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Organic small molecule luminescent material and organic electroluminescent device prepared from same

A technology of electroluminescent devices and luminescent materials, applied in 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 definite molecular weight Effect

Active Publication Date: 2016-01-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Organic small molecule luminescent material and organic electroluminescent device prepared from same
  • Organic small molecule luminescent material and organic electroluminescent device prepared from same
  • Organic small molecule luminescent material and organic electroluminescent device prepared from same

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Experimental program
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Embodiment 1

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

[0029] m 1 Synthesis of : Methyl 2-aminobenzoate (50mmol, 7.588g) was dissolved in 100ml of THF, cooled to 0°C, and methylmagnesium bromide (3.0MinTHF, 66.6mL, 200mmol) was added dropwise, and reacted for 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 (0.5ml...

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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Abstract

The invention belongs to the field of organic photoelectric material technology, and discloses an organic small molecule luminescent material and an organic electroluminescent device prepared from same. The organic small molecule luminescent material uses 9,9-dimethyl-10- phenyl acridine or 10-phenyl phenoxazine as an electron providing unit, and is connected with a different electron withdrawing unit at 2-site of the acridine group or the 3-site of the phenoxazine group to obtain a series of novel efficient organic small molecule luminescent materials. The organic small molecule luminescent material can change the characteristic of intramolecular charge transfer in the material, can make the luminescence peak of the luminescent material has a blue-shift, can be used as a luminescent layer for the organic electroluminescent device, and has a 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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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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