Condensed ring compound containing boron atom, nitrogen atom and selenium atom or tellurium atom and organic electroluminescent device

A nitrogen atom and boron atom technology is applied in the field of fused ring compounds and organic electroluminescence devices, which can solve the problems of complex device structure and reduced external quantum efficiency of the device, and achieve high luminous efficiency, narrow electroluminescence half-peak width, The effect of high device external quantum efficiency

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

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Problems solved by technology

However, this D-A structure usually exhibits a large Stokes shift due to the vibrational relaxation of the excited state, and the luminescence spectrum is wide, and the half-maximum width (FWHM) is generally 70-100nm. In practi

Method used

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  • Condensed ring compound containing boron atom, nitrogen atom and selenium atom or tellurium atom and organic electroluminescent device
  • Condensed ring compound containing boron atom, nitrogen atom and selenium atom or tellurium atom and organic electroluminescent device
  • Condensed ring compound containing boron atom, nitrogen atom and selenium atom or tellurium atom and organic electroluminescent device

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preparation example Construction

[0050] 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:

[0051] After the compound shown in formula (II) is reacted with alkyllithium, then reacted with boron trihalide and organic amine to obtain the condensed ring compound shown in formula (I); said alkyllithium is preferably butyllithium, secondary One or more of butyllithium, tert-butyllithium, methyllithium and ethyllithium; the boron trihalide is preferably boron trifluoride, boron trichloride, boron tribromide and boron triiodide One or more of them; the organic amine is preferably one or more of N, N-diisopropylethylamine, triethylamine and tri-n-butylamine;

[0052]

[0053] Lu 1 It is halogen; other code names are the same as above, and will not be repeated here.

[0054] Alternatively, a typical preparation process thereof is as follows:

[0055] The compound shown in formula (III) is reacted with...

Embodiment 1

[0075] The reaction formula is as follows:

[0076]

[0077] Add 1-1(2-bromo-1-fluoro-3-iodobenzene) (79.4g, 264.0mmol), aniline (11.2 g, 120.0mmol), Pd 2 (dba) 3 (3.3g, 3.6mmol), t-Bu 3 P·BF 4 (4.18g, 14.4mmol) and sodium tert-butoxide (26.0g, 270.0mmol), take 500mL of toluene and add it to the bottle, heat up to 110°C, stir the reaction for 24 hours under the protection of argon, then cool to room temperature, at 50°C After the toluene was removed under reduced pressure, the reaction solution was washed with deionized water, extracted with ether to separate the organic phase, and then dried by adding anhydrous sodium sulfate. The organic phase was filtered to remove the solvent, and the crude product was separated by silica gel column to obtain product 1-2 (44.7 g, yield: 85%). Elemental analysis of its structure (C 18 h 11 Br 2 f 2 N): theoretical value C, 49.24; H, 2.53; N, 3.19; test value C, 49.31; H, 2.50; N, 3.23. MALDI-TOF MS analysis: theoretical value 43...

Embodiment 2

[0083] The reaction formula is as follows:

[0084]

[0085] 2-1 (2,7-dibromo-9-phenylcarbazole) (28.8g, 72.0mmol), 4-tert-butylphenylselenol (12.84g, 60.0mmol), Pd 2 (dba) 3 (1.37g, 1.5mmol), Xantphos (1.74g, 3.0mmol) and N,N-diisopropylethylamine (15.5g, 20.9mL, 120.0mmol), add 300mL 1,4-dioxane to the bottle , heated to reflux, stirred and reacted for 12 hours under the protection of argon, then cooled to room temperature, poured the reaction solution into 1.2L deionized water, stirred for 1 hour, extracted with dichloromethane to separate the organic phase, and then added anhydrous sulfuric acid After drying over sodium, the organic phase obtained by filtration was removed from the solvent, and the crude product was separated through a silica gel column to obtain product 2-2 (23.0 g, yield: 72%). Elemental analysis of its structure (C 28 h 24 BrNSe): theoretical value C, 63.05; H, 4.54; N, 2.63; found value C, 63.15; H, 4.50; N, 2.65. MALDI-TOF MS analysis: theoret...

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Abstract

The invention provides a fused ring compound containing boron atoms, nitrogen atoms and selenium atoms or tellurium atoms. The fused ring compound is shown as a formula (I). The condensed ring compound containing boron atoms, nitrogen atoms and selenium atoms or tellurium atoms is used as a luminescent material, on one hand, the relaxation degree of an excited state structure can be reduced by using a rigid skeleton structure of the condensed 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.

Description

technical field [0001] The invention belongs to the technical field of materials, in particular to a condensed ring compound containing boron atoms, nitrogen atoms, selenium atoms or tellurium 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 between the cathode and the anode. The device structure is sequentially composed of a transparent ITO anode, a hole injection layer (TIL), a hole transport layer (HTL), For the 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 required. The mechanism of light emission is to form a voltage between two electrodes, inject electrons from the cathode and inject holes from the anode, the electrons and holes combine in the light-emitting layer to form an excited state, and then radiate back to th...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F7/30C07F7/10C07F9/6596C09K11/06H01L51/54H01L51/50
CPCC07F5/027C07F7/0816C07F9/6596C07F7/30C07F7/0812C09K11/06C09K2211/104C09K2211/107C09K2211/1055C09K2211/1085C09K2211/1007C09K2211/1011C09K2211/1033C09K2211/1014C09K2211/1029H10K85/624H10K85/636H10K85/654H10K85/657H10K85/40H10K85/6572H10K50/11
Inventor 王利祥邵世洋杜宝云李伟利吕剑虹王兴东赵磊王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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