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Organic electrogenerated orange red light-emitting material and preparation method thereof

An orange-red light and organic technology, applied in the field of organic electroluminescent materials, can solve the problems of low luminous efficiency, shortened device life, difficult to achieve accurate quantitative dye doping, etc., to achieve stable luminous color, good thermal stability, Effects of avoiding phase separation and interface degradation

Active Publication Date: 2014-05-14
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the performance of the device has been improved, due to the large number of OLED layers, the manufacturing process is complicated, the lighting voltage is high, and the luminous efficiency is low.
There is also a plan to use a single-emitting layer doping structure, but the concentration of dye doping is difficult to quantify accurately, and the phase separation and interface degradation caused by doping will reduce the service life of the device

Method used

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  • Organic electrogenerated orange red light-emitting material and preparation method thereof
  • Organic electrogenerated orange red light-emitting material and preparation method thereof
  • Organic electrogenerated orange red light-emitting material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of an organic electroluminescent orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 10% of the total molar weight of the polymer (x=0.1)

[0027] 1) Synthesis of 2,7-dibromo-9,9-dioctylfluorene

[0028]

[0029] Add 200mL of dimethyl sulfoxide and 14g of 2,7-dibromofluorene into a three-necked flask, stir to dissolve 2,7-dibromofluorene, raise the temperature to 75°C, add 0.12g of tetrabutylammonium bromide, 50wt% hydrogen Sodium oxide solution 50mL, stir to dissolve completely, add 1-bromooctane 20g, stir and react for 24h to obtain a mixed solution;

[0030] Dilute the mixed solution with 100 mL of ethyl acetate, wash with deionized water 3 times, add 50 mL of water each time, stir and wash for 25 min, and extract to obtain a light yellow organic phase solution;

[0031] Add 30 g of desiccant anhydrous magnesium sulfate to the light yellow solution, stir for 25 minutes, and filter to obtain a light yellow liquid;...

Embodiment 2

[0052] Example 2: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 5% of the total molar weight of the polymer (x=0.05)

[0053] In a three-necked flask, 0.9 mmol (0.494 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.1mmol (0.050g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0054] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain an orange-red solid; add 200mL of 2mol / L hydrochloric acid solution to the orange-red solid, stir, then add 50mL of chloroform, extract, collect the or...

Embodiment 3

[0056] Example 3: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 1% of the total molar weight of the polymer (x=0.01)

[0057] In the three-necked flask, 0.98 mmol (0.537 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.02mmol (0.010g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0058] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain a dark red solid; add 200mL of 2mol / L hydrochloric acid solution to the dark red solid, stir, then add 50mL of chloroform, extract, collect the org...

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Abstract

The invention discloses an organic electrogenerated orange red light-emitting material and a preparation method thereof. The organic electrogenerated orange red light-emitting material has a general structural formula shown in the patent specification, wherein x is in a range of 0.01 to 0.5. The preparation method comprises the following steps that 2,7-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene, 2,7-dibromo-9,9-dioctylfluorene and 2,7-di(5-bromo-2-thienyl)-9-fluorenone are mixed according to a mole ratio of 100: (0 to 98): (2 to 100); and the mixture is added with tetrakis(triphenylphosphine)palladium and methyl trioctyl ammonium chloride and then undergoes a reaction in toluene and a sodium carbonate solution having the content of 2mol / L at a temperature of 60 to 120 DEG C in a nitrogen protective atmosphere under the conditions of backflow and stirring to produce the organic electrogenerated orange red light-emitting material. A device prepared from the organic electrogenerated orange red light-emitting material and having a structure of ITO / PEDOT / the organic electrogenerated orange red light-emitting material / Ca / Al has an electrogenerated orange red light-emitting characteristic. In an electrogenerated light-emitting spectrum of the organic electrogenerated orange red light-emitting material, an obvious orange red light peak exists.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic electroluminescent material, in particular to an electroluminescent polymer material capable of emitting orange-red light, and a preparation method of the organic electroluminescent material. Background technique [0002] Organic electroluminescent device (OLED) is a new type of flat display device, which has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight and thin thickness. [0003] In 1990, Burroughs et al. at the University of Cambridge reported the electroluminescence of poly(p-phenylene vinylene) (PPV) for the first time. Due to the characteristics of simple process and easy realization of large-screen display and flexible display, people have become more interested in electroluminescent polymer materials and devices, and a series of in-depth res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C08G61/12
Inventor 许并社徐阳武钰铃王华苗艳勤高志翔许慧侠
Owner TAIYUAN UNIV OF TECH
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