Synthesis and Application of 1,3,4,5,7,8-Hexafluorotetracyanonaphthoquinodimethane (F6-TNAP): A Conductivity Dopant for Organic Light-Emitting Devices

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• 作者：Phillip K. Koech ; Asanga B. Padmaperuma ; Liang Wang ; James S. Swensen ; Evgueni Polikarpov ; Jens T. Darsell ; James E. Rainbolt ; Daniel J. Gaspar
• 刊名：Chemistry of Materials
• 出版年：2010
• 出版时间：July 13, 2010
• 年：2010
• 卷：22
• 期：13
• 页码：3926-3932
• 全文大小：868K
• 年卷期：v.22,no.13(July 13, 2010)
• ISSN：1520-5002

文摘

Conductivity dopants are used in organic light-emitting devices (OLEDs) to reduce the operating voltage and consequently improve the power efficiency. Here, we report the synthesis, as well as photophysical and electroluminescent properties, of an organic molecular p-type conductivity dopant: 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TNAP). F6-TNAP was obtained in a three-step two-pot synthesis from commercially available octafluoronaphthalene. When 1%−5% of F6-TNAP was coevaporated with N,N′-di-1-naphthyl-N,N′-diphenyl-1,1′-biphenyl-4,4′diamine (α-NPD) an absorption band at 950 nm was formed, which is attributed to charge transfer and assigned to the F6-TNAP radical anion. Single-carrier (hole-only) devices fabricated with F6-TNAP doped into α-NPD as the hole transport layer (HTL) show a >2 V decrease in operating voltage, compared to the undoped device. A decrease in operating voltage was also demonstrated in blue OLED devices using a F6-TNAP-doped HTL, with only a slight decrease in external quantum efficiency, thus resulting in a net improvement in power efficiency. These results demonstrate that F6-TNAP may be useful in generating high-efficiency OLEDs.