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Red thermal induction delay fluorescent polymer and preparation and application thereof

A delayed fluorescence and polymer technology, applied in the manufacture of semiconductor/solid-state devices, luminescent materials, semiconductor devices, etc., can solve the problems of reduced radiation rate index rate, high non-radiative decay rate, and low photoluminescence efficiency of dyes, reaching The effect of suppressing efficiency roll-off, simple preparation method, and high external quantum efficiency

Active Publication Date: 2018-05-04
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, these polymer-based thermally-induced delayed fluorescent materials are mainly concentrated in blue-green, green, yellow-green and yellow light, while red-light polymer-based thermally-induced delayed fluorescent materials are difficult to achieve, mainly because pure organic materials are in long-wavelength The non-radiative decay rate of the region is large (energy gap rule) and increases exponentially with decreasing energy level difference, resulting in a rapid exponential rate decrease of the radiative rate, making the photoluminescence efficiency of the dye very low

Method used

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  • Red thermal induction delay fluorescent polymer and preparation and application thereof
  • Red thermal induction delay fluorescent polymer and preparation and application thereof
  • Red thermal induction delay fluorescent polymer and preparation and application thereof

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preparation example Construction

[0084] The present invention also provides a preparation method of the red heat-induced delayed fluorescent polymer of the present invention, comprising:

[0085] Copolymerize the compound with the structure of formula (II), the compound with the structure of formula (III) and the compound with the structure of formula (IV) to obtain the polymer with the structure shown in formula (I);

[0086]

[0087] Wherein, Ar1 is 2,7-fluorene derivative or 2,7-carbazole derivative;

[0088] Ar2 is the aryl group of C6~C20;

[0089] R 1 , R 2 , R 3 , R 4 and R 5 independently selected from hydrogen, C1-C30 alkyl, C1-C30 alkoxy or C6-C50 substituted aryl;

[0090] x is 0

[0091] n is 1-200.

[0092] In the present invention, the compound having the structure of formula (II), the compound of formula (III) and the compound of formula (IV) are copolymerized to obtain the polymer of the structure shown in formula (I); wherein, R in the structure 1 , R 2 , R 3 , R 4 , R ...

Embodiment 1

[0096] Embodiment 1: the synthesis of polymer PFSOTAQ0.5

[0097] The preparation process is shown in the following formula:

[0098]

[0099] The specific steps are:

[0100] 3,7-Dibromo-2,8-dioctyl-S,S-dioxo-dibenzothiophene (296.2mg, 0.495mmol), 9,9-dioctyl-2,7-dipinacol Borate fluorene (321.3mg, 0.5mmol), 2-(4-(bis(4-bromophenyl)amino)phenyl)-9,10-anthraquinone (3.0mg, 0.005mmol), palladium acetate ( 3mg) and tricyclohexylphosphine (6mg) were added to a 50mL Schlenk bottle, and the gas was changed three times, protected by argon, and deoxygenated toluene (8mL) was added, and heated at 82°C until the raw materials were completely dissolved; the deoxygenated tetraethyl A mixture of ammonium hydroxide (2mL) and water (2mL) was added to the reaction solution, and reacted at 80-85°C for 18h; phenylboronic acid (69mg, 0.6mmol) dissolved in 1mL of tetrahydrofuran was added to the reaction solution, and reacted for 6h, Add 1 mL of bromobenzene to the reaction solution and re...

Embodiment 2

[0102] Example 2: Synthesis of Polymer PFSOTAQ1

[0103] The preparation process is shown in the following formula:

[0104]

[0105] The specific steps are:

[0106] 3,7-Dibromo-2,8-dioctyl-S,S-dioxo-dibenzothiophene (293.3mg, 0.49mmol), 9,9-dioctyl-2,7-dipinacol Borate fluorene (321.3mg, 0.5mmol), 2-(4-(bis(4-bromophenyl)amino)phenyl)-9,10-anthraquinone (6.1mg, 0.01mmol), palladium acetate ( 3mg) and tricyclohexylphosphine (6mg) were added to a 50mL Schlenk bottle, and the gas was changed three times, protected by argon, and deoxygenated toluene (8mL) was added, and heated at 82°C until the raw materials were completely dissolved; the deoxygenated tetraethyl A mixture of ammonium hydroxide (2mL) and water (2mL) was added to the reaction solution, and reacted at 80-85°C for 18h; phenylboronic acid (69mg, 0.6mmol) dissolved in 1mL of tetrahydrofuran was added to the reaction solution, and reacted for 6h, Add 1 mL of bromobenzene to the reaction solution and react for 6 h...

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Abstract

The invention provides a red thermal induction delay fluorescent polymer with a structure as shown in the formula (I). The provided polymer has a smaller energy level difference between a first excited singlet state and a first excited triplet state, and achieves thermal induction delay fluorescence emission; the provided polymer chooses a specific polymerization unit and the specific ratio of thepolymerization units, so that the external quantum efficiency of an obtained electroluminescent device is high when the obtained polymer is applied to the electroluminescent device, and the roll-offthe efficiency of the electroluminescent device can be inhibited. In addition, the preparation method of the provided polymer is simple, the obtained polymer can use the simple solution processing mode like spin-coating and ink-jet printing when being used to manufacture a device, so that the manufacturing process of the electroluminescent device is greatly simplified.

Description

technical field [0001] The invention relates to the field of organic polymer luminescent materials, in particular to a red heat-induced delayed fluorescent polymer and its preparation and application. Background technique [0002] In 2012, Adachi's research group reported a pure organic compound fluorescent material with an internal quantum efficiency of 100% (Nature, 2012, 492, 234-238), the first singlet excited state and the first triplet excited state of this type of material The energy level difference between them is small (<0.3eV), the triplet excitons can absorb the heat generated in the surrounding environment, and upconvert to singlet excitons through anti-intersystem crossing, and then the radiative transition produces thermally induced delayed fluorescence ( TADF). The luminescent mechanism can make full use of singlet excitons and triplet excitons, and its internal quantum efficiency can reach up to 100% when applied to electroluminescent devices. At the sa...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C08G61/124C08G61/126C08G2261/3241C08G2261/3243C08G2261/344C08G2261/5222C08G2261/3142C08G2261/122C08G2261/1428C08G2261/1412C08G2261/95C09K2211/1416C09K2211/1425C09K2211/1458H10K85/113H10K85/151H10K50/11
Inventor 程延祥王彦杰朱运会杨一可战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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