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Compound containing carbazole unit and use thereof

A technology for carbazole units and compounds, which is applied in the field of compounds containing carbazole units, and can solve problems such as poor performance, poor compound planarity, and weak self-assembly ability.

Active Publication Date: 2018-04-17
HEBEI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still big problems with the existing carbazole compounds: the poor planarity of the compound leads to its weak self-assembly ability, which makes it low in mobility / conductivity when used as a hole transport material, resulting in The poor performance of hole transport materials in the above-mentioned devices greatly limits the application of carbazole compounds in the above-mentioned devices (Adv.Mater., 2014, 26, 6629-6634; Chem.Commun., 2014 ,50,14161-14163)

Method used

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  • Compound containing carbazole unit and use thereof
  • Compound containing carbazole unit and use thereof
  • Compound containing carbazole unit and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of hole transport material compound 16 (in its structural formula, R1=R2=CH3, R3=benzene ring, R4=benzene ring)

[0030]

[0031] In a 100mL one-mouth bottle, add 1.00g (5.99mmol) carbazole, dissolve it with tetrahydrofuran, place the one-mouth bottle in an ice bath and avoid light, then dissolve 2.67g (15mmol) NBS with tetrahydrofuran and pour it into constant pressure The dropping funnel was slowly dropped into a 100mL single-necked bottle, and stirred in an ice bath under the protection of nitrogen for 4h. The reactant was poured into 100mL water, extracted three times with ethyl acetate, the obtained liquid was spin-dried, and column chromatography was carried out with ethyl acetate:petroleum ether=1:200 to obtain 1.56g (4.8mmol) white solid, compound 2, yield 80%. 1 H NMR (500Hz, CDCl 3 )δ8.16 (s, 2H), 8.09 (s, 1H), 7.55 (d, J = 8.5Hz, 2H), 7.33 (d, J = 8.5Hz, 2H).

[0032]

[0033] In a 250mL single-necked bottle, add 3.35g (10.31mmol)...

Embodiment 2

[0050] Example 2 Synthesis of hole transport material compound 24 (in its structural formula, R1=OC8H17, R2=CH3, R3=benzene ring, R4=benzene ring)

[0051]

[0052] In a 250mL single-necked bottle, add 3.35g (10.31mmol) of compound 2, 6.19g (24.76mmol) of compound 17, 5.66g (41.01mmol) of sodium carbonate, 14mL of water, 26mL of ethanol, then add 30mL of solvent toluene, and then bubble for 30min Remove oxygen, then add 0.3g (0.26mmol) tetrakistriphenylphosphine palladium, reflux and stir at 80°C for 12h under the protection of nitrogen, add 20mL of dichloromethane after cooling, wash the organic phase with ice water 3 times, wash with anhydrous sodium sulfate After drying, the filtrate was filtered and evaporated to obtain a crude product, which was subjected to column chromatography with ethyl acetate:petroleum ether=1:200 to obtain 4.32 g (7.5 mmol) of compound 18 with a yield of 73%. 1 H NMR (500Hz, CDCl 3 )δ8.27(s,2H),8.06(s,1H),7.63(d,J=8.5Hz,6H),7.47(d,J=8.5Hz,2H),7...

Embodiment 3

[0065] Example 3 Synthesis of hole transport material compound 28 (wherein R1=OC8H17, R2=CH3, R3=benzene ring, R4=thiophene ring)

[0066]

[0067] In a 100mL single-necked bottle, add 3.84g (30mmol) of compound 25, 3.14g (10mmol) of compound 12, add 4mL of 2mol / L potassium carbonate, add 60mL of tetrahydrofuran, then bubble for 30min to remove oxygen, then add 0.1g (0.09 mmol) tetrakistriphenylphosphine palladium, reflux and stir at 80°C for 12h under the protection of nitrogen, add ethyl acetate 20mL after cooling, wash the organic phase with ice water 3 times, dry with anhydrous sodium sulfate, then filter and evaporate the filtrate to obtain the crude product , Column chromatography was performed with ethyl acetate:petroleum ether=1:100 to obtain 2.36g of compound 26 with a yield of 73%. 1 H NMR (500Hz, CDCl 3 )δ8.18 (s, 3H), 7.78 (d, J = 2.5Hz, 3H), 7.51 (d, J = 2.5Hz, 3H), 7.23 (t, J = 2.5Hz, 3H).

[0068]

[0069] In a 100mL one-mouth bottle, dissolve 2.36g of t...

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Abstract

The invention discloses a compound containing a carbazole unit and a use thereof. The carbazole compound has a structure represented by formula (I): (img file='re-DDA0001591266690000011.TIF' wi='1229'he='1359' / ), in the formula (I), R1 is a C1-C12 hydrocarbon group or a C1-C12 alkoxy group or a C4-C20 heterocyclic group, wherein a hetero-atom in the heterocyclic group is N or S or O; R2 is a C1-C12 hydrocarbon group; and R3 and R4 are the same or different aromatic hydrocarbon groups or heterocyclic aromatic hydrocarbon groups. The carbazole compound disclosed by the invention can be used asa hole transport material in perovskite solar cells, organic small molecule solar cells, electroluminescent devices and other photoelectric devices.

Description

technical field [0001] The present invention relates to an organic compound, in particular to a compound containing a carbazole unit and its application. Background technique [0002] With the development of society, mineral resources such as coal, oil and natural gas are increasingly depleted, and the resulting energy crisis and environmental pollution have become urgent problems to be solved. People urgently need to find other new alternative energy sources. Organic thin-film solar cells, such as dye-sensitized solar cells, perovskite solar cells, and organic small molecule solar cells, have potential practical value due to their low cost. Among the above-mentioned photovoltaic devices, perovskite solar cells and organic small molecule solar cells are the hotspots of current research, among which perovskite solar cells are rapidly becoming the most promising new technologies due to their high photoelectric conversion efficiency which is almost comparable to that of inorga...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/54
CPCC07D519/00H10K85/655H10K85/6572Y02E10/549
Inventor 刘博张晓敏张凤玉王亚军
Owner HEBEI NORMAL UNIV
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