Hyperbranched phosphorescent polymer and preparation method thereof

A technology of polymers and compounds, applied in the field of hyperbranched phosphorescent polymers and their preparation, can solve the problems of widening optical band gap, unsatisfactory electroluminescence efficiency, concentration quenching effect, etc. The effect of improving electroluminescence efficiency and improving electroluminescence efficiency

Inactive Publication Date: 2020-09-11
徐海琴
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when fluorescent compounds are used to form light-emitting layers in organic light-emitting devices, they have the disadvantage that triplet excitons generated in hosts are wasted. Therefore, when phosphorescent compounds have been gradually used to form light-emitting layers, due to It uses singlet excitons and triplet excitons at the same time, and its internal quantum efficiency is much higher than that of the fluorescent light-emitting layer.
However, when the phosphorescent polymer material is applied to double-layer electroluminescent devices, the concentration quenching effect of the complex is very likely to be caused due to aggregation, and the optical band gap is widened, which in turn causes the electroluminescent efficiency of the phosphorescent emitting material to be not very high. ideal
Therefore, the wide optical bandgap of existing phosphorescent emission materials and the unsatisfactory electroluminescent efficiency have become technical problems to be solved urgently by those skilled in the art.

Method used

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  • Hyperbranched phosphorescent polymer and preparation method thereof
  • Hyperbranched phosphorescent polymer and preparation method thereof
  • Hyperbranched phosphorescent polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 4-iodophenol (220mg, 1.00mmol), K 2 CO 3 (276mg, 2.00mmol) and a solution of (4-((10-bromodecyl)oxy)cyclohexyl)benzene (396mg, 1.00mmol) dissolved in 20mL of DMF were added to a 50ml three-necked flask and heated at 110°C Heat for 16 hours. After cooling to room temperature, dichloromethane was added to the reaction mixture. with H 2 The organic layer was washed with O and washed with Na 2 SO 4 dried, and the dried residue was removed from CH 2 Cl 2 / methanol (volume ratio is 4:1) and precipitates out, obtains white solid I-Y, (451mg, productive rate 84.0%), and reaction equation is:

[0029]

Embodiment 2

[0031] N-(3-aminophenyl)-2,7-dibromocarbazole (532 mg, 1 mmol), I-Y (1541.6 mg, 2.8 mmol), Pd(OAc) 2 (12 mg, 0.06 mmol), t-BuONa (384 mg, 4.0 mmol), toluene (10 mL) and 10 wt% P(t-Bu) dissolved in hexane 3 (290mL, 1mmol) was added into a 500ml three-necked flask, stirred at a speed of 300r / min and reacted at 120°C for 48h. After cooling to room temperature, petroleum ether was added to the reaction mixture. The organic layer was washed with toluene and washed with Na 2 SO 4 dry. After evaporation, the residue was dissolved in petroleum ether / CH 2 Cl 2 (7:1) is carried out silica gel column chromatography purification as eluent, obtains the compound shown in formula (II) (500mg, productive rate 70.0%), and chemical reaction equation is:

[0032]

Embodiment 3

[0034] 2,2'-(9,9-dibutyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborin alkane) (265.18mg, 0.5mmol), compound represented by formula (II) (491.736mg, 0.4mmol), 2,5-bis(4-bromophenyl)-1,3,4-oxadiazole (19.0mg , 0.05mmol), the compound represented by formula (III) (19.6mg, 0.02mmol), 10mL of purified toluene and 10mL of dehydrated tetrahydrofuran were added to a 50mL two-necked flask, and 5mg of Pd(OAc) was sequentially added under the protection of argon. 2 and 6mgPCy 3 , heated to 80°C and reacted for 2 hours, added 6mL of 20% organic base, refluxed for 36 hours, then added 2mgPCy 3 and 1mgPd(OAc) 2 Capping, after reacting for 10h, inject 0.3mL bromobenzene to capping again. After 12 hours, the reaction liquid was precipitated in methanol, and then extracted with methanol and acetone for 12 hours respectively, and the obtained concentrated extract was precipitated in methanol. The precipitate was dissolved in toluene, and carried out silica gel column chroma...

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Abstract

The invention belongs to the technical field of luminescent materials, and particularly relates to a hyperbranched phosphorescent polymer and a preparation method thereof. The invention provides a hyperbranched phosphorescent polymer. The structure of the hyperbranched phosphorescent polymer is shown as a formula (I). The invention also provides a preparation method of the hyperbranched phosphorescent polymer, which comprises the following steps: 1, carrying out nucleophilic substitution reaction on 4-iodophenol and (4-((10-bromodecane)oxy)cyclohexyl)benzene to obtain I-Y; 2, carrying out electrophilic substitution reaction on N-(3-aminophenyl)-2,7-dibromo carbazole, I-Y and t-BuONa to obtain a compound shown as a formula (II); and 3, carrying out a Suzuki coupling reaction on 2,2'-(9,9-dibutyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane), the compound represented by the formula (II), 2,5-bis (4-bromophenyl)-1,3,4-oxadiazole and the compound represented by the formula (III) to obtain the formula (I). The technical problems that an existing phosphorescent emission material is wide in optical band gap and unsatisfactory in luminous efficiency are solved.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to a hyperbranched phosphorescent polymer and a preparation method thereof. Background technique [0002] Generally, an organic light emitting device includes: an anode on a substrate; a hole transport layer, a light emitting layer, an electron transport layer, etc. as an organic layer on the anode. Compounds used to form a light emitting layer of an organic light emitting device are classified into fluorescent compounds using singlet excitons and phosphorescent compounds using triplet excitons according to a light emitting mechanism. However, when fluorescent compounds are used to form light-emitting layers in organic light-emitting devices, they have the disadvantage that triplet excitons generated in hosts are wasted. Therefore, when phosphorescent compounds have been gradually used to form light-emitting layers, due to It uses singlet excitons and trip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/10C08G61/12C09K11/06
CPCC08G61/10C08G61/124C09K11/06C08G2261/12C08G2261/132C08G2261/1412C08G2261/3142C08G2261/3228C08G2261/3241C08G2261/411C08G2261/5242C09K2211/185C09K2211/1475C09K2211/1466C09K2211/1416
Inventor 徐海琴
Owner 徐海琴
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