Aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance, and preparation method and applications thereof

A technology of aggregation-induced luminescence and thermal activation delay, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc. , the effect of high yield and high luminous brightness

Active Publication Date: 2019-11-19
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current research on aggregation-induced luminescent materials with both circularly polarized luminescence and thermally activated delayed fluorescence emission properties is still in its infancy, and the types and quantities of materials are extremely rare, and the performance needs to be further improved.

Method used

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  • Aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance, and preparation method and applications thereof
  • Aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance, and preparation method and applications thereof
  • Aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Synthesis of target compound (I):

[0080] 1) Synthesis of compound 1:

[0081] Under argon protection, 4-bromophthalic anhydride (1.50g, 6.64mmol) and (R)-1,2,3,4-tetrahydro-1-naphthol (0.98g, 6.64mmol) were added into a three-neck flask, dissolved with 15 mL of DMF, and stirred at 150°C for 24 hours. After the reaction solution was cooled to room temperature, pour it into 150mL water to precipitate the solid, filter it with suction, and use the mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2 as the mobile phase to separate and purify the crude product by silica gel column chromatography and dry it in vacuo Obtain white powder 1.84g (compound 1, R-ImNBr) afterward, about 78% of productive rate, reaction formula is as follows:

[0082]

[0083] 2) Synthesis of target compound (I):

[0084] Compound 1 (1.00g, 2.82mmol), phenoxazine compound (0.70g, 3.52mmol), anhydrous potassium phosphate (0.75g, 3.52mmol), 2-dicyclohexylphosphine-2...

Embodiment 2

[0087] Synthesis of target compound (I):

[0088] 1) Synthesis of compound 1:

[0089] Under argon protection, 4-bromophthalic anhydride (1.50g, 6.64mmol) and (S)-1,2,3,4-tetrahydro-1-naphthol (0.98g, 6.64mmol) were added into a three-neck flask, dissolved with 15 mL of DMF, and stirred at 150°C for 24 hours. After the reaction liquid is cooled to room temperature, pour it into 150mL water to precipitate the solid, filter it with suction, and use the mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2 as the mobile phase to separate and purify the crude product by silica gel column chromatography and dry it in vacuo Obtain white powder 1.89g (compound 1, S-ImNBr) afterward, about 80% of productive rate, reaction formula is as follows:

[0090]

[0091] 2) Synthesis of target compound (I):

[0092] Compound 1 (1.00g, 2.82mmol), phenoxazine compound (0.70g, 3.52mmol), anhydrous potassium phosphate (0.75g, 3.52mmol), Ruphos (0.26g, 0.56mmol) wer...

Embodiment 3

[0095] Synthesis of target compound (II):

[0096] 1) Synthesis of compound 1:

[0097] The synthetic method of compound 1 is the same as the synthetic method of compound 1 in embodiment 1;

[0098] 2) Synthesis of target compound (II):

[0099] Add compound 1 (1.00g, 2.82mmol), dimethylacridine compound (0.74g, 3.52mmol), anhydrous potassium phosphate (0.75g, 3.52mmol), Ruphos (0.26g, 0.56mmol) into the three-necked flask , dissolved in 30 mL of toluene, stirred and bubbled with argon for 30 minutes, then added Pd 2 (dba) 3 (80mg, 0.14mmol), stirred and reacted at 120°C for 24 hours under the protection of argon. After the reaction solution was cooled to room temperature, it was filtered with suction, and the solvent was distilled off by a rotary evaporator under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography using a mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2 as the mobile p...

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PUM

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Abstract

The invention discloses an aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance, and a preparationmethod and applications thereof. According to the preparation method, molecular design is adopted to synthesize the organic luminescent material with CPL, TADF, and AIE performance; regulation of material aggregation-induced emission, thermally activated delayed fluorescence emission, and circular polarization emission performance can be realized through changing electronic donor groups and chiral groups. The synthesis method and purifying technology of the aggregation-induced emission luminescent material with both circular polarization luminescent and thermally activated delayed fluorescence emission performance are simple; yield is high; the preparation method is suitable for large scale production; and organic electroluminescent devices prepared from the aggregation-induced emission luminescent material with circular polarization luminescent and thermally activated delayed fluorescence emission performance are high in luminance, internal quantum efficiency, and external quantum efficiency, and practical requirements are satisfied.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to an aggregation-induced luminescence material with circularly polarized luminescence and thermally activated delayed fluorescence emission, and a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diodes, OLEDs) have unique advantages such as quick response, wide viewing angle, rich colors, light and thin volume, self-illumination and bendable, rollable and even foldable, so they are called the most potential next-generation technology. This generation of display technology is expected to be widely used in electronic products such as mobile phones, TVs, tablet computers, VR (virtual reality, head-mounted displays) and wearable smart devices. In view of its huge economic and social benefits, OLED display technology has been highly valued by academia, industry and even the governments of various...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D401/04C09K11/06H01L51/54
CPCC07D413/04C07D401/04C09K11/06C09K2211/1029C09K2211/1033C09K2211/1007C09K2211/1011H10K85/615H10K85/657H10K85/6572
Inventor 许炳佳杨新哲陈奕彤石光宋子存黄凯航唐小勇
Owner SOUTH CHINA NORMAL UNIVERSITY
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