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Conjugated polymer and preparation method thereof

A conjugated polymer and polymer technology, applied in the field of conjugated polymers and their preparation, can solve problems such as far from reaching performance, difficulty in delaying fluorescence emission, increasing material cost and difficulty in structural modification, etc., to achieve good luminescence performance effect

Active Publication Date: 2016-07-20
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

However, the external quantum efficiency of traditional conjugated polymer fluorescent materials can only reach 5-6%.
An effective way to improve device performance is to introduce "chemical doping" of phosphorescent units of heavy metal complexes in polymers, thereby making full use of the singlet and triplet excitons produced, and the external quantum efficiency can reach 20% (J.Am .Chem.Soc.2012,134,15189; Adv.Funct.Mater.2008,18,1430), but the introduction of phosphorescent units increases the cost of materials and the difficulty of structural modification
The inherent characteristics of conjugated polymers such as large conjugated delocalization systems make it difficult to achieve delayed fluorescence emission, although non-conjugated polymers with E-type delayed fluorescence can be obtained through flexible connections and ingenious synthesis methods (Adv. Mater ,doi:10.1002 / adma.201501090), but it is far from the expected performance, therefore, how to obtain a conjugated polymer with a simple synthesis method and high-efficiency E-type delayed fluorescence emission properties is a technical problem that needs to be solved at present

Method used

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  • Conjugated polymer and preparation method thereof
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  • Conjugated polymer and preparation method thereof

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preparation example Construction

[0066] The present invention also provides a kind of preparation method of polymer described in the present invention, comprising:

[0067] Copolymerize the compound with the structure of formula (II) and the compound of the structure of formula (III) to obtain the compound of the structure shown in formula (I);

[0068]

[0069] Wherein, R is an alkyl group of C1-C30 or an aryl group of C7-C50;

[0070] Ar is a C6-C50 aryl group or a C4-C50 heteroaryl group;

[0071] A is a C6-C50 aryl group containing an electron-withdrawing group;

[0072] n is 1-200;

[0073] x is changed to 0

[0074] According to the present invention, the present invention will have the compound of formula (II) structure and the compound of formula (III) structure copolymerization, obtain the compound of structure shown in formula (I); Wherein, the compound of formula (II) structure and formula (III) Among the substituents in the compound of structure, the R is preferably a C3-C25 alkyl grou...

Embodiment 1

[0087] Example 1: Synthesis of Polymer PAPhF

[0088] (1) Synthesis of 9,9-dihexyl-9,10-dihydroacridine

[0089] The preparation process is shown in the following formula:

[0090]

[0091] The specific steps are:

[0092] Methyl N-phenyl anthranilate (20.5g, 90mmol) and 80ml of dry tetrahydrofuran were added into a 250ml three-necked flask, the gas was exchanged, and the ether solution of hexylmagnesium bromide (130ml, 2mol / l) dropwise added to the stirred reaction system, the dropwise addition was completed, and stirred at room temperature for 5h; the reaction solution was poured into 200ml water, extracted with water and ether, and the organic phase was rotary evaporated under reduced pressure to obtain the intermediate; the intermediate, 100ml glacial acetic acid Add 30ml of concentrated hydrochloric acid into a 250ml single-necked flask, reflux at 90°C for 24h, cool to room temperature, pour the reaction solution into 200ml of water, extract with water and ethyl ace...

Embodiment 2

[0112] Embodiment 2: the synthesis of polymer PAPTC

[0113] 1) Preparation of unbrominated formula (II) structural compound

[0114] The preparation process is shown in the following formula:

[0115]

[0116] The specific steps are:

[0117] 9,9-dihexyl-9,10-dihydroacridine (2.0 g, 3.7 mmol), 4,6-di-tert-butyl-2-p-bromophenyl- 1,3,5-triazine (1.3g, 3.7mmol), Pd2(dba)3 (0.003g, 0.04mmol), DPPF (0.005g, 0.08mmol), sodium tert-butoxide (0.71g, 7.4mmol) were added Into a 100ml three-neck flask, add 20ml of dry toluene, ventilate, under argon protection, condense at 80°C for 20h, cool to room temperature, extract with water and dichloromethane, rotate the organic phase, and separate by column to obtain 2.0g of the product , 90% yield.

[0118] The obtained product is carried out nuclear magnetic resonance detection, and its hydrogen spectrum is: 1 HNMR (400MHz, CDCl 3)δ8.84(d, J=8.3Hz, 2H), 7.40(d, J=8.3Hz, 2H), 7.30(m, 2H), 6.94–6.81(m, 4H), 6.19(d, J=8.8 Hz, 2H), 2.02...

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Abstract

The invention provides a conjugated polymer and a preparation method thereof. The polymer provided by the invention has a structure represented by a formula (I). The energy level difference between the first excitation singlet state and the first excitation triplet state of the polymer is relatively low, such that the polymer has E-type delayed fluorescence emission. The polymer has good luminescence properties when applied in electroluminescent devices.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a conjugated polymer and a preparation method thereof. Background technique [0002] E-type delayed fluorescence was first discovered in the organic fluorescent dye eosin (Eosin), which was named because of the same lifetime of phosphorescence associated with it. E-type delayed fluorescence compounds include common organic small molecules such as fluorescein and acridine yellow (Acridine), and the fluorescence intensity of these compounds increases with temperature within a certain range, so E-type delayed fluorescence is also called It is heat-assisted or heat-induced delayed fluorescence [thermoassistantorthermallyactivateddelayedfluorescence (TADF)]. The basic reason for the E-type delayed fluorescence is that the energy level difference between the first excited singlet state and the first excited triplet state is small enough. At this time, the compound that can emit th...

Claims

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Application Information

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IPC IPC(8): C08G61/12
Inventor 程延祥朱运会王彦杰战宏梅李晓张子龙
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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