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Indeno[1,2-b]fluorene unit-based A-D-A conjugate micro-molecule, and application thereof in photoelectric devices

A small molecule, A-D-A technology, applied in A-D-A conjugated small molecules and its application in optoelectronic devices, to achieve excellent carrier transport and strong absorption effects

Active Publication Date: 2017-04-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of A-D-A conjugated small molecules based on such inden[1,2-b]fluorene units as donors and acceptor materials in solar cells or as electron transport materials in optoelectronic devices has not been reported yet.

Method used

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  • Indeno[1,2-b]fluorene unit-based A-D-A conjugate micro-molecule, and application thereof in photoelectric devices
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  • Indeno[1,2-b]fluorene unit-based A-D-A conjugate micro-molecule, and application thereof in photoelectric devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthetic route of A-D-A conjugated small molecule 1 based on indeno[1,2-b]fluorene unit is as follows:

[0057]

[0058] (1) Add a (1g, 1.05mmol), compound b (1.08g, 5.65mmol), tetrakis(triphenylphosphine) palladium (61mg, 0.052mmol) into a three-necked round bottom flask, and nitrogen gas for 15 minutes. Add toluene (10ml), tetrahydrofuran (2.5ml), ethanol (4ml), and 3.5ml of 2M potassium carbonate aqueous solution, heat to reflux and stir the reaction, after reacting for 15 hours, take a sample, monitor by TLC, the reaction is complete, stop heating. After being cooled to room temperature, extracted with dichloromethane, concentrated, and purified by silica gel (200-300 mesh) column chromatography, the eluent was petroleum ether / dichloromethane (2:1), to obtain intermediate c (0.67g, 70%). This preparation method was also used in Examples 2, 3, and 4 below. 1 H NMR (500MHz, CDCl 3 )δ9.91(s,2H),7.79(m,4H),7.71(dd,J=7.9,1.6Hz,2H),7.65(s,2H),7.64(d,J=1.3Hz,2H)...

Embodiment 2

[0062]

[0063] The synthesis route of A-D-A conjugated small molecule 2 based on inden[1,2-b]fluorene unit is as follows:

[0064] Add compound c (92mg, 0.1mmol) and malononitrile (66mg, 1mmol) into a two-necked round-bottomed flask, add 30ml of chloroform, blow nitrogen for 15 minutes, add 0.1ml of triethylamine, react at room temperature for 15 minutes, and monitor the reaction with TLC , after the reaction, separated and purified by column chromatography, the eluent was petroleum ether / dichloromethane (2:1~1:1), to obtain the product 2 (88mg, 87%). 1 H NMR (500MHz, CDCl 3 )δ7.81(m,4H),7.78–7.71(m,4H),7.66(s,2H),7.64(s,2H),7.54(d,J=3.3Hz,2H),2.09(m,8H ),1.20–0.95(m,40H),0.76(t,J=7.1Hz,12H),0.65(m,8H). 13 C NMR (126MHz, CDCl 3 )δ157.76,152.70,151.25,150.65,143.87,140.58,140.46,133.99,130.94,126.03,124.54,120.78,120.69,114.71,114.52,113.70,76.08,55.34,40.60,31.90,29.99,29.33,29.26,23.88,22.70 ,14.18.MS(MALDI-TOF):m / z 1018(M + ).

[0065] The UV-Vis absorption spectru...

Embodiment 3

[0067]

[0068] Add compound c (130mg, 0.14mmol) and compound 1,3-diethyl-2-thiobarbituric acid (170mg, 0.85mmol) into a two-necked round-bottomed flask, add 30ml of chloroform, blow nitrogen for 15 minutes, add 0.1ml of pyridine, heated to 65°C, stirred and reacted for 12 hours, monitored the reaction with TLC, after the reaction, separated and purified by column chromatography, the eluent was petroleum ether / dichloromethane (2:1~1:1), to obtain Product 3 (125 mg, 69%). 1 H NMR (500MHz, CDCl 3 )δ8.70 (s, 2H), 7.92 (d, J = 4.3Hz, 2H), 7.88 (dd, J = 8.0, 1.6Hz, 2H), 7.82 (d, J = 8.0Hz, 2H), 7.77 ( s,2H),7.68(s,2H),7.64(d,J=4.2Hz,2H),4.66(m,4H),4.60(m,4H),2.19–2.04(m,8H),1.40(t ,J=7.0Hz,6H),1.34(t,J=7.0Hz,6H),1.20–0.97(m,40H),0.76(t,J=7.1Hz,12H),0.73–0.59(m,8H) . 13 C NMR (126MHz, CDCl 3 )δ178.84,162.79,161.27,160.18,152.53,151.27,149.80,147.80,143.82,140.69,136.65,131.88,126.29,125.05,121.00,120.55,114.65,109.97,55.35,44.15,43.29,40.69,31.89,30.04,29.35 ,29.28,23.89,22...

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Abstract

The invention discloses an indeno[1,2-b]fluorene unit-based A-D-A conjugate micro-molecule, and an application thereof in photoelectric devices. The conjugate micro-molecule is centered on an indeno[1,2-b]fluorine unit, and adopts a conjugate unit as a bridge bond and different electron withdrawing units as end groups. The conjugate micro-molecule has good absorption and appropriate energy grade in the visible range, and can be applied to donor materials and receptor materials in organic solar cells to make the devices have a good efficiency.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to an A-D-A conjugated small molecule based on indene[1,2-b]fluorene unit and its application in photoelectric devices. Background technique [0002] With the continuous development of human society, the continuous improvement of living standards, and the rapid growth of energy demand, the global energy crisis is becoming increasingly severe. The frequent shortage of non-renewable energy such as coal and oil has made the energy problem a bottleneck restricting the development of human society and economy. Under this background, it is imminent to develop clean and renewable energy technologies. As an abundant clean energy, solar energy has great development value. Among them, as a new type of thin-film photovoltaic cell technology, organic solar cells (OPV) have outstanding advantages such as all-solid-state, highly adjustable photovoltaic material properties, flexible c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24C07D409/14H01L51/46
CPCC07D333/24C07D409/14H10K85/623H10K85/655H10K85/654Y02E10/549
Inventor 黄飞贾建超郑楠楠胡志诚曹镛
Owner SOUTH CHINA UNIV OF TECH
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