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Organic room-temperature electrophosphorescent material, preparation method and organic electroluminescent diode thereof

An electrophosphorescence and electroluminescence technology, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as restricting the application of OLED devices, and achieve the effect of enhancing the spin-orbit coupling effect and suppressing non-radiative attenuation.

Pending Publication Date: 2022-03-08
YUNNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the non-radiative decay of triplet excitons and / or the quenching of the surrounding environment, such pure organic room-temperature phosphorescent materials do not emit light in the amorphous state, but strong room-temperature phosphorescence can only be observed in the crystalline state, which severely restricts its application in OLED devices

Method used

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  • Organic room-temperature electrophosphorescent material, preparation method and organic electroluminescent diode thereof
  • Organic room-temperature electrophosphorescent material, preparation method and organic electroluminescent diode thereof
  • Organic room-temperature electrophosphorescent material, preparation method and organic electroluminescent diode thereof

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preparation example Construction

[0084] The present invention provides a method for preparing an organic room temperature electrophosphorescent material described in the above technical solution, comprising the following steps:

[0085] In a protective atmosphere, the intermediate D-XH, the intermediate F-A, an organic solvent, a dehydrating agent and a basic catalyst are subjected to a nucleophilic substitution reaction to obtain the organic room-temperature electrophosphorescent material having the structure of formula I.

[0086] In the present invention, -XH is connected to the benzene ring in the D structure.

[0087] In the present invention, the D-XH is specifically the intermediate D-OH or the intermediate D-SH.

[0088] The present invention has no special requirements on the source of the intermediate D-XH, and commercially available or self-made products can be used. In the present invention, when the intermediate D-OH or the intermediate D-SH is preferably a self-made product, the present inventi...

Embodiment 1

[0172] Add M1 (1g, 3.32mmol) and potassium carbonate (0.55g, 3.98mmol) into a three-necked reaction flask, and under the protection of argon, add 5mL of N-methylpyrrolidone and 5mL of toluene. Carry out at 140°C, and reflux with a condenser connected to a water separator. After 2h, the reaction was cooled to room temperature. Add 5mL of M2 (0.86g, 2.59mmol) dissolved in N-methylpyrrolidone, raise the temperature to 190°C for affinity substitution reaction for 18h, and detect the reaction by thin-layer chromatography. After the reaction was completed, it was washed three times with deionized water, and the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated. Silica gel column chromatography, eluting with a mixed solvent of petroleum ether:dichloromethane with a volume ratio of 5:1, and drying to obtain a white solid organic room temperature electrophosphorescent material with the structural formula I-26, 1.554 g, and a yield ...

Embodiment 2

[0178] Add M3 (0.36g, 1.53mmol) and potassium carbonate (0.25g, 1.83mmol) into a three-necked reaction flask, and under the protection of argon, add 5mL of N-methylpyrrolidone and 5mL of toluene. Carry out at 140°C, and reflux with a condenser connected to a water separator. After 2h, the reaction was cooled to room temperature. Add 5mL of M2 (0.396g, 1.19mmol) dissolved in N-methylpyrrolidone, heat up to 190°C, and detect the reaction by thin-layer chromatography. After the reaction, the filtrate was washed with deionized water, the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated. Silica gel column chromatography, eluting with a mixed solvent of petroleum ether:dichloromethane 8:1, obtained a white solid organic room temperature electrophosphorescent material with the structural formula I-25, 0.5 g, and the yield was 76.9%. 1 H NMR (500MHz, CDCl 3 ,δppm):8.75(m,6H),7.59(m,6H),7.43(dd,J=7.6,1.5Hz,1H),7.29(m,1H),7.24(d,...

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Abstract

The invention belongs to the technical field of photoelectric materials, and particularly relates to an organic room-temperature electrophosphorescent material, a preparation method and an organic electroluminescent diode thereof. The organic room-temperature electrophosphorescent material provided by the invention has the characteristic structures of a fused arylamine electron donor D and an electron acceptor A. The fused arylamine electron donor D has the structure as shown in formula II-1 or II-2, and the fused arylamine electron donor provides molecular rigidity and inhibits non-radiative attenuation of triplet excitons; x regulates and controls intramolecular charge transfer and enhances the spin-orbit coupling effect, A serves as an electron acceptor to receive electrons provided by D, and finally effective room-temperature phosphorescence is obtained in an amorphous state.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic room temperature electrophosphorescent material, a preparation method and an organic electroluminescence diode. Background technique [0002] Compared with liquid crystal display (LCD), organic light-emitting display (OLED) has outstanding characteristics such as self-illumination, wide viewing angle, high response speed, ultra-thin, and low temperature resistance, and has become a new generation of display technology that is being developed internationally. According to the luminescent mechanism, the existing organic electroluminescent materials can be divided into fluorescent materials, phosphorescent metal complexes and thermally activated delayed fluorescent materials. For fluorescent materials, only 25% of the singlet excitons can be utilized, and 75% of the triplet excitons are lost by non-radiative attenuation, so the maximum theoreti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/06C07D265/38C07D279/22C07D401/12C07D409/12C07D413/12C07D417/12C07D471/04C07D471/14C07D471/16C07D487/04C07D487/06C07D498/04C07D513/04C07D513/16C07D513/22C07D519/00C07F5/02C07F9/6578C09K11/06H01L51/54H01L51/50
CPCC07D219/06C07D265/38C07D279/22C07D471/04C07D513/04C07D487/04C07D498/04C07D401/12C07D417/12C07D513/16C07D471/14C07F9/6578C07F5/027C07D487/06C07D513/22C07D519/00C07D471/16C07D413/12C07D409/12C09K11/06C09K2211/1029C09K2211/1044C09K2211/1051C09K2211/1037C09K2211/1048C09K2211/1059C09K2211/1096C09K2211/1011C09K2211/1014H10K85/654H10K85/657H10K85/6576H10K85/6572H10K50/11
Inventor 丁军桥徐露琳
Owner YUNNAN UNIV
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