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Organic optoelectronic material with indeno-phenanthroline structure and preparing method and application thereof

An organic photoelectric material, indenophenanthroline technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of rare electron transport materials, achieve good industrialization prospects, high glass transition Effect of temperature and high thermal stability

Active Publication Date: 2016-09-07
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although there are many electron transport materials for organic light-emitting devices, there are not many electron transport materials that can meet the above conditions.

Method used

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  • Organic optoelectronic material with indeno-phenanthroline structure and preparing method and application thereof
  • Organic optoelectronic material with indeno-phenanthroline structure and preparing method and application thereof
  • Organic optoelectronic material with indeno-phenanthroline structure and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1: Preparation of the aforementioned compound E01

[0074] Preparation of intermediate one (a):

[0075]

[0076] At -78°C and under the protection of nitrogen, take 67.6g of 4,7-dibromophenanthroline (200.0mmol) and disperse it in 500g of tetrahydrofuran, then add dropwise 176mL of 2.5mol / L containing n-butyl Lithium n-hexane solution, after the dropwise addition, keep it warm for 2.0 hours, then add 33.0g of trimethylchlorosilane dropwise at -78°C, keep it warm for 2.0 hours after the drop, and then slowly warm the reaction system to room temperature , then poured the system into 200g of water, stirred and reacted for 30min, then added 500g of ethyl acetate for extraction, the system was layered, washed with water, and finally the organic phase was desolvated under reduced pressure until there was no fraction, and 64.7g of intermediate- (a), without further purification.

[0077] Preparation of intermediate one (b):

[0078]

[0079] At -78°C and unde...

Embodiment 2

[0099] Example 2: Preparation of the aforementioned compound E26

[0100] The preparation of intermediate two (a):

[0101]

[0102] At -78°C and under the protection of nitrogen, 52.1 g of 4-bromodibenzofuran (211.0 mmol) was dispersed in 400 g of tetrahydrofuran, and then 93 mL of n-butyllithium containing 2.5 mol / L was added dropwise. After the addition of the n-hexane solution is complete, keep it warm for 2.0 hours, and then slowly raise the temperature to -10°C for storage until use.

[0103] Take 32.5g of intermediate one (c) (100.0mmol) and dissolve it in 300g of tetrahydrofuran, add the above-mentioned phenyllithium solution dropwise at -10°C, keep the reaction for 2.0 hours after dropping, and then slowly raise the temperature of the reaction system to room temperature , and then poured the system into 200g of water, stirred and reacted for 30min, then added 500g of dichloromethane for extraction, the system was layered, washed with water, and dried over anhydrou...

Embodiment 3

[0122] Example 3: Preparation of the aforementioned compound E38

[0123] Preparation of intermediate three (a):

[0124]

[0125] At -78°C and under the protection of nitrogen, take 16.6g of bromobenzene (105.0mmol) and disperse it in 150g of tetrahydrofuran, then add dropwise 47mL of n-hexane solution containing n-butyllithium with a concentration of 2.5mol / L, dropwise After the addition, keep the reaction for 2.0 hours, and then slowly raise the temperature to -10°C for storage until use.

[0126] Take 24.5g of intermediate bis(a) (50.0mmol) and dissolve it in 120g of tetrahydrofuran, add the above-mentioned phenyllithium solution dropwise at -10°C, keep the reaction for 2.0 hours after dropping, and then slowly raise the temperature of the reaction system to room temperature , and then poured the system into 150g of water, stirred and reacted for 30min, then added 300g of dichloromethane for extraction, the system was layered, washed with water, and dried over anhydrou...

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Abstract

The invention discloses an organic optoelectronic material with the indeno-phenanthroline structure and a preparing method and application thereof, and belongs to the technical field of organic optoelectronic materials. The organic optoelectronic material has the molecular structure shown in the formula I (please see the specification), wherein R1 and R2 are one of hydrogen, phenyl and dibenzofuran, R3 is one of hydrogen, phenyl, polycyclic conjugation aryl with the 10-60 carbon number and aromatic heterocyclic radical containing N, S and O atoms. As the organic optoelectronic material contains the indeno-phenanthroline structure, the larger rigid flat structure is formed, the high electron mobility and the large electron affinity are provided, and transmission of injected electrons is greatly improved.

Description

technical field [0001] The invention relates to an organic photoelectric material containing an indenophenanthroline structure and a preparation method and application thereof, belonging to the technical field of organic photoelectric materials. Background technique [0002] In recent years, organic light emitting diodes (organic light emitting diode, OLED) have become a very popular emerging flat-panel display at home and abroad, because OLED displays have self-illumination, wide viewing angle (up to 175°C or more), short response time, high luminous efficiency, Wide color gamut, low operating voltage (3-10V), thin panel, large-size and flexible panel can be produced, and simple manufacturing process, and it has the potential of low cost. It is considered to be the star of the next generation of ultra-thin flat panel display devices. Although many research institutions and companies around the world have invested a lot of energy in the research and development of organic e...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1011H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 林存生孙晟源张善国付文岗胡葆华许琰
Owner VALIANT CO LTD
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