Functional modified branch-shaped conjugated compounds, ink, membranes and applications

A conjugated compound and conjugation technology, applied in the direction of silicon organic compounds, applications, compounds of group 4/14 elements of the periodic table, etc., can solve the problems of inability to fully utilize the solar spectrum and low collection capacity, and achieve the regulation of charge transfer The effect of reducing the spectral band gap and reducing the spectral bandwidth

Inactive Publication Date: 2017-12-12
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on all-thiophene dendritic conjugated oligothiophene, it can be used to prepare organic thin film solar cells (Adv. Funct. Mater. 2008, 18, 3323–3331)

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
  • Functional modified branch-shaped conjugated compounds, ink, membranes and applications
  • Functional modified branch-shaped conjugated compounds, ink, membranes and applications
  • Functional modified branch-shaped conjugated compounds, ink, membranes and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1: Synthesis of compound 3

[0140]

[0141] Weigh compound 1 (1.0g, 984μmol), compound 2 (1.25g, 2.4mmol), Pd 2 (dba) 3 .CHCl 3 (120mg, 116μmol), HP(tBu) 3 BF 4 (70mg, 241μmol) was added to a 500mL two-necked round bottom flask under a nitrogen atmosphere, degassed THF (300mL) was added to the above two-necked flask, and then K was added dropwise to the reaction system 2 CO 3 Aqueous solution (1M, 15.0 mL, 15.0 mmol), stirring at room temperature overnight. The reaction system gradually turned blue. After 24 hours, first evaporate and concentrate most of the solvent in the solution, then extract the solution with dichloromethane / water, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, remove the solvent by rotary evaporation, and separate with a silica gel column The product, the eluent was dichloromethane: n-hexane (1:4), 1.4 g of blue solid compound 3 was obtained, and the yield was 88%. The characterization data are as fol...

Embodiment 2

[0143] Example 2: Synthesis of Compound 4

[0144]

[0145] The compound TBAF (270 mg, 855 μmol) was weighed and dissolved in 2 mL of THF to form a homogeneous solution. Take another 50mL reaction flask, weigh compound 3 (120mg, 73.2μmol) and dissolve it in 5mL THF, and dissolve it fully. 2ml of TBAF in THF was added dropwise to the compound 3 solution, and stirred at room temperature for 15 minutes. The reaction mixture was dropped into 30 ml of methanol, and the resulting precipitate was collected. The crude product obtained by precipitation was purified and separated by a silica gel chromatography column, and the eluent was dichloromethane: n-hexane (1: 3) to obtain 90 mg of compound 4 with a yield of 90%. The characterization data are as follows:

[0146] 1 H NMR(CDCl 3 ,400MHz):δ=8.92(d,J=3.80Hz;2H),7.32-7.33(m;8H),7.15-7.16(m;2H),7.10(m;2H),7.01-7.05(m;4H) ),4.04(d,J=7.76Hz;4H),1.98(br;2H),1.20-1.34(m;64H),0.82-0.87ppm(m;12H).MALDI-TOF MS:m / z calcd for C 78 H 100 N 2 O 2...

Embodiment 3

[0147] Example 3: Synthesis of Compound 6

[0148]

[0149] Weigh compound 1 (258mg, 254μmol), compound 5 (900mg, 780mmol), Pd 2 (dba) 3 .CHCl 3 (60mg, 57.9μmol), HP(tBu) 3 BF 4 (30mg, 104μmol) was added to a 250mL two-necked round bottom flask under a nitrogen atmosphere, degassed THF (135mL) was added to the above two-necked flask, and then K was added dropwise to the reaction system 2 CO 3 Aqueous solution (1M, 5.0 mL, 5.0 mmol), stirring at room temperature overnight. The reaction system gradually turned blue. After 24 hours, first evaporate and concentrate most of the solvent in the solution, then extract the solution with dichloromethane / water, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, remove the solvent by rotary evaporation, and separate with a silica gel column After removing small molecule by-products and catalysts. It was purified and separated again by gel permeation chromatography, using THF as the eluent to obtain 614 m...

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 discloses functional modified branch-shaped conjugated compounds, ink, membranes and applications. The branch-shaped compounds have structures represented by a formula (I) or (II), wherein B is a branched conjugated link unit, and the B is selected from a unit which is formed by a five-membered or six-membered aromatic unit and has a branched structure; Core is a kernel functional modified unit; FG is a tail-end functional modified unit; m is a branching degree of the B, and m is selected from 2 or 3; and n is a number of an iteration time of a repeating unit, and n is one selected from 1, 2, 3, and 4. The invention also discloses the ink, the membranes, preparation methods of the ink and the membranes and applications, wherein the ink and the membranes are based on the branch-shaped conjugated compounds, the applications comprises an application in photoelectric response devices. The branch-shaped conjugated compounds provided by the invention have the advantages of high molecular weights, good solution workability, single and decided molecular structures, narrow spectrum band gaps, good sunlight spectral response in a long-wave direction, easiness to material purification, good repeatability and the like, and the branch-shaped conjugated compounds are more beneficial for applications in organic semiconductor devices.

Description

Technical field [0001] The invention relates to an organic conjugated semiconductor material, in particular to a functionalized modified tree-shaped conjugated compound, an ink and a film based on the compound, and a preparation method and application thereof, belonging to the field of organic photoelectric semiconductor materials and applications. Background technique [0002] Organic semiconductor materials have the characteristics of easy availability of raw materials, low cost, photoelectric properties that can be tailored through molecular design, light weight, compatibility with flexible substrates, and easy large-area processing and preparation into films, and have a broader market prospect. [0003] Organic semiconductor materials are mainly divided into two types: conjugated polymer materials and conjugated organic small molecule materials. Conjugated polymer materials have the advantages of large molecular weight, good film-forming properties, and easy large-scale large-s...

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): C07F7/08C09D11/02C09D11/30C07D417/14C07D519/00H01L51/46
CPCC09D11/02C07D417/14C07D519/00C07F7/0814H10K85/655H10K85/657H10K85/6572Y02E10/549
Inventor 高威窦军彦马昌期崔铮
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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