Charge-Transporting Molecular Glasses

Strohriegl, Peter; Gražulevičius, Juozas V.

doi:10.1002/1521-4095(20021016)14:20<1439::aid-adma1439>3.0.co;2-h

Cited by 499 publications

(266 citation statements)

References 85 publications

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“…The most widely studied and used representatives of this class of electroactive compounds N,N-diphenyl-N,Nbis(3-methylphenyl)-(1,1 -biphenyl)-4,4 -diamine (TPD) and 1,1-bis(di-4-tolylaminophenyl) cyclohexane (TAPC) exhibit very good charge-transport properties [1]. Polymers containing triphenylamine moiety, such as poly(4-diphenyl-aminostyrene) have been also reported [2,3].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photopolymerization of new triphenylamine-based oxiranes

Andrulevičiūtė

Lazauskaité

Gražulevičius

2007

Designed Monomers and Polymers

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Abstract-Synthesis and cationic photopolymerization of new triphenylamine-based oxiranes, i.e., 4-[(oxiranylmethoxy) methyl] triphenylamine, 4-hydroxymethyl-4 -(2-oxiranylmethoxymethyl) triphenylamine and 4-[4-(oxiranylmethoxymethyl) phenylphenylamino]-4 -(diphenylamino) biphenyl are reported. Di-(tert-butylphenyl) iodonium tetrafluoroborate (BPIT), diphenyliodonium tetrafluoroborate (DPIT) and (η 5 -2,4-cyclopentadien-1-yl) [1,2,3,4,5-η)-(1-methylethyl) benzene]-iron (+)-hexafluorophosphate (−1) (Irgacure 261) were used as photoinitiators. These photopolymerizations give products with a degree of polymerization varying between 4 and 108. The photopolymerization of the triphenylamine based hydroxyl group containing oxirane apparently occurs by activated monomer mechanism in its final stage. Photopolymerization of 4-[(oxiranylmethoxy) methyl] triphenylamine was studied in more detail. The influence of photoinitiator, temperature, and photoinitiator concentration on the rate of polymerization and conversion limit is discussed.

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Section: Introductionmentioning

confidence: 99%

Synthesis and photopolymerization of new triphenylamine-based oxiranes

Andrulevičiūtė

Lazauskaité

Gražulevičius

2007

Designed Monomers and Polymers

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“…Low molecular mass organic compounds with internal charge transfer properties are widely adopted for organic photonics such as materials for the creation of molecular electronics elements, organic magnets, solar cells and organic light emitting diodes (OLEDs) for full display panels [1][2][3]. One of the most widely used red light-emitting materials contains pyranylidene (4H-pyran-4-ylidene) or isophorene (5,5-dimethylcyclohex-2-enylidene) fragments as backbone of the molecule (see Fig.1), which are conjugated in a system with electron acceptor and electron donor fragments [1,.…”

Section: Introductionmentioning

confidence: 99%

“…One of the most widely used red light-emitting materials contains pyranylidene (4H-pyran-4-ylidene) or isophorene (5,5-dimethylcyclohex-2-enylidene) fragments as backbone of the molecule (see Fig.1), which are conjugated in a system with electron acceptor and electron donor fragments [1,. In many cases the light-emitting layer from such commercially available compounds is prepared by thermal evaporation in vacuum [1][2][25][26][27]. Some of them are used as dopants in a polymer matrix and spin-coated onto a hole transport layer from solution [1,12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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“…Because of their good solid film-forming capabilities, various triarylamine derivatives have been utilized as hole-transporting materials. [2][3][4] Recently, considerable efforts have been devoted to the development of new amorphous triarylamines possessing high morphologic stability. [5][6][7][8][9][10] Certain tetraaminobiphenyl derivatives are known to have photoconductive properties.…”

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confidence: 99%

Improved Performance of Organic Light-emitting Diodes with a New Hole-transporting Material

Kim¹,

Hwang²

2005

Chemistry Letters

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A new compound, 2,2 0 -dimethyl-3,3 0 ,5,5 0 -tetrakis(p-tolyldiamino)biphenyl (DTTAB), was synthesized and investigated as a hole-transporting material for organic light-emitting diodes. The luminous efficiency of electroluminescent device was improved by using DTTAB instead of NPB at lower driving voltage, suggesting that the DTTAB layer can efficiently accept holes from the hole-injecting layer and transport holes into an adjacent emitting layer.Since the first report of multilayered organic light-emitting diodes (OLEDs), many studies focused on improving device efficiency and enhancing the durability of OLEDs.1 Particularly hole-transporting material is one of the significant factors of the device performance. For the hole-transporting layer, high thermal stability, especially high T g of above 100C, good holetransport ability, excellent film formability are essentially needed. A number of hole-transporting materials based on aromatic amine structure have been reported so far. Because of their good solid film-forming capabilities, various triarylamine derivatives have been utilized as hole-transporting materials.2-4 Recently, considerable efforts have been devoted to the development of new amorphous triarylamines possessing high morphologic stability.5-10 Certain tetraaminobiphenyl derivatives are known to have photoconductive properties. They have been used for electrophotographic applications.11 Despite the relatively good charge-transporting properties of tetraaminobiphenyls now known, no hole-transporting properties for OLEDs have yet been reported. In this study, we synthesized a novel amorphous compound, 2,2 0 -dimethyl-3,3 0 ,5,5 0 -tetrakis(p-tolyldiamino)biphenyl (DTTAB) as a hole-transporting materials with higher glasstransition temperature. We report here the preparation and properties of DTTAB and the application for the EL device.According to the literature, tetraaminobiphenyls can be obtained from tetrahydroxybiphenyl, primary arylamine, and aryl halide.11 In this case, the coupling reaction of the arylhydroxybiphenyl and arylamines was not so convenient. We have found the more efficient amination reaction by using palladium catalyst. The general synthetic routes to tetraaminobiphenyls are outlined in Scheme 1. For the amination reaction, 2,2 0 -dimethyl-3,3 0 ,5,5 0 -tetrabromobiphenyl (1) was synthesized by the lithiation of 2,4,6-tribromotoluene following oxidative coupling. 12DTTAB was successfully prepared from 1 and di-p-tolylamine in toluene in the presence of Pd 2 (dba) 3 /P(t-Bu) 3 /NaOt-Bu at 110 C. 13 The palladium catalyst is very effective, giving the corresponding tetraaminobiphenyl product in good yield with only a low amount of the palladium catalyst. The thermal stability data of 2,2 0 -dimethyl-3,3 0 5,5 0 -tetraaminobiphenyl (DTTAB) was investigated by differential scanning calorimetry and thermogravimetric analysis: The results were summarized in Table 1 with the most well-known hole-transporting materials TPD and NPB for comparison.As shown in Table 1, DTTAB has higher val...

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Charge-Transporting Molecular Glasses

Cited by 499 publications

References 85 publications

Synthesis and photopolymerization of new triphenylamine-based oxiranes

Synthesis and photopolymerization of new triphenylamine-based oxiranes

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Improved Performance of Organic Light-emitting Diodes with a New Hole-transporting Material

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