94847-10-6Relevant academic research and scientific papers
Carbazole/oligofluorene end-capped hexanes: Solution-processable host materials for phosphorescent organic light-emitting diodes
Li, Huanhuan,Tao, Ye,Chen, Runfeng,Xie, Guohua,Zheng, Chao,Huang, Wei
, p. 4442 - 4447 (2017)
Alkyl substituents are promising in improving the solubility and film morphology of aromatic compounds for the solution processing of organic optoelectronic devices. However, the introduction of electronically inert alkyls will generally hinder hole and electron injection and transport into/between the aromatic units, leading to lower electronic properties of the material and thus inferior device performance. Here, we propose an alternative method by using alkyl groups via aromatic double end-capping alkylization, where aromatic carbazole and oligofluorenes were linked at both ends of a hexyl chain to obtain a series of carbazole/oligofluorene end-capped hexanes. These newly designed compounds show high solubility, good film morphology, high thermal stability, blue emission, high triplet energy, and suitable frontier orbital energy levels with good charge transport properties; when used as host materials in solution-processed phosphorescent organic light-emitting diodes (PhOLEDs), these molecules exhibit high device performance with maximum current efficiency of 28.0 cd A-1 and external quantum efficiency up to 7.8%. Our strategy of integrating both the advantages of alkyl and aromatic units offers an effective approach to design high-performance solution-processable organic optoelectronic materials.
Self-aggregation behavior of fluorescent carbazole-tailed imidazolium ionic liquids in aqueous solutions
Dong, Bin,Gao, Yan'an,Su, Yijin,Zheng, Liqiang,Xu, Jingkun,Inoue, Tohru
, p. 340 - 348 (2010)
Three amphiphilic imidazolium ionic liquids (ILs), 1-[n-(N-carbazole)alkyl] -3-methylimidazolium bromide [carbazoleCnmim]Br (n = 6, 10, and 12), that incorporate a fluorescent carbazole moiety at the terminal of the hydrocarbon chain, were designed and synthesized. Their surface activity, aggregation behavior, and thermodynamics of micelle formation in aqueous solutions were systematically investigated by surface tension, electrical conductivity, and 1H NMR spectroscopy. The incorporation of bulky carbazole groups led to the loose arrangement of [carbazoleCnmim]Br molecules at the air-water interface. Both the enhanced hydrophobicity and the ??-?? interaction due to the incorporation of carbazole groups contributed to the lower critical micelle concentration (cmc) and higher micellar aggregation number, reflecting a strong capability of the designed carbazole-tailed imidazolium ILs for the formation of micelle. The analysis of 1H NMR spectra revealed that the carbazole moieties may overlap with the middle methylenes of the alkyl chains. The amphiphilic carbazole-tailed imidazolium ILs demonstrated strong and stable fluorescence properties, indicating their potential application in the combined field of surface chemistry and photochemistry. ? 2010 American Chemical Society.
