Organic electroluminescent device with an aromatic amine‐containing polymer as a hole transport layer (I): Poly[N‐[p‐N′ ‐phenyl‐N′‐[1,1′‐biphenyl‐4′‐[N″‐phenyl‐N″‐(2‐methylphenyl)amino]‐4‐amino]]phenyl methacrylamide]

Kido, Junji; Komada, Masaki; Harada, Gaku; Nagai, Katsutoshi

doi:10.1002/pat.1995.220061104

Cited by 6 publications

(6 citation statements)

References 13 publications

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“…A considerable amount of research has focused on developing new materials for hole-transporting layers in OLEDs. − Several requirements must be fulfilled for these materials to be viable in their use as HTLs. The material must have a low barrier to hole injection from the anode, have a high hole mobility, a low barrier to hole injection into the ETL or emissive layer, and be thermally stable in an amorphous or glassy state.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Triaryldiamines as Thermally Stable Hole Transporting Layers for Organic Light-Emitting Devices

1998

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The synthesis of a series of asymmetric triaryldiamines has provided a number of materials with a wide range of thermal, electrochemical, and spectroscopic properties. The asymmetric materials described herein have two different diarylamine groups bound to a 1,4-phenylene or 4,4‘-biphenylene core, i.e., Ar1Ar2N−C6H4−NAr1‘Ar3 or Ar1Ar2N-biphenyl-NAr1‘Ar3, respectively. The diarylamines studied include diphenylamine, phenyl-m-tolylamine, naphthylphenylamine, iminostilbene, iminodibenzyl, and carbazole. These materials were prepared by copper- and palladium-catalyzed coupling of aryl halides and diarylamines. The asymmetry inherent in these compounds prevents these low molecular mass compounds from crystallizing, thus yielding higher thermal stability over that of the symmetric derivatives. In all cases, the asymmetric diamines form stable glasses, with glass transition temperatures up to 125 °C. HOMO levels for these materials, estimated by cyclic voltammetry, show a broad range of values, with oxidation potentials both lower and higher than those of common hole transport materials used in organic light emitting devices.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Triaryldiamines as Thermally Stable Hole Transporting Layers for Organic Light-Emitting Devices

1998

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“…2 (a-1, b-1) can be assigned to the reduction of the monocation of the consecutively formed dimeric form (tetraphenylbenzidine). Similarly, the formation of tetraarylbenzidines was also reported 16,[18][19][20][21][22] . We confirmed this dimerization process by having performed in situ UV-VIS electrochemical oxidation.…”

Section: Resultsmentioning

confidence: 80%

“…The hole-transporting and electrochemical properties of compounds 1-3 have already been described, and they have also been employed in OLEDs 3, [15][16][17][18][19][20][21][22] .…”

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confidence: 99%

Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization

Faber

Mielke

Rapta

et al. 2000

Collect. Czech. Chem. Commun.

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Dedicated to Professor udovít Treindl in honour of his 70th birthday.Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald amination. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and EPR spectroscopy, and in situ spectroelectrochemical measurements. N,N,N′,N′-Tetraphenylbenzidine (1), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (2), and triphenylamine (3) served as model substances in the study of the synthesized complex compounds 4 and 5. In structure 4, two triphenylamine centres are linked with a non-conjugated fluorene bridge; in structure 5, two tetraarylbenzidine skeletons with two nitrogens are linked with a conjugated biphenylbridge system. In addition, structure 5 contains a non-conjugated fluorene bridge. The presence of the fluorene moiety in the molecular design has a significant influence on the investigated properties of the new materials. In the anodic oxidation of the tetraarylbenzidinetype compounds (1, 2, and 5), two well-defined reversible oxidation peaks were observed. However, the oxidation of the triphenylamine-type structures (3 and 4) is more complex, due to fast consecutive reactions. The dimer-like structures (4 and 5) are characterized by two independent oxidation centres that are simultaneously oxidized at approximately the same potentials. This was confirmed by quantitative cyclovoltammetric as well as UV-VIS investigations.

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“…A related perennial problem is the fundamental understanding of the underlying structure−property relationships in the materials. Polymers containing triphenylamine units, such as N , N ‘-diphenyl- N , N ‘-bis(3-methylphenyl)-(1,1‘-biphenyl)-4,4‘-diamine ( m -TPD) invented by Xerox, in the main chain or side chain of polymers represent one of the areas of investigation relative to these problems. , Research in the past decade has led to important progress in the experimental and theoretical understanding of electronic and electrical properties in these polymers and achievement of drift mobility on the order of 10 -5 cm 2 /(V s) in several polymers introducing N , N ‘-diphenyl- N , N ‘-bis(4-methylphenyl)-(1,1‘-biphenyl)-4,4‘-diamine (TPD) . To prepare charge transporting polymers, however, many investigators prepared a monomer by introducing one or two functional groups to a molecule having charge transporting ability. − This method needed a long sequence of reaction steps for preparation of monomers and its polymerization.…”

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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Organic electroluminescent device with an aromatic amine‐containing polymer as a hole transport layer (I): Poly[N‐[p‐N′ ‐phenyl‐N′‐[1,1′‐biphenyl‐4′‐[N″‐phenyl‐N″‐(2‐methylphenyl)amino]‐4‐amino]]phenyl methacrylamide]

Cited by 6 publications

References 13 publications

Asymmetric Triaryldiamines as Thermally Stable Hole Transporting Layers for Organic Light-Emitting Devices

Asymmetric Triaryldiamines as Thermally Stable Hole Transporting Layers for Organic Light-Emitting Devices

Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization

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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