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Dendritic fused ring compound containing boron atoms and oxygen atoms, preparation method and application thereof and organic electroluminescent device

A technology of dendritic and boron atoms, applied in the field of dendritic condensed ring compounds and organic electroluminescent devices, can solve the problems of low color purity and wide emission spectrum.

Pending Publication Date: 2022-05-27
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Dendritic fused ring compound containing boron atoms and oxygen atoms, preparation method and application thereof and organic electroluminescent device
  • Dendritic fused ring compound containing boron atoms and oxygen atoms, preparation method and application thereof and organic electroluminescent device
  • Dendritic fused ring compound containing boron atoms and oxygen atoms, preparation method and application thereof and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Example 1: Preparation of compounds of formula I-1

[0154] The synthetic route and process are as follows:

[0155]

[0156] Under an argon atmosphere, in a 500 mL three-necked flask, weigh the compound of formula 1-1 (13.6 g, 0.05 mol), phenol (4.7 g, 0.05 mol), thiophenol (5.5 g, 0.05 mol) and K 2 CO 3(13.8g, 0.10mol), add 80mL N-methylpyrrolidone (NMP) into the bottle, heat up to 150°C, stir and react under argon protection for 10 hours, then cool to room temperature, dilute the reaction solution with toluene, pour it out Pour into water, separate the organic phase, add anhydrous sodium sulfate to dry, remove the solvent from the organic phase obtained by filtration, and separate the crude product column to obtain product 1-2 (8.7 g, yield: 40%). Elemental Analysis: Theoretical C, 49.57; H, 2.77; S, 7.35; Tested C, 49.67; H, 2.97; S, 7.15. Electrospray ionization mass spectrometry (ESI-MS): theoretical value 433.9, experimental value 433.9 (M + ).

[0157] U...

Embodiment 2

[0161] Example 2: Preparation of compounds of formula 1-5

[0162] The synthetic route and process are as follows:

[0163]

[0164] Under argon atmosphere, in a 500mL three-necked flask, weigh the compound of formula 1-1 (13.6g, 0.05mol), 4-pyridinethiol (11.1g, 0.10mol) and K 2 CO 3 (13.8g, 0.10mol), add 80mL N-methylpyrrolidone (NMP) into the bottle, heat up to 150°C, stir and react under argon protection for 10 hours, then cool to room temperature, dilute the reaction solution with toluene, pour it out Pour into water, separate the organic phase, add anhydrous sodium sulfate to dry, remove the solvent from the organic phase obtained by filtration, and separate the crude product column to obtain product 2-2 (9.1 g, yield: 40%). Elemental analysis: theoretical C, 42.31; H, 2.22; N, 6.17; S, 14.12; found C, 42.41; H, 2.32; N, 6.11; S, 14.11. ESI-MS: theoretical value 451.8, experimental value 452.9 ([M+H] + ).

[0165] Under argon atmosphere, the compound of formula 2...

Embodiment 3

[0168] Example 3: Preparation of compounds of formula I-11

[0169] The synthetic route and process are as follows:

[0170]

[0171] Under an argon atmosphere, weigh the compound of formula 1-1 (13.6 g, 0.05 mol), 4-hydroxy-9,9'-dimethylfluorene (21.0 g, 0.10 mol) and K in a 500 mL three-necked flask 2 CO 3 (13.8g, 0.10mol), add 80mL N-methylpyrrolidone (NMP) into the bottle, heat up to 150°C, stir and react under argon protection for 10 hours, then cool to room temperature, dilute the reaction solution with toluene, pour it out Pour into water, separate the organic phase, add anhydrous sodium sulfate to dry, remove the solvent from the organic phase obtained by filtration, and obtain the product 3-2 (13.0 g, yield: 40%) by column separation of the crude product. Elemental Analysis: Theoretical C, 66.27; H, 4.33; Tested C, 66.31; H, 4.45. ESI-MS: theoretical value 650.0; experimental value 651.0 ([M+H] + ).

[0172] Under an argon atmosphere, the compound of formula 3...

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Abstract

The invention provides a dendritic fused ring compound containing boron atoms and oxygen atoms, a preparation method and application thereof and an organic electroluminescent device. The dendritic fused ring compound containing the boron atoms and the chalcogenide atoms is composed of a fused ring center containing the boron atoms and the chalcogenide atoms (one or more of oxygen, sulfur, selenium and tellurium) and peripheral branches. The compound with the specific structure can utilize the resonance effect between boron atoms and oxygen group atoms (oxygen / sulfur / selenium / tellurium) to realize separation of front line orbits so as to realize relatively small delta EST and TADF effects, and can also utilize a rigid framework structure of a specific condensed ring unit to reduce the excited state relaxation degree so as to realize relatively high luminous efficiency and relatively narrow luminescent spectrum.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a dendritic condensed ring compound containing boron atoms and oxygen atoms, a preparation method and application thereof, and an organic electroluminescent device. Background technique [0002] Organic light-emitting devices (OLEDs) are considered to be the most promising next-generation flat-panel display and solid-state lighting technologies due to their rich colors, thin thickness, wide viewing angle, fast response, and the ability to fabricate flexible devices. 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 (EIL) and cathode, 1 to 2 organic layers can be omitted as needed, and excitons are formed by combining holes (Hole) and electrons (Electron) injected by the positive and negativ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F9/6561C09K11/06H01L51/54H01L51/50
CPCC07F5/027C07F9/6561C09K11/06C09K2211/1029C09K2211/1096C09K2211/1014C09K2211/1007C09K2211/1059C09K2211/1048C09K2211/1055C09K2211/1033C09K2211/1037H10K85/6565H10K85/631H10K85/654H10K85/657H10K85/6572H10K50/11Y02E10/549
Inventor 王利祥邵世洋王兴东李伟利赵磊吕剑虹王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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