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2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine: Uses, Synthesis and Application

Dec 14,2022

Physicochemical property

2, 4-diphenyl -6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan 2-yl)phenyl]-1,3,5-triazine is white powder or crystal for phenyl. It has a melting point of 204 °C. Its boiling point is predicted to be 641.3±57.0 °C and its density is predicted to be 1.21±0.1 g/cm3.

Synthetic routes

The synthetic step 1 of 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

Fig. 2 The synthetic step 1 of 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

Add Pd (PPh3)4 (0.345 g, 0.3 mmol) quickly to a mixture of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (5.35 g, 20 mmol), 3-bromophenylboronic acid (4.01 g, 20 mmol) and Na2CO3 aqueous solution (2 mol L .-.1, 20 mL) in toluene (100 mL) and ethanol (20 mL) under nitrogen. Stir the reaction at 90 °C for 12 h and cool to room temperature. Remove the volatile under reduced pressure and extract the residue with CH2Cl2/H2O. Separate the combined organic layer and dry over anhydrous MgSO4. Filter and concentrate in vacuo. Purify the crude product by column chromatography using petroleum ether as eluent. Scale gram 1H NMR (500 MHz, CDCl3) δ 8.89 (t,J= 1.75 Hz, 1H), 8.80.-.8.74 (m, 4H), 8.73.-.8.68 (m, 1H), 7.76.-.7.71 (m, 1H), 7.66.-.7.55 (m, 6H), 7.45 (t, J= 7.8 Hz, 1H) [1].

The synthetic step 2 of 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

Fig. 3 The synthetic step 2 of 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

Add Pd (PPh3)2Cl2 (0.11 g, 0.15 mmol) to a mixture of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (3.88 g, 10 mmol), bis (pinacolato) diboron (3.04 g, 12 mmol) and anhydrous KOAc (2.94 g, 30 mmol) in THF (80 mL) under nitrogen. Stir the reaction at 80°C for 12 h and cool to room temperature. Remove the volatile under reduced pressure and extract the residue with CH2Cl2/H2O. Separate the combined organic layer and dry over anhydrous MgSO4. Filter and concentrate in vacuo. Purify by column chromatography using petroleum ether/CH2Cl2 (v/v = 1/1) as eluent. 1H NMR  (500 MHz, CDCl3) δ 9.14 (s, 1H), 8.88.-.8.86 (m, 1H), 8.83.-.8.75 (m, 4H), 8.05.-.8.07 (m, 1H), 7.74.-.7.46 (m, 7H), 1.41 (s, 12H) [1].

Application

An electron-transport triarylphosphine oxide-triazine

An organic electron-transport compound for phosphorescent OLEDs is reported, which possesses the advantages of low molecular weight, enhanced glass transition temperature and electron mobility upon doping with 8-hydroxyquinolatolithium (Liq) as well as facile synthesis and purification. There is 2, 4-Diphenyl -6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan 2-yl)phenyl]-1,3,5-triazine in synthesis. The analytically pure NaAN-m-TRZ (m/z=611.73) is obtained through coupling the 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine linker with 10-(naphth-2-yl)-anthracen-9-yl moiety. The residual bromo intermediate could be easily removed by column chromatography and/or recrystallization from CH2Cl2, hence eliminating a high-risk factor for OLED stability. Thermal analyses show that it exhibits a Tg of 157℃ and decomposition temperature of 353℃ at 1% weight loss. NaAN-m-TRZ has a HOMO level of -5.76 eV determined by the ultraviolet photoelectron spectroscopy measurement and an estimated LUMO level of -2.84 eV. Doping NaAN- m-TRZ with 50% (mass fraction) Liq yields impressive electron mobility of 6.23×10-5~7.19×10-4 cm2·V-1·s-1@E=(2~5)×105 V·cm-1 using space-charge-limited current model, which contributes to suppressing triplet-polaron annihilation in the phosphorescent OLEDs. Consequently, based on the single NaAN-m-TRZ:Liq electron-transport layer, the top-emission green phosphorescent OLED involving Ir(ppy)2(m-mbppy) produces extraordinary durability with projected lifetime t97 of 2 567 h@1 000 cd·m-2 as well as a luminous efficiency of 72.2 cd·A-1 and power efficiency of 81 lm·W-1@1 000 cd·m-2 [2].

