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Compound with heterocyclic ligand and preparation method and application thereof

A compound and heterocycle technology, applied in the field of compounds containing heterocycle ligands and its preparation, can solve problems such as poor luminous efficiency and thermal stability

Active Publication Date: 2016-06-29
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, currently disclosed luminescent materials, especially blue luminescent materials, have relatively poor luminous efficiency and thermal stability.

Method used

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  • Compound with heterocyclic ligand and preparation method and application thereof
  • Compound with heterocyclic ligand and preparation method and application thereof
  • Compound with heterocyclic ligand and preparation method and application thereof

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preparation example Construction

[0080] The present invention also provides a method for preparing the above compound containing heterocyclic ligands, comprising:

[0081] A) Mixing and reacting the compound having the structure of formula (II) and the compound having the structure of formula (III) to obtain the compound of the structure of formula (IV);

[0082]

[0083] B) reacting the compound with the structure of formula (IV), the compound with the structure of formula (V) and the compound with the structure of formula (VI) to obtain the compound with the structure of formula (I);

[0084] HO——R 10 Formula (Ⅵ);

[0085] where the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently selected from hydrogen, halogen, cyano, substituted C1-C30 alkyl, unsubstituted C1-C30 alkyl, substituted C1-C30 cycloalkyl, unsubstituted C1-C30 cycloalkyl , substituted C1-C30 alkoxy, unsubstituted C1-C30 alkoxy, substituted C5-C60 heterocyclic group, unsubstituted C5-C60 heterocyclic group, substitut...

Embodiment 1

[0106] Preparation of Embodiment 1 Intermediate 5-fluoro-2-nitro-N-phenylaniline (formula (II-1-1))

[0107] Add 15.6 g of 5-fluoro-2-aminonitrobenzene into the reaction flask, add 300 mL of anhydrous toluene, stir, add 19.2 g of sodium tert-butoxide, and react for 1 hour under nitrogen protection. Then 30 grams of iodobenzene and 2.8 grams of tris(dibenzylideneacetone) dipalladium were added in sequence, and 4 grams of ligand tri-tert-butylphosphine were added by injection, and the temperature of the reaction was raised to 60° C. overnight.

[0108] After the reaction was completed, the temperature was lowered, 100 mL of water was added to stop the reaction, the water layer was separated, and the toluene layer was dried with anhydrous magnesium sulfate for 30 minutes. The toluene was spin-dried to obtain a dark oil, which was passed through the column, washed with dichloromethane:petroleum ether=1:4, monitored by spot plate, and the product point of RF=0.3 was collected. Aft...

Embodiment 2

[0164] Embodiment 2 has the preparation of the compound of formula (I-2-8) structure

[0165]Add 5 g of the compound having the structure of formula (IV-1-30) into 100 mL of toluene and stir, then add a mixture of 1.8 g of aluminum isopropoxide and water, and stir at 60° C. for 2 h. At the same time, dissolve 1.48g of 4-hydroxybiphenyl in 50mL of methanol and add it dropwise after 2 hours. A white solid precipitates out. After reacting overnight, the white solid is obtained by suction filtration. Rinse with water, then with methanol, and finally with PE to obtain 5g The final product has the compound of formula (I-2-8), yield = 83%. The mass spectral value of this product is 866.29. Above-mentioned reaction process is shown in the following formula:

[0166]

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Abstract

The invention provides a compound with a heterocyclic ligand and a preparation method and application thereof. According to the compound with the heterocyclic ligand, the specific heterocyclic ligand is selected to be combined with metal aluminum, so that after the obtained organic compound is applied to an organic light-emitting device, the light-emitting efficiency of the device is improved, and the service life is long.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a compound containing a heterocyclic ligand and a preparation method and application thereof. Background technique [0002] An organic light-emitting device (OLED) is composed of a cathode, an anode, and an organic layer inserted between the cathode and the anode, that is, the device is composed of a transparent ITO anode, a hole injection layer (TIL), a hole transport layer (HTL), Light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) and cathode are formed, and 1~2 organic layers can be omitted as required. The working mechanism of OLED is that a voltage is formed between two electrodes, one side injects electrons from the cathode, and the other side injects holes from the anode, and the electrons and holes recombine in the light-emitting layer to form an excited state. The excited state returns to a stab...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C09K11/06H01L51/54
CPCC09K11/06C07F5/069C09K2211/1029C09K2211/1044C09K2211/186H10K85/321H10K85/6572H10K50/00
Inventor 高春吉贺金新崔敦洙尹恩心李明王钊
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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