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Polyspirofluorene and Organic Electroluminescent Devices

A technology selected from polyspirofluorene, which is applied in the field of polyspirofluorene and organic electroluminescent devices, and can solve the problems of polyspirofluorene without charge transfer, red shift of polymer spectrum, and reduction of fluorescence quantum efficiency.

Active Publication Date: 2020-07-07
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

For example Hintschich (Journal of Physical Chemistry B, 2008, 112, 16300-16306), Wu (Applied Physics Letters, 2005, 87) and Kim (Journal of Luminescence, 2005, 115, 109-116), Wang (Polym Chem, 2014, 5, 6444.) and others reported that the alkoxy chain on the side chain of polyspirofluorene has a strong electron-donating effect, which causes charge transfer between the main chain and the side chain, which in turn leads to a red shift of the polymer spectrum and a decrease in the fluorescence quantum efficiency. Many unfavorable factors such as prolonged fluorescence lifetime
Up to now, how to make the modified polyspirofluorene do not have this kind of charge transfer method has not been reported yet.

Method used

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  • Polyspirofluorene and Organic Electroluminescent Devices
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  • Polyspirofluorene and Organic Electroluminescent Devices

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preparation example Construction

[0119] The invention provides a preparation method of polyspirofluorene, comprising:

[0120] The dihalogen monomer with the structure of formula (II) and the diboron derivative monomer with the structure of formula (III) are polymerized in the presence of a palladium compound, a basic compound, an organic phosphine compound, a solvent, and a catalyst to obtain polyspirofluorene;

[0121] Or the dihalogen monomer of the formula (II) structure, the diboron derivative monomer of the formula (III) structure and the aromatic compound are polymerized in the presence of a palladium compound, a basic compound, an organic phosphine compound, a solvent, and a catalyst to obtain a polymer Spirofluorene;

[0122]

[0123] Among them, R 1 , R 2 , R 3 , R 4 Independently selected from C1-C22 straight-chain alkyl, C1-C22 branched-chain alkyl, C3-C22 cycloalkyl, C1-C22 alkoxy or C1-C22 heteroalkyl;

[0124] M is selected from one of chlorine trifluoromethanesulfonate and halogen; B i...

Embodiment 1

[0169] Carbazole (50g, 0.3mol), AlCl 3 (88.0g, 0.66mol) and dry dichloromethane (300mL) were added to a 1L three-necked flask, and mechanical stirring was turned on to dissolve; Pass into the sodium hydroxide solution; after the dropwise addition, the temperature is raised to reflux at 45°C, and the reaction is carried out for 12 hours. 3M HCl (300mL) solution was added dropwise in the system, and the solvent dichloromethane was distilled off to obtain a brown solid washed with a large amount of distilled water to obtain 82.8g of 3,6-bis(1-octanoyl)carbazole powder. 65.8%. The purity is 99.0%. The product obtained is carried out nuclear magnetic analysis, and the result is: 1 HNMR (400MHz, CDCl 3 ,δ):8.79(d,J=1.1Hz,2H),8.61(s,1H),8.15(dd,J=8.5,1.5Hz,2H),7.50(d,J=8.6Hz,2H),3.11 (t, J = 7.5Hz, 4H), 1.88–1.75 (m, 4H), 1.49–1.25 (m, J = 47.7, 8.0Hz, 16H), 0.90 (t, J = 6.9Hz, 6H).

Embodiment 2

[0171] The 3,6-di(1-octanoyl)carbazole powder (57.0g, 136mmol) obtained in Example 1, hydrazine hydrate (132mL, 2.17mol), sodium hydroxide (54.4g, 1.36mol) and a Diethylene glycol (500mL) was added to a 1L three-necked flask, and the three necks of the flask were respectively equipped with a mechanical stirring device, a built-in thermometer and a water separator; the stirring was turned on, the temperature was raised to 110°C for 4 hours, the temperature was raised to 150°C for 12 hours, and the temperature was raised to React at 190°C for 6h, release the generated gas and moisture, then raise the temperature to 210°C for 6h. After the reaction was completed, the system was cooled to room temperature, poured into a large amount of water, filtered, and the filter cake was drained. Using 200-300 mesh silica gel as the stationary phase and dichloromethane as the eluent, 43 g of light yellow solid 3,6-dioctylcarbazole was obtained by column separation, with a yield of 65%. The p...

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Abstract

The invention provides a polyspirofluorene having a structure represented by formula (I); the invention introduces a carbazole group into the side chain of spirofluorene to synthesize a polymer containing carbazole spirofluorene. The polymer of carbazole spirofluorene prepared by the present invention does not have intramolecular charge transfer from the main chain to the side chain, and at the same time, due to the modification of carbazole, the polymer has good hole transport ability and can retain the purity of pure blue light Under the advantage of , a good device efficiency can be achieved. At the same time, the polyspirofluorene of the invention introduced with aromatic groups can obtain three primary colors of blue, green and red emission, and achieve good device efficiency.

Description

technical field [0001] The invention relates to the field of a polymer preparation method, in particular to polyspirofluorene and an organic electroluminescent device. Background technique [0002] Polymer light-emitting diodes (PLEDs) can be prepared by solution processing (such as inkjet, spin coating, etc.), and have the advantages of low cost, easy realization of large area and flexible display, so they are favored in the field of light emission. . Current polymer blue light materials are mainly polymers such as polyphenylene (PPP), polycarbazole (PCz), and polyfluorene (PF). Among them, polyfluorene and its derivatives are widely considered to be the best among these materials, and there have been a large number of literature and patent reports. Moreover, the blue polyfluorene derivative is used as a skeleton, and other primary colors of red and green can be produced after copolymerization of other monomers, thereby realizing a full-color display device. [0003] How...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/10C08G61/12H01L51/50H01L51/54
CPCC08G61/10C08G61/126C08G2261/11C08G2261/122C08G2261/3243C08G2261/312C08G2261/149C08G2261/5222C08G2261/411C08G2261/354C08G2261/3246C08G2261/91H10K85/113H10K85/111H10K50/00H10K2102/00H10K2102/301
Inventor 王利祥丁军桥白科研赵磊
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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