Coumarin green light dyestuff containing triphenylamine ethylene side chain
A technology of triphenylamine ethylene and coumarin, which is applied in coumarin dyes, luminescent materials, organic chemistry and other directions, can solve the problems of sensitive processing technology, and achieve the effect of stable emission spectrum and insensitive preparation process.
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Embodiment 1
[0043] The synthesis of embodiment 1 green light dye GT1:
[0044] For its synthetic route, see figure 1 shown.
[0045] (1) Synthesis of compound 2a
[0046]
[0047] Synthetic steps: Add compound 1a (6.48g, 20mmol) (commercially available), potassium vinylfluoroborate (3.22g, 24mmol), tetrakistriphenylphosphine palladium (8.3g, 5%), K 2 CO 3 (6.48g, 60mmol), toluene (70mL) and water (14mL). Nitrogen was evacuated 3 times, heated up to 80° C., kept at this temperature, and reacted for 8 hours. TLC detected that the reaction of compound 1a was complete.
[0048] Post-reaction treatment: Stop heating, lower the temperature to 20°C, pour the reaction liquid into water, extract and separate the liquids with EA (100 mL*3), combine the organic layers, dry with anhydrous sodium sulfate, and evaporate to dryness under reduced pressure. The crude product was obtained by column chromatography as a white compound 2a (4 g, yield 73.7%). 1 H NMR (400MHz, CHLOROFORM-d) ppm 5.15 (d...
Embodiment 2
[0058] The synthesis of embodiment 2 green light dye GT2:
[0059] For its synthetic route, see figure 2 shown.
[0060] (1) Synthesis of compound 3b
[0061]
[0062] Synthetic steps: add compound 1b (4.58g, 20mmol) (commercially available) in 250mL reaction flask, compound 2b (commercially available) (8.5g, 30mmol), Pd 2 (dba) 3 (920mg, 5%), tri-tert-butylphosphine (400mg, 10%), sodium tert-butoxide (4.58g, 40mmol) and toluene (100mL). Nitrogen was evacuated 3 times, heated up to 110° C., kept at this temperature, and reacted for 12 hours. TLC detected that the reaction of compound 1b was complete.
[0063] Post-reaction treatment: Stop heating, lower the temperature to 20°C, pour the reaction liquid into water, extract and separate the liquids with ethyl acetate (10 mL*2), combine the organic layers, dry over anhydrous sodium sulfate, and evaporate to dryness under reduced pressure. The crude product was subjected to column chromatography to obtain pale yellow comp...
Embodiment 3
[0071] The photophysical property test of embodiment 3 green light dyes GT1 and GT2:
[0072] The test of photophysical properties of green light dyes GT1 and GT2 in solution is to dissolve the corresponding dyes in toluene or dichloromethane, and the concentration of the solution is 1×10 -5 mol / L, the dye-based CCF film was prepared by dissolving the dye and the corresponding proportion of PMMA in toluene, and then drying it. The photophysical properties of the dye film were measured after the dye was dissolved in THF and then spin-coated to prepare the film. The effect of CCF films prepared with GT1 and GT2 on background blue light (λ max ≈450nm) has good absorption, see image 3 , Figure 5 , the emitted light is green light, see Figure 4 , Figure 6 . GT1 and GT2 have strong luminescence (the quantum yield EQE is close to 70%), are not sensitive to the preparation process, and their emission spectra are very stable in a large range of doping concentration and tempera...
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Abstract
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