Leaving substituent-containing compound, organic semiconductor material formed therefrom, organic electronic device, organic thin-film transistor and display device using the organic semiconductor material, method for producing film-like product, pi-electron conjugated compound and method for producing the pi-electron conjugated compound
A technology of conjugated compounds and substituents, applied in the field of compounds containing leaving substituents
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[0490] In the preparation method of the present invention, the precursor of the present invention represented by the general formula (I) is contained in a precursor-containing film, and the film is coated on a substrate (support) such as a plastic substrate, a metal substrate, a silicon wafer by, for example, and glass substrates. The precursor is converted into a compound represented by general formula (Ia) (specific compound) and a compound represented by general formula (II) (eliminated component) by energy.
[0491] Several isomers of the compound represented by the general formula (I) exist depending on the stereo configuration of the substituent. However, these isomers are all converted to specific compounds represented by general formula (Ia) to yield the same eliminated components.
[0492] The groups X and Y eliminated from the compound represented by the general formula (I) are defined as leaving substituents, and X-Y formed therefrom are defined as eliminated compo...
Embodiment 1 and 2
[0765]
[0766] According to the following reaction formula (scheme), the compound of Ex.1 and the compound of Ex.2 were synthesized.
[0767]
[0768] Charge compound (7-1) (550mg, 1.49mmol), compound (8) (346mg, 0.74mmol) and N,N-dimethylformamide (hereinafter abbreviated as "DMF" in a 100mL round bottom flask, 10mL). The resulting mixture was bubbled with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (18.3 mg, 0.02 mmol) and tris(o-tolyl)phosphine (24.4 mg, 0.08 mmol) were added to the mixture, which was then stirred at room temperature under argon atmosphere for 24 hours . The reaction solution was diluted with dichloromethane, and water was added to the mixture to separate the organic layer. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed successively with saturated potassium fluoride aqueous solution and saturated brine, dried over magnesium sulfate, and then filtered. The filtrate was passe...
Embodiment 3
[0781]
[0782] According to the following reaction formula (scheme), the compound of Ex.3 was synthesized.
[0783]
[0784] The method of Example 1 was repeated except that compound (7-1) was changed to compound (7-2), thereby obtaining Ex.3 compound as yellow crystals (yield: 253 mg, yield: 75%).
[0785] The analysis results of the compound of Ex.3 are shown below.
[0786] [Ex.3 compound];
[0787] 1 H NMR (500MHz, CDCl 3 ,TMS,δ):2.60-2.70(m,4H),3.38(s,6H),5.90(t,2H,J=5.2Hz),6.03-6.09(m,4H),6.63(d,2H,J =9.7Hz),7.40(d,4H,J=8.1Hz),7.49(s,2H),7.50(dd,2H,J 1 =7.7Hz,J 2 =2.3Hz)
[0788] High precision mass spectrometry (LC-TofMS) (m / z): 456.127 (measured), 456.122 (calculated)
[0789] According to the above analysis results, it was confirmed that the structure of the synthesized product was consistent with the compound of Ex.3.
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