Designing a bipolar host material for blue phosphorescent OLEDs: Phenoxy-carbazole substituted triazine

Rothmann, Michael; Fuchs, Evelyn; Schildknecht, Christian; Langer, Nicolle; Lennartz, Christian; Münster, Ingo; Strohriegl, Peter

doi:10.1016/j.orgel.2011.03.038

Cited by 48 publications

(24 citation statements)

References 22 publications

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“…151,[212][213][214][215][216] Modification of the host CBP by replacing one phenyl ring in the biphenyl unit with a pyridine or a pyrimidine ring, CPPY and CPHP (Fig. As discussed in Section 3.7.1.3, nitrogencontaining six-membered heterocyclic groups such as pyridine, pyrimidine and triazine are electron-deficient structures and can be combined with a triphenylamine moiety to synthesize bipolar host materials and show good performance in PHOLEDs.…”

Section: 723mentioning

confidence: 99%

Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices

2015

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Phosphorescent organic light-emitting devices (OLEDs) have attracted increased attention from both academic and industrial communities due to their potential practical application in high-resolution full-color displays and energy-saving solid-state lightings. The performance of phosphorescent OLEDs is mainly limited by the phosphorescent transition metal complexes (such as iridium(III), platinum(II), gold(III), ruthenium(II), copper(I) and osmium(II) complexes, etc.) which can play a crucial role in furnishing efficient energy transfer, balanced charge injection/transporting character and high quantum efficiency in the devices. It has been shown that functionalized main-group element (such as boron, silicon, nitrogen, phosphorus, oxygen, sulfur and fluorine, etc.) moieties can be incorporated into phosphorescent emitters and their host materials to tune their triplet energies, frontier molecular orbital energies, charge injection/transporting behavior, photophysical properties and thermal stability and hence bring about highly efficient phosphorescent OLEDs. So, in this review, the recent advances in the phosphorescent emitters and their host materials functionalized with various main-group moieties will be introduced from the point of view of their structure-property relationship. The main emphasis lies on the important role played by the main-group element groups in addressing the key issues of both phosphorescent emitters and their host materials to fulfill high-performance phosphorescent OLEDs.

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Section: 723mentioning

confidence: 99%

Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices

2015

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“…[4][5][6][7][8][9] In the past few years, much effort has been devoted to theoretical and experimental investigations on 1,3,5-triazine and its derivatives. [10][11][12][13][14][15][16] In this paper, the compound 2-(2-hydroxy-styryl)-4,6-dimethyl-1,3,5-triazine (P1) with a D--A structure composed of the electron-donating phenol ring and the electron-withdrawing 1,3, 5-triazine ring, as shown in Fig. 1, was devised by molecular design theory and synthesized experimentally for the purpose of validation.…”

Section: Introductionmentioning

confidence: 99%

A novel nitrogen-containing compound with D-π-A structure: theoretical and experimental study

et al. 2014

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2-(2-Hydroxy-styryl)-4,6-dimethyl-1,3,5-triazine (P1), a novel compound with D--A structure, possesses a variety of isomers. Density functional theory calculations were employed to explore the isomerization mechanisms of its various isomers at the 6-311+G** level. The calculated results show that the phenol configurations of compound P1 are more stable than the quinoid configurations, whether they exist as monomers, complexes, with methanol or dimers. The most stable structure of compound P1 was used to calculate the UV-vis and fluorescence spectra. To validate the calculated results, the title compound was synthesized and characterized by 1 H NMR and 13 C NMR techniques. The measured absorption and fluorescence spectra of P1 in methanol and N,N-dimethylformamide are in good agreement with the calculated ones.Résumé : La 2-(2-hydroxy-styryl)-4,6-diméthyl-1,3,5-triazine (P1), un nouveau composé comportant une structure D--A, possède une grande variété d'isomères. Les calculs de la théorie de la fonctionnelle de la densité ont été utilisés pour explorer les mécanismes d'isomérisation de des différents isomères de ce composé au niveau 6-311+G**. Les résultats des calculs montrent que les structures phénoliques du composé P1 sont plus stables que les structures quinoïdiques, qu'elles se présentent sous forme de monomères, de complexes de méthanol ou de dimères. La configuration la plus stable du composé P1 a servi à calculer les spectres UV-vis et de fluorescence. Pour valider les résultats des calculs, le composé P1 a été synthétisé et caractérisé à l'aide des techniques de RMN 1 H et RMN 13 C. Les spectres d'absorption et de fluorescence de P1 mesurés dans du méthanol et du N,N-diméthylformamide coïncident bien avec ceux qui avaient été calculés. [Traduit par la Rédaction]Mots-clés : 1;3;5-triazine, synthèse, mécanisme d'isomérisation, transfert de proton, théorie de la fonctionnelle de la densité.