Self-assembly of carbazole-containing gelators: alignment of the chromophore in fibrous aggregates
Yabuuchi, Kazuhiro,Tochigi, Yusuke,Mizoshita, Norihiro,Hanabusa, Kenji,Kato, Takashi
, p. 7358 - 7365 (2007)
Carbazole-containing gelators derived from l-isoleucine have been developed. They form elongated self-assembled fibers in common organic solvents and in liquid crystals, leading to the efficient gelation of these solvents. Spectroscopic studies indicate t
Synthesis and application of amine-containing conjugated small molecules for the automatic formation of an electron transporting layer: Via spontaneous phase separation from the bulk-heterojunction layer
Kim, Juae,Kim, Yong Ryun,Kim, Minji,Jin, Jong Sung,Sung, Ji Yeong,Back, Hyungcheol,Kim, Heejoo,Lee, Kwanghee,Suh, Hongsuk
, p. 31867 - 31876 (2019)
Carbazole-based conjugated small molecule electrolytes (CSEs) containing different numbers of amine groups were synthesized and applied to bulk-heterojunction (BHJ) organic solar cells for the formation of a spontaneous self-assembled electron transporting layer (ETL). The active layer was spin-coated with a mixture solution containing the BHJ materials and a small amount of CSE, and a thin layer of CSE was formed underneath the active layer (CSE/BHJ bi-layer) via spontaneous phase separation, which is confirmed by the depth profile of the time of flight secondary ion mass spectroscopy (ToF-SIMS) spectrum. The amino groups in the CSEs form hydrogen-bonds with the surface of indium tin oxide (ITO), which acts as an ETL in BHJ solar cells. Moreover, the formed CSE layer is capable of changing the effective work function (WF) of ITO. An increasing number of amino groups in the CSEs (from Cz1N to Cz3N) provides more reduction of the effective WF of ITO, which results in a lower internal resistance and a higher power conversion efficiency (PCE). Furthermore, the enhanced hydrogen bonding between the amines and ITO with an increased number of amine groups has been studied by XPS. This result suggests that one-step processing provides a reduction of the manufacturing cost, which can provide an attractive design concept for ETL fabrication.
Electrochemical-coupling layer-by-layer (ECC-LbL) assembly
Li, Mao,Ishihara, Shinsuke,Akada, Misaho,Liao, Meiyong,Sang, Liwen,Hill, Jonathan P.,Krishnan, Venkata,Ma, Yuguang,Ariga, Katsuhiko
, p. 7348 - 7351 (2011)
Electrochemical-coupling layer-by-layer (ECC-LbL) assembly is introduced as a novel fabrication methodology for preparing layered thin films. This method allows us to covalently immobilize functional units (e.g., porphyrin, fullerene, and fluorene) into thin films having desired thicknesses and designable sequences for both homo-and heteroassemblies while ensuring efficient layer-to-layer electronic interactions. Films were prepared using a conventional electrochemical setup by a simple and inexpensive process from which various layering sequences can be obtained, and the photovoltaic functions of a prototype p/n heterojunction device were demonstrated.
Solution-processed blue and blue-green phosphorescent organic light-emitting devices using iridium(III) complexes based on 9-(6-(4-phenyl-1H-1,2,3-triazol-1-yl)hexyl)-9H–carbazole ligand
Xu, Huixia,Sun, Peng,Wang, Kexiang,Zhang, Xiaolin,Ren, Jingkun,Yang, Tingting,Zhang, Xinwen,Hao, Yuying,Wang, Hua,Xu, Bingshe,Wong, Wai-Yeung
, p. 148 - 154 (2016)
We have designed and successfully synthesized a series of solution-processed iridium(III) complexes of (Czphtz)2Ir(N?N) bearing main ligand of 9-(6-(4-phenyl-1H-1,2,3 -triazol-1-yl)hexyl)-9H-carbazole, namely (Czphtz)2Ir(tfmptz) (Ir1) (Czphtz)2Ir(pptz) (Ir2) and (Czphtz)2Ir(fpptz) (Ir3). The hole-transporting carbazole and electron-transporting 1, 2, 4-trizole moieties were introduced through hexyl to balance carrier transport. The solution-processed host-free and doped phosphorescent organic light-emitting devices (PhOLEDs) were fabricated. Here, in this paper, we will present the photophysical, electrochemical properties and performances in devices of three complexes. All of them exhibit excellent solubilities in common organic solvents. The pure-blue-light-emitting Ir1 with the maximum emission peak at 463?nm was attained by varying the structure of ancillary ligand and have the CIE coordinate of (0.19, 0.18) in host-free PhOLED. Our work shows that the rational structure modification of ancillary ligand is an effective approach to develop deep blue-light-emitting materials.
