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Organic white light material with thermal activation delay and aggregation-induced emission performance and synthetic method and application thereof

A technology of aggregation-induced luminescence and thermal activation delay, applied in the field of OLED devices, can solve the problems of difficult control of host-guest ratio, complicated preparation process, etc., to overcome aggregation luminescence quenching, simple synthesis method and purification process, and high yield Effect

Active Publication Date: 2016-04-13
SUN YAT SEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this doping method has disadvantages such as complex preparation process, phase separation between host and guest, and difficulty in controlling the ratio between host and guest during vacuum evaporation.

Method used

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  • Organic white light material with thermal activation delay and aggregation-induced emission performance and synthetic method and application thereof
  • Organic white light material with thermal activation delay and aggregation-induced emission performance and synthetic method and application thereof
  • Organic white light material with thermal activation delay and aggregation-induced emission performance and synthetic method and application thereof

Examples

Experimental program
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preparation example Construction

[0042] The synthesis method of the organic white light material of the present invention, such as figure 1 shown, including the following steps:

[0043] Step one: provide fluorobenzene and 4-bromobenzenesulfonyl chloride (or 4-iodobenzenesulfonyl chloride) or 4-bromobenzoyl chloride (or 4-iodobenzoyl chloride), take dichloromethane (DCM) as solvent in three Under the catalysis of ferric chloride, fluorobenzene is connected to 4-bromobenzenesulfonyl (or 4-iodobenzenesulfonyl) or 4-bromobenzoyl (or 4-iodobenzoyl) by Friedel-Crafts reaction, and synthesized to obtain first intermediate or third intermediate.

[0044] Step 2: Provide phenothiazine, use N,N-dimethylformamide (DMF) as a solvent to react with the first intermediate or the third intermediate under the action of potassium tert-butoxide, and synthesize the corresponding second intermediate or the fourth intermediate, Ar with a phenothiazine substituent 1 The halide; the halogen element of the halide is bromine or io...

Embodiment 1

[0048] Example 1: Synthesis of 10-(4-(4-(9-phenylanthracenyl-10-yl)benzenesulfonyl)phenyl)-10H-phenothiazine

[0049] (1) Synthesis of the first intermediate 1-(4-fluorobenzenesulfonyl)-4-bromobenzene, the synthetic route is as follows:

[0050]

[0051] Add 4-bromobenzenesulfonyl chloride (5.00g, 19.69mmol) and fluorobenzene (2.84g, 29.54mmol) into a 250mL three-necked flask, dissolve in 20mL of dichloromethane, add ferric chloride (6.33g, 39.38mmol) Afterwards, the reaction solution was heated to 40° C. and stirred for 6 h. The reaction solution was cooled to room temperature, and 30 mL of dichloromethane and 50 mL of 1M dilute hydrochloric acid were slowly added successively and stirred for 10 min. layer, and dried with anhydrous sodium sulfate, suction filtered, and the obtained filtrate was spin-dried with the solvent by a rotary evaporator, and the remaining solid was vacuum-dried to obtain 5.54 g of a white powder, with a yield of 90%.

[0052] (2) Synthesizing the...

Embodiment 2

[0058] Example 2: Synthesis of 10-(4-((4-(dibenzothiophen-4-yl)phenyl)sulfonyl)phenyl)-10H-phenothiazine

[0059] Synthesize the target product 10-(4-((4-(dibenzothiophen-4-yl)phenyl)sulfonyl)phenyl)-10H-phenothiazine, the synthetic route is as follows:

[0060]

[0061] The third intermediate 10-(4-(4-bromobenzenesulfonyl)phenyl)-10H-phenothiazine (0.50g, 1.01mmol) and dibenzothiophene-4-boronic acid (0.35g, 1.52mmol) Add it into a three-neck flask, dissolve it with 30mL tetrahydrofuran (THF), add 2MK 2 CO 3 Aqueous solution 1.5mL, argon and stirred for 30min, added 0.05gPd(PPh 3 ) 4 After that, it was heated to 75°C for 16h. After the reaction solution was cooled to room temperature, 20 mL of ethanol was added and spin-dried in a rotary evaporator under vacuum. The crude product was separated and purified by silica gel column chromatography using a mixed solution of n-hexane and dichloromethane with a volume ratio of 1:1 as the eluent. The obtained solid was a white ...

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Abstract

The invention provides an organic white light material with the terminal activation delay and aggregation-induced emission performance and a synthetic method and application thereof. The general molecular formula of the white light material is Ar-Ar1-Ar2, wherein Ar is a phenothiazine electron-donating substituent group, Ar1 is a strong electron-withdrawing group, and Ar2 is an aromatic fused ring or heterocyclic aromatic substituent group except phenothiazine. The synthetic method of the material is simple, the thermal performance, luminous efficiency and white light color purity of an end product can be adjusted through connection of different aromatic fused ring or heterocyclic aromatic groups, the white light material has the thermal activation delay and aggregation-induced emission properties, the glass transition temperature is high, and the emission performance is excellent. The obtained white light material is a light emitting layer applied to preparing a non-doped OLED device, the illumination brightness is high, the stability is good, and the practicability requirement can be met.

Description

technical field [0001] The invention relates to an asymmetric thermally activated delayed fluorescent material, its synthesis method and an OLED device using the thermally activated delayed fluorescent material, in particular to an agglomeration-induced emission (AIE) property and a thermally activated delayed fluorescent (TADF) emission A white light material with properties, a synthesis method thereof and an OLED device using the white light material as a light-emitting layer. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted great attention from the scientific and industrial circles due to their advantages such as fast response, low driving voltage, flexibility, and active light emission. Large-area lighting has important applications, so the design and synthesis of organic white light materials have been a hot spot in the research and development of OLED materials in recent years. However, since white light is composite light, which is u...

Claims

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Application Information

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IPC IPC(8): C07D279/22C07D417/12C09K11/06H01L51/54
CPCC09K11/06C07D279/22C07D417/12C09K2211/1092C09K2211/1037H10K85/615H10K85/657H10K85/6576H10K50/00
Inventor 许炳佳谢宗良王乐宇毛竹刘婷婷杨志涌于涛池振国张艺刘四委许家瑞吴元均吕伯彦
Owner SUN YAT SEN UNIV
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