Synthesis of Bis(phenazasiline) Compounds and Their Application for TFT as a Model of Phenazasiline-Containing Polymers

Abstract

New bis(phenazasiline) compounds were prepared and a thin film transistor (TFT) device containing bis(phenazasiline) derivatives was fabricated. The bis(phenazasiline)s, prepared from 2-bromo-8-methylphenazasiline, were effective materials for TFT. Obtained bis(phenazasiline) derivatives were considered to be model compounds of phenazasiline-containing polymers in the prediction of TFT properties.

Preparation and Comparison of Chemical Properties of Phenazasiline Monomer, Dimer, Trimer, and Polymer

“…[15] Previously, we have prepared some phenazasiline-containing polymers with various substituents, and investigated their applications. [17][18][19][20][21] On the other hand, in order to develop new functional materials, it is important to investigate the effect of the substituents on the compound. Previously, we have synthesized various phenazasiline derivatives, and investigated their substituent effects.…”

“…[20] In addition, various phenazasiline-containing poly(arylene)type π-conjugated copolymers have been prepared, and their applications have also been investigated. [15][16][17] The phenazasiline-containing copolymers have been prepared from the reaction of dibromophenazasiline with an activated aromatic compound (diboronic acid (and its ester), [15,17] distannane, [17,20] etc. ), however, phenazasilinediboronic acid derivatives have not been prepared yet.…”

High‐Performance All‐Aryl Phenazasilines via Metal‐Free Radical‐Mediated CH Silylation for Organic Light‐Emitting Diodes

“…Phenazasilines, which contain both Si and N heteroatoms in a fused six‐membered ring, are typical examples . Structurally similar to the popular donor moiety of 9,10‐dihydroacridine by replacing its 9‐C with Si, phenazasilines can benefit from both 9,10‐dihydroacridine‐alike architecture and Si incorporation, exhibiting intrinsically promising properties as hole‐transporting materials for organic field effect transistors with a hole mobility of 10 −4 cm 2 V −1 s −1 and an ON–OFF ratio close to 10 5 , thermally activated delayed fluorescence (TADF) emitters for organic light emitting diodes (OLEDs) with external quantum efficiency (EQE) up to 22.3%, and host materials for phosphorescent OLEDs (PhOLEDs) with EQE of 12%. Nevertheless, the synthesis of phenazasilines, either traditionally through extended heating of diphenylsilane with phenothiazines and cyclization reaction between 2,2′‐dilithiodiarylamine intermediates and dichlorosilanes, or recently by rhodium‐catalyzed double activation of SiH and CH bonds for dehydrogenation and SiC coupling, suffers from the low yields, complicated precursors, long synthetic routes, or high chemical costs.…”

Preparation, Properties and use for Functional Additive of Poly (Dibenzazepine)s

“…への展開が行われている。その一方で，筆者らも，種々のモノ シラン架橋型ジフェニルアミンであるフェナザシリンをはじめ とした種々の架橋ジフェニルアミン系ポリマーの合成を行い， その特性評価およびその特性評価を行ってきている [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] 。 その中で，筆者らは，フェナザシリン含有ポリマーについて， 有機トランジスタ 13,14) や有機EL素子 [14][15][16] ，エレクトロクロ ミック素子 15,17) といった電子デバイスの構成材料や，DNAと の複合化 18,19) やプラスチック材料に蛍光性機能をもたせるた めの添加剤 20,21)…”

“…林 英 樹 ＊, † ・村 上 恵 次 ＊＊ ・尾 之 内 千 夫 ＊＊ ・小 田 三 都 郎 ＊ ・中 尾 秀 信 ＊＊＊ ＊ 名古屋市工業研究所 愛知県名古屋市熱田区六番3-4-41(〒456-0058) ＊＊ 13,16,34) PPhenaz-Meは，トリフルオロ酢酸からキャストすること に よ りIRス ペ ク ト ル に 違 い が 見 ら れ た (Fig 5(b) 点 線 部 分)のに対し，PAzep-Meはトリフルオロ酢酸キャストによる スペクトルの変化は見られなかった (Fig 5(a)…”