An organic small molecule luminescent material and an organic electroluminescent device prepared therefrom

A technology of electroluminescent devices and luminescent materials, which is applied in the direction of luminescent materials, electric solid devices, electrical components, etc., can solve the problems of large CIE chromaticity coordinate y value, etc., and achieve good reproducibility, high device efficiency, and easy purification Effect

Active Publication Date: 2018-06-29
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to the intramolecular charge transfer characteristics of thermally excited delayed fluorescent organic materials, the half-peak width of the luminescence spectrum of the material is relatively large, and the CIE chromaticity coordinate y value of the electroluminescent device made of thermally excited delayed fluorescent organic materials is usually large, so More stable and efficient blue light materials need to be further developed

Method used

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  • An organic small molecule luminescent material and an organic electroluminescent device prepared therefrom
  • An organic small molecule luminescent material and an organic electroluminescent device prepared therefrom
  • An organic small molecule luminescent material and an organic electroluminescent device prepared therefrom

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Experimental program
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Effect test

Embodiment 1

[0028] This embodiment P 1 The preparation comprises the following preparation steps:

[0029] m 1 Synthesis of 2-aminobenzoic acid methyl ester (50mmol, 7.588g) was dissolved in 100ml of THF, cooled to 0°C, and then methylmagnesium bromide (3.0M in THF, 66.6mL, 200mmol) was added dropwise, Reaction 24h. After the reaction was completed, THF was removed with a rotary evaporator, extracted with dichloromethane, and 6.19 g of a brown liquid was obtained after column separation, with a yield of 82%. 1 HNMR (500MHz, CDCl 3 , δ, ppm): 7.0-7.15 (m, 2H), 6.5-6.7 (m, 2H), 3.2-4.2 (s, 2H), 1.5-1.6 (s, 6H). The above reaction is shown in the following formula:

[0030]

[0031] m 2 Synthesis of: under the protection of argon, 4,4'-dibromodiphenyl sulfone (10mmol, 3.76g), M 1 (20mmol, 3.02g) were dropped into a 250ml three-necked reaction flask, and 100ml of toluene was added to dissolve them. After dissolving, sodium tert-butyl alkoxide (4.8g, 50mmol), tri-tert-butylphosphine...

Embodiment 2

[0036] This embodiment P 2 The preparation comprises the following preparation steps:

[0037] m 4 Synthesis of: under the protection of argon, 4,4'-dibromobenzophenone (10mmol, 3.4g), M 1(20mmol, 3.02g) were dropped into a 250ml three-necked reaction flask, and 100ml of toluene was added to dissolve them. After dissolving, sodium tert-butyl alkoxide (4.8g, 50mmol), tri-tert-butylphosphine (0.5ml, 1M / L) and palladium acetate (112mg, 0.5mmol) were added sequentially, and the system turned dark green. After feeding, heat to 110°C, reflux, and react for 24 hours. After the reaction was completed, the product was extracted with dichloromethane and washed with water, and 3.98 g of a yellow solid was obtained after column separation, with a yield of 83%. 1 HNMR (500MHz, DMSO, δ, ppm): 8.7-8.8 (s, 2H), 7.5-7.7 (d, 4H), 7.3-7.4 (d, 4H), 7.1-7.2 (d, 2H), 6.9-7.1 ( d, 2H), 5.2-5.3 (s, 2H), 1.5-1.6 (s, 12H).

[0038] m 5 The synthesis of: under the protection of argon, the M 4 (1...

Embodiment 3

[0042] This embodiment P 3 The preparation comprises the following preparation steps:

[0043] m 6 Synthesis of: under the protection of argon, 4-bromodiphenyl sulfone (10mmol, 2.97g), M 1 (20mmol, 3.02g) were dropped into a 250ml three-necked reaction flask, and 100ml of toluene was added to dissolve them. After dissolving, sodium tert-butyl alkoxide (4.8g, 50mmol), tri-tert-butylphosphine (0.5ml, 1M / L) and palladium acetate (112mg, 0.5mmol) were added sequentially, and the system turned dark green. After feeding, heat to 110°C, reflux, and react for 24 hours. After the reaction was completed, extracted with dichloromethane, washed with water, and separated by a column to obtain 3.19 g of a yellow solid with a yield of 87%. 1 HNMR (500MHz, DMSO, δ, ppm): 8.7-8.8 (s, 2H), 7.5-7.7 (d, 4H), 7.3-7.4 (d, 4H), 7.1-7.2 (d, 2H), 6.9-7.1 ( d, 2H), 5.2-5.3 (s, 2H), 1.5-1.6 (s, 12H).

[0044] m 7 The synthesis of: under the protection of argon, the M 6 (10mmol, 3.67g), 50ml of a...

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PUM

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses an organic small molecule luminescent material and an organic electroluminescence device prepared therefrom. The organic small molecule luminescent material uses 9,9-dimethyl-10-phenylacridine or 10-phenylphenoxazine as the electron-donating unit, through the 2-position of the acridine unit or the phenoxazine The 3 positions of the unit are connected with different electron-withdrawing units, and a series of new high-efficiency organic small molecule light-emitting materials are obtained. The organic small molecule luminescent material of the invention changes the charge transfer characteristics within the material, so that the luminescence peak of the luminescent material is blue-shifted, and can be used as a luminescent layer in an organic electroluminescent device with high device efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an organic small molecule luminescent material and an organic electroluminescent device prepared therefrom. Background technique [0002] After more than 20 years of development, organic light-emitting diodes have entered the stage of industrialization in terms of flat-panel display and lighting. Compared with polymers, organic light-emitting small molecules can obtain higher device efficiency and longer lifetime due to fewer preparation steps, definite structure, and easier purification, and are easier to obtain commercial applications. [0003] In traditional organic small molecule fluorescent materials, since 75% of the triplet excitons are spin-forbidden, radiative luminescence cannot occur, so only 25% of the singlet excitons can emit light, and the luminous efficiency is low. In contrast, organic phosphorescent materials based on metal c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D219/04C07D401/04C07D411/04C07D411/14C07D405/14C07D409/04C07D409/14C07D401/10C07D265/38C07D413/14C07D413/04C07D413/10C09K11/06H01L51/54
CPCC09K11/06C07D219/04C07D265/38C07D401/04C07D401/10C07D405/14C07D409/04C07D409/14C07D411/04C07D411/14C07D413/04C07D413/10C07D413/14C09K2211/1059C09K2211/1029C09K2211/1088C09K2211/1085C09K2211/1092H10K85/657H10K85/6574H10K85/6576H10K85/6572
Inventor 苏仕健高斌李祥龙彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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