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A kind of boron-nitrogen bond-containing perylene imide optoelectronic small molecule material and its preparation method and application

A perylene imide and small molecule technology, which is applied in the field of perylene imide photoelectric small molecule materials and its preparation, can solve the problems of less research on electron transport materials, achieve broad application prospects, short process flow, high electronic and The effect of hole mobility

Active Publication Date: 2021-03-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In recent years, there have been extensive studies on electron-donor materials in the active layer, and relatively few studies on electron-transport materials.

Method used

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  • A kind of boron-nitrogen bond-containing perylene imide optoelectronic small molecule material and its preparation method and application
  • A kind of boron-nitrogen bond-containing perylene imide optoelectronic small molecule material and its preparation method and application
  • A kind of boron-nitrogen bond-containing perylene imide optoelectronic small molecule material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation of peryleneimide photoelectric small molecule material PDIBN-T containing boron nitrogen bond, the reaction equation is as follows:

[0040]

[0041] (1) In a 500mL three-neck flask, under nitrogen protection, add compound M1 (856mg, 0.1mmol) and propylamine (59mg, 0.1mmol), then add 15mL tetrahydrofuran as a solvent, react at room temperature for 12 hours, and determine by spotting Reaction process; after the reaction, the reaction mixture was put into a one-necked bottle for direct rotary evaporation, and purified by column chromatography (dichloromethane) to obtain 700 mg of a yellow-orange dark green solid, namely compound M2, with a yield of 80%;

[0042] (2) In a 500mL three-necked flask, under nitrogen protection, add compound M2 (292mg, 0.35mmol) and dichloro(phenyl)borane (0.4ml); then add 1mL of catalyst triethylamine and 30mL of Toluene, the solvent, started to heat up after the dropwise addition, and heated to 100°C for 12 hours of reactio...

Embodiment 2

[0050]

[0051] Under nitrogen protection, in a 500mL three-necked flask, add compound M3 (230mg, 0.25mmol) and 5,5'-bis(trimethyltin)-2,2'-dithiophene (58mg, 0.12mmol), and then Toluene (10 mL) was added as a solvent and tetrakis(triphenylphosphine) palladium (9 mg) was added as a catalyst. After the addition, the temperature began to rise, and the mixture was heated to 130° C. for 12 hours. After the reaction, extract with dichloromethane (DCM), while stirring silica gel powder, the crude product is purified with silica gel column (petroleum ether:dichloromethane volume ratio is 2:5). Finally, recrystallization was carried out with methanol and tetrahydrofuran to finally obtain 216 mg of dark red solid, which is the small molecule material PDIBN-DT, with a yield of 72%. 1 H NMR: (500MHz, CDCl 3 )δ9.27–9.08(m,8H),8.65(s,2H),7.71–7.54(m,10H),7.51(s,2H),7.32(s,2H),5.22(s,4H),4.56 (s,4H),2.25(d,J=8.6 Hz,8H),2.07–1.98(m,4H),1.87(d,J=14.0Hz,8H),1.54–1.03(m,44H),0.96( t, J=7....

Embodiment 3

[0053] Fabrication of battery devices

[0054] With PBDB-T (poly[[4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b']dithiophene-2, 6-diyl]-2,5-thiophenediyl[5,7-bis(2-ethylhexyl)-4,8-dioxo-4H,8H-benzo[1,2-c:4, 5-b'] dithiophene-1,3-diyl]]) and the small molecule material PDIBN-T prepared in Example 1 are blended as the battery active layer material to make an organic solar cell, and the active layer material donor PBDB- The ratio of T to acceptor PDIBN-T was 1:1.5 (w / w).

[0055] Formal device: ITO glass (indium tin oxide conductive glass) is treated with oxygen-Plasma after ultrasonic cleaning, and PEDOT:PSS (polyethylene dioxythiophene) film (thickness 40nm) is used as a hole transport layer on ITO , and then use PBDB-T and the PDIBN-T blend solution prepared in Example 1 to spin the film, which is the active layer (thickness 100nm), and anneal the active layer at 100° C. for 5 minutes. A layer of PFN (poly[9,9dioctylfluorene-9,9-bis(N,N dimethylamino-hexyl)fluorene])...

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Abstract

The invention discloses a boron-nitrogen bond-containing perylene imide photoelectric small molecular material, a preparation method and application thereof. The boron-nitrogen bond-containing peryleneimide optoelectronic small molecule material of the present invention has a LUMO energy level of -3.75V and has a wide absorption of the solar spectrum. The introduction of the boron-nitrogen bond makes the material have bipolar characteristics, and at the same time The material also has good electron mobility and hole mobility, so that the material has good photoelectric properties, can be used as a light-emitting layer or an active layer, and has broad application prospects in organic light-emitting diodes, organic field effect transistors, and organic solar cells. . The method for preparing the boron-nitrogen bond-containing perylene imide optoelectronic small molecule material is simple and convenient, the process flow is short, and it is beneficial to industrial production.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials and devices, and in particular relates to a boron-nitrogen bond-containing perylene imide optoelectronic small molecule material and its preparation method and application. Background technique [0002] Due to the advantages of light weight, low cost, flexibility and rollability, and the ability to be applied to large-area processing such as roll-to-roll, organic solar cells have attracted widespread attention in recent years and are considered to be a very promising technology among many new energy technologies. one. The active layer material of an organic solar cell plays a key role in determining the photoelectric energy conversion efficiency of the cell. Active layer materials can be divided into electron transport materials and hole transport materials according to the types of transport carriers, which are also called electron acceptors and electron donors accordingly. [...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07F5/02H10K85/655H10K85/657H10K30/00H10K50/00H10K2102/00H10K2102/301Y02E10/549Y02P70/50
Inventor 黄飞王仕亮刘熙曹镛
Owner SOUTH CHINA UNIV OF TECH
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