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Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof

An electroluminescent device and derivative technology, which is applied in the preparation of organic compounds, silicon organic compounds, aminohydroxy compounds, etc. Level transition smooth effect

Pending Publication Date: 2020-11-20
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the present invention provides a kind of benzanthracene derivative as the mother nucleus and different active sites on it are connected with side chains to obtain a luminescence auxiliary layer material with better performance, which can solve the problem of existing organic electroluminescence The technical problem of unsatisfactory luminous efficiency and service life of the device

Method used

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  • Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof
  • Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof
  • Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the preparation of compound 9

[0056]

[0057] After adding reactant A-9 (50mmol) and reactant B-9 (55mmol) in 200ml of toluene in the reaction vessel, add Pd under nitrogen atmosphere 2 (dba) 3 (0.56mmol), P(t-Bu) 3 (2.8 mmol), t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 °C, and the mixture was stirred for 10 h. Use diatomaceous earth to filter while hot to remove salt and catalyst. After the filtrate is cooled to room temperature, distilled water is added to the filtrate for washing. After liquid separation, the organic phase is retained, and the aqueous phase is extracted with ethyl acetate. The combined organic layers were then dried using magnesium sulfate, and the solvent was removed using a rotary evaporator. Using dichloromethane:petroleum ether at a volume ratio of 1:9 as the eluent, the remaining substance was purified by column chromatography to obtain the final product 9 (21.7 g, yield 78%, ...

Embodiment 2

[0058] Embodiment 2: the preparation of compound 23

[0059]

[0060] step 1:

[0061] After adding chemical formula reactant A-23 (50mmol) and reactant B-23 (55mmol) in 200ml toluene in the reaction vessel, add Pd under nitrogen atmosphere 2 (dba) 3 (0.56mmol), P(t-Bu) 3 (2.8 mmol), t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 °C, and the mixture was stirred for 10 h. Use diatomaceous earth to filter while hot to remove salt and catalyst. After the filtrate is cooled to room temperature, distilled water is added to the filtrate for washing. After liquid separation, the organic phase is retained, and the aqueous phase is extracted with ethyl acetate. The combined organic layers were then dried using magnesium sulfate, and the solvent was removed using a rotary evaporator. Using dichloromethane:petroleum ether volume ratio: 9 as eluent, the remaining substance was purified by column chromatography to obtain intermediate C-23 ...

Embodiment 3

[0064] Embodiment 3: the preparation of compound 44

[0065]

[0066] step 1:

[0067] After adding chemical formula reactant A-44 (50mmol) and reactant B-44 (55mmol) in 200ml toluene in the reaction vessel, add Pd under nitrogen atmosphere 2 (dba) 3 (0.56mmol), P(t-Bu) 3 (2.8 mmol), t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 °C, and the mixture was stirred for 10 h. Use diatomaceous earth to filter while hot to remove salt and catalyst. After the filtrate is cooled to room temperature, distilled water is added to the filtrate for washing. After liquid separation, the organic phase is retained, and the aqueous phase is extracted with ethyl acetate. The combined organic layers were then dried using magnesium sulfate, and the solvent was removed using a rotary evaporator. Using dichloromethane:petroleum ether at a volume ratio of 1:9 as the eluent, the remaining substance was purified by column chromatography to obtain inter...

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Abstract

The invention discloses an organic electroluminescent compound of a benzanthracene derivative. The structural general formula of the organic electroluminescent compound of the benzanthracene derivative is shown as a chemical formula 1 shown in the specification, wherein X is a chemical bond, O, S, Si(R4R5), C(R6R7) or NR8; and Ar1, Ar2 and R1-R3 are independently selected from hydrogen, a substituted or non-substituted C1-C10 alkyl group, a substituted or non-substituted C6-C30 aryl group, a substituted or non-substituted 3-membered-30-membered heteroaryl group, a substituted or unsubstitutedC10-C30 fused ring group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkyl sulfydryl group, a substituted or unsubstituted C6-C30 arylamino group, and asubstituted or unsubstituted C6-C30 aryloxy group. The organic electroluminescent compound provided by the invention has the advantages of short synthetic route, simple process, easily available raw materials and low cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescence compound of benzanthracene derivatives and a preparation method and application thereof. Background technique [0002] An organic electrical element utilizing the organic light emitting phenomenon generally has a structure including an anode, a cathode and an organic layer therebetween. Here, the organic layer is generally formed into a multilayer structure composed of various substances in order to improve the efficiency and stability of organic electrical components, for example, it can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, etc. And electron injection layer etc. are formed. [0003] Among them, hole-transporting materials usually have low highest occupied molecular orbital (HOMO) values, which tend to reduce the efficiency when using materials with fast ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C217/84C07D217/02C07C217/78C07D307/91C07D333/76C07C217/80C07D409/12C07D335/04C07D311/78C07D405/04C07D405/10C07F7/08C07D221/18C07D401/04C07D401/10C07C209/68C07C213/02C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07C217/84C07D217/02C07C217/78C07D307/91C07D333/76C07C217/80C07D409/12C07D335/04C07D311/78C07D405/04C07D405/10C07F7/0816C07F7/083C07D221/18C07D401/04C07D401/10C09K11/06C07C2603/94C07C2603/18C07C2603/42C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1096H10K85/625H10K85/622H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/40H10K85/6572H10K50/15H10K50/16H10K50/17H10K50/171H10K50/11
Inventor 汪康张雪李明孙峰陈明姜志远曹淼
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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