A novel carbazole-based gold(i) complex with interesting solid-state, multistimuli-responsive characteristics
Chen, Zhao,Liang, Jinhua,Nie, Yuting,Xu, Xuqingfeng,Yu, Guang-Ao,Yin, Jun,Liu, Sheng Hua
, p. 17473 - 17477 (2015)
A new carbazole-based mononuclear gold(i) complex was designed and synthesized. The novel luminogen shows significative solid-state reversible mechanochromism, dual-responsive thermochromism and sensitive thin-film vapochromism properties. In addition, we
Intramolecular charge transfer in bipolar molecules for electron and hole transporting materials
Karpicz,Gulbinas,Undzenas,Grazulevicius,Lygaitis
, p. 2276 - 2280 (2004)
The excited state relaxation of 6-(9H-carbazole)hexyl-9,10,10-trioxo-9H-3- thioxanthenecarboxyl (CHTT) molecules containing electron donating and electron accepting groups was investigated in solutions by means of picosecond pump-probe absorption spectros
Synthesis and optoelectronic properties of dinuclear cyclometalated platinum (II) complexes containing naphthalene-functionalized carbazole groups in the single-emissive-layer WPLEDs
Hao, Zhaoran,Liu, Yu,Huang, Ying,Meng, Fanyuan,Wang, Yafei,Tan, Hua,Su, Shijian,Zhu, Weiguo
, p. 52 - 59 (2017)
To tune excimer/aggregation emission and obtain single emissive dopants for white polymer light-emitting diodes (WPLEDs), two novel star-shaped dinuclear cyclometalated platinum (II) complexes, namely DPtF(pic)C6TPhC6D(dHCz) and DPtF(pic)C6TPhC6D(dNaCz), have been synthesized and characterized, where DPtF(pic) is dinuclear platinum (II) [(4,6-difluorophenyl)-pyridinato-N,C2′](picolinate) blue-emitting phosphorescent chromophore, D(dHCz) and D(dNaCz) are blue emitting fluorescent chromophores containing carbazole or naphthalene functionalized carbazole group, respectively, TPh is p-terphenyl used as central bridging core, finally, each parts of molecular skeleton are wired through nonconjugated hexyloxy ether linkage (C6). Their thermal, electrochemical and optophysical properties were primarily investigated. The device fabricated with these complexes doped into a host polyvinylcarbazole (PVK) blend with 30?wt % of an electron transport material 1,3-bis-(5-(4-(tert-butyl)phenyl)-1,3,4-oxadiazol-2-yl)benzene (OXD-7) showed near-white emission at lower dopant concentration. At 1?wt % dopant concentration, DPtF(pic)C6TPhC6D(dHCz) exhibited near-white emission with a luminous efficiency (LE) of 1.12?cd/A and a maximum external quantum efficiency (EQE) of 0.57% (Commission Internationale de I'Eclairage(CIE) chromaticity coordinates: (0.27, 0.40)) at 2.72?mA/cm2. At the same dopant concentration, DPtF(pic)C6TPhC6D(dNaCz) showed much tunable near-white emission with a LE of 0.99?cd/A and a EQE of 0.51% (CIE: 0.30, 0.41) at 0.87?mA/cm2.
Synthesis and study of 2-alkoxy(2-alkylsulfanyl)-4,6-distyrylpyrimidines containing a terminal carbazole group
Komissarova, Ekaterina A.,Lunegov, Igor V.,Shklyaeva, Elena V.,Abashev, Georgii G.
, p. 257 - 261 (2016)
[Figure not available: see fulltext.] We report the synthesis of new 4,6-distyrylpyrimidines containing an unsubstituted carbazole ring linked with the pyrimidine moiety by a flexible aliphatic seven-membered –O(CH2)6– or –S(CH2)6– bridge. The electrochemical and spectral properties of the synthesized compounds were studied; optical band gaps were calculated from the relevant UV absorption onsets and were found to be equal to 2.55 and 2.54 eV, respectively. A thin film based on the derivative with sulfur-containing bridge (–S(CH2)6–) was deposited on a conductive material and demonstrated to have a smooth surface and hole conductivity.
