Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof

An organic semiconductor, 2-c technology, applied in the application field of organic photoelectric technology, can solve the problems of difficult purification, limited application, low electron cloud density of aromatic ring, etc., and achieve cost reduction, solubility and planar balance, good Effect of solution processability

Active Publication Date: 2011-05-18
SOUTH CHINA UNIV OF TECH
View PDF3 Cites 49 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole has not attracted attention, and there are few reports, the main reason is that naphthalene[1,2-c:5,6 -c] bis[1,2,5]thiadiazole has strong electron deficiency, low electron cloud density of aromatic ring, poor chemical reactivity, and difficult substitution reaction, so it is difficult t...

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
  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof
  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof
  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0036] The preparation of the organic semiconductor material of the present invention: directly halogenate naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole, and introduce alkylated thiophene or bithiophene and other auxiliary The aromatic group Ar of the soluble group reacts with the halogenated product through a transition metal-catalyzed coupling reaction to obtain a naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole structure Organic semiconductor materials. Using the aromatic group Ar as a bridge, the solubility of Ar can be adjusted, and active groups can also be introduced at the reactive sites on the Ar group. In this way, the problems of solubility and chemical modification of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole are solved, better performance is obtained, and the problem of naphthalene [1,2-c:5,6-c]bis[1,2,5]thiadiazole processability problem, expanding naphthalene[1,2-c:5,6-c]bis[1,2 , The reactivity and application of this structure of 5] thiadiazole can obtain a...

Embodiment 13

[0039] Example 13, Preparation of 7-dithiophene-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0040] The synthetic route is as follows:

[0041]

[0042] (1) Preparation of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0043] Add 0.49g (2mmol) of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole into a 50ml single-necked bottle with a stirring bar, and add 10ml of concentrated sulfuric acid, stir to dissolve and Heat to 60°C, then add 0.78g NBS (4.4mmol), and react in the dark for 24 hours. After the reaction, pour the reaction solution into water, and the precipitated solid is the crude product. Filter, wash with water until neutral, and then wash with ethanol After washing and drying, 0.72 g of crude product was obtained, which was directly carried out to the next reaction without purification.

[0044] (2) Preparation of 3,7-bis(thiophen-5-yl)-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0045] Add 0.72g of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]...

Embodiment 2

[0046] Example 2 Poly{N-9-heptadecyl-2,7-carbazole-alternating-2,2-[3',7'-bis(3-octylthiophen-5-yl)-naphthalene[1 ', 2'-c: 5', 6'-c] two [1', 2', 5'] thiadiazole]} (abbreviated as PCz-DOTNBT) preparation

[0047] The synthetic route is as follows:

[0048]

[0049] 3-octyl-5-tributyltinthiophene reagent was prepared according to literature [Voituriez, Arnaud; Mellah, Mohamed; Schulz, Emmanuelle.Synthetic Metals 2006, 156 (2-4), 166-175.], 2,7-bis( 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-diyl)-N-9-heptadecylcarbazole According to literature [N.Blouin, A.Michaud, M . Leclerc, Adv. Mater. 2007, 19, 2295-2300] Preparation.

[0050] (1) Preparation of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0051] Add 0.73g (3mmol) of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole into a 50ml single-necked bottle with a stirring bar, and add 10ml of concentrated sulfuric acid, stir to dissolve And heated to 60 ℃, then add 1.17g (6.6mmol) NBS, avoid light reaction, thin chr...

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 relates to an organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof, wherein the organic semiconductor material is prepared by reacting the halogenated derivatives with the monomer containing an aromatic group structure under the metal catalyst, wherein the halogenated derivatives are obtained by halogenating the naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole; the aromatic group is connected with a naphthalene [1, 2-c:5, 6-c] di [1, 2, 5] thiadiazole unit in a conjugate manner. The organic semiconductor material is characterized by containing 3, 7 substituted decorative[1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole chemical groups; as the naphthalene [1, 2-c:5, 6-c] di [1, 2, 5] thiadiazole has excellent electron-withdrawing ability and planarity, the organic semiconductor material can excellently adjust the photoelectric property, has excellent photoelectric performance, and is applied to the field of organic photoelectric components.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of organic semiconductor materials containing naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole and its application in the field of organic photoelectric technology Applications. Background technique [0002] Organic photoelectric materials and devices are very suitable for industrial production and promotion due to their easy-to-obtain materials, simple preparation process, low cost, flexibility, and large-area film formation, and have very broad commercialization prospects. Since 1987, Deng Qingyun Research Group [Tang, C.W.; Van Slyke S.A.et.al; Appl.Phys.Lett.1987, 51, 913.] of Kodak Company of the United States proposed an organic small molecule thin film electroluminescent device and in 1990, Cambridge, UK Since the R.H.Friend research group [Burroughes, J.H.; Bradley, D.D.C.; Friend, R.H; Holmes, A.B.et al; Nature 1990, 347, 539.] proposed the ...

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
IPC IPC(8): C08G61/12H01L51/54H01L51/30H01L51/46
CPCY02E10/50Y02E10/549
Inventor 黄飞曹镛王明
Owner SOUTH CHINA UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap