Heat-inducible delayed fluorescence polymer with main chain comprising diphenyl silane and carbazole unit and preparation method of heat-inducible delayed fluorescence polymer

A technology of diphenylsilicon and carbazole units is applied in the field of thermally induced delayed fluorescent polymers and their preparation, which can solve the problems of low triplet energy level, affecting the full utilization of triplet excitons, and difficult to achieve full-color luminescence, etc. Achieve high triplet energy level, efficient thermally induced delayed fluorescence emission properties, and easy industrial production.

Active Publication Date: 2018-08-10
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, the triplet energy levels of the currently disclosed polymers are still low, making it difficult to achieve full-color luminescence, while affecting the full utilization of electrically generated triplet excitons.

Method used

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  • Heat-inducible delayed fluorescence polymer with main chain comprising diphenyl silane and carbazole unit and preparation method of heat-inducible delayed fluorescence polymer
  • Heat-inducible delayed fluorescence polymer with main chain comprising diphenyl silane and carbazole unit and preparation method of heat-inducible delayed fluorescence polymer
  • Heat-inducible delayed fluorescence polymer with main chain comprising diphenyl silane and carbazole unit and preparation method of heat-inducible delayed fluorescence polymer

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preparation example Construction

[0054] The present invention also provides a method for preparing a heat-induced delayed fluorescent polymer whose main chain contains diphenylsilicon and carbazole units according to claim 1, comprising:

[0055] Copolymerize the monomers with the structures of formula (III), formula (IV) and formula (V) to obtain the polymer shown in formula (I),

[0056]

[0057] Among them, R 1 , R 2 independently selected from C1-C20 alkyl groups or C6-C30 aryl groups;

[0058] A is a fluorescent dye unit containing an electron donor / acceptor twisted structural unit;

[0059] x is 0

[0060] n is 2-200.

[0061] According to the present invention, the present invention copolymerizes the monomers having the structures of formula (III), formula (IV) and formula (V) to obtain the polymer shown in formula (I), wherein, the present invention has no special requirements on the conditions of copolymerization , any copolymerization method known in the art can be used, and the catal...

Embodiment 1

[0064] Embodiment 1: the synthesis of polymer I-1

[0065] (1) Preparation of two (4-bromophenyl) diphenyl silicon

[0066] The preparation process is shown in the following reaction equation:

[0067]

[0068] The specific steps are: add p-dibromobenzene (9.44g, 40.0mmol) and dry 100ml tetrahydrofuran into a 250ml flask, pump and exchange gas, protect with argon, and dry ice acetone bath. Take 16ml of n-butyllithium (2.5M) in a constant pressure dropping funnel, and slowly add it dropwise to the stirred reaction solution until the dropwise addition is complete. After keeping the reaction at low temperature for 1 h, inject diphenyl silicon dichloride (4.2 ml, 20.0 mmol) into the reaction liquid, return to room temperature naturally, and react overnight. The reaction solution was poured into 200ml of water, extracted twice with 100ml of ether, the organic phase was collected, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was re...

Embodiment 2

[0081] Embodiment 2: the synthesis of polymer I-2

[0082] (1) Preparation of 3,6-dibromo-9-(4-(4',6'-phenyl-1,3,5-triazine))phenylcarbazole

[0083]

[0084] The specific steps are: 3,6-dibromocarbazole (1.30g, 4.0mmol), 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1.14g , 3.5mmol) and cesium carbonate (2.60g, 8.0mmol) in 30ml of N,N-dimethylformamide, gas exchanged, stirred at 150°C for 20h under the protection of argon. Cool to room temperature, pour the reaction solution into 200ml of water, precipitate a large amount of solids, filter with suction, wash with water, collect the filter cake and disperse it in 30ml of ethanol, ultrasonicate for 5 minutes, heat and stir at 70°C for 10 minutes, filter with suction, repeat twice, and dry to obtain 2.0 g of light yellow solid, yield 90%. The mass spectrometry test is 630.0 (M + ).

[0085] (2) Synthesis of polymer I-2

[0086]

[0087] The specific steps are the same as those of polymer I-1, the monomer 3,6-dibromo-9...

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Abstract

The invention provides a heat-inducible delayed fluorescence polymer with a main chain comprising diphenyl silane and carbazole unit and having a structure as shown in formula (I) and a preparation method. The detection discovers that an energy gap between a first excited singlet state and a first excited triplet state of the polymer is small and has a property for thermally inducing the delay ofthe fluorescence emission. By introducing the diphenyl silane and the carbazole unit, the polymer has a high triplet state energy level, and can effectively shielding a quenching effect between luminescence units, so that the polymer has high-efficient property for thermally inducing the delay of the fluorescence emission. When the polymer is applied to electroluminescence, the full-color luminescence can be realized, and the high-efficient fluorescence emission at a pure-film state can be realized; and additionally, the preparation method of the polymer is simple, and the polymer is expectedto be applied to an electroluminescent device of the solution processing.

Description

technical field [0001] The invention belongs to the field of organic light-emitting materials, and in particular relates to a heat-induced delayed fluorescent polymer whose main chain contains diphenyl silicon and carbazole units and a preparation method thereof. Background technique [0002] Small-molecule organic compounds with thermally induced delayed fluorescence emission properties have been widely used in organic electroluminescent devices due to their efficient utilization of triplet excitons. Such as literature Nature, 2012, 492,234; Nature Photon, 2014, 8,326; Adv.Mater.2015, 27, 2096; CN201310413578; CN201310733731; Luminescent properties. The performance of electroluminescent devices made of such compounds as light-emitting materials is comparable to that of devices made of heavy metal compound phosphorescent materials. However, when small molecule compounds are used in light-emitting devices, they often need to be produced by evaporation, which is complicated. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/124C08G2261/122C08G2261/1412C08G2261/1428C08G2261/143C08G2261/145C08G2261/146C08G2261/149C08G2261/15C08G2261/18C08G2261/3241C08G2261/344C08G2261/411C08G2261/5222C08G2261/95
Inventor 程延祥朱运会王彦杰杨一可战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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