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A condensed ring compound containing two boron atoms and two oxygen group atoms and an organic electroluminescent device

A compound and boron atom technology, applied in the field of organic light-emitting materials, can solve the problems of complex device structure and reduced external quantum efficiency of the device, and achieve the effects of reducing the degree of relaxation, narrowing the half-peak width, and narrowing the half-peak width of electroluminescence

Active Publication Date: 2022-06-07
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, this D-A structure exhibits a large Stokes shift due to the vibrational relaxation of its excited state, and the luminescence spectrum is wide, and the half-maximum width (FWHM) is generally 70-100nm. In practical applications, filters or Constructing optical microcavities to improve color purity, but this will lead to a decrease in the external quantum efficiency of the device or a complex device structure

Method used

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  • A condensed ring compound containing two boron atoms and two oxygen group atoms and an organic electroluminescent device
  • A condensed ring compound containing two boron atoms and two oxygen group atoms and an organic electroluminescent device
  • A condensed ring compound containing two boron atoms and two oxygen group atoms and an organic electroluminescent device

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[0106] The present invention also provides a method for preparing the above-mentioned fused ring compound containing two boron atoms and two oxygen atoms, comprising: combining the compound represented by formula (III) or the compound represented by formula (IV) with an alkyl group After the lithium reaction, react with boron trihalide and organic amine to obtain a fused ring compound represented by formula (I) or formula (II); the alkyl lithium is preferably butyllithium, sec-butyllithium, tert-butyllithium One or more of lithium, methyl lithium and ethyl lithium; the boron trihalide is preferably one or more of boron trifluoride, boron trichloride, boron tribromide and boron triiodide ; The organic amine is preferably one or more of N,N-diisopropylethylamine, triethylamine and tri-n-butylamine.

[0107]

[0108] Among them, Lu 1 ~Lu 4 It is hydrogen or halogen; other codes are the same as above, and will not be repeated here.

[0109] The present invention also provide...

Embodiment 1

[0124] The reaction formula is as follows:

[0125]

[0126] Under argon atmosphere, 1-1 (10.0g, 0.037mol), bis(4-tert-butylphenyl)amine (20.7g, 0.074mol), tris(dibenzylideneacetone) were added to a 500mL three-necked flask Dipalladium (1.7 g, 1.85 mmol), tri-tert-butylphosphorus tetrafluoroborate (2.1 g, 7.4 mmol) and sodium tert-butoxide (10.7 g, 0.11 mol) were added with 250 mL of toluene. The temperature was raised to 105°C, and the reaction was stirred for 3 hours. After cooling to room temperature, the reaction solution was extracted with 200 mL of ether, washed with saturated brine three times (200 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Product 1-2 (19.4 g, yield: 78%).

[0127] Elemental Analysis Structure (C 46 H 54 F 2 N 2 ): Theoretical C, 82.10; H, 8.09; F, 5.65; N, 4.16 Tested C, 82.10; H, 8.09; N, 4.16.

[0128] Matrix-assisted laser desorption ionization ti...

Embodiment 2

[0141] The reaction formula is as follows:

[0142]

[0143] Under an argon atmosphere, 2-1 (30.0 g, 0.097 mol), 3,6-di-tert-butylcarbazole (53.0 g, 0.19 mol) and cesium carbonate (142.4 g, 0.44 mol) were added to a 500 mL three-necked flask , take 200 mL of N,N-dimethylformamide (DMF) into the bottle, heat up to 130 ° C, stir and react for 3 hours, after cooling to room temperature, add the reaction solution to 400 mL of saturated brine to settle, filter, and vacuum dry. The obtained The solid was separated by silica gel column to obtain product 2-2 (36.1 g, yield: 45%).

[0144] Elemental Analysis Structure (C 46 H 48 Br 2 F 2 N 2 ): Theoretical C, 66.83; H, 5.85; Br, 19,33; F, 4.60; N, 3.39 Tested C, 66.82; H, 5.89; N, 3.28.

[0145] MALDI-TOF mass spectrum: theoretical value 824.2; experimental value 824.3 (M + ).

[0146] Under argon atmosphere, add 2-2 (10.0g, 12.10mmol), thiophenol (3.4g, 25.40mmol) and sodium carbonate (2.7g, 25.40mmol) to a 500mL three-neck...

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Abstract

The present invention provides a condensed ring compound containing two boron atoms and two oxygen group atoms, as shown in formula (I) or formula (II). Compared with the prior art, the present invention uses a condensed ring compound containing two boron atoms and two oxygen group atoms as the light-emitting unit. On the one hand, the resonance effect between boron atoms and oxygen group atoms can be used to realize the separation of HOMO and LUMO , thus achieving a smaller ΔE ST and TADF effect, while the hybrid fused ring unit of boron atom and oxygen atom has a rigid skeleton structure, which can reduce the degree of relaxation of the excited state structure, thereby achieving a narrower half-width; on the other hand, through the skeleton of the fused ring unit The introduction of different substituents can further adjust the delayed fluorescence lifetime and half-peak width.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and particularly relates to a condensed ring compound containing two boron atoms and two oxygen atoms and an organic electroluminescent device. Background technique [0002] Organic light-emitting devices (OLEDs) are usually composed of a cathode, an anode, and an organic layer interposed between the cathode and the anode. (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 the mechanism of action is to form a voltage between the two electrodes , while injecting electrons from the cathode and injecting holes from the anode, the electrons and holes combine in the light-emitting layer to form an excited state, and the excited state radiates back to the ground state, thereby realizing the device emitting light. Organic electroluminescent materials are considered to b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F7/08C07F9/6596C09K11/06H01L51/50H01L51/54
CPCC07F5/02C07F9/6596C07F7/0816C09K11/06C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/104C09K2211/1055C09K2211/1059C09K2211/107C09K2211/1085C09K2211/1096H10K85/622H10K85/636H10K85/626H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/657H10K85/40H10K50/11Y02E10/549
Inventor 王利祥邵世洋王一诺王兴东赵磊王淑萌吕剑虹田洪坤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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