Thin film and compound used in the same
A compound and thin film technology, applied in bismuth organic compounds, electrical components, circuits, etc., can solve problems such as expensive and resource depletion
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[0332] Hereinafter, the present invention will be more specifically described based on examples, but the present invention is not limited to the following examples.
[0333] 1 H and 13 C NMR spectrum was measured using JEOL Model JNM-EX-270 spectrometer and JEOL Model JNM-EX-400. MS spectra were measured using SHIMADZU-GCMS-QP5050A. For the measurement of FAB-MS, a SX102A double focus mass spectrometer manufactured by JEOL Ltd was used. GPC for cyclic fractionation was detected by RI using Shodex Kf001 and KF002 as fillers in GL Science LC-908 MODEL576. Gas chromatography (hereinafter, sometimes abbreviated as GC) was used for measurement using Shimadzu Corporation GC-14B equipped with a Silicon OV-17 (2%-1m) packing column. Silica gel is used for thin layer chromatography (hereinafter sometimes abbreviated as TLC). The emission spectrum was measured with a fluorescence spectrophotometer (manufactured by JASCO Corporation, trade name: FP-6500) at an excitation wavelength ...
Synthetic example 1
[0342] (Synthesis Example 1) Synthesis of 1-phenyl-3,6-bis(trimethylsilyl)dithienobismuthol
[0343] [chem 37]
[0344]
[0345] The above synthesis reaction can be carried out in the following procedure to synthesize 1-phenyl-3,6-bis(trimethylsilyl)dithienobismuthole. In the formula, TMS represents a trimethylsilyl group.
[0346] Put 4,4'-dibromo-2,2'-bis(trimethylsilyl)bithiophene 0.446g (0.952mmol) and ether 10mL in a 30mL two-necked flask with a reflux cooling tube, and cool to -80°C. 1.25 mL of n-butyllithium (1.59 M hexane solution, 1.98 mmol) was added thereto, and the mixture was slowly returned to room temperature and stirred for about 1 hour. About 0.2 mL was collected and hydrolyzed, and the production of the dilithium was confirmed by GC (gas chromatography). On the other hand, 10 mL of THF and 0.514 g (0.952 mmol) of diiodophenylbismuth were placed in a 30 mL two-neck flask equipped with a dropping funnel and a reflux cooling tube, and the synthesized dili...
Synthetic example 2
[0351] (Synthesis Example 2) Synthesis of 1-phenyl-2,7-dimethyl-3,6-bis(trimethylsilyl)dithienobismuthol
[0352] [chem 38]
[0353]
[0354] The above synthesis reaction was carried out in the following order to synthesize 1-phenyl-2,7-dimethyl-3,6-bis(trimethylsilyl)dithienobismuthol.
[0355] Put 0.468 g (1 mmol) of 4,4'-dibromo-3,3'-dimethyl-2,2'-bis(trimethylsilyl)bithiophene and 5 mL of ether into a 10 mL two-necked flask , cooled to -80°C. 1.27 mL of n-butyllithium (1.56 M hexane solution, 2 mmol) was added thereto, slowly returned to room temperature, stirred for about 1 hour, and about 0.2 mL was collected for hydrolysis, and the formation of a dilithium was confirmed by GC. On the other hand, 5 mL of THF and 0.540 g (1 mmol) of diiodophenylbismuth were added to a 20 mL Schlenk tube with a dropping funnel, cooled to 0° C. in an ice bath, and di The lithiated body was kept at 0°C and stirred overnight. After confirming the disappearance of the dilithium by TLC (...
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