Synthesis of poly(N‐9‐ethylcarbazole‐exo‐norbornene‐5,6‐dicarboximide) for hole‐transporting layer in hybrid organic light‐emitting devices

Abstract

We synthesized new polynorbornene dicarboximide (PCaNI) functionalized with hole‐transporting carbazole moieties and its copolymer (PCaNA) by ring‐opening metathesis polymerization (ROMP), where the PCaNA was further reacted with 3‐amino‐triethoxysilane to prepare PCaNI/silica hybrid. We also investigated the feasibility of PCaNI and PCaNI/silica hybrid (PCaSi) as a hole‐transporting material for hybrid organic light emitting devices (HOLEDs). To improve the performance of the PCaNI‐based HOLEDs, N,N′‐diphenyl‐N,N′‐(3‐methylphenyl)‐[1,1′‐biphenyl]‐4‐4′‐diamine (TPD) was also introduced into the PCaNI matrix. Results showed that PCaNI exhibited high glass transition temperature (∼260 °C) and high optical transparency in the visible region. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of PCaNI were measured as 5.6 and 2.2 eV, while the TPD‐doped PCaNI showed 5.7 eV (HOMO) and 2.6 eV (LUMO). The PCaNI/silica hybrid nanolayers showed excellent solvent resistance due to the formation of covalent bonds between ITO and PCaNI. The HOLEDs with PCaNI/TPD or PCaSi/TPD hybrid nanolayers exhibited relatively higher luminance (∼10,000 cd/m2), lower operating voltage (∼6.5 V at 300 cd/m2), and higher current efficiency (∼2.7 cd/A). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

The preparation of well-controlled poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide) polymers

“…3 A small selection of these interesting applications include cell adhesion materials, membranes, insulating materials and various optics applications. [4][5][6][7][8][9] This breadth of applications can be attributed to the fact that, as a polymer class, poly(NDI)s have been demonstrated to exhibit favorable thermal and mechanical properties, which greatly extend their range of practical applications. [10][11][12][13][14] Furthermore, ring-opening metathesis polymerization allows the preparation of well-defined random, block and alternating copolymers that extend the utility of poly(NDI)s as a system to prepare reactive and functional polymers.…”

“…[10][11][12][13][14] Furthermore, ring-opening metathesis polymerization allows the preparation of well-defined random, block and alternating copolymers that extend the utility of poly(NDI)s as a system to prepare reactive and functional polymers. 15,16 Therefore, a systematic study of the influence of the Grubbs initiator on the precise controllability of the molecular weight and stereochemistry of a standard NDI monomer is of practical utility. Monomer preparation for poly(NDI)s is simple and easy.…”

Synthesis and Ring-Opening Metathesis Polymerization of a New Norbornene Dicarboximide with a Pendant Carbazole Moiety

“…Therefore, ROMP appears to be an interesting method also for fabricating side chain-type carbazole-containing polymers. Some examples of ROMP of norbornene-based monomers containing carbazole groups promoted by Grubbs catalysts are described in the literature [38][39][40][41]. Recently, Zeng et al also reported the synthesis of highly efficient blue thermally activated delayed fluorescence polymers and copolymers based on side chain-type carbazole-containing polymers obtained by using Grubbs second-generation catalyst [42].…”

Preparation of neutrally colorless, transparent polynorbornenes with multiple redox‐active chromophores via ring‐opening metathesis polymerization toward electrochromic applications

“…Ring‐opening metathesis polymerization (ROMP) offers an effective way to polymerize norbornene monomers with different side chain substitutes 26. Grubbs' ruthenium (Ru) carbene complexes efficiently catalyze ROMP under ambient conditions, with a high tolerance for polar functional groups 27–32. Thus, the use of a Ru‐based catalyst in ROMP is a promising route to prepare polynorbornenes with colorless, transparent, and easily solution‐processable properties.…”