Organic semiconductor compound and its preparation method and uses

A technology of organic semiconductors and organic photoconductors, applied in the preparation of organic compounds, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problems of deteriorating working environment and easy oxidation of devices, and achieve wide application prospects and excellent photoconductive properties , Facilitate the effect of mass synthesis

Inactive Publication Date: 2009-01-28
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When negatively charged, the corona device produces O 3 Make the working environment worse, the device is easy to oxidize

Method used

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  • Organic semiconductor compound and its preparation method and uses
  • Organic semiconductor compound and its preparation method and uses
  • Organic semiconductor compound and its preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1, using titanium tetrachloride and N-methylmorpholine as a catalyst to synthesize 2,2',2"-(5H-tribenzo[a,f,k]triindene-5,10,15-triethylene base) tris(2-cyanoacetate methyl ester) (compound VIII, C 39 h 21 N 3 o 6 )

[0038] Take 0.77g (2mmol) of irindone and 1.8ml (20mmol) of methyl cyanoacetate, and add 50ml of dichloromethane as a reaction solvent. The mixture was predispersed using ultrasound for 30 min, and then 1.3 ml of titanium tetrachloride (12 mmol) and 4.0 ml of N-methylmorpholine (36 mmol) were sequentially added dropwise under stirring. The reaction system was sealed, placed in an ultrasonic water bath, and reacted at 25° C. for 5 h. 120ml of water was added to the reaction system, and then 150ml of dichloromethane was added for extraction. The organic phase was taken and the solvent was evaporated to dryness to obtain a dark red solid. The solid was washed successively with ethyl acetate and methanol, and finally recrystallized in a mixed so...

Embodiment 2

[0042] Embodiment 2, using titanium tetrachloride and pyridine as a catalyst to synthesize compound 2,2',2 "-(5H-tribenzo[a,f,k]triindene-5,10,15-triylidene) three ( 2-Ethyl cyanoacetate) (Compound IX, C 42 h 27 N 3 o 6 )

[0043] Take 0.77g (2mmol) of irindone and 1.8ml (20mmol) of methyl cyanoacetate, and add 50ml of dichloromethane as a reaction solvent. The mixture was predispersed using ultrasound for 30 min, and then 1.3 ml of titanium tetrachloride (12 mmol) and 2.9 ml of pyridine (36 mmol) were sequentially added dropwise with stirring. The reaction system was sealed, placed in an ultrasonic water bath, and reacted at 25° C. for 5 h. 120ml of water was added to the reaction system, and then 150ml of dichloromethane was added for extraction. The organic phase was taken and the solvent was evaporated to dryness to obtain a dark red solid. The solid was washed successively with ethyl acetate and methanol, and finally recrystallized in a mixed solvent of ethanol and...

Embodiment 3

[0047] Embodiment 3, use titanium tetrachloride and N-methylmorpholine as catalyst synthesis compound IX

[0048] Take 0.77g (2mmol) of irindone and 2.1ml (20mmol) of ethyl cyanoacetate, and add 50ml of dichloromethane as a reaction solvent. The mixture was pre-dispersed by ultrasound for 30 min, and then 1.3 ml of titanium tetrachloride (12 mmol) and 4.4 ml of N-methylmorpholine (40 mmol) were sequentially added dropwise under stirring as a catalyst. The reaction system was sealed, placed in an ultrasonic water bath, and reacted at 25° C. for 5 h. 120ml of water was added to the reaction system, and then 150ml of dichloromethane was added for extraction. The organic phase was taken and concentrated, and the concentrated solution was passed through a 200-300 mesh silica gel column with dichloromethane as the eluent to collect the red component therein. Finally, it was recrystallized in a mixed solvent of ethanol and dichloromethane to obtain 0.68 g of red flaky crystals (51%...

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Abstract

The invention discloses an organic semi-conductor compound and preparing method and application, which possesses structural formula as formula I, wherein R1, R2 and R3 is ethyl cyanoacetate subunit or O atom as formula II, which is not O atom at the same time; the R in the formula II is C1-8 alkyl. The invention possesses superior electronic transmission property, which is convenient to do mass synthesis.

Description

technical field [0001] The invention relates to an organic semiconductor compound and its preparation method and application. Background technique [0002] Semiconductor devices based on semiconductor materials are the foundation of the modern electronics industry. In the field of semiconductor material research, although inorganic semiconductor materials represented by silicon have been widely used and occupy a dominant position in many electronic products, organic semiconductor materials have also received much attention in recent years because of their characteristics that many inorganic semiconductor materials do not have. received widespread attention. For example, organic semiconductors have the characteristics of easy structure-performance modulation, suitable for making flexible devices, and low processing costs. Organic photoconductors represented by phthalocyanine compounds and organic hole transport materials represented by polyarylamines and hydrazone compounds...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/40C07C253/30C07C255/14C07C49/563H01L51/50
Inventor 王远张鑫然晁伟马严郝锐
Owner PEKING UNIV
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