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Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof

A technology of thianthrene oxide and aromatic amine is applied in the field of organic light-emitting materials to achieve the effects of simple material structure, delayed fluorescence characteristics and molecular weight determination

Inactive Publication Date: 2015-05-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through several years of research, thermally excited delayed fluorescent organic materials have made great progress, but in order to meet the requirements of light-emitting devices, more efficient and stable blue, green and red light materials need to be further developed
[0005] Up to now, most of the evaporated molecules used in thermally excited delayed fluorescence organic light-emitting devices have units such as diphenyl sulfone, thioxanthone, and triazine as the core, while organic light-emitting small molecules with thianthrene oxide as the core are not. never reported

Method used

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  • Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof
  • Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof
  • Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In this example, the preparation of thianthrene oxide-aromatic amine organic light-emitting small molecule T1, the specific synthesis route is as follows:

[0036]

[0037] Concrete preparation process is as follows:

[0038] (1) Preparation of intermediate 2-bromothianthrene (S1): The raw material thianthrene (6.5 g, 30 mmol) was put into a 250 ml three-necked reaction flask, and 60 ml of glacial acetic acid was added to dissolve it. Under the protection of argon, slowly add 1.2eq of liquid bromine (5.76g, 36mmol) dropwise. After the dropwise addition, heat to 80°C. After reacting for 5h, add 100ml of sodium bisulfite solution (1.58M) to quench the reaction , after extracting with dichloromethane, washed 3 times with saturated sodium chloride solution, added anhydrous magnesium sulfate to dry, and spin-dried with a rotary evaporator; the resulting solid was recrystallized with n-hexane to obtain 7.35 g of a white solid, the yield 83.5%. 1HNMR (600MHz, CDCl 3 , δ,...

Embodiment 2

[0042] In this example, the preparation of thianthrene oxide-aromatic amine organic light-emitting small molecule T2, the specific synthesis route is as follows:

[0043]

[0044] Concrete preparation process is as follows:

[0045](1) Preparation of intermediate 2,3,6,7-tetrabromothianthrene (S3): Put the raw material thianthrene (4.32g, 20mmol) into a 250ml three-necked reaction flask, and add 50ml of glacial acetic acid to dissolve it , under the protection of argon, slowly drop 8eq of liquid bromine (25.6g, 160mmol), after the dropwise addition, heat to 80°C, after reacting for 5h, add 150ml of sodium bisulfite solution (2M) to quench the reaction; After extracting with dichloromethane, wash 3 times with saturated sodium chloride solution, add anhydrous magnesium sulfate to dry, and spin dry with a rotary evaporator; the obtained solid is recrystallized with n-hexane to obtain 10 g of a white solid with a yield of 84%. . 1HNMR (600MHz, CDCl 3 , δ, ppm) 7.63 (s, 4H); ...

Embodiment 3

[0049] In this example, the preparation of thianthrene oxide-aromatic amine organic light-emitting small molecule T3, the specific synthesis route is as follows:

[0050]

[0051] Concrete preparation process is as follows:

[0052] (1) Prepare intermediate 2-bromothianthrene (S1) according to step (1) in Example 1;

[0053] (2) Preparation of intermediate 2-carbazolethianthrene (S5): under argon protection, intermediate S1 (2g, 6.78mmol), carbazole (1.2g, 7.14mmol), anhydrous potassium carbonate (3.3 g, 23.8mmol) and cuprous iodide (3.3g, 17mmol) into a 100ml three-necked flask, add 25ml1,3-dimethylpropylene urea (DMPU) to dissolve them, then add phase catalyst 18 crown 6 (300mg) , stirred at room temperature for 20 minutes, then heated to 180 ° C, and reacted for 24 hours; after the reaction, the inorganic salt was removed by suction filtration, then extracted with dichloromethane, washed 3 times with saturated sodium chloride solution, dried by adding anhydrous magnesiu...

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Abstract

The invention belongs to the technical field of organic luminescent materials and discloses a thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and an application thereof. The thianthrene oxide-aromatic amine organic luminescent small molecule has a structure formula as shown in the specification, wherein at least one of Ar1, Ar2, Ar3 and Ar4 is a group with an aromatic amine structure, and the rest is hydrogen. The preparation method comprises the following steps: (1) carrying out reaction on thianthrene and liquid bromine to obtain bromo-substituted thianthrene; (2) carrying out reaction on the bromo-substituted thianthrene and hydrogen peroxide to obtain bromo-substituted thianthrene oxide; and (3) carrying out reaction on the bromo-substituted thianthrene oxide and a compound with an aromatic amine structure to obtain the thianthrene oxide-aromatic amine organic luminescent small molecule. The thianthrene oxide-aromatic amine organic luminescent small molecule is good in luminescent property and can be used for preparing organic luminescent devices as a luminescent layer material.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a thianthrene oxide-aromatic amine organic luminescent small molecule and its preparation and application. Background technique [0002] After more than 20 years of development, organic light-emitting diodes have entered the industrial stage in terms of flat-panel display and lighting. Compared with polymers, organic light-emitting small molecules have fewer preparation steps, stable structures, and can be purified, so higher device efficiency can be obtained so that they can be commercially applied. [0003] Traditional organic small molecule fluorescent materials, because 75% of the triplet excitons are spin-forbidden, cannot produce radiative luminescence, so only 25% of the singlet excitons can emit light, and the luminous efficiency is low. In contrast, organic phosphorescent materials based on metal complexes such as iridium and platinum c...

Claims

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Application Information

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IPC IPC(8): C07D339/08C07D409/04C07D409/14C07D417/14C07D409/10C07D417/10C07D417/04C09K11/06H01L51/54
CPCC09K11/06C07D339/08C07D409/04C07D409/10C07D409/14C07D417/04C07D417/10C07D417/14C09K2211/1029C09K2211/1014C09K2211/1007C09K2211/1092C09K2211/1037H10K85/631H10K85/636H10K85/657H10K85/6576H10K85/6572
Inventor 苏仕健谢高瞻李云川
Owner SOUTH CHINA UNIV OF TECH
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