High Solid‐State Near Infrared Emissive Organic Fluorophores from Thiadiazole[3,4‐c]Pyridine Derivatives for Efficient Simple Solution‐Processed Nondoped Near Infrared OLEDs

• Published in: Advanced functional materials Vol. 30; no. 31
• Main Authors: Therdkatanyuphong, Pattarawadee, Chasing, Pongsakorn, Kaiyasuan, Chokchai, Boonnab, Sumita, Sudyoadsuk, Taweesak, Promarak, Vinich
• Format: Journal Article
• Language: English
• Published: 01.08.2020
• Subjects: high solid‐state emission; near infrared emissive fluorophores; solution‐processed nondoped OLEDs; thiadiazole[3,4‐c]pyridine
• ISSN: 1616-301X; 1616-3028
• DOI: 10.1002/adfm.202002481

Many efforts have been dedicated to developing near infrared (NIR) fluorescent emitters with strong emission especially in the range of 700–1000 nm due to their potential applications in biomedical and optoelectronic fields. However, high solid state NIR emission fluorophores are still rare for applications. Herein, two efficient donor‐π‐acceptor type NIR emitters, C3HTP and C4HTP, are designed and synthesized by end‐capping two isomeric bis(n‐hexylthienyl)thiadiazole[3,4‐c]pyridines as π‐acceptor with structural bulky, electron rich tercarbazole moiety. They exhibit excellent solid state NIR emission with an emission peak at 725 nm, especially C3HTP, reaching a record high photoluminescence quantum yield (ΦPL) of 34% for NIR organic fluorescent materials. By taking advantage of their ΦPL values in the film state (ΦPL = 10–34%), suitable energy levels (highest occupied molecular orbital (HOMO) level ≈ −5.3 eV), high hole mobility (5.49 × 10−8 cm2 V−1 s−1) as well as good amorphous film forming ability by solution casting, they are used to fabricate a nondoped emissive layer (EML) in simple double‐layer solution processed NIR electroluminescent (EL) devices. The device containing C3HTP as the EML shows a NIR emission peaking at 726 nm and excellent EL performance with a high external quantum efficiency of 1.51%, which is the best solution processed nondoped NIR organic light‐emitting diodes reported to date. Importantly, this represents an advance in near infrared organic fluorescent materials and EL devices that meet the requirements of many applications. New thiadiazole[3,4‐c]pyridine derivatives exhibit superior solid state near infrared (NIR) emission with hole‐transporting property and the best solution processed nondoped NIR organic light‐emitting diodes reported to date.