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Pyrrolyl group-containing compound, polymer, mixture, composition, and organic electronic device

A compound, pyrrole-based technology, applied in the fields of polymers, compositions and their organic electronic devices, mixtures, and pyrrole-containing compounds, to achieve the effects of improving luminescence performance and lifespan, high external quantum efficiency, and long device lifespan

Inactive Publication Date: 2020-11-03
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still a lot of room for improvement in terms of device stability.

Method used

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  • Pyrrolyl group-containing compound, polymer, mixture, composition, and organic electronic device
  • Pyrrolyl group-containing compound, polymer, mixture, composition, and organic electronic device
  • Pyrrolyl group-containing compound, polymer, mixture, composition, and organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0169] Synthesis of compound (3):

[0170]

[0171] synthetic route:

[0172]

[0173] 1) Synthesis of intermediate 3-3: under nitrogen atmosphere, (22.3g, 100mmol) compound 3-1, (20.4g, 100mmol) compound 3-2, (9.55g, 50mmol) cuprous iodide, (5.7 g, 50mmol) trans-cyclohexanediamine, (31.8g, 100mmol) potassium phosphate and 250mL toluene were added to a 500mL three-neck flask, heated and stirred to 110°C for 12 hours, the reaction was completed, cooled to room temperature, and the filtrate was suction filtered , most of the solvent was evaporated by rotary evaporation, and washed three times with dichloromethane dissolved in water, and the organic phase was collected and mixed with silica gel to pass through a column for purification, and the yield was 75%.

[0174] 2) Synthesis of intermediate 3-4: under nitrogen atmosphere, add (18g, 60mmol) compound 3-3 and 150mL anhydrous tetrahydrofuran into a 500mL three-necked flask, cool down to -78°C, and slowly add 60mmol n-but...

Embodiment 2

[0181] Synthesis of compound (5):

[0182]

[0183] synthetic route:

[0184]

[0185] 1) Synthesis of intermediate 5-3: According to the synthesis method of intermediate 3-3, compounds 5-1 and 5-2 were substituted for compounds 3-1 and 3-2, and the yield was 75%.

[0186]2) Synthesis of intermediate 5-4: under nitrogen atmosphere, (11.3 g, 60 mmol) of compound 5-3 and 150 mL of triethyl phosphite were added into a 250 mL three-necked flask, heated at 160° C., and reacted for 12 hours. The reaction was stopped, and the liquid in the reaction solution was distilled out with a vacuum distillation device. The remaining solid was recrystallized with dichloromethane and ethanol solution, and the yield was about 80%.

[0187] 3) Synthesis of intermediate 5-5: under nitrogen atmosphere, (6.2g, 40mmol) compound 5-4, (8.2g, 40mmol) iodobenzene, (3.8g, 20mmol) cuprous iodide, (2.3g, 20mmol) trans-cyclohexanediamine, (12.7g, 40mmol) potassium phosphate and 100mL toluene were add...

Embodiment 3

[0192] Synthesis of compound (9):

[0193]

[0194] synthetic route:

[0195]

[0196] 1) Synthesis of intermediate 9-2: according to the synthesis method of intermediate 3-3, compounds 5-1 and 9-1 were substituted for compounds 3-1 and 3-2, and the yield was 70%.

[0197] 2) Synthesis of intermediate 9-3: (12.3g, 60mmol) compound 9-2, (17g, 120mmol) phosphorus pentoxide and 60mL trifluoromethanesulfonic acid were added to a 150mL three-necked flask, stirred at room temperature for 24 hours, To finish the reaction, slowly invert the reaction solution in 300°C of ice water, filter with suction, wash the filter residue with water, aqueous sodium bicarbonate solution, and water several times, collect the filter residue, dry it, place it in 50mL of pyridine, reflux for 12 hours, and cool After reaching room temperature, most of the solvent was evaporated by rotary evaporation, and extracted three times with dichloromethane, and the organic phase was collected and mixed with...

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Abstract

The invention discloses a pyrrolyl-containing compound, a high polymer, a mixture, a composition and an organic electronic device. The pyrrolyl-containing compound contains a structure represented bya general formula (1), forms a condensed ring with other functional units through a pyrrolyl group, and is adjusted in the aspects of molecular stability and transmission performance. The pyrrolyl-containing compound disclosed by the invention is used in an OLED, particularly used as a light emitting layer material, and can provide higher device performance.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on August 8, 2019, with the application number 2019107287503, and the title of the invention is "a class of pyrrolyl-containing compounds and their applications", the entire content of which is incorporated by reference In this application. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to a class of pyrrolyl-containing compounds, high polymers, mixtures, compositions and organic electronic devices. Background technique [0003] Organic semiconductor materials have great potential for applications in optoelectronic devices such as organic light-emitting diodes (OLEDs), such as flat-panel displays and lighting, due to their structural diversity, relatively low fabrication cost, and superior optoelectronic performance. [0004] In order to improve the light-emitting performance of organic light-e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10C07D487/04C07D513/04C07D471/04C07D519/00C07D487/16C09K11/06H01L51/50H01L51/54
CPCC07D487/10C07D487/04C07D513/04C07D471/04C07D519/00C07D487/16C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1014C09K2211/1037C09K2211/1048C09K2211/1088C09K2211/1092H10K85/631H10K85/654H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/15H10K50/11
Inventor 何锐锋吴灿洁宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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