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Room temperature phosphorescent compound and composition and application thereof

A room temperature phosphorescence, compound technology, applied in the field of phosphorescence compounds, can solve problems such as inability to achieve electroluminescence

Inactive Publication Date: 2019-10-29
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The problem to be solved by the present invention is that the existing pure organic phosphorescent materials at room temperature cannot realize electroluminescence, and a room temperature phosphorescent compound based on phenothiazine or phenoxazine and its derivatives instead of naphthalene or naphthalene derivatives is provided, Composition and its application

Method used

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  • Room temperature phosphorescent compound and composition and application thereof
  • Room temperature phosphorescent compound and composition and application thereof
  • Room temperature phosphorescent compound and composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Table 1. Summary of Synthesis Example Product Data.

[0092]

[0093]

[0094] 3mmol of raw material-1 (ie 2,6-dibromonaphthalene or its derivatives: N-1 to N-62), 6.6mmol of raw material-2 (ie phenothiazine or its derivatives: PTZ-1 to PTZ -25), 19.8mmol sodium tert-butoxide, 0.15mmol palladium acetate and 0.15mmol tri-tert-butylphosphine were added to 35mL toluene, refluxed for 24 hours under the protection of nitrogen, then cooled to room temperature, the reaction solution was filtered, and added to the filtrate Add 100mL water, extract the organic phase with 100mL dichloromethane, separate the organic phase and concentrate to 5.5mL, carry out column chromatography separation with dichloromethane and petroleum ether (volume ratio 1:3) eluent to obtain the target product, then The pure product was obtained by vacuum sublimation. The relevant data of the target compounds obtained are shown in Table 1.

[0095] Taking compound 1 as an example to illustrate the s...

Embodiment 2

[0097] Table 2. Summary of Synthesis Example Product Data.

[0098]

[0099] 3 mmol of 1,4 dibromonaphthalene or its derivatives (raw material-1: N-63 to N-123), 6.6 mmol of phenothiazine or its derivatives (raw material-2: PTZ-1 to PTZ-25), Add 19.8mmol sodium tert-butoxide, 0.15mmol palladium acetate and 0.15mmol tri-tert-butylphosphine to 35mL toluene, reflux for 24 hours under nitrogen protection, then cool to room temperature, filter the reaction solution, add 100mL water to the filtrate, Extract the organic phase with 100mL dichloromethane, separate the organic phase and concentrate to 5.5mL, use dichloromethane and petroleum ether (volume ratio 1:3) eluent to carry out column chromatography separation to obtain the target product, and then obtain the target product by vacuum sublimation Pure. The relevant data of the obtained target compounds are shown in Table 2.

[0100] Taking compound 76 as an example to illustrate the specific details of the synthesis example ...

Embodiment 3

[0102] With 3mmol of raw material-1 (ie 2,6-dibromonaphthalene or its derivatives: N-1 to N-62), 6.6mmol of raw material-2 (ie subthiazine or its derivatives: PXZ-1 to PXZ -25), 19.8mmol cesium carbonate, 0.15mmol bis(dibenzylideneacetone) palladium and 0.15mmol tri-tert-butylphosphine were added to 35mL o-dichlorobenzene, heated to reflux for 24 hours under the protection of nitrogen, and then cooled To room temperature, filter the reaction solution, add 100mL water to the filtrate, extract the organic phase with 100mL dichloromethane, separate the organic phase and concentrate to 5.5mL, elute with dichloromethane and petroleum ether (volume ratio 1:3) Reagents were separated by column chromatography to obtain the target product, and then the pure product was obtained by vacuum sublimation. The relevant data of the obtained target compounds are shown in Table 3.

[0103] Taking compound 123 as an example to illustrate the specific details of the experiment in the synthesis e...

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Abstract

The invention relates to a room temperature phosphorescent compound and composition and application thereof based on phenothiazine or phenoxazine and derivatives substituting naphthalene or naphthalene derivatives, and belongs to the technical field of phosphorescent compounds. The room temperature phosphorescent compound is represented in a formula (1) or (2), and has room temperature phosphorescence characteristics. The invention further provides a room temperature phosphorescent composition with high luminous efficiency, and the room temperature phosphorescent composition is composed of thecompound represented by the formula (1) or (2) and a compound containing a 1,3,5-triazine group. The phosphorescent compound has the characteristics of room temperature phosphorescence emission in both the crystalline state and the amorphous state, and the compound and the composition are used as a luminescent material for preparing a luminescent layer of an organic electroluminescent device, andthe prepared organic electroluminescence device achieves an important breakthrough in pure organic electrophosphorescent devices.

Description

technical field [0001] The invention belongs to the technical field of phosphorescent compounds, in particular to a room temperature phosphorescent compound based on phenothiazine or phenoxazine and its derivatives substituted naphthalene or naphthalene derivatives, a composition and an application thereof. Background technique [0002] Due to the broad application prospects in the fields of smart phones, TVs, wearable displays and solid-state lighting, organic light-emitting diodes (OLED: Organic Light Emitting Diodes) have been extensively researched and accepted in the scientific and industrial circles in recent decades. focus on. According to the statistical rules of quantum spin, OLED devices based on traditional fluorescent materials can use up to 25% of the singlet excitons generated by electrical excitation, and when the light output efficiency of the device is 20-30%, the maximum external quantum efficiency is 5.0-7.5 % (assuming that the photoluminescent efficienc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D265/38C07D403/10C07D403/14C07D413/14C07D401/14C07D413/10C07D401/10C07D251/24C07D519/00C07D471/04C09K11/06H01L51/50H01L27/32
CPCC07D279/22C07D265/38C07D403/10C07D403/14C07D413/14C07D401/14C07D413/10C07D401/10C07D251/24C07D519/00C07D471/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059H10K85/622H10K85/626H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 王悦
Owner JILIN UNIV
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