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Crosslinkable polymers based on Diels-Alder reaction and their applications in organic electronic devices

An organic electronic device, polymer technology, applied in the direction of electric solid devices, electrical components, semiconductor devices, etc., can solve the problem of device life to be improved, and achieve excellent solvent resistance, good cross-linking effect, and short time.

Active Publication Date: 2020-10-16
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the performance of solution-processed OLEDs based on cross-linked polymers based on these cross-linking groups, especially the device life, still needs to be improved.

Method used

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  • Crosslinkable polymers based on Diels-Alder reaction and their applications in organic electronic devices
  • Crosslinkable polymers based on Diels-Alder reaction and their applications in organic electronic devices
  • Crosslinkable polymers based on Diels-Alder reaction and their applications in organic electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0257] Example 1: Synthesis of polymer P1 containing conjugated diene functional group D

[0258]

[0259] Synthesis of 2,5-diphenyl-p-xylene (3):

[0260] Add 26.40g (0.1mol) of 2,5-dibromo-p-xylene and 24.39g (0.2mmol) of phenylboronic acid into a 250ml three-neck round bottom flask, add 250ml of toluene, stir to dissolve, then add 50ml of water and 21.2g of Na 2 CO 3 (0.2mol), stir until the solids are all dissolved, add 0.5ml Aliquat 336 and 75mg triphenylphosphine tetrahelical palladium catalyst (o) (PPh 3 ) 4 Pd, nitrogen protection for 10min, then heating to reflux (92-100°C), reflux for 20min, turn off nitrogen to keep the system sealed, reflux reaction overnight, after cooling, extract the reaction solution with toluene (50mlx4), combine the organic phase, and sequentially use NaCl saturated solution Washed with water, distilled off the solvent and dried to obtain 22.48 g of white crystals, the theoretical value was 25.84 g, and the yield was about 87%. M.P.180...

Embodiment 2

[0283] Example 2: Synthesis of polymer P2 containing conjugated diene functional group D

[0284]

[0285] Synthesis of 2,7-Dibromofluorene (15)

[0286] Add fluorene (14) (100g, 602mmol) and iron powder (0.8g, 1.4mmol) into a 1-liter three-necked round-bottomed flask, add 500mL of chloroform to dissolve it completely, cool it to about 0-5°C in an ice-water bath, and slowly A mixture of liquid bromine (69 mL, 1337 mmol) and 100 mL of chloroform was added dropwise, protected from light, and after 1 hour of dropwise addition, reacted at room temperature for 10 hours, and a large amount of white solids precipitated. During the reaction process, the reaction was monitored by thin-layer chromatography. After the reaction was completed, saturated aqueous sodium bisulfite was added to remove excess unreacted liquid bromine. A large amount of white solid in the reaction mixture was filtered, the filtrate was washed three times with water, the oil layer was separated, concentrated,...

Embodiment 3

[0294] Example 3: Synthesis of Polymer P3 Containing Dienophile Functional Group A

[0295]

[0296] Synthesis of 4-Bromophenyl Acrylate (19)

[0297] Add 60% sodium hydride (3.68g, 91.6mol) to a tetrahydrofuran solution of p-bromobenzyl alcohol (16.3g, 87.3mol) under ice-cooling, react for 30min, then add acryloyl chloride (8.3g, 91.6mol), and the reaction continues Stir for 30min. Water was then added to terminate the reaction, and the organic solvent was removed by rotary evaporation. The residue was extracted with ethyl acetate, washed with saturated brine, and then mixed with silica gel powder to pass through the column. The ratio of ethyl acetate:petroleum ether was 80:20 as a rinse solution. 16 g of oil was obtained with a yield of 95%. 1 H-NMR (CDCl 3)δ: 6.03 (1H, dd, J = 10.5, 1.1Hz), 6.31 (1H, dd, J = 17.3, 10.5Hz), 6.61 (1H, dd, J = 17.3, 1.1Hz), 7.03 (2H, d , J=9.1 Hz), 7.50 (2H, d, J=9.1 Hz).

[0298] Synthesis of 4-(Diphenylamino)phenyl Acrylate (20)

[...

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Abstract

The invention provides a kind of mixture that can take place Diels-Alder reaction, comprise polymer (I) and polymer (II), the structure of described polymer (I) and polymer (II) is as follows: x1 , y1, x2, y2, z1 and z2 are molar percentages; said x1>0, x2>0, y1>0, y2>0, z1≥0, z2≥0; x1+y1+z1=1, x2+y2+z2=1Ar1, Ar2, Ar2‑1, Ar3, Ar4 and Ar4‑1 are each independently selected from: aryl or heteroaryl groups containing 5‑40 ring atoms; R1 and R2 are each independently A linking group; D is a conjugated diene functional group, A is a dienophilic functional group; n1 is greater than 0, and n2 is greater than 0. The above-mentioned mixtures for the Diels-Alder reaction have very good optical properties.

Description

[0001] This application is required to be submitted to the Chinese Patent Office on December 22, 2016, the application number is 201611201706.X, and the title of the invention is "Crosslinkable polymer based on Diels-Alder reaction and its application in organic electronic devices" The priority of the Chinese patent application of , the entire content of which is incorporated in this application by reference. technical field [0002] The invention relates to the field of organic polymer optoelectronic materials, in particular to a kind of mixture based on Diels-Alder reaction to construct cross-linkable polymers, another mixture containing it, a composition, an organic electronic device and applications thereof. Background technique [0003] Since the invention of polymer light-emitting diodes (O / PLEDs), polymer light-emitting diodes (O / PLEDs) have been in the There is great potential for applications in optoelectronic devices such as flat panel displays and lighting. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/54C08G61/12
CPCC08G61/12C08G2261/334C08G2261/344C08G2261/3162C08G2261/3142C08G2261/135C08G2261/76C08G2261/46C08G2261/149C08G2261/95C08G2261/512Y02E10/549H10K85/151H10K50/155C08G2261/3325H10K85/113H10K85/631H10K85/653H10K85/654H10K85/655H10K85/6574H10K85/6576
Inventor 潘君友刘升建
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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