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Fluorene organic electroluminescent material and preparation method thereof

An electroluminescent material and luminescent technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems that luminescent materials cannot meet the requirements of OLED use, and achieve improved efficiency, increased yield, and high purity Effect

Active Publication Date: 2015-05-20
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the technical problem that indenofluorene light-emitting materials in the prior art cannot meet the use requirements of OLEDs, the present invention provides an indenofluorene-based organic electroluminescent material with simple preparation method, high luminous efficiency and long service life And its preparation method and application

Method used

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  • Fluorene organic electroluminescent material and preparation method thereof
  • Fluorene organic electroluminescent material and preparation method thereof
  • Fluorene organic electroluminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of compound 001

[0034] The specific synthetic route is shown in the following formula:

[0035]

[0036] Add 10.54g (10mmol) of bromostyryl indenofluorene derivatives, 6.88g (40mmol) of 2-naphthalene boronic acid, 3.18g (30mmol) of sodium carbonate, 200ml of tetrahydrofuran and 100ml of water into a three-necked flask, degas, and add four three Phenylphosphopalladium 0.12g (0.10mmol), heated to 70°C, reacted for 24 hours, cooled to room temperature, filtered with suction, washed the filter cake with water, ethanol and ether, and dried to obtain star-shaped indeno 8.96 g of fluorene olefin derivatives, the yield is more than 75%, and the HPLC purity is greater than 98%. Mass spectrum: Calculated value is 1195.61; found value is 1195.62. Elemental analysis: Calculated value: C: 93.42%; H: 6.58%; Tested value: C: 93.41%; H: 6.59%.

[0037]

Embodiment 2

[0038] Embodiment 2: the synthesis of compound 002

[0039] The specific synthetic route is shown in the following formula:

[0040]

[0041]Add 10.54g (10mmol) of bromostyrylindenofluorene derivatives, 11.07g (45mmol) of 2-pyrenylboronic acid, 3.39g (32mmol) of sodium carbonate, 200ml of tetrahydrofuran and 100ml of water into a three-necked flask, degas, and add four Triphenylphosphopalladium 0.14g (0.12mmol), heated to 72°C, reacted for 25 hours, cooled to room temperature, filtered with suction, washed the filter cake with water, ethanol and ether, and dried to obtain star-shaped indene 10.77 g of fluorene olefin derivatives, the yield is over 76%, and the HPLC purity is greater than 98%. Mass spectrum: Calculated value 1417.85; found value 1417.83. Elemental analysis: Calculated value: C: 94.03%; H: 5.97%; Tested value: C: 94.04%; H: 5.96%.

[0042]

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 003

[0044] The specific synthetic route is shown in the following formula:

[0045]

[0046] Add 10.54g (10mmol) of bromostyryl indenofluorene derivatives, 14.35g (50mmol) of N-phenylcarbazolylboronic acid, 3.60g (34mmol) of sodium carbonate, 200ml of tetrahydrofuran and 100ml of water into a three-necked flask and degas , add 0.16g (0.14mmol) tetrakistriphenylphosphopalladium, heat up to 74°C, react for 26 hours, cool to room temperature, after the solid precipitates, filter with suction, wash the filter cake with water, ethanol and ether, and dry to obtain 11.56 g of star-shaped indenofluorene olefin derivatives, the yield is over 75%, and the HPLC purity is over 98%. Mass Spectrum: Calculated value: 1541.01; Tested value: 1541.03. Elemental analysis: Calculated value: C: 91.19%; H: 6.08%; N: 2.73%; Tested value: C: 91.18%; H: 6.09%; N: 2.73%.

[0047]

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Abstract

The invention relates to an organic electroluminescent material and a preparation method thereof, and aims to solve the technical problem that the luminescent efficiency of conventional luminescent materials cannot fulfill the requirements of OLED. The novel organic electroluminescent material is prepared by introducing substituents into a base material (indenofluorene compounds). By introducing different substituents, the provided material has a better planar structure and conjugate structure compared with common indenofluorene compounds, and the luminescent peaks can be adjusted by modulating the electron transition so as to obtain the required light-blue organic electroluminescent material. The luminescent efficiency of the provided material in a diluted solution is 96%, the luminescent efficiency in film is 83%, and the results show that the indenofluorene compounds have high luminescent efficiency. Compared with 5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-diindenofluorene, the provided preparation method of indenofluorene organic electroluminescent material has the advantages of simpler synthesis and purification, and lower cost, and is capable of fulfilling the industrial development requirements. The product yield is largely improved, the product purity is high, the HPLC purity is greater than 98%, the obtained material can prominently improve the efficiency, and the film-forming property and service life of the obtained material are both improved obviously.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an indenofluorene-based organic electroluminescence material and a preparation method and application thereof. Background technique [0002] Among many organic electroluminescent materials, compounds containing indenofluorene structures are important components. Indenofluorene compounds, like fluorene, have relatively rigid structures. In addition, these compounds also have good thermal stability. , High luminous efficiency and other advantages, therefore, both thermal stability and fluorescence quantum efficiency are good, it is an ideal precursor for the development of new OLED materials. [0003] Isotriindene is an isomer of triindene. Due to the difference in structure, the benzene rings of the two compounds are directly conjugated to each other and their names are different. Traditional synthetic methods are tedious and harsh to regulate, and the yield is low,...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C13/62C07C1/32C07D209/86C07C211/54C07C209/68
Inventor 马晓宇李文军李贺张英
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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