Selenium-containing pi extension naphthalene tetracarboxylic diimide compound, and preparation method and application thereof

A technology of naphthalene tetracarboxylic acid diimide and compound, which is applied in the field of naphthalene tetracarboxylic acid diimide derivatives, and can solve problems such as limited application

Active Publication Date: 2015-07-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the optimal properties of these N-alkyl-substituted NDI-DTYM2 series n-type materials largely depend on the high-temperature annealing (≥150°C) of their thin-film devices, which limits their application to a certain extent. Applications in Flexible Electronics on Plastic Substrates

Method used

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  • Selenium-containing pi extension naphthalene tetracarboxylic diimide compound, and preparation method and application thereof
  • Selenium-containing pi extension naphthalene tetracarboxylic diimide compound, and preparation method and application thereof
  • Selenium-containing pi extension naphthalene tetracarboxylic diimide compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] N,N′-bis(2-butyl-octyl)-[2,3-d:6,7-d′]-bis[1,3-diseleno-2-yrylene-propanedicyanide Synthesis of ]-naphthalene-1,4,5,8-tetracarboxylic diimide (compound 1)

[0093] Concrete synthetic steps are:

[0094]Under the protection of nitrogen, the compound N,N′-bis(2-butyl-octyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide Amine (918mg, 1.00mmol), potassium 1,1-dicyanoethylene-2,2-diselenate (700mg, 2.50mmol) were added into 160mL THF, heated to 50°C, and stirred for 2.5 hours. Cool to room temperature, spin off the solvent under reduced pressure, use dichloromethane / petroleum ether (2 / 1) as eluent, separate and purify the crude product with silica gel chromatography, and obtain 448 mg of blue-purple solid product (compound 1), Yield 42%.

[0095] Mass Spectrum: [MS(TOF)]m / z:1068.1(M+H) + .

[0096] Elemental analysis: Molecular formula: C 46 h 50 N 6 o 4 Se 4 ; Theoretical: C, 51.79; H, 4.72; N, 7.88; Found: C, 51.76; H, 4.77; N, 7.76.

[0097] Pro...

Embodiment 2

[0100] N,N′-bis(2-octyl-dodecyl)-[2,3-d:6,7-d′]-bis[1,3-diseleno-2-yaryne-propane Synthesis of dicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (compound 2)

[0101] Concrete synthetic steps are:

[0102] Replace N with N,N′-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, N'-bis(2-butyl-octyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, the synthesis method is the same as in Example 1 step, a blue-purple solid (compound 2) was prepared with a yield of 28%.

[0103] Mass Spectrum: [MS(TOF)]m / z:1292.5(M+H) + .

[0104] Elemental analysis: Molecular formula: C 62 h 82 N 6 o 4 Se 4 ; Theoretical: C, 57.67; H, 6.40; N, 6.51; Found: C, 57.66; H, 6.39; N, 6.31.

[0105] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.85–0.87(m,6H,–CH 3 ),1.25(m,32H,–CH 2 –),2.01(m,1H,CH),4.23(d,2H,J=7.50Hz,–CH 2 –N).

[0106] After testing, compound 2 is soluble in common organic solvents, such as dichloromethane, chloroform...

Embodiment 3

[0108] N,N′-bis(3-hexyl-undecyl)-[2,3-d:6,7-d′]-bis[1,3-diseleno-2-yaryne-propanedi Synthesis of cyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (compound 3)

[0109] Concrete synthetic steps are:

[0110] Use N,N′-bis(3-hexyl-undecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide instead of N,N ′-bis(2-butyl-octyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, the synthesis method is the same as that in Example 1 , a blue-purple solid (compound 3) was prepared with a yield of 28%.

[0111] Mass Spectrum: [MS(TOF)]m / z:1206.3(M + ).

[0112] Elemental analysis: Molecular formula: C 56 h 70 N 6 o 4 Se 4 ; Theoretical: C, 55.72; H, 5.85; N, 6.96; Found: C, 55.99; H, 5.80; N, 7.05.

[0113] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.85–0.94(m,6H,–CH 3 ),1.23–1.33(m,24H,–CH 2 –),1.52(br,1H,CH),1.74(br,2H,–CH 2 –),4.02–4.06(m,2H,–CH 2 –N).

[0114] After testing, compound 3 is soluble in common organic solvents, such as dic...

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Abstract

The invention discloses a selenium-containing pi extension naphthalene tetracarboxylic diimide compound, and a preparation method and an application thereof. The structure of the above naphthalene tetracarboxylic diimide derivative is represented as in the specification and claim, and is prepared through a reaction of 2,3,6,7-tetrahalogenonaphthalene tetracarboxylic diimide and 1,1-dicyanoethylene-2,2-diselenol or 1,1-dicyanoethylene-2,2-diselenol and 1,1-dicyanoethylene-2,2-dithiolate in an organic solvent. The naphthalene tetracarboxylic diimide derivative can be used as an organic thin film transistor of a semiconductor layer without heat treatment of the semiconductor film, the electron mobility of the derivative can reach 1.0cm<2>V<-1>s<-1>, the on/off ratio of the derivative is greater than 10<6>, the electron mobility of the monocrystalline field effect transistor device of the derivative an reach 2.0cm<2>V<-1>s<-1>, and the on/off ratio of the device is greater than 10<5>.

Description

technical field [0001] The present invention relates to naphthalene tetracarboxylic acid diimide derivatives, in particular to a class of selenium-containing π-extended naphthalene tetracarboxylic acid diimide compounds, its preparation method and its use as an organic semiconductor material in an organic thin film field effect transistor Applications. Background technique [0002] Organic thin film transistors (OTFT for short) are active devices that control the conductivity of organic semiconductor materials through an electric field. OTFT has the advantages of simple preparation process, [0003] With the advantages of low cost, light weight, flexibility, and good compatibility with plastic substrates, it has broad application prospects in flexible displays, organic radio frequency electronic labels (ORFID), organic sensors, etc. (Nature.2004, 428, 911-918 ;Science2009,326,1516-1519.;Nat.Mater.2010,9,859-864.;Adv.Mater.2010,22,3778-3798.;Science2010,327,1603-1607.Specia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D517/22C09B57/08H01L51/30H01L51/10
CPCC09B57/08H10K85/621H10K85/657H10K10/466
Inventor 高希珂韩文杰王中丽朱道本
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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