Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

N-type organic semiconductor material containing oblique line type naphthalimide unit

An organic semiconductor and diimide technology, which is applied in the field of n-type semiconductor materials, can solve the problems of lack of high electron mobility, air-stable n-type organic semiconductor materials, and few types.

Active Publication Date: 2012-06-27
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with p-type organic semiconductor materials, there are fewer types of n-type organic semiconductor materials, especially n-type organic semiconductor materials with high electron mobility, air stability, and solution processability.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N-type organic semiconductor material containing oblique line type naphthalimide unit
  • N-type organic semiconductor material containing oblique line type naphthalimide unit
  • N-type organic semiconductor material containing oblique line type naphthalimide unit

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0020] Preparation 1: 1,2,5,6-naphthalene tetracarboxylic acid

[0021] Add 0.85 g of 1,5-dicyano-2,6-dimethylnaphthalene and 20 mL of K 2 Cr 2 o 7 (3.56g) and NaOH (0.33g) in water. After the mixture was stirred for half an hour, it was sealed in a stainless steel jar, heated to 220°C and maintained for 10 hours. After cooling, it was filtered, and the filtrate was treated with ether, and the aqueous layer was acidified by adding concentrated hydrochloric acid to obtain a yellow solid (1.06 g, yield 85%). Preparation 2: 1,2,5,6-naphthalene tetracarboxylic anhydride

preparation example 2

[0022] Add 1.0 g of 1,2,5,6-naphthalene tetracarboxylic acid obtained in the previous step into 50 mL of acetic anhydride, stir and reflux in a 100 mL round bottom flask for 3 hours, distill off most of the solvent under reduced pressure, vacuum filter, and the residue After washing with methanol, 0.79 g of product was obtained with a yield of 90%.

preparation example 3

[0023] Preparation Example 3: N, N'-bis(4-(trifluoromethyl)phenyl)-naphthalene-1,2,5,6-bis(dicarboxamide)

[0024]

[0025] The acid anhydride (0.586g, 2.2mmol) obtained in the previous step reaction and excess 4-trifluoromethylbenzylamine (6.6mmol) and zinc acetate (1.54mmol) were added in a 25mL round bottom flask, and 6mL quinoline was added, Heating to above 200°C, stirring and reacting at this temperature for 3 hours. After cooling, vacuum filter, and successively use hot dilute Na 2 CO 3 solution, water, toluene, methanol wash. 1.06 g of crude product were obtained, yield 83%. The further extraction of the product was purified by vacuum sublimation. Elemental analysis: calcd for C, 61.86; H, 2.77; N, 4.81; found: C, 62.03; H, 2.77, N, 4.87.Mp 317-318℃.MALDI-TOF / MS, m / z calcd for C 30 h 16 f 6 N 2 o 4 :582.1, found: 582.1; 1 H NMR (400MHz, CDCl 3 , ppm): δ=4.97(s, 4H), 7.60(s, 8H), 8.12(d, J=8.4Hz, 2H), 9.35(d, J=8.4Hz, 2H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides an N-type organic semiconductor material containing an oblique line type naphthalimide unit, which can be used for an organic diaphragm field effect transistor. In the material, the characteristic of the prior linear type naphthalimide moleculars that carboxylic acid imine hexatomic rings are connected to the positions of 1, 8 and 4, 5 is changed, and the carboxylic acid imine hexatomic rings are connected to the positions of 1, 2 and 5, 6 to form five-membered rings and oblique line type, so charge distribution and electron energy level of the moleculars of the material can be changed. The structure is conductive to introducing polymerizable groups in the positions of 3, 7 of a naphthalene ring so as to synthesize a polymer containing the oblique line type aromatic naphthalimide unit.

Description

technical field [0001] The invention relates to an n-type semiconductor material used in an organic thin film field effect transistor, in particular to an organic small molecule n-type semiconductor material containing oblique naphthalene cyclodiimide units. Background technique [0002] Field Effect Transistor (FET) is an active device that uses an electric field to control the conductivity of solid materials, and has become one of the important components in the microelectronics industry. At present, field-effect transistors are close to the natural limit of miniaturization, and the cost is high, which is not conducive to the preparation of large surface area devices. The characteristics of organic field-effect transistors (OFET) can just overcome the above-mentioned shortcomings: wide sources of materials, can be made into flexible devices, can be made into large-area devices, suitable for low-temperature processing, can be processed into films by solution, suitable for l...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04H01L51/30
Inventor 郑庆东陈善慈
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com