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A light-emitting compound containing a dibenzo seven-membered heterocyclic structure, its preparation method and organic electroluminescent device

A light-emitting compound and a seven-membered heterocycle technology, applied in the field of organic electroluminescent devices, can solve the problems of high driving voltage, low luminous efficiency, and short life, and achieve reduced driving voltage, high photothermal stability, and delayed phosphorescence life Effect

Active Publication Date: 2022-07-19
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are many new discoveries about high-efficiency heavy metal phosphors on the market, their driving voltage is relatively high, their lifetime is relatively short, and their luminous efficiency is relatively low; The luminous efficiency of organophosphorus light-emitting compounds and organic electroluminescent devices is a technical problem that those skilled in the art need to solve urgently

Method used

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  • A light-emitting compound containing a dibenzo seven-membered heterocyclic structure, its preparation method and organic electroluminescent device
  • A light-emitting compound containing a dibenzo seven-membered heterocyclic structure, its preparation method and organic electroluminescent device
  • A light-emitting compound containing a dibenzo seven-membered heterocyclic structure, its preparation method and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] This embodiment provides a light-emitting compound containing a dibenzo seven-membered heterocyclic structure, and the preparation method thereof is as follows:

[0053]

[0054] S1, in N 2 Under protection, take raw material A-6 (60.00mmol), IrCl 3 ·3H 2 O (20.00 mmol) was added to a mixed solution of 100.00 mL of ethylene glycol ether and 30.00 mL of water, heated under reflux at 120 °C for 24 h, and then cooled to room temperature. Rinse with water ethanol and petroleum ether, and dry to obtain powdery bridging ligand B-6 (10.26 g, yield: 60.04%);

[0055]

[0056] S2. Under the protection of N2, weigh the bridging ligand B-6 (5.85mmol), add silver trifluoromethanesulfonate (11.70mmol), then add 100.00mL of dichloromethane, 30.00mL of methanol solution to the system, 55 The reaction was heated under reflux for 24 h, then cooled to room temperature, and the filtrate by column chromatography (short column) was concentrated to solid precipitation, and dried to ...

Embodiment 2

[0068] This embodiment provides a light-emitting compound containing a dibenzo seven-membered heterocyclic structure, and the preparation method thereof is as follows:

[0069]

[0070] S1, under nitrogen protection system, weigh raw material A-44 (60.00mmol), IrCl 3 ·3H 2 O (20.00 mmol) was added to a mixed solution of 240.00 mL of ethylene glycol ether and 80.00 mL of water, heated under reflux at 120 °C for 24 h, and then cooled to room temperature. Rinse with water ethanol and petroleum ether, and dry to obtain powdery bridging ligand B-6 (12.60 g, yield: 59.64%);

[0071]

[0072] S2. Under the protection of N2, weigh the bridging ligand B-44 (5.68mmol), add silver trifluoromethanesulfonate (11.36mmol), then add 90.00mL of dichloromethane, 30.00mL of methanol solution to the system, 55 The reaction was heated under reflux for 24 h, then cooled to room temperature, and the filtrate by column chromatography (short column) was concentrated to solid precipitation, and...

Embodiment 3

[0084] This embodiment provides a light-emitting compound containing a dibenzo seven-membered heterocyclic structure, and the preparation method thereof is as follows:

[0085]

[0086] S1, under nitrogen protection system, weigh raw material A-64 (60.00mmol), IrCl 3 ·3H 2 O (20.00 mmol) was added to a mixed solution of 210.00 mL of ethylene glycol ether and 70.00 mL of water, heated under reflux at 120°C for 24 hours, and then cooled to room temperature. Rinse with water ethanol and petroleum ether, and dry to obtain powdery bridging ligand B-6 (11.28 g, yield: 59.58%);

[0087]

[0088] S2. Under the protection of N2, weigh the bridging ligand B-64 (5.81mmol), add silver trifluoromethanesulfonate (11.62mmol), then add 90.00mL of dichloromethane, 40.00mL of methanol solution to the system, 55 The reaction was heated under reflux for 24 h, then cooled to room temperature, and the filtrate of column chromatography (short column) was concentrated to solid precipitation, ...

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Abstract

The invention discloses a light-emitting compound containing a dibenzo seven-membered heterocyclic structure, a preparation method and an organic electroluminescent device, and belongs to the technical field of chemistry and light-emitting compounds. The general structural formula of the light-emitting compound is: In the formula, X Selected from connecting key, ‑O‑, ‑S‑, ‑SO 2 ‑, ‑C(R 3 )(R 4 )‑,‑N(R 5 )‑,‑Si(R 6 )(R 7 )‑,‑Sn(R 8 )(R 9 )‑and‑Ge(R 10 )(R 11 ) in one; n takes 2 or 3; Ar represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 yuan) heteroaryl, substituted or At least one of unsubstituted (C6-C30) arylamino, substituted or unsubstituted (3-30-membered) heteroarylamino. The organic electroluminescent device containing the light-emitting compound has lower driving voltage, higher lifetime and higher efficiency.

Description

technical field [0001] The invention relates to the technical field of chemical and light-emitting compounds, in particular to a light-emitting compound containing a dibenzo-seven-membered heterocyclic structure, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] 2002-2005 is the growth stage of organic light-emitting diodes. At this stage, people have been able to widely access products with organic light-emitting diodes, including vehicle monitors, PDAs, mobile phones, DVDs, digital cameras, helmet-use microdisplays and home appliances. Organic light-emitting diode products officially entered the market, mainly in the display fields such as traditional LCD and VFD. This period is still dominated by passive drive, monochrome or multi-color display, panels below 10 inches, but active drive, full color and more than 10 inches panels have also begun to be used. After 2005, in the mature stage of organic light-emitting diodes,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/12
Inventor 马晓宇汪康王进政黄悦张鹤张雪王永光
Owner JILIN OPTICAL & ELECTRONICS MATERIALS