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Organoboron fused ring compound containing dendritic structure and organic electroluminescent device

A molecular structure, organic boron technology, applied in the field of materials, can solve the problems of wide emission spectrum, low color purity, etc.

Pending Publication Date: 2022-05-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, most dendritic thermally activated delayed fluorescent materials use non-condensed ring units such as triphenyltriazine, diphenyl sulfone, and benzophenone as the central core, and their excited state structures relax strongly, resulting in a broad emission spectrum (semi The peak width is generally 70-100nm, Mater.Chem.Front., 2018, 2, 1097; J.Mater.Chem.C, 2016, 4, 2442; Dye.Pigm.2016, 133, 380e386) and the color purity is not high question

Method used

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  • Organoboron fused ring compound containing dendritic structure and organic electroluminescent device
  • Organoboron fused ring compound containing dendritic structure and organic electroluminescent device
  • Organoboron fused ring compound containing dendritic structure and organic electroluminescent device

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preparation example Construction

[0057] The present invention has no special limitation on the preparation method of the condensed ring compound, and a typical preparation process thereof is as follows:

[0058] The compound represented by formula (II) is reacted with the compound represented by formula (III) in a solvent to obtain the condensed ring compound represented by formula (I).

[0059]

[0060] Among them Lu 1 、Lu 2 、Lu 3 each independently selected from hydrogen, halogen, hydroxyl, mercapto, amino,

[0061] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode; the organic thin film layer includes the condensed ring compound shown in the above formula (I) .

[0062] The present invention has no special restrictions on the structure of the organic electroluminescent device, and conventional organic electroluminescent devices well known to those skilled in the art can be use...

Embodiment 1

[0078] The chemical structure and synthetic route of I-1 are as follows:

[0079]

[0080] Under an argon atmosphere, add 1-1((3,5-dichlorophenyl)-diphenylamine) (6.91 g, 22 mmol), N,N'-diphenyl-m-benzenediphenylamine to a 50 mL Schlenk bottle Amine (2.6g, 10mmol), Pd 2 (dba) 3 (0.46g, 0.5mmol), t-Bu 3 PHBF 4 (0.58g, 2mmol), t-BuONa (3.84g, 40mmol), then inject 20mL of toluene, and react at 110°C for 24 hours. Cool down to room temperature, add deionized water and 100 mL of dichloromethane for extraction, and wash with deionized water several times. The organic phase was separated, and the product 1-2 (4.5 g, yield: 55%) was obtained by column separation and desolventization. Elemental analysis: theoretical value C, 79.50; H, 4.94; N, 6.87; test value C, 79.47; H, 4.91; N, 6.89. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF (m / z)): theoretical value 814.3; experimental value 814.3 (M + ).

[0081] Under argon atmosphere, wei...

Embodiment 2

[0085] The chemical structure and synthetic route of I-2 are as follows:

[0086]

[0087] Under argon atmosphere, weigh 2-1((5-chloro-3-fluorophenyl)-diphenylamine) (2.98g, 10mmol), m-bromophenol (1.73g, 10mmol) and K 2 CO 3 (2.76g, 20mmol), take 40mL DMF and add in the bottle, heat up to 90°C, stir and react under argon protection for 8 hours, then cool to room temperature, pour the reaction solution into water after diluting the reaction solution with toluene, separate the organic phase, Anhydrous sodium sulfate was added to dry, and the obtained organic phase was filtered to remove the solvent, and the crude product was separated by column to obtain product 2-2 (2.9 g, yield: 65%). Elemental analysis: theoretical value C, 63.95; H, 3.80; N, 3.11; test value C, 63.91; H, 3.77; N, 3.14. Electrospray ionization mass spectrometry (ESI-MS): theoretical value 449.0; experimental value 449.0 (M+).

[0088] Under argon atmosphere, in a 50 mL Schlenk bottle, add 1-1 (3.1 g, 10 ...

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Abstract

The invention provides an organoboron fused ring compound containing a dendritic molecular structure. The organoboron fused ring compound is shown as a formula (I). On one hand, the relaxation degree of an excited state structure can be reduced by utilizing a rigid skeleton structure of the fused ring compound, so that relatively narrow half-peak width is realized; on the other hand, anti-intersystem crossing is promoted through the heavy atom effect of selenium atoms or tellurium atoms, so that the delayed fluorescence effect is obtained, and high luminous efficiency is achieved. Meanwhile, by changing the types of aromatic rings or heteroaromatic rings contained in the fused ring compound, the delayed fluorescence lifetime and the half-peak width can be further adjusted. Experimental results show that when the luminescent compound is used as a luminescent layer of the electroluminescent device, narrow electroluminescent half-peak width can be realized without an optical filter and a microcavity structure, and high external quantum efficiency of the device can also be realized. Experimental results show that the fused ring compound provided by the invention not only has a TADF effect, but also has the characteristics of high luminous efficiency and narrow luminescent spectrum.

Description

technical field [0001] The invention relates to the technical field of materials, in particular to an organic boron condensed ring compound containing a dendritic molecular structure and an organic electroluminescence device. Background technique [0002] Organic light-emitting devices (OLEDs) have the characteristics of rich colors, thin thickness, wide viewing angle, fast response, and flexible devices, and are considered to be the most promising next-generation flat panel display and solid-state lighting technologies. Generally speaking, OLED is composed of ITO anode, hole injection layer (TIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer Composition of (EIL) and cathode, 1-2 organic layers can be omitted as required, and the holes (Hole) injected from the positive and negative electrodes on the organic film combine with electrons (Electron) to form excitons (Exciton). When the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/6561C09K11/06H01L51/54H01L51/50
CPCC07F5/027C07F9/65611C09K11/06C09K2211/1029C09K2211/1085C09K2211/107C09K2211/1055C09K2211/104C09K2211/1096C09K2211/1007C09K2211/1011C09K2211/1014H10K85/636H10K85/626H10K85/633H10K85/631H10K85/657H10K85/6572H10K50/11
Inventor 王利祥邵世洋王兴东赵磊李伟利吕剑虹王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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