Fused ring compound containing two boron atoms and two oxygen atoms and organic electroluminescent device

A technology of compound and boron atom, which is applied in the field of organic light-emitting materials, can solve the problems of reduced external quantum efficiency and complex structure of devices, and achieve the effects of narrow half-peak width, reduced relaxation degree, and narrow electroluminescent half-peak width

Active Publication Date: 2021-04-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

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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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  • Fused ring compound containing two boron atoms and two oxygen atoms and organic electroluminescent device
  • Fused ring compound containing two boron atoms and two oxygen atoms and organic electroluminescent device
  • Fused ring compound containing two boron atoms and two oxygen atoms and organic electroluminescent device

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preparation example Construction

[0106] The present invention also provides a method for preparing the above-mentioned condensed ring compound containing two boron atoms and two oxygen group atoms, comprising: combining the compound shown in formula (III) or the compound shown in formula (IV) with an alkyl After lithium reaction, react with boron trihalide and organic amine again, obtain the condensed ring compound shown in formula (I) or formula (II); Described alkyllithium is preferably butyllithium, sec-butyllithium, tert-butyl 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 provides the use...

Embodiment 1

[0124] The reaction formula is as follows:

[0125]

[0126] Under argon atmosphere, add 1-1 (10.0g, 0.037mol), di(4-tert-butylphenyl)amine (20.7g, 0.074mol), tris(dibenzylideneacetone) into a 500mL three-necked flask Dipalladium (1.7g, 1.85mmol), tri-tert-butylphosphonium tetrafluoroborate (2.1g, 7.4mmol) and sodium tert-butoxide (10.7g, 0.11mol) were added to 250mL 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 three times with saturated brine (200 mL×3), the organic phases were combined, dried by adding anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained solid was separated through a silica gel column to obtain Product 1-2 (19.4 g, yield: 78%).

[0127] Elemental analysis structure (C 46 h 54 f 2 N 2 ): theoretical value C, 82.10; H, 8.09; F, 5.65; N, 4.16 test value C, 82.10...

Embodiment 2

[0141] The reaction formula is as follows:

[0142]

[0143] Under argon atmosphere, 2-1 (30.0g, 0.097mol), 3,6-di-tert-butylcarbazole (53.0g, 0.19mol) and cesium carbonate (142.4g, 0.44mol) were added to a 500mL three-necked flask , put 200mL 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 400mL of saturated saline for sedimentation, filter, and vacuum-dry to obtain The solid was separated through a 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 value C, 66.83; H, 5.85; Br, 19,33; F, 4.60; N, 3.39 test value 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, 2-2 (10.0g, 12.10mmol), thiophenol (3.4g, 25.40mmol) and sodium carbonate (2.7g, 25.40mmol) were added to a 50...

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Abstract

The invention provides a fused ring compound containing two boron atoms and two oxygen atoms. The fused ring compound is represented by a formula (I) or a formula (II). Compared with the prior art, the fused ring compound containing two boron atoms and two oxygen atoms is used as a light-emitting unit, on one hand, separation of HOMO and LUMO can be achieved through the resonance effect between the boron atoms and the oxygen atoms, and thus the small [delta]EST and TADF effects are achieved; meanwhile, a hybrid fused ring unit of the boron atoms and the oxygen atoms has a rigid skeleton structure, so that the relaxation degree of an excited state structure can be reduced, and a relatively narrow half-peak width is realized; on the other hand, different substituents are introduced into the skeleton of the fused ring unit, so that the delayed fluorescence lifetime and the half-peak width can be further adjusted.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, in particular to a condensed ring compound containing two boron atoms and two oxygen group 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 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), and a light-emitting layer. (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) and cathode composition, 1~2 organic layers can be omitted as required, the mechanism of action is to form a voltage between the two electrodes , while electrons are injected from the cathode and holes are injected from the anode, the electrons and holes combine to form an excited state in the light-emitting layer, and the ...

Claims

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Application Information

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Patent Type & Authority Applications(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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