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Fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and preparation method and applications thereof

A fluorescent quantum and molecular material technology, applied in the field of organic semiconductor materials, achieves the effects of high fluorescent quantum efficiency, multiple options, and simple steps

Active Publication Date: 2017-02-15
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The simultaneous integration of steric functionalization and the introduction of electron acceptor units is still a challenge from the perspective of material design

Method used

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  • Fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and preparation method and applications thereof
  • Fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and preparation method and applications thereof
  • Fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] High fluorescence quantum efficiency fluorene-based donor-acceptor H-type molecular material M1, wherein: Ar 1 , Ar 2 , Ar 3 , Ar 4 is phenyl, Ar 5 , Ar 6 is p-bromooctoxybenzene, Ar 7 , Ar 8 , Ar 9 , Ar 10 is fluorenyl tertiary alcohol, Ar 11 It is 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole, and the preparation method includes the following steps:

[0053] (1) 3-Octylthiophene (5.0g, 25.5mmol) was added to 80mL of anhydrous THF, cooled to -78°C, n-butyllithium (2.4M in hexanes, 11.7ml, 28.0mmol) was slowly added dropwise, the dropwise addition was completed , stirred at -78 ° C for 1 hour, raised to room temperature and reacted for 1 hour, the reaction system was cooled to -78 ° C, and the THF solution of 2M trimethyltin chloride (9.1 g, 28.0 mmol) was added to the reaction system through a syringe for 1 After hours, the reaction was warmed to room temperature and stirred overnight. 20 mL of KF aqueous solution was added to the reactant to quenc...

Embodiment 2

[0059] High fluorescence quantum efficiency fluorene-based donor-acceptor H-type molecular material M2, wherein: Ar1 , Ar 2 , Ar 3 , Ar 4 is phenyl, Ar 5 , Ar 6 is p-bromooctoxybenzene, Ar 7 , Ar 8 , Ar 9 , Ar 10 for fluorene, Ar 11 It is 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole, and the preparation method is the same as that in Example 1, except that the fluorenyl group in Example 1 The boronate ester 5a of tertiary alcohol was replaced with boronate ester 5b of fluorene, and finally the product M2 (40%) was obtained as a yellow oil. 1 H NMR (400MHz, CDCl 3 ): δ(ppm): 8.05(s, 2H), 7.88(m, 8H), 7.70(m, 12H), 7.58(m, 10H), 7.49(d, J=8.8Hz, 8H), 7.31(m ,12H),6.83(d,J=8.8Hz,4H),3.90(t,J=6.4Hz,4H),2.26(m,4H),1.97(m,16H),1.73(m,4H),1.18 (br,124H),0.88(m,34H).0.65(m,12H). 13 C NMR (101MHz, CDCl 3 )δ158.43,152.60,152.23,151.42,151.00,143.80,141.74,141.27,140.73,140.45,140.05,138.50,136.58,135.18,131.56,128.56,127.16,126.98,126.75,126.09,125.47,125.38,124.8...

Embodiment 3

[0061] High fluorescence quantum efficiency fluorene-based donor-acceptor H-type molecular material M3, wherein: Ar 1 , Ar 2 , Ar 3 , Ar 4 is phenyl, Ar 5 , Ar 6 is p-bromooctoxybenzene, Ar 7 , Ar 8 , Ar 9 , Ar 10 for pyrene, Ar 11 It is 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole, and the preparation method includes the following steps:

[0062] (1) Compound 3 (0.5 g, 0.92 mmol), pyrene boronate 6 (0.36 g, 1.1 mmol), Pd (PPh 3 ) 4 (53mg, 0.045mmol) was added to a 150ml round bottom flask, K 2 CO 3 (10ml, 2M) and toluene (15ml) were separately purged with nitrogen for 30min before use to remove oxygen from the solution. The above solutions were poured into round-bottomed flasks, respectively, and the solution was heated to 100° C. and refluxed for 48 hours. The solution was cooled to room temperature, poured into 80 mL of deionized water, extracted with dichloromethane, the combined organic layers were washed with water and saturated brine, then dried...

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Abstract

The invention discloses a fluorenyl donor-acceptor H type molecular material with high fluorescence quantum efficiency and a preparation method and applications thereof. The bridging electron acceptor unit of Friedel-Crafts reactions of tertiary alcohol of a halogenated aryl group is taken as the bridging group; the aryl group is coupled to a chromophoric group through the halogen to form the H type molecular material, the structural formula of the molecular material is shown in the description, in the structural formula, Ar1, Ar2, Ar3, Ar4, and Ar11 individually represent an aryl group, Ar11 is an electron acceptor unit, Ar5, Ar6, Ar7, Ar8, Ar9, and Ar10 individually represent an aryl group or a non-aryl group; and SG1, SG2, SG3, and SG4 represent an aryl group or a non-aryl group. The synthesis of the material is in a modularization mode, the selection range of electron acceptor units is wide, the reaction steps are simple, the conditions are mild, and moreover, the molecular material has high thermal stability, electrochemical stability, and optical stability, and is an organic optoelectronic functional material with a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a class of high fluorescence quantum efficiency fluorenyl donor acceptor H-type molecular materials and a preparation method and application thereof. [0002] technical background [0003] Due to the advantages of low production cost, simple manufacturing process, and the ability to prepare flexible large-area devices, organic optoelectronic devices have become a hot research topic for scientists at home and abroad. Organic small molecule materials have been widely used in organic solar cells, organic electroluminescence, organic light detection, organic storage, organic lasers and other fields due to their advantages of definite structure and easy purification. Since 1993, WynbergH. et al. [Havinga1E.E., Hoeve W.ten, Wynberg H..Synthetic Metals, 1993, 299] proposed the molecular design of electron donor-electron acceptor and in 1998 Huang Wei e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06H01L51/54H01L51/46
CPCC09K11/06C07D417/14C09K2211/1007C09K2211/1011C09K2211/1051C09K2211/1092H10K85/657Y02E10/549
Inventor 解令海卞临沂刘宁郭峰宁余洋章杨仪明东黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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