Organic electron-transport materials are an essential component to boost performances and stability of organic light-emitting diodes. We present a robust organic electron-transport compound 3-(6-(3-(4,6-bis(4-biphenylyl)-l,3,5-triazin-2-yl)phenyl)pyridin-2-yl)phenyldiphenylphosphine oxide by facilely coupling the triphenylphosphine oxide moiety to the 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine unit via a 2,6-pyridinylene linker. It is well soluble in weakly polar solvents and possesses a high Tg of 123 °C with an exceptional Td≈470 °C at 1% weight loss and deep HOMO/LUMO levels of ca. ?6.45/-3.06 eV. The phos-phorescent spectrum measured in solid state at 77 K reveals a notable triplet energy of 2.88 eV. n-Doping with 8-hydroxyquinolatolithium (Liq) produces the electron mobility value of 4.66×10?5-3.21×10?4 cm V?1s?1 @(2–5)×10?5 V cm?1. Moreover, the contrasting solubility of the bromo reaction intermediate and the new compound in alcoholic solvents facilitates separation. The characterizations of bottom- and top-emission green phosphorescent OLEDs involving this single Liq-doped electron-transport layer reveal long stability. In particular, the latter provides outstanding performances with 77.4 cd A?1 (corresponding to an EQE of 18.7%) and 86.8 lm W?1@ca. 1000 cd m?2, based on the green emitter bis(2-phenylpyridine)(2-(4-methyl-3-phenylphenyl)pyridine)iridium(III). Moreover, driven by a constant current for ca. 640 h, the initial luminance of 1000 cd m?2 appears almost no decay [3].

There has been an increasing demand for high-performance and cost-effective organic electron-transport materials for organic light-emitting diodes (OLEDs). In this contribution, we present a simple compound 3-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline(there is 2, 4-diphenyl -6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan 2-yl)phenyl]-1,3,5-triazine in synthesis)through the facile Pd-catalyzed coupling of a triphenyltriazine boronic ester with 3-bromo-1,10-phenanthroline. It shows a high Tg of 112?°C. The ultraviolet photoelectron spectroscopy measurements reveal a deep HOMO level of ?6.5?eV. The LUMO level is derived as ?3.0?eV, based on the optical bandgap. The low-temperature solid-state phosphorescent spectrum gives a triplet energy of ~2.36?eV. 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (Liq, 1:1) leads to considerably improved electron mobility of 5.2?×?10?6–5.8?×?10?5?cm2?V?1?s?1 at E?=?(2–5)?×?105?V?cm?1, in contrast with the triarylphosphine oxide-phenantroline molecular conjugate we reported previously. It has been shown that through optimizing the device structure and hence suppressing polaron-exciton annihilation, introducing this single Liq-doped electron-transport layer could offer high-efficiency and stable phosphorescent OLEDs [1].

Highly efficient bipolar host material

Two novel indole-based, bipolar, host materials were designed and synthesized by introducing the triazine unit to the 5-position of indole moiety with a meta-linking strategy. The two host materials exhibited excellence bipolar transport abilities and the meta-linking analog presented a high Tg value (>120 °C). Furthermore, their electrochemical and photo-physical properties were also fully characterized and all the results exhibited that the meta-linking strategy made a significant effect on the physical properties of the two hosts. Moreover, the PHOLED devices using 9-(4-(5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1H-indol-1-yl) phenyl)-9H-carbazole and 9-(4-(5-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1H-indol-1-yl)phenyl)-9H-carbazole(these two compounds are synthesized from 2, 4-diphenyl -6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan 2-yl)phenyl]-1,3,5-triazine) as hosts were also fabricated to evaluate the practical utilities of host materials. The devices achieved the maximum external quantum efficiencies of 17.53% for para-linking compound and 14.53% for meta-linking analog, respectively. In particular, para-linking compound based device revealed the maximum external quantum efficiency was twice that of the device using 2,4-Diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine as the host [4].

References

[1] Jin G, Liu J Z, Zou J H, et al. Appending triphenyltriazine to 1, 10-phenanthroline: a robust electron-transport material for stable organic light-emitting diodes[J]. Science Bulletin, 2018, 63(7): 446-451.

[2] Ling-ling C, Lin-ye W, Shu X, et al. Triazine-based electron-transport material for stable phosphorescent organic light-emitting diodes[J]. Chinese Journal of Liquid Crystal & Displays, 2021, 36(1).

[3] Chen L L, Peng L, Wang L Y, et al. Molecular engineering of an electron-transport triarylphosphine oxide-triazine conjugate toward high-performance phosphorescent organic light-emitting diodes with remarkable stability[J]. Science China Chemistry, 2020, 63(7): 904-910.

[4] Chen Y, Xie J, Wang Z, et al. Highly efficient bipolar host material based-on indole and triazine moiety for red phosphorescent light-emitting diodes[J]. Dyes and Pigments, 2016, 124: 188-195.

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