Conjugated Silole and Carbazole Copolymers: Synthesis, Characterization, Single‐Layer Light‐Emitting Diode, and Field Effect Carrier Mobility

Abstract

Summary: Soluble conjugated random and alternating copolymers (PCz‐PSP) derived from N‐hexyl‐3,6‐carbazole (Cz) and 1,1‐dimethyl‐2,3,4,5‐tetraphenylsilole (PSP) were synthesized by palladium(0)‐catalyzed Suzuki coupling reactions. The feed ratios of Cz to PSP were 95:5, 90:10, 80:20, 70:30, and 50:50. Chemical structures and optoelectronic properties of the copolymers were characterized by 1H NMR, 13C NMR, UV absorption, cyclic voltammetry, photoluminescence, electroluminescence, and field effect transistor. HOMO levels of the copolymers are between −5.15 and −5.34 eV. Single‐layer devices with a configuration of ITO/copolymer/Ba/Al were fabricated and the copolymer with PSP content of 20% displayed the highest external quantum efficiency of 0.77%. Field effect transistors with tantalum pentoxide‐polyacrylonitrile double insulators demonstrated that hole mobilities of the copolymers decreased with their PSP contents, and the hole mobility up to 9.3 × 10−6 cm2 · (V · s)−1 could be achieved.Synthesis of coplymers derived from 3,6‐carbazole and silole.magnified imageSynthesis of coplymers derived from 3,6‐carbazole and silole.

Silole‐Containing Polymers: Chemistry and Optoelectronic Properties

“…[110] The M w of the copolymers ranged from 11 100 to 16 700 with M w =M n 1.7. From the absorption spectrum of the alternating copolymer, the absorption peak for the silole units was 395 nm.…”

Conjugated Organosilicon Materials for Organic Electronics and Photonics

“…Chen and coauthors incorporated N-hexyl-3,6-carbazole (Cz) and 1,1-dimethyl-2,3,4,5-tetraphenylsilole (PSP) to yield random and alternating copolymers (PCz-PSP) (Fig. 47b) by Suzuki coupling reactions [219]. The molecular weights were around 11-17 kDa (M w , polydispersity between 1.3 and 1.7).…”

“…In contrast to the random copolymer, the alternating copolymer exhibited a broad absorption band which obviously results from the mixed configuration dominated by the TST segment. In films with a low 47 Structural formulas of (a) 9,9-dioctylfluorene (FO) and 1,1-dimethyl-3,4-diphenyl-2,5-bis(2 -thienyl)silole (TST) copolymers PFO-TST [218] and (b) N-hexyl-3,6-carbazole (Cz) and 1,1-dimethyl-2,3,4,5-tetraphenylsilole (PSP) copolymers PCz-PSP [219] TST content the excitation energy completely transferred from the PFO to the TST segment. In OLEDs (layer structure ITO/PEDOT/PVK/copolymer/Ba/Al) the emitted light from the copolymers was found to be red-shifted.…”

A New Carbazole‐Constructed Hyperbranched Polymer: Convenient One‐Pot Synthesis, Hole‐Transporting Ability, and Field‐Effect Transistor Properties

“…3,6-Dibromo-9-N-butanecarbazole (1), 3,6-diiodocarbazole (4), 3-bromo-9-N-hexyl-carbazole (8), and 9-hexyl-9H-carbazol-3-ylboronic acid (9) were synthesized according to the literature methods and our previous work [28,46]. All other reagents were used as received.…”

“…Compound 2 was obtained as a white solid in 50% yield, according to the literature. [28] The tetrabromocarbazole 7 was synthesized through four steps, similar to the method reported in the literature. [29] First, di-iodocarbazole 4 was prepared from 9H-carbazole by a Tucker iodination reaction, [30] which was then alkylated with 1-bromobutane in the presence of KOH as a base to afford 5.…”