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2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material and preparation method thereof

A technology of oxadiazole spiro aromatic hydrocarbons and luminescent materials, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., and can solve the problems of reducing the yield rate of device products, increasing the difficulty of device manufacturing, and increasing production costs, etc. , to achieve good photoelectric performance, large steric hindrance effect, and good thermal stability

Inactive Publication Date: 2017-11-24
XINYANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the low-concentration doping mechanism can effectively suppress high-concentration aggregation quenching, the fabrication process is cumbersome and time-consuming.
In addition, in the case of low-concentration doping, the device performance is greatly affected by the concentration of the guest material, which increases the difficulty of device fabrication, reduces the yield of device products, and increases production costs.

Method used

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  • 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material and preparation method thereof
  • 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material and preparation method thereof
  • 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of 2,5-bis(2-(spiro-9,9'-oxanthrene fluorene)phenyl)-1,3,4--oxadiazole

[0039] The first step: 2,5-bis(2-bromophenyl)-1,3,4--oxadiazole

[0040] Dissolve 5.0 mL of 2-bromophenylacetyl chloride in 40 mL of tetrahydrofuran, and slowly drop it into 0.85 mL of 80% hydrazine hydrate solution in 0.85 mL of tetrahydrofuran (20 mL) through a constant-pressure low-liquid funnel at 0° C., and react for 1 hour. Then react at room temperature for 2 hours, wash with saturated sodium bicarbonate solution until alkaline, filter with suction to obtain a white solid, wash with water, and dry to obtain 2,5-bis(2-bromophenyl)-1,3,4-oxo Oxadiazole product, (yield: 91%), LC-MS (EI) m / z 380.9127 [M + ].

[0041] The second step: Synthesis of 2-spiro-9,9′-xanthene fluorenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0042] Add 2-bromo-spiro-9,9′-xanthene fluorene (0.4110g, 1.0mmol) and 50mL tetrahydrofuran into a single-necked round bottom flask, stir at low temperature ...

Embodiment 2

[0045] Example 2: Synthesis of 2,5-bis(2-(spiro-9,9'-thiaxanthene fluorene)phenyl)-1,3,4--oxadiazole

[0046] The first and second steps are the same as the first and second steps of Example 1,

[0047] The third step: 2,5-bis(2-bromophenyl)-1,3,4-oxadiazole (0.3800g, 1.0mmol), 2-spiro-9,9′-thioxanthene fluorenyl -4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.9480g, 2.0mmol), tetrakistriphenylphosphopalladium (0.2311g, 0.2mmol), potassium carbonate solution (10.0 mL, 2.0mol / L) and toluene into a three-necked round-bottomed flask, heated and stirred for 5-72 hours under nitrogen protection and light-proof conditions, and then cooled to room temperature after the reaction was evaporated and concentrated by a rotary evaporator, washed with water, Dichloromethane was extracted several times, and the organic phase was combined and dried with anhydrous magnesium sulfate; Crude product; then column chromatography, using ethyl acetate and petroleum ether as detergents, after purification...

Embodiment 3

[0048] Example 3: Synthesis of 2,5-bis(2-(spiro-9,9'-dioxathioxanthene fluorene)phenyl)-1,3,4--oxadiazole

[0049] The first and second steps are the same as the first and second steps of Example 1,

[0050] The third step: 2,5-bis(2-bromophenyl)-1,3,4-oxadiazole (0.3800g, 1.0mmol), 2-spiro-9,9′-dioxathioxanthene Fluorenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.0120g, 2.0mmol), tetrakistriphenylphosphopalladium (0.2311g, 0.2mmol), potassium carbonate solution (10.0mL, 2.0mol / L) and toluene were added to a three-necked round-bottomed flask, under nitrogen protection and light-shielding conditions, heated and stirred for 5-72 hours, and then the reaction was cooled to room temperature, evaporated and concentrated by a rotary evaporator, Washing with water and extracting with dichloromethane several times, combining the organic phases and drying with anhydrous magnesium sulfate; after drying, suction filtration under reduced pressure and washing the desiccant with dichlorometh...

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Abstract

The invention discloses a 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material and a preparation method thereof, and relates to third-generation light-emitting display materials and techniques. The 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material has a high triplet-state energy level because of the favorable electron transport performance of 2,5-diphenyl-1,3,4-oxadiazole and the excellent hole transport performance and the bulk-mass spatial steric hindrance effect of a spirocyclic aromatic hydrocarbon and the non-conjugated connection of the 2,5-diphenyl-1,3,4-oxadiazole spirocyclic aromatic hydrocarbon steric hindrance type bipolar light-emitting material; a compound is enabled to have excellent bipolar transport performance; the material is enabled to have a three-dimensional bulk-mass spatial steric hindrance effect by the introduction of a bulk-mass spirocyclic aromatic hydrocarbon functional group, can be used for greatly improving the stability of the amorphous state of the material, and therefore, can be widely used for an organic light-emitting diode. The material has the following characteristics of (1), the high triplet-state energy level, (2), high light-emitting efficiency, high thermal decomposition temperature and glass-transition temperature, (3), a bipolar transport property, (4), the three-dimensional bulk-mass spatial steric hindrance effect, and (5), a simple and easy synthesis method.

Description

technical field [0001] The present invention specifically relates to a preparation method based on the functional modification of 2,5-diphenyl-1,3,4-oxadiazole using spiro aromatic hydrocarbons, and relates to the steps and raw materials used in the preparation process of these materials . Background technique [0002] Since the pioneering work first reported by Tang et al. in 1987, organic light-emitting diodes (OLEDs) have been favored due to their light weight, wide viewing angle, high contrast, wide and cheap source of raw materials, self-illumination, large-area flexible display, and fast response. Applications are gaining increasing attention in the areas of flat panel displays and solid state lighting. However, traditional fluorescent organic light-emitting diodes are limited by a maximum internal quantum efficiency of 25% because they can only use singlet excitons to emit light, and their external quantum efficiency can only reach a maximum of 5%. Phosphorescent or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C09K11/06H01L51/54
CPCC09K11/06C07D413/14C09K2211/1048C09K2211/1007C09K2211/1092C09K2211/1088H10K85/6565H10K85/6576H10K85/6574
Inventor 赵祥华黎小胜王莉敏唐林
Owner XINYANG NORMAL UNIVERSITY
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