B/N organic electroluminescent material and preparation method and application thereof

An electroluminescence, electromechanical technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as poor color purity, and achieve low-efficiency roll-off, high-efficiency thermally activated delayed fluorescence, and high fluorescence quantum yield. Effect

Active Publication Date: 2022-03-08
SUZHOU UNIV
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Problems solved by technology

Up to now, although the introduction of TADF materials as luminescent dyes in OLED devices can achieve high efficiency, the color purity is very poor in most cases, which cannot meet the technical requirements for high color purity of ultra-high-definition full-color display technology (Rec.2020 standard). New material systems with high efficiency and high color purity need to be developed urgently
In recent years, although new TADF materials with multiple resonance effects (MR) have been reported to achieve high color purity luminescence, (Adv. Mater., 28, 2777-2781 (2016); Nat. Photonics (2019) DOI: 10.1038 / s41566 -019-0476-5; Angew.Chem.Int.Ed.,57,11316-11320(2018);Adv.Opt.Mater.,1801536(2019);ACS Appl.Mater.Interfaces 11,13472-13480(2019 )), but for green OLED devices, the CIE of the highest quality green OLED device currently reported is only (0.16,0.71) (Angew.Chem.Int.Ed., 60, 23142-23147), which is still far lower According to the Rec.2020 green light standard (CIE is (0.20,0.80), where CIEy represents the proportion of green light in the luminescence, the higher the green, the purer it is)

Method used

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  • B/N organic electroluminescent material and preparation method and application thereof
  • B/N organic electroluminescent material and preparation method and application thereof
  • B/N organic electroluminescent material and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of DBTN-1 and DBTN-2

[0028]

[0029] 1. Synthesis of Intermediate 1:

[0030] Under nitrogen protection, 5.6g (20mmol) of 3,6-di-tert-butylcarbazole, 4.2g (20mmol) of 2-fluoro-6-bromochlorobenzene, and 9.8g (30mmol) of cesium carbonate were successively added to a 250mL two-necked flask. And 200mL ultra-dry N,N-dimethylformamide solvent. After nitrogen replacement, the resulting reaction solution was heated to 150° C. and stirred for 24 hours. After the reaction was cooled to room temperature, it was slowly poured into 500 mL of deionized water, stirred and filtered to obtain a white filter cake. Using PE:DCM (6:1) as the eluent, it was further purified by silica gel column chromatography to obtain 9.0 g of pure white solid with a yield of 96%.

[0031] Product characterization: 1 H NMR (600MHz, CDCl 3 -d) δ8.16(dd, J=3.5,1.8Hz,2H),7.80(dt,J=8.1,1.2Hz,1H),7.45(ddt,J=8.2,6.1,1.7Hz,3H),7.31 (t,J=8.0Hz,1H),7.00(dd,J=8.5,2.0Hz,2H),1.47...

Embodiment 2

[0039] 1. Synthesis of intermediate 1:

[0040] Under nitrogen protection, 5.6 g (20 mmol) of 3,6-di-tert-butylcarbazole, 4.2 g (20 mmol) of 2-fluoro-6-bromochlorobenzene, and potassium tert-butoxide (30 mmol) were successively added to a 250 mL two-necked flask. And 200mL ultra-dry N,N-dimethylformamide solvent. After nitrogen replacement, the resulting reaction solution was heated to 150° C. and stirred for 24 hours. After the reaction was cooled to room temperature, it was slowly poured into 500 mL of deionized water, stirred and filtered to obtain a white filter cake. Using PE:DCM (6:1) as eluent, it was further purified by silica gel column chromatography to obtain 9.6 g of pure white solid.

[0041] 2. Synthesis of intermediate 2:

[0042] Under nitrogen protection, 5.2g intermediate 1 (11mmol), 4-tert-butylaniline 746mg (5mmol), palladium acetate (0.5mmol), tri-tert-butylphosphine tetrafluoroborate 290mg ( 1mmol), sodium tert-butoxide 2.0g (30mmol) and 150mL ultra-d...

Embodiment 3

[0045] 1. Synthesis of intermediate 1:

[0046] Under nitrogen protection, 5.6 g (20 mmol) of 3,6-di-tert-butylcarbazole, 4.2 g (20 mmol) of 2-fluoro-6-bromochlorobenzene, and sodium tert-butoxide (30 mmol) were successively added to a 250 mL two-necked flask. and 200 mL of ultra-dry meta-xylene solvent. After nitrogen replacement, the resulting reaction solution was heated to 150° C. and stirred for 24 hours. After the reaction was cooled to room temperature, it was slowly poured into 500 mL of deionized water, stirred and filtered to obtain a white filter cake. Using PE:DCM (6:1) as the eluent, it was further purified by silica gel column chromatography to obtain 8.5 g of pure white solid.

[0047] 2. Synthesis of intermediate 2:

[0048] Under the protection of nitrogen, 5.2g of intermediate 1 (11mmol), 746mg (5mmol) of 4-tert-butylaniline, palladium chloride (0.5mmol), and 290mg of tri-tert-butylphosphine tetrafluoroborate were successively added to a 250mL two-necked r...

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Abstract

The invention provides a B / N organic electroluminescent material as well as a preparation method and application thereof, and further relates to an organic electroluminescent device. The novel B / N organic electroluminescent materials DBTN-1 and DBTN-2 provided by the invention have extremely high fluorescence quantum yield and efficient narrow-band green light emitting property of thermally activated delayed fluorescence in a solution and in a film-doped state. Particularly, the organic electroluminescent device prepared from the fluorescent dye has the advantages of high efficiency, high color purity and ultra-pure green light emission, and can be applied to an ultra-high-definition display technology and the like.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent dyes, in particular to a B / N type organic electroluminescent material and its preparation method and application. Background technique [0002] Organic luminescent dyes have a wide range of applications in electronic devices. For example, in an organic electroluminescent device (OLED), by connecting a voltage across the cathode (Al) and the anode (ITO), the carrier electrons and holes are respectively injected, and the electrons and holes are respectively passed through the electron transport layer ( ETL) and hole transport layer (HTL) reach the emissive layer (EML) containing organic luminescent dyes, in the emissive layer (EML), electrons and holes recombine to generate excitons that emit photons in the process of fluorescence or phosphorescence device. OLED technology has the advantages of wide viewing angle, ultra-thin, fast response, high luminous efficiency, and flexible displa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54H01L51/50
CPCC07F5/02C09K11/06C09K2211/107H10K85/657H10K50/12Y02E10/549
Inventor 张晓宏范孝春王凯
Owner SUZHOU UNIV
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