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1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material, preparation method and applications thereof

A technology of hole transport materials and cyclohexane groups, which is applied in the preparation of amino hydroxyl compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of poor thermal stability and low HOMO value, and achieve high yield , good solubility, high glass transition temperature and thermal stability

Inactive Publication Date: 2017-04-19
VALIANT CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] TAPC (1,1-bis[4-[N,N-bis(p-tolyl)amino]phenyl]cyclohexane) is a good hole transport material with very high transport capacity; but unfortunately Because of its poor thermal stability, the glass transition temperature is only 78°C (Adv Mater, 1993, 5:662); and for perovskite materials, the HOMO value of TAPC is low

Method used

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  • 1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material, preparation method and applications thereof
  • 1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material, preparation method and applications thereof
  • 1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material, preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation of embodiment one compound 1

[0065] The reaction scheme is as follows:

[0066]

[0067] Add 2.66g (0.01mol) 1,1-bis(4-aminophenyl) cyclohexane, 9.75g (0.045mol) 2,4-dimethoxybromobenzene, 5.60g (0.05mol) Potassium tert-butoxide, 53.2 g toluene. Add 0.366g (4.0×10 -4 mol)Pd 2 (dba) 3 , 0.232g (8.0×10 -4 mol)(t-Bu) 3 PH·BF 4 , the temperature was raised to 100° C. to 108° C. for reflux reaction for 8 hours. After the reaction was completed, the reaction liquid was filtered, and the filter cake was rinsed with 20 g of toluene. The filtrate was passed through a silica gel column, and the solvent was removed under reduced pressure to obtain a reddish-brown viscous liquid. The above crude product was recrystallized by THF and toluene (mass ratio 3:3) to obtain 6.1 g of off-white solid, yield: 74.9%. LC-MS: [M] + = 691.46. 1 H-NMR(500MHz,d6-DMSO)δ / ppm: 7.15~7.18(d,4H),6.65~6.67(d,4H),6.51~6.53(d,4H),6.40~6.45(m,8H), 3.93(s,24H), 2.14~2.17(t,4H...

Embodiment 2

[0068] The preparation of embodiment two compound 2

[0069] The reaction scheme is as follows:

[0070]

[0071] Add 3.00g (0.011mol) 1,1-bis(4-aminophenyl) cyclohexane, 11.00g (0.051mol) 3,4-dimethoxybromobenzene, 6.32g (0.056mol) to a 250mL three-necked flask Potassium tert-butoxide, 60.0 g toluene. Add 0.412g (4.5×10 -4 mol)Pd 2 (dba) 3 , 0.261g (9.0×10 -4 mol)(t-Bu) 3 PH·BF 4 , the temperature was raised to 100° C. to 108° C. for reflux reaction for 8 hours. After the reaction was completed, the reaction solution was filtered, and the filter cake was rinsed with 25 g of toluene. The filtrate was passed through a silica gel column, and the solvent was removed under reduced pressure to obtain a reddish-brown viscous liquid. The above crude product was recrystallized through THF and toluene (mass ratio 3:3) to obtain 6.9 g of off-white solid, yield: 75.2%. LC-MS: [M] + = 691.46. 1 H-NMR(500MHz,d6-DMSO)δ / ppm: 7.15~7.17(d,4H),6.73~6.76(d,4H),6.65~6.67(d,4H),6.17~...

Embodiment 3

[0072] The preparation of embodiment three compound 3

[0073] The reaction scheme is as follows:

[0074]

[0075]Add 2.41g (9.0×10 -3 mol) 1,1-bis(4-aminophenyl)cyclohexane, 8.84 g (0.041 mol) 3,5-dimethoxybromobenzene, 5.08 g (0.045 mol) potassium tert-butoxide, 48.2 g toluene. Add 0.331g (3.6×10 -4 mol)Pd 2 (dba) 3 , 0.210g (7.2×10 -4 mol)(t-Bu) 3 PH·BF 4 , the temperature was raised to 100° C. to 108° C. for reflux reaction for 8 hours. After the reaction was completed, 50 g of water was added to wash twice, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a brown viscous liquid. The above crude product was recrystallized through THF and ethyl acetate (mass ratio 5:5) to obtain 5.6 g of off-white powder, yield: 76.8%. LC-MS: [M] + =811.41. 1 H-NMR (500MHz,d6-DMSO)δ / ppm: 7.15~7.17(d,4H),6.65~6.67(d,4H),5.74(s,12H),3.93(s,24H),2.14~2.17( t,4H), 1.52~1.56(t,6H).

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Abstract

The present invention discloses a 1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material, a preparation method and applications thereof, and belongs to the technical field of perovskite solar cells, wherein the 1,1-bis(4'-aminophenyl)cyclohexane group-containing hole transport material has a structure represented by a formula 1, R is represented by a formula 2 or formula 3 or formula 4 or formula 5 or formula 6 or formula 7 or formula 8 or formula 9 or formula 10. The invention further discloses a preparation method and applications of the hole transport material. According to the present invention, the hole transport material is easy to prepare and refine, has characteristics of high yield and good solubility, is easily dissolved in common organic solvents, has high HOMO energy level, can be well matched to the energy level of the perovskite material, further has characteristics of high hole mobility, high glass transition temperature and high thermal stability, and easily forms the good amorphous film.

Description

technical field [0001] The invention relates to a hole transport material containing 1,1-bis(4-aminophenyl)cyclohexane group, a preparation method and application thereof, and belongs to the technical field of perovskite solar cells. Background technique [0002] With the growth of the world's population and the increasing development of industry, global warming and the exhaustion of fossil energy, it is imminent for human beings to develop clean and renewable new energy sources. Among various new energy technologies, solar photovoltaic power generation is undoubtedly one of the most promising directions. Although traditional silicon-based solar cells have achieved industrialization and the market is relatively mature, their cost performance cannot compete with traditional energy sources, and the pollution and energy consumption problems in the manufacturing process have affected their wide application. Therefore, it is necessary to research and develop new solar cells with...

Claims

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Application Information

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IPC IPC(8): C07C217/92C07C213/02C07C217/94C07D319/18H01L51/42H01L51/46
CPCC07C213/00C07C213/02C07C213/08C07C217/92C07C217/94C07D319/18H10K85/631H10K85/6574H10K30/00Y02E10/549
Inventor 胡臻玉任辉彩曹原庞茂印陈帅田绍振王永磊罗伟胡葆华孟凡民
Owner VALIANT CO LTD
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