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“…4 Host-embeded phosphorescent emitters are generally used to avoid this defect. Additionly, energy transfer between host and dopant molecule is used in PHOLEDs to achieve high efficiency.…”

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confidence: 99%

“…7 However, the number of triazine derivatives with bipolar character is very limited, 4,7 therefore, there is still a strong need for the development of triazine based compounds. Our interest focuses on the development of efficient host materials based on triazine because of their unique thermal and optical properties.…”

mentioning

confidence: 99%

“…During our ongoing efforts on the development of luminescent materials and host for PHOLEDs, 8 we have found that triazine based molecules, such as 2,4,6-tris(3-methyl-4-(thiophen-2-yl)phenyl)-1,3,5-triazine (TTPT) and 2,4,6-tris(3-methyl-4-(trimethylsilyl)phenyl)-1,3,5-triazine (TSPT) exhibit good glass-forming nature, low-lying HOMO energy and unique optical/electrochemical behaviors as compared to those of other triazine derivatives. 4 Based on these facts, we envisioned that these molecules would potentially be good hosts for red guest in PHOLEDs. The facts have also prompted us to investigate electroluminescent (EL) characteristics of these materials.…”

mentioning

confidence: 99%

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Efficient Host Material Containing 1,3,5-Triazine Moiety for Red Phosphorescent Organic light-emitting diodes (OLEDs)

Jung¹,

Lee²,

Kim³

et al. 2011

Bulletin of the Korean Chemical Society

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Organic light-emitting diodes (OLEDs) using organic fluorescent dyes as emitting materials have multilayered structure of the following order in general: cathode/hole injection layer/hole transporting layer/emissive layer/electron-transporting layer/electron-injection layer/anode.1 The internal quantum efficiency of fluorescent dye, however, is limited up to 25% maximum because of the singlet exciton it utilizes.2 Phosphorescent organic light-emitting diodes have also received a great deal of attention because of their high internal efficiency (nearly 100%) from the utilization of both singlet and triplet excitons.3 In spite of a number of advantages in phosphorescence organic light-emitting diodes (PHOLEDs), several drawbacks still remain, most notably is concentration quenching of the emitter.4 Host-embeded phosphorescent emitters are generally used to avoid this defect. Additionly, energy transfer between host and dopant molecule is used in PHOLEDs to achieve high efficiency. 5Therefore, the development of suitable host materials in accordance with a dopant is considered major issue because the emission in the emissive layer depends on the energy matching of the host and guest molecule.Recently, a few report have demonstrated that triazine based heterocycles with bipolar character showed high efficiency in OLEDs performance.7 However, the number of triazine derivatives with bipolar character is very limited, 4,7 therefore, there is still a strong need for the development of triazine based compounds. Our interest focuses on the development of efficient host materials based on triazine because of their unique thermal and optical properties. During our ongoing efforts on the development of luminescent materials and host for PHOLEDs, 8 we have found that triazine based molecules, such as 2,4,6-tris(3-methyl-4-(thiophen-2-yl)phenyl)-1,3,5-triazine (TTPT) and 2,4,6-tris(3-methyl-4-(trimethylsilyl)phenyl)-1,3,5-triazine (TSPT) exhibit good glass-forming nature, low-lying HOMO energy and unique optical/electrochemical behaviors as compared to those of other triazine derivatives.4 Based on these facts, we envisioned that these molecules would potentially be good hosts for red guest in PHOLEDs. The facts have also prompted us to investigate electroluminescent (EL) characteristics of these materials. We herein report the synthesis, characterization and OLED performance of triazine-based compounds. Result and DiscussionStarting material 1 was synthesized by a slight modification of a previous synthetic methodology reported by Kostas et al., as shown in Scheme 1. (See experimental section)7 By cyclotrimerization of 4-bromo-3-methylbenzonitrile with trifluoromethanesulfonic acid in dry chloroform, compound 1 was obtained in a high yield. TTPT was then synthesized using a Suzuki coupling by the reaction of 2-bromothiophene with 2,4,6-tris(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine and was obtained in good yields (~85%). All compounds were fully characterized by varied spectroscopic metho...

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Designing a bipolar host material for blue phosphorescent OLEDs: Phenoxy-carbazole substituted triazine

Cited by 48 publications

References 22 publications

Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices

Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices

A novel nitrogen-containing compound with D-π-A structure: theoretical and experimental study

Efficient Host Material Containing 1,3,5-Triazine Moiety for Red Phosphorescent Organic light-emitting diodes (OLEDs)

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