Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof

A technology of grafting perylene diimide and perylene diimide, which is applied in organic chemistry, semiconductor/solid-state device manufacturing, electric solid-state device, etc., to achieve good solubility, improve electron affinity, and simple synthesis method

Active Publication Date: 2020-02-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0003] The object of the present invention is to provide a kind of hydroxyquinoline-based metal organic small molecule complex material grafted with perylene diimide and aromatic group for the current organic semiconductor materials

Method used

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  • Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof
  • Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof
  • Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 5-(3-hexyl-5-(trimethyltin)thiophen-2-yl)-8-hydroxyquinoline (F)

[0032] (1) Under nitrogen atmosphere, add compound A (7-fluoro-8-hydroxyquinoline) (1.5g, 10.0mmol), iron powder (10.0mg, 0.18mmol) and 50mL of chloroform into a 150mL three-necked flask, Cool in an ice-water bath; add 5 mL of liquid bromine (3.3 g, 21.0 mmol) / chloroform mixed solution dropwise, and the temperature in the bottle does not exceed 5°C during the dropwise addition. After the reaction was completed, it was filtered and recrystallized from chloroform to obtain light yellow solid B (5-bromo-7-fluoro-8-hydroxyquinoline) (1.6 g, yield 72%).

[0033]

[0034] (2) Under nitrogen atmosphere, add compound B (1.3g, 6.0mmol), compound C (2.0g, 6.0mmol), catalyst Pd (PPh 3 ) 4 (0.19g, 0.17mmol), then add 100mL tetrahydrofuran as a solvent, and react at 105°C for 12h. Post-treatment: when the reaction mixture is put into a single-necked bottle, it is mixed with silica gel powder for ...

Embodiment 2

[0041] 5-(2-(N,N'-bis(n-tridecyl)-1,4,5,8-tetraketoneperylenediimide)-4-hexylthiophene)-7-fluoro-8-hydroxyl Preparation of quinoline (M1)

[0042] (1) Under nitrogen atmosphere, add compound F (1.19g, 2.5mmol) and compound G (N,N'-bis(n-tridecyl)-2-bromo-1,4,5 , 8-tetraketone perylene diimide) (2.08g, 2.5mmol), catalyst Pd (PPh 3 ) 4 (0.06g, 0.05mmol), then added toluene (100mL), heated to 105°C for 12 hours. Post-treatment: when the reaction mixture is put into a single-necked bottle, it is mixed with silica gel powder for rotary evaporation, and then purified through a column with a silica gel column (the eluent is selected petroleum ether: dichloromethane is 2:1 (v / v)), to obtain Yellow solid compound H (5-(2-(N,N'-bis(2-octyldodecyl)-1,4,5,8-tetraketoneperylenediimide)-4-hexylthiophene) -7-fluoro-8-hydroxyquinoline) (2.00 g, 75% yield).

[0043]

[0044] (2) Under nitrogen atmosphere, add compound H (1.60g, 1.5mmol) and I to a 250mL two-necked bottle 2 (0.46g, 1.8...

Embodiment 3

[0047] 5-(2-(N,N'-bis(2-hexyldecyl)-1,4,5,8-tetraketone perylenediimide)-4-hexylthiophene)-7-fluoro-8-hydroxyl Preparation of quinoline (M2)

[0048] (1) Under nitrogen atmosphere, add compound F (1.19g, 2.5mmol) and compound I (N,N'-bis(2-hexyldecyl)-2-bromo-1,4,5 , 8-tetraketone perylene diimide) (2.30g, 2.5mmol), catalyst Pd (PPh 3 ) 4 (0.06g, 0.05mmol), then added toluene (100mL), heated to 105°C for 12 hours. Post-treatment: when the reaction mixture is put into a single-necked bottle, it is mixed with silica gel powder for rotary evaporation, and then the column is purified with a silica gel column (the eluent is selected petroleum ether: dichloromethane is 2:1 (v / v)), Compound J (5-(2-(N,N'-bis(2-octyldodecyl)-1,4,5,8-tetraketoneperylenediimide)-4-hexylthiophene was obtained as a yellow solid )-7-fluoro-8-hydroxyquinoline) (2.07 g, 72% yield).

[0049]

[0050] (2) Under nitrogen atmosphere, add compound J (1.72g, 1.5mmol) and I to a 250mL two-necked bottle 2 (...

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Abstract

The invention discloses a hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, a preparation method and applications thereof.According to the invention, the hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups is obtained through a Stille coupling reaction and a metal coordination reaction; the metal organic small molecule cooperation compound belongs to branched small molecules, the structure of the metal organic small molecule cooperation compound uses a metal as a core, and a branched chain contains hydroxyquinoline and a perylene diimide and electron-donating aromatic group unit; hydroxyquinoline has high electron withdrawing capacity, the grafted perylene diimide unit is beneficial to improving the crystallization capacity and the electron affinity of small molecules, the electron donating capacity is enhanced by linking the electrondonating aromatic group to the perylene diimide unit, and the push-pull electron effect is easily formed with the hydroxyquinoline; and the structure small molecule and the polymer donor form energylevel matching, so that the structure small molecule is suitable for being used as a small molecule acceptor material.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to the synthesis of hydroxyquinoline-based metal organic small molecule complex materials grafted with perylene diimide and aromatic groups, and to the application of such materials in organic field effect transistors, organic solar energy Applications in the field of organic light-emitting technologies such as batteries and organic electroluminescence. Background technique [0002] With the development of social population, the human demand for traditional petrochemical energy such as oil and coal is increasing day by day. In order to solve the gap in energy demand and measure the impact on the ecological environment at the same time, academia and industry have turned their attention to renewable solar energy, that is, using solar cells to directly convert solar energy into electricity. However, although silicon-based solar cells have achieved high efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/16H01L51/42H01L51/46
CPCC07D495/16H10K85/324H10K30/00Y02E10/549
Inventor 应磊李康钟知鸣黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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