Charge transporting and thermally activated delayed fluorescence materials for OLED applications

Abstract

The design and synthesis of efficient charge transporting and TADF materials for OLEDs is a real challenge, and serious considerations are required.

The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration

“…Structure determination: The 1 H NMR spectra of 11A-16A showed characteristic signals in the range of 6.39-8.41 ppm due to the PCH group and coupling constants of 2 J PH from 7.5 to 11.0 Hz, and they showed signals in the range of 5.03-6.46 ppm and the corresponding coupling constants of 5 J PH from 6.7 to 11.3 Hz due to the CHOH proton (Table 1). Relatively large long-range coupling constants 5 J PH are characteristic of cyclic bisallyl systems [25,26]. In the 13 C{ 1 H} NMR spectra, typical signals from the benzyl group in the range of 78.7-81.9 ppm and 1 J CP coupling constants from 55.7 to 65.0 Hz were observed.…”

“…Isomer ratio trans/cis: 3.6:1. 1 H NMR (CDCl 3 ) δ 7.90-7.80 (m, 6H, major + minor) 7.72-7.57 (m, 23H, major + minor, CHP major), 7.40 (d, 2 J PH = 8.0 Hz, 1H, CHP, minor), 7.37-7.24 (m, 6H, major + minor), 7.21 (dd, J = 7.5, 7.5 Hz, 2H, major), 7.18-7.11 (m, 2H, major), 7.06 (dd, J = 7.7, 7.7 Hz, 2H, minor), 7.00 (d, J = 7.6 Hz, 1H, minor), 6.87 (d, 3 J HH = 7.6 Hz, 1H, major), 6.75 (d, 3 J HH = 7.7 Hz, 1H, major), 6.55 (d, J HH = 7.8 Hz, 1H, minor), 6.46 (d, J HH = 7.5 Hz, 2H, minor), 6.36 (dd, 5 J PH = 11.3, 5 J HH = 2.3 Hz, 1H, CHOH, minor), 5.15 (dd, 5 J PH = 7.5, 5 J HH = 2.3 Hz, 1H, CHOH, major) ppm. 13 1 J CP = 57.0 Hz, CHP, major), 79.9 (d, 1 J CP = 56.0 Hz, CHP, minor) ppm.…”

“…31 P{ 1 H} NMR (CDCl 3 ) δ 18.5 (minor), 18.2 (major) ppm. 19 5 J PH = 11.0 Hz, 1H, CHOH, minor), 5.71 (dd, 5 J PH = 7.1, 5 J HH = 2.7 Hz, 1H, CHOH, major), 3.82 (s, 1H, OH, major), 2.55 (d, J = 13.3 Hz, 3H, PMe, major), 2.41 (d, J = 13.4 Hz, 3H, PMe, minor), 1.78 (s, 1H, OH, minor). 13 (10-hydroxy-9,10-dihydroanthr-9-yl)methyldiphenylphosphonium methanesulfonate (14MsO).…”

“…Isomer ratio trans/cis: 1.3:1. 1 H NMR (CD 2 Cl 2 ) δ 8.09-7.49 (m, 23H, major + minor), 7.48-7.17 (m, 13H, major + minor) 7.14 (d, J = 7.7 Hz, 1H, major), 7.10-7.03 (m, 6H, major + minor), 6.92 (d, J = 6.4 Hz, 1H, major), 6.83-6.75 (m, 4H, major + minor), 6.27 (dd, 5 J PH = 10.7; 5 J HH =2.9 Hz, 1H, CHOH, minor), 5.59 (dd, 5 J PH = 7.2; 5 J HH =2.7 Hz, 1H, CHOH, major), 2.69 (d, 2 J PH = 13.6 Hz, 3H, major), 2.57 (d, 2 J PH = 13.6 Hz, 3H, minor), 2.32 (s, 6H, major + minor) ppm. 13 3 J HH = 7.6 Hz, 1H, CH An , major), 6.93 (dd, 3 J HH = 7.7, 4 J PH = 1.2 Hz, 1H, CH An , major), 6.88 (dd, 2 J PH = 8.7, J HH = 2.8 Hz, 1H, CHP, minor), 6.70 (d, 3 J HH = 7.8 Hz, 1H, CH An , minor), 6.42 (s, 2H, major), 6.41 (dd, 5 J PH = 7.1, J HH = 2.8 Hz, 1H, CHOH, minor), 6.29 (s, 2H, minor), 5.67 (dd, 5 J PH = 7.0, 3 J HH = 2.8 Hz, 1H, CHOH, major), 3.77 (s, 3H, minor), 3.75 (s, 6H, major), 3.71 (s, 3H, major), 3.68 (s, 6H, minor), 2.50 (d, J = 13.3 Hz, 3H, major), 2.34 (d, J = 13.4 Hz, 3H, minor), 1.87 (br s, 1H, OH) ppm.…”

“…Organic electronics and optoelectronics are relatively new fields of basic knowledge and technology that have become a subject of interest to chemists, physicists and process engineers [1][2][3][4]. Therefore, the search for organic fluorescent and semiconducting materials for the construction of new-generation electronic devices, such as organic light-emitting diodes (OLEDs) [5], organic field-effect transistors (OFETs) [6], organic solar cells (OPVs) [7], organic solar concentrators (OSCs) [8], organic lasers [9], etc., has drawn the attention of numerous multidisciplinary joint laboratories. Among the aromatic hydrocarbons, linearly fused acenes are being considered as key organic compounds for achieving these goals [10].…”