Synthesis of Polyacetylenes Having Pendant Carbazole Groups and Their Photo- and Electroluminescence Properties

Abstract

Novel carbazole-containing polymers, i.e., poly (3,6-di-tert-butyl-N-(p-ethynylphenyl)carbazole) [poly(t-Bu 2CzPA)] and poly(N-(p-ethynylbenzoyl)carbazole) [poly(CzCOPA)] were synthesized by the polymerization of the corresponding carbazole-containing acetylene monomers using [(norbornadiene)-RhCl]2-Et3N, WCl6-n-Bu4Sn, and WCl4 catalysts. The UV-vis absorption band edge wavelengths of the polymers obtained by the polymerization with W catalysts were longer than those of the Rh-based polymers. The photoluminescence quantum yield of the W-based poly(t-Bu2CzPA) was 55%, while that of the Rh-based one was as low as 3.6%. The photocurrent of poly(t-Bu2CzPA) was 40-50 times higher than the dark current. Poly(t-Bu2CzPA) in conjunction with iridium complexes exhibited electroluminescence (13-18 cd/m 2 ).

Enhanced Photoluminescence, Mesomorphism and Conformation of Liquid‐Crystalline Conjugated Polymers with Terphenyl Mesogen Pendants

“…The quantum yields of 30 and 31 are found to increase with the spacer lengths, agreeing with the results of previous work. [119][120][121][122] Compared with 32, the light emitting profile of polymer 31 is much stronger and slightly red-shifted to 428 nm (Table 5, no. 1, 2, 3), due to the push-pull pairs favoring the photoluminescence (shown in Figure 6).…”

Synthesis and Electroluminescent Properties of Disubstituted Polyacetylene Derivatives Containing Multi‐Fluorophenyl and Cyclohexylphenyl Side Groups

“…These polymers exhibit photoconductivity and EL properties upon doping with an iridium complex. [10] The best performance was reported with a multilayer EL device using poly[1-phenyl-5-(a-naphthoxy)pentyne] blended with poly(vinylcarbazole) (PVK) as the emitting layer, bathocuproine as a hole blocking layer, and 8-hydroxyquinoline aluminum (Alq3) as an electron transporting layer. [12] A similar multilayer EL device using silole-containing PA as the active layer emitted blue-green light of 496 nm with a maximum brightness and current efficiency of 1118 cd Á m À2 and 1.45 cd Á A À1 , respectively.…”

“…In the past few years, Masuda et al, [7][8][9][10] Tang et al, [11][12][13][14] and our laboratory [15][16][17] have synthesized several series of substituted PA derivatives that are stable in air and soluble in common organic solvents. Although the conductivity of these PA derivatives is not as high as that of nonsubstituted PA, they show both PL and EL properties in the…”

Synthesis and Properties of Polyacetylenes Connecting Carbazole at the 2‐ and 3‐Positions: Effect of Polymerization Catalysts and Substitution Positions on the Optoelectronic Properties

“…The polymer in conjunction with iridium complexes exhibits electroluminescence. [10] On the other hand, poly(phenylacetylene)s connecting the carbazole moiety through methylene spacers show small fluorescence. [11] Consequently, it is considered that direct connection of carbazole moiety to conjugated polyacetylene backbone is a key importance for drawing the optoelectronic properties of carbazole.…”