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Thienopyrroloquinone compound, a preparation method and application thereof as a semiconductor active layer in an organic field effect transistor

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 limited quantity, low bipolar field-effect mobility, etc., and achieve strong self-assembly ability , Low LUMO energy level, narrow energy level bandgap effect

Active Publication Date: 2016-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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: Reid J.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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  • Thienopyrroloquinone compound, a preparation method and application thereof as a semiconductor active layer in an organic field effect transistor
  • Thienopyrroloquinone compound, a preparation method and application thereof as a semiconductor active layer in an organic field effect transistor
  • Thienopyrroloquinone compound, a preparation method and application thereof as a semiconductor active layer in an organic field effect transistor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of Compound Ia

[0038]

[0039] To a 20 mL three-necked flask containing sodium hydride (56.0 mg, 60 wt%, 1.4 mmol) and 1,2-dimethoxyethane (5 mL) at 0°C under nitrogen protection, malononitrile (46.2 mL) was added in one portion. mg, 0.7 mmol), the foam was removed and the reaction was raised to room temperature 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-necked flask of ethyl ethane (10 mL), the reaction was heated and refluxed for 3 hours under nitrogen protection. Then the reaction temperature was lowered to room temperature and exposed to air, diluted hydrochloric acid (10 mL, 1 M) was added, stirred in an ice-water bath for 30 minutes, extracted with ether (30 mL×3), the organic phases were combined and washed with saturated brine, After dryin...

Embodiment 2

[0040] Example 2: Synthesis of Compound IIa

[0041]

[0042] To a 10 mL three-necked flask containing compound IV (130.2 mg, 0.18 mmol) and tetrahydrofuran (2 mL) at -78 °C under nitrogen protection, n-butyllithium (1.6 M in hexane, 248 μL, 0.396 mmol) was slowly added dropwise, 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) for quenching, extract with ether (30mL×3), The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain the crude product 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 )δ144.0,129.9,121.2,120.8,116.3,68.8,53.5,39.0,31.9,31.7,31.0,29.9,29.6,29.4,29.3,26.13,26.09,22.7,22.6,1...

Embodiment 3

[0043] Example 3: Synthesis of Compound IV

[0044]

[0045] Compound V (282.0 mg, 0.5 mmol), sodium tert-butoxide (768.8 mg, 8.0 mmol), bis(dibenzylideneacetone) palladium (28.8 mg, 0.05 mmol), 1,1' were added to a 50 mL three-necked flask. -Bis(diphenylphosphino)ferrocene (110.9 mg, 0.2 mmol) and toluene (10 mL), stirred at 25°C for 20 minutes, added compound VI (280.1 mg, 1.16 mmol), heated to 110°C and reacted for 10 hours . After cooling to room temperature, water (20 mL) was added, extracted with ether (30 mL×3), the organic phases were combined and washed with saturated brine, dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation. 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...

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Abstract

The invention discloses a thienopyrroloquinone compound, a preparation method and application thereof as a semiconductor active layer in an organic field effect transistor. These compound has the advantages of good planarity, strong self-assembly ability, low LUMO energy level, narrow energy band gap, and insensitivity to oxygen and water. The introduction of pyrrole structure facilitates the regulation of solubleness of a sample by modification of substituents, and facilitates solution processing. The organic field-effect transistor with compound Ia as a semiconductor layer prepared by a spin-coating method has excellent bipolar field-effect properties (muh = 5.3*10<-3> cm <2> / V s, m e = 7.7*10<-3> cm<2> / V s). The switching current ratio is higher than 10<4>; and the compound is stable in the air, and has important application value.

Description

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

Claims

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Application Information

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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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