyes to mimic candlelight. The resultant BPMO-based simple structured candlelight organic LED device permitted a maximum exposure limit of 57,700 s, much longer than did a candle (2750 s) or an incandescent bulb (1100 s) at 100 lx. The resulting device showed a color temperature of 1690 K, which is significantly much lower than that of oil lamps (1800 K), candles (1900 K), or incandescent bulbs (2500 K). The device showed a melatonin suppression sensitivity of 1.33%, upon exposure for 1.5 h at night, which is 66% and 88% less than the candle and incandescent bulb, respectively. Its maximum power efficacy is 23.1 lm/W, current efficacy 22.4 cd/A, and external quantum efficiency 10.2%, all much higher than the CBP-based devices. These results encourage a scalable synthesis of novel host materials to design and manufacture high-efficiency candlelight organic LEDs

Pyridinyl-Carbazole Fragments Containing Host Materials for Efficient Green and Blue Phosphorescent OLEDs

Pyridinyl-carbazole fragments containing low molar mass compounds as host derivatives H1 and H2 were synthesized, investigated, and used for the preparation of electro-phosphorescent organic light-emitting devices (PhOLEDs). The materials demonstrated high stability against thermal decomposition with the decomposition temperatures of 361–386 °C and were suitable for the preparation of thin amorphous and homogeneous layers with very high values of glass transition temperatures of 127–139 °C. It was determined that triplet energy values of the derivatives are, correspondingly, 2.82 eV for the derivative H1 and 2.81 eV for the host H2. The new derivatives were tested as hosts of emitting layers in blue, as well as in green phosphorescent OLEDs. The blue device with 15 wt.% of the iridium(III)[bis(4,6-difluorophenyl)-pyridinato-N,C2′]picolinate (FIrpic) emitter doping ratio in host material H2 exhibited the best overall characteristics with a power efficiency of 24.9 lm/W, a current efficiency of 23.9 cd/A, and high value of 10.3% of external quantum efficiency at 100 cd/m2. The most efficient green PhOLED with 10 wt% of Ir(ppy)3 {tris(2-phenylpyridine)iridium(III)} in the H2 host showed a power efficiency of 34.1 lm/W, current efficiency of 33.9 cd/A, and a high value of 9.4% for external quantum efficiency at a high brightness of 1000 cd/m2, which is required for lighting applications. These characteristics were obtained in non-optimized PhOLEDs under an ordinary laboratory atmosphere and could be improved in the optimization process. The results demonstrate that some of the new host materials are very promising components for the development of efficient phosphorescent devices