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Photoelectric material and preparation method thereof and application to organic electronic device

A technology of optoelectronic materials and synthesis methods, which is applied in the fields of electric solid state devices, photovoltaic power generation, electrical components, etc., can solve the problems of high cost and complicated preparation process of optoelectronic materials, and achieve the effects of low manufacturing cost, easy purification and good yield.

Active Publication Date: 2016-06-15
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to solve the problem of complex preparation process and high cost of photoelectric materials in the prior art, and provide a new photoelectric material that can be processed by solution, produced in large area and low cost

Method used

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  • Photoelectric material and preparation method thereof and application to organic electronic device
  • Photoelectric material and preparation method thereof and application to organic electronic device
  • Photoelectric material and preparation method thereof and application to organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Synthesis of P1-SO

[0053] (1) Synthesis of dibromodiphenyl sulfoxide

[0054] Diphenylsulfide (2.34mL, 20mmol) was dissolved in CH 2 Cl 2 and H 2 O (1:1, 150mL) mixed solvent, add 30% H 2 o 2 (0.86mL, 36mmol) and liquid bromine (4.1mL, 80mmol), and then the reaction solution was stirred continuously at room temperature for 6h. After the reaction was completed, excess liquid bromine was removed with saturated sodium sulfite solution, and then extracted with water and dichloromethane , after the organic phase was dried with anhydrous magnesium sulfate, spin-dried in vacuum in a rotary evaporator to obtain a crude product, then carried out column chromatographic separation and purification, utilized sherwood oil as an eluent, and finally carried out recrystallization with sherwood oil to obtain 5.88g ( 86%) white solid, 1 H-NMR (500MHz, CDCl 3 ): δ (ppm) = 7.59-7.63 (d, 4H), 7.48-7.52 (d, 4H), due to the good symmetry of this structure, it shows two typ...

Embodiment 2

[0062] Example 2: P2-SO 2 Synthesis

[0063] (1) Synthesis of Dibromodiphenylsulfone

[0064] Dibromodiphenyl sulfide (11.7253g, 34.1mmol), 30% H 2 o 2 (150mL) and HOAc (150mL) were added into a single-necked bottle and heated to reflux in an oil bath overnight. After the reaction was completed, filter and recrystallize with ethanol to obtain pure product dibromodiphenyl sulfone with a yield of 88.5%. 1 H-NMR (500MHz, CDCl 3 ): δ (ppm) = 7.77-7.79 (d, 4H), 7.64-7.67 (d, 4H), due to the good symmetry of this structure, it shows two types of hydrogen, and the nuclear magnetic resonance is in good agreement with it, that is, the product is obtained Dibromodiphenyl sulfone; preparation process is shown in the following formula (6):

[0065] Formula (6):

[0066] (2) With reference to the step (2) of Example 1, 4,4'-to-octyloxyanilinodiphenylsulfone was synthesized, a pale yellow solid with a yield of 88%, 1 H-NMR (500MHz, DMSO-d 6):δ(ppm)=8.56(s,2H),7.57-7.60(d,4H),7.06-...

Embodiment 3

[0068] Example 3: P3-mSO 2 Synthesis.

[0069] (1) Synthesis of meta-dibromodiphenyl sulfone.

[0070] Add NBS (17.8g, 100mmol) in batches to a solution of diphenylsulfone (10.9g, 50.0mmol) in sulfuric acid (50mL), and stir the reaction solution at 100°C for 2h. Poured into 100mL of ice water to obtain a white precipitate, which was filtered and recrystallized with ethanol to obtain the pure product m-dibromodiphenylsulfone with a yield of 58.8%. 1 H-NMR (500MHz, CDCl 3 ): δ (ppm) = 8.07 (s, 2H), 7.86-7.89 (d, 2H), 7.71-7.74 (d, 2H), 7.39-7.43 (m, 2H), the hydrogen at the chemical shift of 8.07, corresponding to The most important thing is the left and right hydrogens sandwiched between the sulfone group and bromine, and the nuclear magnetic resonance is very good, that is, the product m-dibromodiphenyl sulfone is obtained; the preparation process is shown in the following formula (8).

[0071] Formula (8):

[0072] (2) With reference to the step (2) of Example 1, 3,3'-...

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Abstract

The invention discloses a photoelectric material and a preparation method thereof and application to an organic electronic device. The preparation method of the photoelectric material includes the steps that a halogenated compound of M1 or M2 is prepared firstly, wherein M1 or M2 monomers serve as raw materials, N-bromosuccinimide or liquid bromine is added, in an organic solvent of concentrated sulfuric acid or hydrogen peroxide, a reaction is conducted under a normal-temperature or heating and stirring conditions, purification is conducted, and the halogenated compound of M1 or M2 is obtained; then secondary amine is prepared through a C-N coupled reaction, wherein Pd2(dba)3 and DPPF are firstly added to a container, after stirring in a benzene series solvent, the halogenated compound of M1 or M2 is added, primary amine of Ar1 or Ar4 and sodium tert-butoxide are added, and heating reflux is conducted; finally the photoelectric material is prepared. A D-A-D-A type non-conjugate polymer is synthesized through a C-N coupling polymerization method, in addition, a side chain with an electron-donating group is arranged, LUMO and HOMO electron clouds are slightly overlapped, and therefore the characteristic of thermotropic delayed fluorescence can be easily achieved.

Description

technical field [0001] The present invention relates to a novel optoelectronic material, in particular to a optoelectronic material and its preparation method and its application in organic electronic devices. The optoelectronic material at least comprises a main chain skeleton of a D-A structural unit and a side chain group, The application relates to the application in organic electronic devices, especially organic light-emitting devices, including the production method of the corresponding organic electronic devices and its application in lighting and display technology and other occasions. Background technique [0002] Organic light-emitting devices, especially organic light-emitting diodes (OLEDs), due to their self-illumination, surface luminescence, high flexibility, high resolution, high luminous efficiency, fast response time, high brightness, etc., make them the most Promising next-generation display and lighting technologies. In particular, they can form films fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/18C08G75/20H01L51/54
CPCC08G75/18C08G75/20H10K85/111Y02E10/549
Inventor 黄飞胡英元
Owner 东莞伏安光电科技有限公司
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