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A kind of optoelectronic material and its preparation method and application in organic electronic device

A technology for optoelectronic materials and synthesis methods, which is applied in the fields of electrical solid devices, photovoltaic power generation, electrical components, etc., can solve the problems of complex preparation process and high cost of optoelectronic materials, and achieve the effects of easy purification, low manufacturing cost, and good film-forming performance.

Active Publication Date: 2018-06-29
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A kind of optoelectronic material and its preparation method and application in organic electronic device
  • A kind of optoelectronic material and its preparation method and application in organic electronic device
  • A kind of optoelectronic material and its preparation method and application in 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, its preparation method and its application in organic electronic devices. The preparation method is to prepare the halides of M1 or M2 first: take M1 or M2 monomer as raw material, add N-bromosuccinimide or liquid bromine, in the organic solvent of concentrated sulfuric acid or hydrogen peroxide, normal temperature or heating And react and purify under stirring conditions to obtain the halides of M1 or M2; then C-N coupling reaction to prepare secondary amines: first add Pd2(dba)3 and DPPF to the container, stir in a benzene solvent, and then add M1 Or the halide of M2, the primary amine of Ar1 or Ar4 and sodium tert-butoxide, heating to reflux; finally prepare the photoelectric material. The present invention adopts the method of C-N coupling polymerization to synthesize D-A-D-A type non-conjugated polymer, and has a side chain of an electron-donating group in addition, which makes the overlapping of LUMO and HOMO electron clouds smaller , which is conducive to its thermally induced delayed fluorescence characteristics.

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 Patents(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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