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Thermally activated delayed fluorescence host material, preparation method and applications thereof

A technology of delayed fluorescence and host material, applied in the fields of luminescent materials, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of material shortage, low device efficiency and quenching effect

Active Publication Date: 2018-07-13
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the lack of thermally activated delayed fluorescence (TADF) host materials, and there will be a quenching effect between the host and the guest, resulting in low device efficiency

Method used

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  • Thermally activated delayed fluorescence host material, preparation method and applications thereof
  • Thermally activated delayed fluorescence host material, preparation method and applications thereof
  • Thermally activated delayed fluorescence host material, preparation method and applications thereof

Examples

Experimental program
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preparation example Construction

[0058] According to the above-mentioned preparation method, the preparation method comprises the following steps:

[0059] (1) Add 3mmol o-dibromobenzene, 1,2-dibromo-4,5-difluorobenzene, 1,2-dibromo-3,4,5-trifluorobenzene, 2,3-dibromo-1 , 4,5-trifluorobenzene or 1,2-dibromo-3,4,5,6-tetrafluorobenzene was mixed with 10~30mL tetrahydrofuran respectively, stirred at 0~-120℃, and 1~8mmol n- Butyllithium, after reacting for 12-24 hours, add 1-5 mmol of phosphorus trichloride, stir and react for 6-12 hours, and then perform post-treatment to obtain the intermediate;

[0060] (2) Dissolve the intermediate in 10~30mL ether, stir at 0~-120°C, add 1~8mmol of n-butyl lithium dropwise, react for 12~24h, add 1~5mmol of phosphorus trichloride and stir to react 6 ~12h, quench the reaction with water;

[0061] (3) Add hydrogen peroxide and continue the reaction for 2 hours to obtain a crude product, which is recrystallized to obtain compounds having the structures of formula I, formula II,...

Embodiment 1

[0086] Embodiment 1 has the preparation of the TPDPO of formula I structure

[0087] (1) Put 3mmol of o-dibromobenzene and 15ml of tetrahydrofuran in a 50ml three-necked round-bottomed flask that has been baked to remove water, and use a mixture of liquid nitrogen and n-propanol to cool to -120°C and stir. Slowly Add 3.6mmol of n-butyllithium dropwise, after reacting for 20min, slowly add 1mmol of phosphorus trichloride and stir for 12h, quench the reaction with water, extract with dichloromethane, and wash the organic layer with anhydrous Na 2 SO 4 Drying, use a rotary evaporator to spin out the solvent, and the concentrate is purified by column chromatography with a volume ratio of petroleum ether and dichloromethane of 5:1 to obtain the intermediate tris(2-bromophenyl)phosphine;

[0088] (2) Stir 3mmol tris(2-bromophenyl)phosphine and 20ml ether at 0°C, add 3.6mmol n-butyllithium dropwise, react for 1h, add 1mmol phosphorus trichloride and stir for 12h, quench the reacti...

Embodiment 2

[0095] Embodiment 2 has the preparation of the TPDPOF6 of formula II structure

[0096] The experimental procedure is the same as that of Example 1, except that the raw material fluoro-o-dibromobenzene used is 1,2-dibromo-4,5-difluorobenzene, and the obtained intermediate is tris(2-bromo-4,5-difluorobenzene) Fluorophenyl)phosphine; the product is 2,3,7,8,14,15-hexafluoro-5,10-[1,2]-phenylphosphine-5,10-dioxide, and the product is marked as TPDPOF6.

[0097] The intermediate structural formula prepared in embodiment 2 is:

[0098]

[0099] The compound TPDPOF6 structural formula that embodiment 2 prepares is:

[0100]

[0101] The data measured by the mass spectrometer of TPDPOF6 are: m / z: 429.97 (100.0%), 430.98 (19.6%), 431.98 (2.2%) Elemental Analysis: C, 50.26; H, 1.41; F, 26.50; O, 7.44; P ,14.40.

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Abstract

The present invention provides a thermally activated delayed fluorescence host material, a preparation method and applications thereof, wherein a thermally activated delayed fluorescence material based on 9,10-dihydro-9,10-o-benzo-9,10-diphospha anthracene-9,10-dioxide is used as a precursor and is modified with different amounts of fluorine atoms so as to prepare the thermally activated delayed fluorescence host material. According to the present invention, the thermally activated delayed fluorescence electroluminescent device prepared by using the thermally activated delayed fluorescence host material as the electroluminescent material has the turn-on voltage of less than 3.0 V, the maximum external quantum efficiency of higher than 12%, the maximum current efficiency of greater than 25cd.A<-1>, and the maximum power efficiency of greater than 20 lm.W<-1>.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and relates to a thermally excited delayed fluorescent host material and a preparation method and application thereof. Background technique [0002] Entering the 21st century of the "information age", the display of information has been closely integrated with the increase of human knowledge and the improvement of life quality. The display of information depends on the display, and the rapid development of information technology makes people have higher and higher requirements for flat panel displays. Among the current various displays, liquid crystal displays (Liquid Crystal Display, LCD) occupy the vast majority of the entire flat panel display market, but liquid crystal displays have narrow viewing angles, weak contrast, low brightness, long response time, poor temperature characteristics and their own Not emitting light must rely on insurmountable shortcomings such as back...

Claims

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Application Information

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IPC IPC(8): C07F9/6568C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F9/65685C09K2211/1096H10K85/657H10K50/12H10K50/11Y02B20/00
Inventor 许辉高飞飞韩春苗
Owner HEILONGJIANG UNIV
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