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Thionated aromatic bisimides as organic semiconductors and devices incorporating them

A kind of substituent, halogenated alkyl technology, applied in the field of thiosulfuric acid aromatic diimide as organic semiconductor and devices using them

Inactive Publication Date: 2013-02-13
POLYERA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, challenges remain in producing electron-transporting (n-type) organic semiconductors that are stable under standard operating conditions in air

Method used

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  • Thionated aromatic bisimides as organic semiconductors and devices incorporating them
  • Thionated aromatic bisimides as organic semiconductors and devices incorporating them
  • Thionated aromatic bisimides as organic semiconductors and devices incorporating them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0244] Embodiment 1: synthesis

Embodiment 1A

[0245] Example 1A: Preparation of (S, S)-PDI1MP, (S, S)-PDIS 1 1MP, (S,S)-trans-PDIS 2 1MP, (S,S)-cis-PDIS 2 1MP, (S, S)-PDIS 3 1MP and (S,S)-PDIS 4 1MP

[0246]

[0247]

[0248] 13.5g (34.4mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride (Aldrich), 11.4g (113mmol) of (S)-(+)-2-aminohexane (Alfa Aesar, 99+% tolerance) and 130 g of imidazole were heated in a sealed container at 200°C for 2 hours. The mixture was cooled slightly and then treated with 700 mL of 1,4-dioxane. The mixture was stirred at ambient temperature for 2 hours then filtered. The filter cake was washed successively with methanol (100 mL) and diethyl ether (100 mL). The filter cake was dried to yield 17.9 g (93% yield) of (S,S)-PDI1MP as a dark red powder.

[0249] 1 H NMR (CDCl 3 ,500MHz):δ8.62(d,4H,J=8.0),8.51(d,4H,J=8.0),5.32(m,2H),2.25(m,2H),1.98(m,2H),1.67 (d,6H,J=6.9),1.44-1.24(m,8H),0.90(t,6H,J=7.1). 13 C NMR (CDCl 3 ,125MHz): δ163.8,134.3,131.2,129.3,12...

Embodiment 1B

[0259] Example 1B: Preparation of trans-PDIS 2 1MHex and cis-PDIS 2 1MHex (racemic and meso spin mixture)

[0260]

[0261]

[0262] 4.2g (10.7mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride (Aldrich), 4.1g (35.6mmol) of (+ / -)-2-aminoheptane (Aldrich), and A mixture of 40 g of imidazole was heated at 200° C. for 2 hours in a sealed container. The mixture was cooled slightly and then triturated in 70 mL of 1,4-dioxane. The mixture was cooled to room temperature and filtered. The filter cake was refluxed with 180 mL of 1,4-dioxane for 10 minutes, cooled to room temperature, filtered, and then successively washed with 100 mL of methanol and twice with 80 mL of diethyl ether. The filter cake was dried to yield 4.8 g (76% yield) of PDIIMHex as a bright red powder.

[0263] 1 H NMR (CDCl 3 ,500MHz):δ8.68(d,4H,J=8.0),8.63(d,4H,J=8.0),5.30(m,2H),2.23(m,2H),1.94(m,2H),1.61 (d,6H,J=7.5),1.42-1.20(m,12H),0.85(t,6H,J=8.0).C 38 h 38 N 2 o 4 The analytic...

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Abstract

Disclosed are thionated fused-ring (aromatic) imides and diimides that can exhibit desirable electronic properties and can possess processing advantages including solution- processability and / or good stability at ambient conditions.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to and the benefit of U.S. Provisional Patent Application No. 61 / 290,676, filed December 29, 2009, the entire disclosure of which is incorporated herein by reference. Background technique [0003] Organic semiconducting materials are used in a wide variety of electronic applications, including field-effect transistors, light-emitting diodes, and photovoltaic cells. However, challenges remain in producing electron-transporting (n-type) organic semiconductors that are stable under standard operating conditions in air. [0004] Therefore, in this field, for novel air-stable and solution-processable n-type organic There remains a need for semiconducting compounds, compositions and materials. Contents of the invention [0005] In light of the foregoing, the present invention provides organic semiconductors and related devices that overcome various deficiencies and disadvantages of the pri...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06H01L51/00C09B5/62
CPCC07D471/06C09B5/62H01L51/0053H01L51/0558Y02E10/549H10K85/621H10K10/484
Inventor J·奎因郑焱陈志华H·乌斯塔C·纽曼颜河A·菲奇提
Owner POLYERA CORP
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