Tetrasubstituted adamantane derivatives with arylamine groups: Solution-processable hole-transporting and host materials with high triplet energy and good thermal stability for organic light-emitting devices |
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| Affiliation: | 1. Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Department of Chemistry, Wuhan University, Wuhan 430072, People’s Republic of China;2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People’s Republic of China;1. Department of Advanced Science and Engineering, Waseda University, 3-4-1 Ookubo, Shinjuku-ku, Tokyo 169-8555, Japan;2. JXTG Nippon Oil & Energy Corporation, High Performance Materials Company, 8 Chidori-cho, Naka-ku, Yokohama 231-0815, Japan;1. Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus of Espinardo, 30100 Murcia, Spain;2. Institut für Angewandte Photophysik, Technische Universität Dresden, George-Bähr Str. 1, D-01069 Dresden, Germany;3. Current address: Novaled GmbH, Tatzberg 49, 01307 Dresden, Germany;4. Current address: Department of Physics, University of Oxford, Clarendon Laboratory, Parks Road, Oxford OX1 3PU, United Kingdom;1. Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Institute of Functional Nano & Soft Materials (FUNSOM), Soochow University, Suzhou, Jiangsu 215123, People’s Republic of China;2. Microelectronics Department, Soochow University, Suzhou, Jiangsu 215006, People’s Republic of China;3. WENGZHENG College, Soochow University, Suzhou, Jiangsu 215104, People’s Republic of China;4. NXP Semiconductors, Shanghai 200070, People’s Republic of China;5. State Key Laboratory of Functional Materials for Informatics, Shanghai Institute of Micro-system and Information Technology, Chinese Academy of Sciences, Shanghai 200050, People’s Republic of China;1. Department of Advanced Material Chemistry, Korea University Sejong Campus, Sejong-ro 2511, Sejong City, 339-700, Republic of Korea;2. Department of Bio-Nano Chemistry, Wonkwang University, 460 Iksandae, Jeonbuk, 54538, Republic of Korea;1. Department of Materials Science and Engineering, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Republic of Korea;2. Department of Chemistry, Center for Superfunctional Materials, Ulsan National Institute of Science and Technology (UNIST), Ulsan, 44919, South Korea;3. Department of Materials Science and Engineering, Pohang University of Science and Technology (POSTECH), Pohang, Gyeongbuk, 790-784, Republic of Korea;4. Research Institute of Advanced Materials, BK21 PLUS SNU Materials Division for Educating Creative Global Leaders, Nano System Institute (NSI), Institute of Engineering Research, Research Institute of Advanced Materials, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Republic of Korea |
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| Abstract: | Four new host/hole-transporting materials, namely 4,4′,4″,4‴-(adamantane-1,3,5,7-tetrayl)tetrakis(N,N-diphenylaniline) (4TPA-Ad, 1),4,4′,4″,4‴-(adamantane-1,3,5,7-tetrayl)tetrakis(N,N-di-p-tolylaniline) (4MTPA-Ad, 2), 1,3,5,7-tetrakis(4-(9H-carbazol-9-yl)phenyl)adamantane (4Cz-Ad, 3) and 1,3,5,7-tetrakis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)adamantane (4tBuCz-Ad, 4), were designed and synthesized by incorporating four electron-donating arylamine units into the rigid adamantane skeleton via a simple C–N coupling reaction. Their thermal, photophysical and electrochemical properties were investigated. The molecular design endows the materials with high triplet energies of ∼3.0 eV, good solution processability, high thermal stability and appropriate HOMO levels. Two types of electroluminescent devices using 1–4 as hole-transporting or host materials were fabricated. The device based on 2 as solution-processed hole-transporting material and tris(quinolin-8-yloxy)aluminum as an emitter revealed a maximum current efficiency of 4.2 cd A−1, which was comparable with the TAPC-based control device. The sky-blue device employing 2 as solution-processed host material and 4,6-(difluorophenyl)pyridine-N,C2′)picolinate (FIrpic) as an emitter showed a maximum current efficiency of 16.6 cd A−1 with Commission Internationale de I’Eclairage (CIE) coordinates of (0.16, 0.32). |
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| Keywords: | Adamantane OLEDs Hole-transporting materials Host materials |
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