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Spiro-di-thioxanthene-based small-molecule luminescent material and preparation and application thereof

A technology of light-emitting materials and thiaxanthene, which is applied in the fields of light-emitting materials, semiconductor/solid-state device manufacturing, electrical components, etc., to achieve the effects of good reproducibility, easy purification, and single material structure

Inactive Publication Date: 2015-12-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, although there have been many reports on light-emitting materials for organic electroluminescent devices, there are few reports on small organic light-emitting molecules with a spiro-bisthiaxanthene structure as the core.

Method used

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  • Spiro-di-thioxanthene-based small-molecule luminescent material and preparation and application thereof
  • Spiro-di-thioxanthene-based small-molecule luminescent material and preparation and application thereof
  • Spiro-di-thioxanthene-based small-molecule luminescent material and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of a spiro-bisthiaxanthene-based small molecule luminescent material P1 in this example:

[0034] Synthesis of 2-bromodiphenylsulfide: o-bromoiodobenzene (50mmol, 14.3g), diphenyldisulfide (16.625mmol, 3.40g), Cu 2 S(1.194g), Fe(1.05g), K 2 CO 3 (8.625g) was dissolved in 125ml of DMSO, heated to 120°C overnight to obtain 2-bromodiphenylsulfide (3.84g), yield 93%. 1 HNMR: 7.55-7.59 (m, 1H), 7.36-7.48 (m, 5H), 7.13-7.18 (m, 1H), 7.01-7.07 (m, 1H), 6.92-6.96 (m, 1H). The reaction equation is as follows:

[0035]

[0036] For the synthesis of 2,7-dibromothioxanthone, refer to the publication specification of the invention patent application (CN200910048908.9), its structural formula and synthetic route are shown in the following formula, and the synthesis of intermediate M2, its structural formula and synthetic route are shown in the following formula:

[0037]

[0038] Preparation of the above compound 2: KOH (5.45 g, 97.3 mmol) and 60 ml of water wer...

Embodiment 2

[0044] Preparation of a spiro-bisthiaxanthene-based small molecule luminescent material P2 in this example:

[0045] The synthesis of P2, its structural formula and synthetic route are shown in the following formula:

[0046]

[0047]Dissolve 2.2gP1 in 30ML of dichloromethane, add 12ML of acetic acid and 3.0ml of 30% hydrogen peroxide, and react overnight at 80°C. After the reaction is complete, extract with dichloromethane, dry with anhydrous magnesium sulfate, and load the solid as a sample. Petroleum ether: dichloromethane = 2:1 through the column, 2.3g of white solid was isolated. Yield 88%. 1 HNMR: 8.22 (dd, J=8.1, 1.1 Hz, 1H), 7.54-7.46 (m, 1H), 7.42-7.34 (m, 1H), 7.04 (d, J=8.2 Hz, 1H).

Embodiment 3

[0049] Preparation of a spiro-bisthiaxanthene-based small molecule luminescent material P5 and P6 in this example:

[0050] Synthesis of intermediates M4, M5:

[0051]

[0052] The synthesis method of M4 is as in Example 1. Add compound 1 (2.65g, 100mmol) into a low-temperature reaction flask, dissolve it in 60mlTHF, and protect it with nitrogen gas. After sealing the device, add liquid nitrogen to cool to -78°C, and add dropwise within 30min. Butyllithium (1.6Minhexanes, 70mL, 110mmol) was incubated for 40min, then 2.21g of 3,7-dibromothioxanthone in THF was added in one go, and reacted overnight at room temperature. After the reaction is complete, THF is removed with a rotary evaporator, extracted with dichloromethane, and the product alcohol M3 is separated by a column. The product M3 was added with 20ml of acetic acid and an appropriate amount of hydrochloric acid, under nitrogen protection, stirred at 80°C overnight, and separated by column to obtain 0.83g of white so...

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PUM

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a spiro-di-thioxanthene-based small-molecule luminescent material and preparation and application thereof. With spiro-di-thioxanthene nucleuses as framework units, and by changing connecting units at both sides of each spiro-di-thioxanthene nucleus and the number of the spiro-di-thioxanthene nucleuses, the molecular weight, Pi conjugacy and intramolecular charge transfer properties of the small-molecule luminescent material disclosed by the invention can be regulated. A spiro-structure therein can adjust the packing method among molecules. The preparation method of the material disclosed by the invention obtains a target compound with diphenyl sulfide and thioxanthone as original reaction materials by a series of simple reactions. The material structure is uniform, and the molecular weight is determined, and the spiro-di-thioxanthene-based small-molecule luminescent material has good solubility and film-forming property in common solvents. The spiro-di-thioxanthene-based small-molecule luminescent material can be applied as a hole transport material, an electron transport material and a luminescent material in OLED (Organic Light Emitting Diode) devices to improve the performance of the devices, and has profound significance for the development of high-performance devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a spiro-bisthiaxanthene-based small molecule luminescent material and its preparation and application. Background technique [0002] In order to improve the efficiency and lifetime of organic electroluminescent devices, compared with polymers, light-emitting small molecules are more likely to be commercialized due to fewer preparation steps, stable structures, and no disadvantages of polydispersity. The preparation of multilayer devices by evaporation or solution processing of small molecules has received great attention and great progress has been made. [0003] So far, organic light-emitting diodes have made great progress. Through fluorescent phosphorescent hybridization, we can obtain white light devices with simple device structures and high efficiency. However, the efficiency of this fluorescent-phosphorescent hybrid device largely depen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D495/10H01L51/54
Inventor 苏仕健刘坤坤陈东成彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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