Condensation polymerization of triphenylamine with carbonyl compounds

Son, Jhun-Mo; Nakao, Mayumi; Oginö, Kazuhíde; Sato, Hisaya

doi:10.1002/(sici)1521-3935(19990101)200:1<65::aid-macp65>3.0.co;2-s

Cited by 13 publications

(10 citation statements)

References 11 publications

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“…Figure 2 shows their 1 H NMR spectra. According to the chemical shifts of a linear polymer synthesized from TPA and paraformaldehyde, 28 the signals in the aromatic range around 6.95 to 7.23 ppm can be assigned to the aromatic protons. LP showed two types of aliphatic proton signals at 2.4 and 3.8 ppm which can be assigned to methyl (CH 3 ) and methylene (CH 2 ) groups.…”

Section: Structural Characterization Of Lp and Hbpsupporting

confidence: 91%

Synthesis and Characterization of Hyperbranched Polymer Having Hole Transporting Ability

Lee

et al. 2004

Polym J

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ABSTRACT:A hyperbranched polymer (HBP) was prepared by the condensation polymerization of 4-hydroxymethylphenyldiphenylamine (TPA-CH 2 OH) and was compared with the corresponding linear polymer (LP) prepared by condensation polymerization of 4-methyltriphenylamine (MTPA) and formaldehyde (FA). It was found that the HBP had higher molecular weight with same molecular volume by using gel permeation chromatography (GPC) equipped with low angle laser light scattering (LALLS) and refractive index (RI) detectors. Electronic and optical properties of the two types of polymers were also examined. The two types of polymers showed almost same absorption in the UVvisible region, while HBP showed stronger emission than LP and a new excimer band at 470 nm. The cyclic voltammography showed that HBP had a redox peak around 1.22 V versus Ag/AgCl electrode, indicating that it has hole transporting ability. HBP is soluble in common organic solvents and forms good quality thin films. Their excellent morphological and thermal stability renders them advantageous for electroluminescence applications.

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Section: Structural Characterization Of Lp and Hbpsupporting

confidence: 91%

Synthesis and Characterization of Hyperbranched Polymer Having Hole Transporting Ability

Lee

et al. 2004

Polym J

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“…The structure of the polymers was determined by 1 H NMR spectroscopy. The NMR signals were assigned by comparison with spectra of polymers reported previously11, 12 and of phenol–formaldehyde resin 15. Figure 1(a,c) shows the 1 H NMR spectra of polymers TDPA–NBA and TDPA–MFBA.…”

Section: Resultsmentioning

confidence: 99%

“…Our group has reported that condensation polymerization of TPA derivatives with formaldehyde, butyraldehyde, benzaldehyde and acetone may provide a simple preparation method for hole transporting polymers 11. Polycondensation carried out in the presence of an acidic catalyst showed that paraformaldehyde and benzaldehyde had a high reactivity with TDPA, N , N ′‐diphenyl‐ N , N ′‐di‐(4‐methylphenyl)‐1,4‐phenylenediamine (PDA) and N , N ′‐diphenyl‐ N , N ′‐bis(4‐methylphenyl)‐1,1′‐biphenyl‐4,4′‐diamine (TPD) 12.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new 4‐tolyldiphenylamine derivatives for hole transporting polymers

Strzelec

Tsukamoto

Kook

et al. 2001

Polymer International

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New hole transport polymers have been synthesized by condensation polymerization of 4tolyldiphenylamine (TDPA) with various types of aldehyde. The reaction conditions have been investigated to yield polymers with high molecular weight. It is found that the molecular weight and yield of the TDPA±aldehyde polymers strongly depend on the electron donor±acceptor nature of the substituent on the aromatic ring of the aldehyde monomer. Structural characterization by 1 H NMR spectroscopy shows that the addition condensation reaction occurs exclusively at the para position of TDPA. The electrochemical and optical properties of polymers have been investigated by cyclic voltammetry and UV±vis spectroscopy. Cyclic voltammograms of all polymers show well-de®ned pairs of reduction and oxidation peaks, indicating that the polymers are electrochemically active. All polymers show low conductivities of magnitude 10 À14 S cm À1 . Differential scanning calorimetry measurements reveal that TDPA±aldehyde polymers exhibit glass transitions in the range 170±230°C. These polymers possess good solubility and the ®lms show suf®cient morphological stability.

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“…The condensation reactions of triphenylamine derivatives (TPAs) with carbonyl compounds have been studied in the presence of acid catalyst and found that paraform-aldehyde (FA), benzaldehyde (BzA), and paraldehyde had a high reactivity toward TPAs. [8][9][10] In our previous works, when triphenylamine (TPA) was reacted with equal molar FA, structural characterization indicated that the addition condensation reaction occurred exclusively at para positions of TPA. The reaction mixture became viscous due to the molecular weight increase, and finally it provided insoluble gel, because TPA has three reaction points.…”

Section: Introductionmentioning

confidence: 99%

“…It is expected that aldehyde may attack protons at the ortho or para position of TPA to yield a polymer in the presence of an acid catalyst like a phenol−formaldehyde resin, since triphenylamine derivatives (TPAs) have an electron-donating amino nitrogen group. The condensation reactions of triphenylamine derivatives (TPAs) with carbonyl compounds have been studied in the presence of acid catalyst and found that paraformaldehyde (FA), benzaldehyde (BzA), and paraldehyde had a high reactivity toward TPAs. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polymers Having a Hole Transporting Ability by Condensation Polymerization of N,N‘-Diphenyl-N,N‘-bis(4-methylphenyl)-(1,1‘-biphenyl)-4,4‘-diamine and Aldehydes

et al. 1999

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Novel polymers having a hole transport ability were prepared by condensation polymerization of N,N‘-diphenyl-N,N‘-bis(4-methylphenyl)-(1,1‘-biphenyl)-4,4‘-diamine (TPD) and paraformaldehyde (FA) or benzaldehyde (BzA). From NMR spectra, it is revealed that addition condensation reactions occurred exclusively at the para positions of TPD. TPD−FA polymer was linked not only by a methylene linkage but also by a methylene ether linkage, while TPD−BzA polymer was only linked by a methine linkage. The glass transition temperatures of TPD−FA and TPD−BzA were 183 and 239 °C, respectively. The drift mobility of TPD−BzA measured by a standard time-of-flight (TOF) method was found to be on the order of 10-5 and 10-6 cm2/(V s). The multilayer EL devices were fabricated using TPD−FA and TPD−BzA polymers as a hole transport layer and Alq as an electron transport emitting layer. In both devices, the initial driving voltage is about 4 V, and the maximum luminance is above 10 000 cd/m2 at 14 V. It is expected that these polymers can be used as a hole transport material in the EL device.

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Condensation polymerization of triphenylamine with carbonyl compounds

Cited by 13 publications

References 11 publications

Synthesis and Characterization of Hyperbranched Polymer Having Hole Transporting Ability

Synthesis and Characterization of Hyperbranched Polymer Having Hole Transporting Ability

Synthesis and characterization of new 4‐tolyldiphenylamine derivatives for hole transporting polymers

Synthesis of Polymers Having a Hole Transporting Ability by Condensation Polymerization of N,N‘-Diphenyl-N,N‘-bis(4-methylphenyl)-(1,1‘-biphenyl)-4,4‘-diamine and Aldehydes

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