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TICT (twisted intramolecular charge transfer) triplet-state electroluminescent material and device

A technology of electroluminescent materials and electroluminescent devices, which is applied in the direction of luminescent materials, electric solid devices, semiconductor/solid device manufacturing, etc., and can solve the problems of slow triplet radiation attenuation, power dissipation, and inability to apply organic electroluminescence Devices and other issues, to achieve the effect of improving luminous brightness and external quantum efficiency, and excellent performance

Active Publication Date: 2019-08-02
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently popular fluorescent OLEDs have an inherent problem: three-quarters of the electrical energy is dissipated by triplet excitons
However, organic room-temperature phosphorescent (RTP) compounds cannot be applied in organic electroluminescent devices without efficient spin-orbit coupling enhanced by heavy metals due to their very slow triplet radiative decay rate.

Method used

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  • TICT (twisted intramolecular charge transfer) triplet-state electroluminescent material and device
  • TICT (twisted intramolecular charge transfer) triplet-state electroluminescent material and device
  • TICT (twisted intramolecular charge transfer) triplet-state electroluminescent material and device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1 preparation method

[0057] Sodium hydride (0.60 g of a 60% dispersion in mineral oil, 15 mmol) was placed in a 50 mL three-neck round bottom flask connected to a dropping funnel. A solution of carbazole (10 mmol) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was added to the above dropping funnel. The flask was evacuated and purged three times with nitrogen. Another 5 mL of anhydrous THF was injected into the flask and stirred for 5 minutes. The carbazole solution was then added dropwise over 10 minutes. The reaction mixture was heated to 60°C and stirred for 30 minutes, then cooled to 0°C. While stirring, benzoyl chloride (or its derivative) (12 mmol) was added dropwise to this reaction mixture. The resulting mixture was further heated and stirred at 60°C overnight. After cooling, the product was collected by removing THF in vacuo, dissolved in dichloromethane (DCM), washed three times with water, washed over anhydrous Na 2 SO 4 Dry and pur...

Embodiment 2B

[0068] The photophysical characteristic of embodiment 2BCz and BrBCz

[0069] In dilute solution, several important photophysical properties of BCZ and BRBCZ were measured by UV-Vis absorption and photoluminescence (PL), the results are shown in Table 1 and figure 1 middle. attached figure 1 CH at room temperature for BCZ and BRBCZ 2 Cl 2 Spectra in dilute solution state, where 1 is the UV-Vis absorption spectrum, 2 is the excitation spectrum, and 3 is the emission spectrum. The excitation spectrum is measured at the long-wavelength emission position, and the excitation wavelength of the emission spectrum is 300 nm. Under an argon atmosphere, BCz shows a double emission of benzimide: a long wavelength band at 544 nm and a short wavelength band around 350 nm with a very large Stokes shift (229 nm). Unexpectedly, the PL decay curve monitored at 544 nm revealed two components instead of one to coexist in this broadband ( figure 2 superior). The fitted lifetime of the fast-...

Embodiment 3

[0077] The time-resolved emission spectrum of embodiment 3pBCz, BCz-DMe, BCz, BrBCz

[0078] Under the premise of PL enhancement in PMMA films, time-resolved emission spectroscopy (TRES) can conveniently identify overlapping broadband near 500nm in PMMA films. The pre-exponential values ​​(weighted by the lifetime value) of each attenuation component are plotted against wavelength to generate an attenuation-dependent spectrogram. Both BCz and BrBCz have near 465nm (2.67eV) 1 TICT fluorescence, at 505nm (2.46eV) 3 TICT RTP, such as image 3 shown. From 1 TICT and 3 The emission wavelengths of BCz calculated in the TICT state are 459nm and 569nm, respectively; for BrBCz, they are 470nm and 510nm, respectively. In addition to BCz 3 Except for TICT-RTP wavelength, other values ​​are in good agreement with the experimental results.

[0079]For a deeper understanding of the above based on 3 The RTP mechanism of the TICT state, the inventors specifically verified the stereoc...

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Abstract

The invention provides an electroluminescent material and an electroluminescent device utilizing the same as a luminous layer. The electroluminescent material comprises a compound represented in formula I in the description, wherein R1, R2, R3, R4 and R5 are independently selected from H, Cl-C4 alkyl or halogen atom; R6, R7, R8, R9, R10, R11, R12 and R13 are independently selected from H, Cl-C4 alkyl, the halogen atom or carbazolyl.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence. It specifically relates to an intramolecular torsion charge transfer triplet electroluminescent material and an electroluminescent device manufactured by using the electroluminescent material. Background technique [0002] The vigorous development of organic light-emitting diodes (OLEDs) as light sources or display panels in academia or industry shows its great application prospects beyond traditional technologies. Currently popular fluorescent OLEDs have an inherent problem: three-quarters of the electrical energy is dissipated by triplet excitons. Thermally activated delayed fluorescence (TADF) is a method to efficiently utilize the energy of triplet excitons. In contrast, dual radiative channels through singlet and triplet states are a direct route to 100% exciton utilization. However, organic room-temperature phosphorescent (RTP) compounds cannot be applied in organic e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D209/88C09K11/06H01L51/50H01L51/54H01L51/52
CPCC07D209/86C07D209/88C09K2211/1007C09K2211/1029H10K85/6572H10K50/11H10K2101/40H10K50/805
Inventor 刘志伟柳杨卞祖强黄春辉
Owner PEKING UNIV
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