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Organic semiconductors

An organic semiconductor and semiconductor technology, applied in organic chemistry, electrical solid devices, light-emitting materials, etc., can solve the problems of reduced semiconductor band gap stability, short life, poor performance, etc., to improve intermolecular and intramolecular mobility, The effect of extended conjugation

Inactive Publication Date: 2011-10-26
CAMBRIDGE DISPLAY TECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] However, the increased level of conjugation required for the compound to form such a π-π stack also leads to a decrease in the semiconductor's bandgap as well as its stability, which leads to poor performance and short lifetime
Furthermore, these compounds can be highly insoluble due to the molecular sizes required to obtain a wide range of conjugation, which poses particular problems for synthesis and makes their use in efficient transistor production methods such as inkjet printing difficult.

Method used

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  • Organic semiconductors
  • Organic semiconductors
  • Organic semiconductors

Examples

Experimental program
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Effect test

Embodiment 1

[0100]

[0101] A solution of intermediate 4 (1 g, 1.69 mmol) in Eaton's reagent (7 ml) was stirred at room temperature in the dark for 48 hours. The dark green solution was poured into ice water (100ml) and the resulting sticky brown solid was dissolved in pyridine (60ml) and the solution was stirred at reflux for 18 hours. The mixture was cooled, poured into dichloromethane (600ml), and washed thoroughly with 2M HCl and water, then dried (MgSO 4 ) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 5% dichloromethane: hexane) gave Example 1 (240 mg, 35%, HPLC 99.6%) as a white solid; mp (DSC) 126.5°C; 1 H NMR (CDCl 3 , 400MHz)δ ppm 7.57 (2H, d, J = 4.8Hz), 7.37 (2H, d, J = 4.8Hz), 3.27 (4H, t, J = 8Hz), 1.85 (4H, m), 1.61 (4H, m), 1.40 (4H, m), 1.30 (12H, m), 0.88 (6H, t, J = 7.4 Hz).

Embodiment 2

[0103]

[0104] Example 2 was synthesized in a similar manner as described in Example 1 by Suzuki coupling reaction followed by acid-induced intramolecular cyclization.

Embodiment 3

[0106] The organic field effect transistor device using the compound of Example 1 as the active layer was prepared as a top-gate, bottom-contact device. Gold source and drain contacts are defined by lift off on the glass substrate. Channel lengths of 10-200 microns and widths of 2 mm are defined. Devices were prepared by spin-coating the compound of Example 1 from a 2% tetralin solution on a clean substrate at 1000 rpm for 60 seconds. The films were then dried on a hot plate at 80°C for 10 minutes and cooled on a metal block for 1 minute. The fluorinated dielectric material was spin-coated onto the semiconducting layer from a fluorine-containing solvent, dried on a hot plate at 80 °C for 10 min, and cooled on a metal block for 1 min. At a channel length of 100 μm, the highest saturation mobility of 0.71 cm was observed 2 / Vs. get ~10 4 switch ratio. A contact resistance of 27kOhm-cm was calculated by extrapolation under a gate field of -40V Vg or 16V / 100nm[ figure 2 ]....

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Abstract

The present invention relates to an organic semiconductor compound comprising the structure of formula (I) : where Ar1, Ar2, Ar3 and Ar4 independently comprise monocyclic aromatic rings and at least one of Ar1, Ar2, Ar3 and Ar4 is substituted with at least one substituent X, which in each occurrence may be the same or different and is selected from the group consisting of (i) optionally substituted straight, branched or cyclic alkyl chains with 1 to 20 carbon atoms, alkoxy, amino, amido, silyl or alkenyl, or (ii) a polymerisable or reactive group selected from the group consisting of halogens, boronic acids, diboronic acids and esters of boronic acids and diboronic acids, alkylene groups and stannyl groups, and where Ar1, Ar2, Ar3 and Ar4 may each optionally be fused to one or more further rings. The organic semiconducting compound is used as an active layer in an organic semiconducting device such as a thin film transistor.

Description

technical field [0001] The present invention relates generally to organic semiconductor materials, and in particular to organic semiconductors used to form part of thin film transistors. Background technique [0002] Transistors can be divided into two main types: bipolar junction transistors and field effect transistors. Both types have a common structure comprising three electrodes with a semiconductor material disposed between them in the channel region. The three electrodes of a bipolar junction transistor are called emitter, collector, and base, while in field effect transistors, the three electrodes are called source, drain, and gate. Since the current between the emitter and collector is controlled by the current flowing between the base and emitter, bipolar junction transistors can be described as current-operated devices. In contrast, field effect transistors can be described as voltage-operated devices since the current flowing between source and drain is control...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/10H10K99/00
CPCC07D495/22C09K11/06C09K2211/1011C09K2211/1092C09K2211/1416C09K2211/1425C09K2211/1458H05B33/10H10K85/6576H10K10/466C07D333/50C08G61/10C08G61/12C08G61/126H10K50/11
Inventor T·朱贝里S·朱贝里
Owner CAMBRIDGE DISPLAY TECH LTD