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Polymer with main chain containing sulphone unit as well as preparation method and application thereof

A technology of polymers and compounds, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, circuits, etc., can solve problems such as low triplet energy level, difficulty in achieving delayed fluorescence emission, and device performance not reaching the expected level. Efficiency roll-off, simple preparation method, and high external quantum efficiency

Active Publication Date: 2017-07-07
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of polymer TADF also requires the polymer to have a high triplet energy level, but the large conjugated delocalization system of traditional conjugated polymers makes the triplet energy level low and it is difficult to achieve delayed fluorescence emission.
Although polymer TADF emission can be achieved through different TADF unit connections (Adv. Mater. , 49, 4373-4377; Adv.Mater.2016, 28, 4019-4024), but its device performance is far from the expected level, and it is difficult to compare with the small molecule organic compound TADF material

Method used

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  • Polymer with main chain containing sulphone unit as well as preparation method and application thereof
  • Polymer with main chain containing sulphone unit as well as preparation method and application thereof
  • Polymer with main chain containing sulphone unit as well as preparation method and application thereof

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preparation example Construction

[0077] The present invention also provides a method for preparing the polymer containing sulfone units in the main chain of the present invention, comprising:

[0078] 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);

[0079]

[0080] Among them, R 1 , R 2 , R 3 C1-C30 alkyl, C1-C30 alkoxy or C6-C35 substituted aryl;

[0081] A is a C6-C50 aryl group or a C3-C45 heteroaryl group containing an electron-withdrawing group;

[0082] x is 0.001

[0083] n is 1-200;

[0084] According to the present invention, the present invention will have the compound of formula (II) structure, the compound of formula (III) structure and the compound of formula (IV) structure to copolymerize, obtain the polymer of structure shown in formula (I); Wherein, in the structure R 1 , R 2 , R 3 , the selection r...

Embodiment 1

[0089] Example 1: Synthesis of Polymer PCSAPTP25

[0090] The preparation process is shown in the following formula:

[0091]

[0092] The specific steps are:

[0093] Bis(4-(3-bromo-6-(2-ethyl)hexylcarbazole)phenyl)sulfone (139.6mg, 0.15mmol), 2,7-dibromo-9,9-dihexyl-10-( 4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,10-dihydroacridine (122.2mg, 0.15mmol), 9-(4-( Dodecyloxy)phenyl)-3,6-dipinacol borate-9-hydrocarbazole (203.9 mg, 0.3 mmol) and bis(tri-o-methylphenylphosphine)palladium dichloride ( 2.4mg, 0.003mmol) was added to a 100mL Schlenk bottle, the gas was changed three times, and argon protection was added, and oxygen-depleted tetrahydrofuran (10mL) and oxygen-depleted potassium phosphate aqueous solution (2mL, 2M) were added, and the reaction was refluxed at 80°C for 12h; Phenylboronic acid (69mg, 0.6mmol) dissolved in 1mL of tetrahydrofuran was added to the reaction solution, reacted for 6h, then 1mL of bromobenzene was added to the reaction solution, and react...

Embodiment 2

[0095] Example 2: Synthesis of Polymer PCSAPTP10

[0096] The preparation process is shown in the following formula:

[0097]

[0098] The specific steps are:

[0099] Bis(4-(3-bromo-6-(2-ethyl)hexylcarbazole)phenyl)sulfone (223.4mg, 0.24mmol), 2,7-dibromo-9,9-dihexyl-10-( 4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,10-dihydroacridine (49.0mg, 0.06mmol), 9-(4-( Dodecyloxy)phenyl)-3,6-dipinacol borate-9-hydro-carbazole (203.9 mg, 0.3 mmol) and bis(tri-o-methylphenylphosphine)palladium dichloride (2.4mg, 0.003mmol) was added to a 100mL Schlenk bottle, and the gas was exchanged 3 times, protected by argon, and oxygen-depleted tetrahydrofuran (10mL) and oxygen-depleted potassium phosphate aqueous solution (2mL, 2M) were added, and the reaction was refluxed at 80°C for 12h; Phenylboronic acid (69 mg, 0.6 mmol) dissolved in 1 mL of tetrahydrofuran was added to the reaction solution, and reacted for 6 hours, then 1 mL of bromobenzene was added to the reaction solution, and rea...

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Abstract

The invention provides a polymer with a main chain containing a sulphone unit. The polymer is of a structure shown in a formula (I). The polymer provided by the invention has thermally induced delayed fluorescence emission as energy level difference between a first excited singlet state and a first excited triplet state of the polymer provided by the invention is smaller by selecting a specific polymerization unit and selecting a specific polymerization unit ratio; and meanwhile, when the polymer is applied to an electroluminescent device, the obtained external quantum efficiency of the electroluminescent device is high, and efficiency roll-off of the electroluminescent device can be effectively inhibited. Besides, the preparation method of the polymer provided by the invention is simple, and the obtained polymer can be prepared in simple solution processing ways such as spin coating and ink-jet printing when being used for preparing the electroluminescent device, so that a preparation technology 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 polymer containing sulfone units in the main chain, a preparation method and application thereof. Background technique [0002] In 2012, Adachi's research group reported for the first time a new type of organic fluorescent material with an internal quantum efficiency of 100%, called thermally induced delayed fluorescence (TADF) material (Nature, 2012, 492, 234-238). The energy level difference between the first excited singlet state and the first excited triplet state of this type of material is small (<0.3eV), and the triplet excitons can absorb heat in the surrounding environment and convert to Singlet excitons, and then radiative transitions produce thermally induced delayed fluorescence; this mechanism can make full use of singlet excitons and triplet excitons, and the internal quantum efficiency can reach up to 100% when applied to electroluminescent...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/54
CPCC08G61/12C08G61/122C08G61/124C08G2261/411C08G2261/5222C08G2261/122C08G2261/3241H10K85/111
Inventor 程延祥王彦杰朱运会杨一可张保华战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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