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Fused heterocyclic aromatic hydrocarbon derivative as well as preparation and application thereof

A technology of heterocyclic aromatic hydrocarbons and derivatives, which is applied in the field of optoelectronic materials, can solve the problems of limiting the performance and efficiency of organic electroluminescent devices, and achieve the effects of improving light extraction efficiency, avoiding light loss, and increasing the refractive index

Active Publication Date: 2020-06-30
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the limitations of refractive index, extinction coefficient and thermal stability, the optical covering layer materials in the prior art (such as CAP-1, belonging to triazine derivatives) solve the problems caused by total reflection and absorption of light inside the device. The efficiency of light loss is still limited, which greatly limits the further improvement of the performance of organic electroluminescent devices. Therefore, research on other light covering layer materials with high refraction, low absorption and better thermal stability can realize organic electroluminescence. The overall improvement of the performance of light-emitting devices is imperative to promote the full application of cover layer materials in panel production lines and the popularization of OLED terminal products

Method used

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  • Fused heterocyclic aromatic hydrocarbon derivative as well as preparation and application thereof
  • Fused heterocyclic aromatic hydrocarbon derivative as well as preparation and application thereof
  • Fused heterocyclic aromatic hydrocarbon derivative as well as preparation and application thereof

Examples

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preparation example Construction

[0054] The present invention also provides the preparation method of described condensed heterocyclic aromatic hydrocarbon derivatives, comprising the following steps:

[0055] (1) to contain substituent R 1 , R 2 , R 3 and R 4 The boronic acid compound and the halide corresponding to the benzoheterocycle are used as raw materials, and the Suzuki reaction (Suzuki coupling reaction) occurs to obtain the substituent R 1 , R 2 , R 3 and R 4 Halides of benzoheterocycles;

[0056] (2) to contain substituent R 1 , R 2 , R 3 and R 4 The halogenated benzoheterocycle and dioxyphenothiazine are used as raw materials to undergo a Wollmann reaction (Ullmann reaction) to obtain the condensed heterocyclic aromatic hydrocarbon derivative.

[0057] In some embodiments, step (1) is specifically:

[0058] will contain the substituent R 1 , R 2 , R 3 and R 4 The substituted boronic acid compound and the halide corresponding to the benzo heterocycle are fed in a molar ratio of 1-3...

Embodiment 1

[0070] Example 1: The above compound 3 of the present invention can be synthesized by the following method.

[0071]

[0072] (1) In a 1L three-necked flask, add 2-chloro-4,6-dibromobenzothiazole (49.11g, 150mmol), phenylboronic acid (36.58g, 300mmol), potassium carbonate (41.46g, 300mmol), toluene ( 300mL), ethanol (150mL), water (150mL), ultrasonically remove the air, continue to add tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), under the protection of nitrogen, heat up to 85 ° C and reflux for 28h, the liquid phase Monitor the completion of the reaction, cool to room temperature, wash twice with water, and beat twice with ethanol to obtain 32.82 g of 2-chloro-4,6-diphenylbenzothiazole with a yield of 68%;

[0073] (2) In a 1L three-necked flask, add 2-chloro-4,6-diphenylbenzothiazole (32.18g, 100mmol), phenothiazine (21.92g, 110mmol), potassium carbonate (41.46g, 300mmol), Tri-tert-butylphosphine tetrafluoroborate (0.58g, 2mmol), xylene (350mL), ultrasonicall...

Embodiment 2

[0076] Embodiment 2: the above compound 11 of the present invention can be synthesized by the following method

[0077]

[0078] (1) In a 1L three-necked flask, add 2-chloro-7-bromobenzothiazole (37.28g, 150mmol), phenanthrene-4-ylboronic acid (33.31g, 150mmol), potassium carbonate (41.46g, 300mmol), toluene (300mL), ethanol (150mL), water (150mL), ultrasonically remove the air, continue to add tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), under the protection of nitrogen, the temperature was raised to 85°C and heated to reflux for 20h, the liquid After phase monitoring, the reaction was completed, cooled to room temperature, washed twice with water, and beaten twice with ethanol to obtain 36.83 g of 2-chloro-7-(phenanthrene-4-yl)benzothiazole with a yield of 71%;

[0079] (2) In a 1L three-necked flask, add 2-chloro-7-(phenanthrene-4-yl)benzothiazole (34.58g, 100mmol), phenothiazine (21.92g, 110mmol), potassium carbonate (41.46g, 300mmol ), tri-tert-butylphos...

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Abstract

The invention belongs to the technical field of photoelectric material application, and particularly relates to a fused heterocyclic aromatic hydrocarbon derivative, and preparation and application thereof. According to the material, a benzoheterocycle is bridged at an aza site of phenothiazine oxygen; a conjugate site of the benzoheterocycle is further modified to realize compound rigid structureregulation and control and conjugation prolonging, so that the material thermal stability is effectively improved, the light extraction efficiency of devices is greatly improved due to a relatively high refractive index and a relatively low extinction coefficient of the material in a visible light region, and the material is an excellent covering layer material; the fused heterocyclic aromatic hydrocarbon derivative has a structural formula shown as a formula (I), wherein X is selected from O, S or O = S = O; wherein R1, R2, R3 and R4 are independently selected from alkyl, aryl substituted orunsubstituted by a substituent group and having 6-30 ring-forming carbon atoms, heteroaryl substituted or unsubstituted by a substituent group and having 3-30 ring-forming atoms, and triarylamino substituted or unsubstituted by a substituent group.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and more specifically relates to a condensed heterocyclic aromatic hydrocarbon derivative, its preparation and application. Background technique [0002] Organic electroluminescent device (OLED) is a new display technology with ultra-thin, high brightness, wide viewing angle, self-illumination, low power consumption, low cost, bendable and low temperature conditions (the liquid crystal in TFT-LCD is in It will solidify under such conditions) and can work normally. It is praised by the industry as the ideal and most promising next-generation display technology after LCD. [0003] In past studies, people paid more attention to the improvement of internal quantum efficiency (IQE), that is, the conversion of charge-hole injection to photons, so the development of functional materials and device structure design have always been the focus of research in the OLED field. Com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14C09K11/06H01L51/50H01L51/52H01L51/54
CPCC07D417/04C07D417/14C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092H10K85/622H10K85/615H10K85/626H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/00H10K50/85
Inventor 王磊郭闰达庄少卿
Owner HUAZHONG UNIV OF SCI & TECH
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