Thienopyrrole quinone compound, preparation method and semiconductor device comprising the material

A compound and thiophene technology, applied in the field of thienopyrrole quinone compound, preparation method and semiconductor equipment containing the material, can solve the problems of low bipolar field-effect mobility and limited quantity, and achieve low LUMO energy level , Strong self-assembly ability, good planarity effect

Active Publication Date: 2018-07-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, Reid J.Chesterfield et al. first discovered that trithiophene-type tetracyanoquinone compounds exhibit bipolar charge transport at high temperatures, but their bipolar field-effect mobility is low (see: ReidJ.Chesterfield, et al. Adv. Mater. 2003, 15(15), 1278–1282)
Since then, although bipolar organic field effect transistors using quinone compounds as semiconductor layers have been reported (see: Handa S., et al. Chem.Comm.2009(26):3919), the number is very limited

Method used

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  • Thienopyrrole quinone compound, preparation method and semiconductor device comprising the material
  • Thienopyrrole quinone compound, preparation method and semiconductor device comprising the material
  • Thienopyrrole quinone compound, preparation method and semiconductor device comprising the material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of compound Ia

[0038]

[0039] At 0°C, under nitrogen protection, malononitrile (46.2 mg, 0.7mmol), after the foam disappeared, it was raised to room temperature and reacted for 30 minutes. The prepared malononitrile anion solution was transferred via cannula to a solution containing compound IIa (136.5 mg, 0.14 mmol), tetrakis(triphenylphosphine) palladium (32.4 mg, 0.028 mmol) and 1,2-dimethoxy In a 50 mL three-neck flask containing ethyl ethane (10 mL), the reaction was heated under reflux for 3 hours under the protection of nitrogen. Then the reaction temperature was lowered to room temperature, and exposed to the air, dilute hydrochloric acid (10mL, 1M) was added, stirred in an ice-water bath for 30 minutes, extracted with ether (30mL×3), the combined organic phases were washed with saturated brine, and Dry over anhydrous magnesium sulfate, remove the organic solvent by rotary evaporation, and the residue is separated by silica ge...

Embodiment 2

[0040] Embodiment 2: the synthesis of compound IIa

[0041]

[0042] Under nitrogen protection at -78°C, n-butyllithium (1.6M in hexane, 248 μL, 0.396mmol) was slowly added dropwise into a 10mL three-necked flask containing compound IV (130.2mg, 0.18mmol) and tetrahydrofuran (2mL), Keep stirring at low temperature for 30 minutes, add elemental iodine (100.5mg, 0.396mmol), warm to room temperature, continue stirring for 2 hours, add saturated sodium thiosulfate solution (10mL) to quench, and extract with ether (30mL×3), The organic phases were combined and washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain the crude compound IIa (yellow oil, 173.8 mg, yield: 99%). 1 H NMR (400MHz, CDCl 3 )δ7.14(s,2H),4.17(d,J=8.0Hz,4H),1.99(m,2H),1.26–1.12(m,48H),0.89–0.80(m,12H); 13 C NMR (100MHz, CDCl 3 )δ144.0, 129.9, 121.2, 120.8, 116.3, 68.8, 53.5, 39.0, 31.9, 31.7, 31.0, 29.9, 29.6, 29.4, 29.3, 26.13, 26.0...

Embodiment 3

[0043] Embodiment 3: the synthesis of compound IV

[0044]

[0045] Add compound V (282.0mg, 0.5mmol), sodium tert-butoxide (768.8mg, 8.0mmol), bis(dibenzylideneacetone) palladium (28.8mg, 0.05mmol), 1,1' - Bis(diphenylphosphino)ferrocene (110.9mg, 0.2mmol) and toluene (10mL), stirred at 25°C for 20 minutes, then added compound VI (280.1mg, 1.16mmol), heated to 110°C for 10 hours . After cooling to room temperature, water (20 mL) was added, extracted with ether (30 mL×3), the combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate, the organic solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography ( Eluent: n-hexane) to obtain compound IV (white solid, 181.0 mg, yield: 50%). 1 H NMR (400MHz, CDCl 3 )δ7.06(d, J=4.8Hz, 2H), 6.98(d, J=5.6Hz, 2H), 4.26(d, J=8.0Hz, 4H), 2.06(m, 2H), 1.25–1.11( m,48H),0.89–0.81(m,12H); 13 C NMR (100MHz, CDCl 3 )δ144.4,130.6,121.5,116.6,116.1,111.5...

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PUM

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Abstract

The invention discloses a class of thienopyrrole quinone compound, a preparation method and its application as a semiconductor active layer in an organic field effect transistor. This type of compound has the characteristics of good molecular skeleton planarity, strong self-assembly ability, low LUMO energy level, narrow energy level band gap, and insensitivity to oxygen and water. The introduction of the pyrrole structure facilitates adjustment of sample dissolution through modification of substituents Good for solution processing. The organic field effect transistor with compound Ia as the semiconductor layer prepared by spin coating has excellent bipolar field effect performance (μh=5.3×10-3cm2V-1s-1,μe=7.7×10-3cm2V-1s-1) . Its switch current ratio is above 104, and it is stable in the air, so it has important application value.

Description

technical field [0001] The invention relates to a semiconductor material of an organic field effect transistor, in particular to a thienopyrrole quinone compound, a preparation method and a semiconductor device containing the material. Background technique [0002] In recent decades, with the design and synthesis of new organic semiconductor materials and the optimization of device fabrication techniques, organic field-effect transistors (OFETs) have achieved rapid development in terms of device performance. Among them, the development of p-type semiconductor is the fastest, and its highest field effect mobility is comparable to that of traditional inorganic silicon materials, and its air stability is better. N-type semiconductors generally have low field-effect mobility and poor air stability, so their development has been lagging behind. Reports on bipolar semiconductors are even rarer. In view of the important role of bipolar semiconductors in the construction of logic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22H01L51/30
CPCC07D495/22H10K85/657H10K10/46
Inventor 于晓强江华包明冯秀娟
Owner DALIAN UNIV OF TECH
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