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Naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors therefrom

A naphthalene diimide, organic group technology, applied in the field of naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors derived therefrom, can solve the problem of no measurement , undesired, reduced field-effect mobility, etc.

Inactive Publication Date: 2014-06-25
GEORGIA TECH RES CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] NDI compound 1a was reported (see Katz, H.; Johnson, J.; Lovinger, A.; Li, W. J. American Chemical Society 2000, 122, 7787) to demonstrate a 0.16 cm in vacuum 2 V -1 the s -1 The measured field-effect electron mobility of , but almost no field-effect electron mobility was measured in air
reported that PDI compound 1b in H 2 The atmosphere reached 1.7cm 2 V -1 the s -1 , but when the device is exposed to air, its field-effect mobility drops dramatically to 0.11 cm 2 V -1 the s -1 (Chesterfield, R.; McKeen, J.; Newman, C.; Ewbank, P.; da Silva, D.; Bredas, J.; Miller, L.; Mann, K.; Frisbie, C. Journal of the American Chemical Society B2004, 108, 19281)
reported that PDI compound 4 has a 0.64cm 2 V -1 the s -1 Air-stabilized field-effect electron mobility (see Jones, B.; Ahrens, M.; Yoon, M.; Facchetti, A.; Marks, T.; Wasielewski, M. Applied Chemistry International Edition (Angew Chem Int Ed) 2004, 43, 6363), but only 1×10 4 on / off ratio and is subject to an undesirable -20 volt threshold voltage

Method used

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  • Naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors therefrom
  • Naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors therefrom
  • Naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors therefrom

Examples

Experimental program
Comparison scheme
Effect test

example 1-N

[0234] Example 1-N, N'-bis(n-hexyl)-4-bromonaphthalene-1,4:5,8-bis(dicarboximide) synthesis

[0235]

[0236] A solution of naphthalene-1,4:5,8-tetracarboxylic dianhydride (10.0 g, 37.3 mmol) in concentrated sulfuric acid (370 mL) was heated to 85°C. 1,5-dibromo-4,6-dioxo-1,4,5,6-tetrahydro-1,3,5-triazine potassium salt (1,5-dibromo-4,6-dioxo-1 , 4,5,6-tetrahydro-1,3,5-triazin-2-olate) (6.06 g, 18.64 mmol) was dissolved in concentrated sulfuric acid and added by cannula. The mixture was allowed to stir at 85°C for 48 hours. After cooling, the reaction mixture was poured into ice. The resulting yellow precipitate was collected by filtration and washed with methanol, and dried under vacuum. The yellow solid was transferred to a flask with glacial acetic acid (370 mL) and n-hexylamine (15.1 g, 0.149 mol). The reaction mixture was refluxed for 20 minutes, allowed to cool overnight, and poured into 1500 mL of methanol. The resulting precipitate was collected by filtrati...

example 2-2

[0238] Example 2-2,7-Dihexyl-4-(tributylstannyl)naphthalene-1,4:5,8-bis(dicarboxylic acid imine) synthesis

[0239]

[0240] N, N'-bis(n-hexyl)-2-bromonaphthalene-1,4,5,8-bis(dicarboximide) (1.45g, 2.82mmol), 1,1,1,2, A solution of 2,2-hexabutyldistannane (1.64 g, 2.82 mmol) and tri-o-tolylphosphine (0.172 g, 0.565 mmol) in dry toluene (30 mL) was degassed with nitrogen for 5 minutes. Tris(dibenzylideneacetone)dipalladium (0.129 g, 0.141 mmol) was added, and the reaction was heated to 90° C. for 24 hours. After cooling, the reaction mixture was precipitated in methanol, and the solid was removed by filtration, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica, dichloromethane) to give (2,7-dihexyl-4-(tributylstannyl)naphthalene-1,4:5,8-bis (dicarboximide), 1.53 g, 2.11 mmol, 74.9%).

[0241] 1H NMR (400MHz, CDCl3) δ8.94(s, 1H), 8.70(d, J=7.6Hz, 1H), 8.67(d, J=7.6Hz, 1H), 4.18(t, J=7.6Hz, 2H ), 4.16(t,...

example 3

[0242] Example 3-"NDI-T-NDI": 4,4'-(thiophene-2,5-diyl)bis(2,7-dihexylnaphthalene- 1，4：5，8 - Bis(dicarboximide)) Synthesis:

[0243]

[0244] 4-Bromo-2,7-dihexylnaphthalene-1,4:5,8-bis(dicarboximide) (1.00g, 1.95mmol), tri-o-tolylphosphine (0.056g, 0.185 mmol), and a solution of 2,5-bis(tributylstannyl)thiophene (0.610 g, 0.930 mmol) in anhydrous dimethylformamide (20 mL) were degassed with nitrogen for 5 minutes. Add tris(dibenzylideneacetone)dipalladium(0)(Pd 2 (dba) 3 ) (0.046 g, 0.048 mmol), and the reaction was heated to 150° C. for 2 hours. After cooling, the reaction mixture was diluted with chloroform and washed 3 times with deionized water. The solution was dried over anhydrous magnesium sulfate and filtered through a plug of celite. The crude product was purified by flash chromatography (silica gel, 2% ethyl acetate in chloroform). Precipitation of the product from methanol and hexanes yielded the product as a purple solid (4,4'-(thiophene-2,5-diyl)bi...

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Abstract

The various inventions and / or their embodiments disclosed herein relate to certain naphthalene diimide (NDI) compounds wherein the NDI groups are bonded to certain subclasses of bridging heteroaryl (hAr) groups, such as the "NDI-hAr-NDI" oligomeric compounds, wherein hAr is a heteroaryl group chosen to provide desirable electronic and steric properties, and the possible identities of the "Rz" terminal peripheral substituent groups are described herein. Transistor and inverter devices can be prepared.

Description

[0001] technical field of invention [0002] The inventions disclosed and described herein relate to oligomers comprising combinations of naphthalene-diimide-heterocycle-naphthalene diimide groups, their synthesis and use as organic compounds in organic electronic devices such as transistors. use of semiconductors. Background of the invention [0003] Organic semiconductors have attracted attention in the art due to their potential application in the fabrication of large-area, flexible, and low-cost electronic devices, including organic light-emitting diodes (OLEDs), solar cells, and / or transistors. Such organic semiconductors can be relatively low molecular weight "small molecules" that can be vacuum deposited. Alternatively, semiconducting organic oligomers or polymers can be solution processed to form organic semiconducting films at the low cost necessary to enable many new and desired end-use applications. See, eg, the review article by Shirota and Kageyama (Chem. Rev. 2...

Claims

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Application Information

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IPC IPC(8): C07D471/06C07D519/00
CPCC07D471/06H01L51/0067C07D519/00H10K85/655H10K85/6576H10K85/6572H10K85/657Y02E10/549Y02P70/50C07F7/22H10K85/654
Inventor L.E.波兰德S.P.蒂瓦里S.马德B.基佩伦R.R.达萨里Y.A.格特马內科D.K.黃M.费诺尔
Owner GEORGIA TECH RES CORP
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