Ethynyl containing electron transport dyes and compositions
a technology of electron transport dye and ethyl containing, which is applied in the field of compositions, organic electronic devices, compounds, etc., can solve the problems of extremely short operating lifetime of devices based on these materials, and exhibit short operating lifetimes
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example 1
Synthesis of 2-(2,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole
[0246]
Part A: Synthesis of Methyl 4-octoxybenzoate
[0247] Into a flask were introduced methyl 4-hydroxybenzoate (251.0 g, 1.65 mol), potassium carbonate (276.37 g, 1.99 mol) and 1200 g of acetone. This was refluxed for 45 min followed by the drop-wise addition of 1-octylbromide (386.17 g, 1.99 mol) over a 1 hour period. The reaction mixture was refluxed for two days. Filtration of the cooled reaction mixture and evaporation of the filtrate gave an oil. This was taken up in ethyl acetate and extracted with 5% NaOH (2×100 ml) followed by water (2×100 ml). The organic layer was dried (MgSO4), concentrated, and transferred to a pre-weighed 1 L three-necked flask. The contents of the flask were subjected to high vacuum distillation to remove the excess 1-octylbromide. The pot residue gave 376 g (86% yield) of methyl 4-octoxybenzoate.
Part B: Synthesis of 4-Octyloxybenzoic acid Hydrazide
[0248] To the co...
example 2
Synthesis of 2-(3,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole
[0254]
Part A: Synthesis of 2-(3,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole
[0255] By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 1, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octyloxybenzoic acid hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).
Part B: Synthesis of 2-(3,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole
[0256] Using the general method of Example 1, the reaction of Pd(PPh3)4 (71.6 mg, 0.1 mmol) and CuI (23.6 mg, 0.1 mmol) with a mixture of 2,(3,5-dibromophenyl)-5-...
example 3
Synthesis of 2-(3,5-Bis-pyren-1-ylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole
[0257]
[0258] Using the general method of Example 1, the reaction of Pd(PPh3)4 (127.5 mg, 0.1 mmol) and CuI (42.0 mg, 0.2 mmol) with a mixture of 2,(3,5-dibromophenyl)-5-[4-octylxoy)phenyl]-1,3,4-oxadiazole (5.70 g, 11.2 mmol) and 1-etylylpyrene (Lancaster Chemicals)(1.29 g, 12.6 mmol) in 50 mL of dry Et3N gave, after work-up and recrystallization from methylene chloride / hexane, 2-(3,5-bis-pyren-1-ylethynyl-phenyl)-5-(4-octyloxy-phenyl)-[1,3,4]oxadiazole (6.25 g, 70% yield).
[0259]1H-NMR 600 MHz (C6D6) δ 8.89 (d, J=9.06 Hz, 2H, pyrene), 8.5 (d, J=1.29 Hz, 2H), 8.22 (d, J=7.76 Hz, 2H), 8.14 (s, 1H), 8.01 (d, J=6.79 Hz, 2H), 7.99 (d, J=9.06 Hz, 2H, pyrene), 7.94 (d, J=7.44 Hz, 2H, pyrene), 7.92 (d, J=7.44 Hz, 2H, pyrene), 7.81 (d, J=8.41 Hz, 2H, pyrene), 7.78 (d, J=7.76 Hz, 2H, pyrene), 7.76 (d, J=7.44 Hz, 2H, pyrene), 7.72 (d, J=8.74 Hz, 2H, pyrene), 6.77 (d, J=8.74 Hz, 2H), 3.57 (t, J=6.47 Hz, 2H,...
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