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Triphenylene-perylene monoimide dicarboxylate binary compound and its preparation method and application

A compound, triphenylene technology, applied in the active layer field of organic solar cells, can solve the problems of liquid crystal phase transition temperature and temperature range, difficult to control, etc., and achieve the effect of easy adjustment of liquid crystal phase transition temperature and temperature range

Active Publication Date: 2020-05-15
JIANGSU HECHENG ADVANCED MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the ternary compound, the perylene diimide unit is used as a bridge to connect two triphenylene units. Since there are no other side chains on the bridge, it is difficult for the phase transition temperature and temperature range of the liquid crystal to pass through the bridge and the side chains. chain regulation

Method used

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  • Triphenylene-perylene monoimide dicarboxylate binary compound and its preparation method and application
  • Triphenylene-perylene monoimide dicarboxylate binary compound and its preparation method and application
  • Triphenylene-perylene monoimide dicarboxylate binary compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Preparation of TP6-C6-ApeDiH

[0066]

[0067] reaction steps

[0068] Compound 1, preparation of o-dihexyloxybenzene

[0069]

[0070] Catechol (20g, 0.1816mol), 1-bromo-n-hexane (89.9g, 0.5448mol), anhydrous potassium carbonate (75.3g, 0.5448mol) and potassium iodide (6.0g) in absolute ethanol (250ml) Reflux for 48 hours. Cool to room temperature and filter with suction. The filter cake was washed with acetone (150ml), filtered with suction, and repeated twice. The filtrate was concentrated, then distilled under reduced pressure, and the fraction at 149-157°C (0.7mmHg) was collected to obtain 48g of compound 1 (colorless oily liquid), with a yield of 96%. 1 H NMR (300MHz, CDCl 3 )δ:6.89(s,4H),3.99(t,4H,J=6.9Hz),1.83-1.76(m,4H,J=6.9Hz),1.49-1.31(m,12H),0.9(t,6H , J=6.9Hz).

[0071] Compound 2, Preparation of 2-hexyloxyphenol

[0072]

[0073] Catechol (50g, 0.45mol), 1-bromo-n-hexane (75g, 0.45mol), anhydrous potassium carbonate (100g, 0.725mol) and po...

Embodiment 2

[0099] Preparation of TP6-C10-ApeDiH

[0100]

[0101] The preparation of compound 2-(10'-aminodecyloxy)-3,6,7,10,11-penta(hexyloxy)triphenylene refers to the preparation of compound 7 in Experimental Example 1. The only difference is that Br(CH 2 ) 6 Br uses Br(CH 2 ) 10 Br alternative.

[0102] Compound 2-(10’-aminodecyloxy)-3,6,7,10,11-penta(hexyloxy)triphenylene 1 H NMR (300MHz, CDCl 3 )δ:7.84(s,6H),4.26-4.17(m,12H),2.67(t,2H,J=6.9Hz),2.00-1.90(m,12H),1.66-1.32(m,44H),0.94 (t, 15H, J = 6.9 Hz).

[0103] For the preparation of the compound perylenetetracarboxylic monoanhydride diester, see the preparation of compound 9 in Experimental Example 1.

[0104]

[0105] N 2 Under protected conditions, 2-(10'-aminodecyloxy)-3,6,7,10,11-penta(hexyloxy)triphenylene (0.39g, 0.435mmol), perylene monoanhydride diester (0.17g, 0.29mmol) and imidazole (10.5g) were heated to 110°C for 1 hour. Then washed with water, the crude product was purified by silica gel column (elue...

Embodiment 3

[0112] Preparation of compound TP6-C12-ApeDiH

[0113]

[0114] For the preparation method, refer to the preparation method in Example 1. The only difference is that Br(CH 2 ) 6 Br uses Br(CH 2 ) 12 Br alternative.

[0115] of the compound 1 H NMR (500MHz, CDCl 3 )δ: 8.38(d, 2H, J=10Hz), 8.19(q, 4H), 7.96(d, 2H), 7.63(t, 4H), 7.54(s, 2H), 4.27(t, 4H), 4.14 -4.05 (m, 14H), 1.89-1.81 (m, 12H), 1.77-1.66 (m, 8H), 1.33-1.29 (m, 56H), 0.88-0.83 (m, 21H).

[0116] Figure 4 is the DSC trace of compound TP6-C12-ApeDiH. During the heating process of compound TP6-C12-ApeDiH, 73.1℃ is the melting point, at which point the crystal starts to change into liquid crystal; 113.6℃ is the clearing point, at which time the liquid crystal becomes isotropic liquid; Change from isotropic liquid to liquid crystal, continue to cool down, solidify at 62.8°C, and change from liquid crystal to crystal. The used DSC thermal analyzer (model is Q600) is produced by American Thermal Analysis C...

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Abstract

The present invention provides a triphenylene-perylene monoimide diformate binary compound, which has a structure represented by a general formula I. The present invention further provides a preparation method of the triphenylene-perylene monoimide diformate binary compound, and applications of the triphenylene-perylene monoimide diformate binary compound as an organic solar cell active layer. Compared to the compound in the prior art, the compound of the present invention has advantages of easy adjustment of liquid crystal phase change temperature and temperature range, such that the compound has optical, electronic and electro-optical uses, and especially has uses as the organic solar cell active layer. The general formula (I) is defined in the specification.

Description

technical field [0001] The present invention relates to a triphenylene-perylene monoimide dicarboxylate binary compound, which has optical, electro-optical and electronic purposes, especially as an active layer of an organic solar cell. Background technique [0002] Columnar phase When the discotic liquid crystal material is in the liquid crystal phase, it is easy to self-assemble into ordered molecular columns due to the strong π-π electron interaction between the discotic nuclei. As a result, there is a higher carrier mobility along the axial direction of the molecular column (Zhao, B.; Liu, B.; Png, R.; Zhang, K.; Lim, K.; Luo, J.; Shao, J.; Ho, P.; Chi, C.; J. Chem. Mater. 2010, 22, 435-449), can be used as the modification layer and active layer of optoelectronic devices. [0003] Due to the simple preparation method, high yield and easy purification, the triphenylene liquid crystal material is the most widely studied discotic liquid crystal material. Bacher et al. re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/18C09K19/34H01L51/46
CPCY02E10/549
Inventor 孔翔飞黄达王桂霞靳灿辉谭玉东
Owner JIANGSU HECHENG ADVANCED MATERIALS
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