Thiophene or furan derivative and organic light emitting device using the derivative

A technology of organic light-emitting devices and furan derivatives, applied in the field of organic optoelectronic materials, can solve the problems of slower electron mobility than hole mobility, achieve high electron transport performance, solve carrier imbalance, and high luminous efficiency Effect

Inactive Publication Date: 2017-08-18
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron mobility is generally slower than the hole mobility. In order to combine holes and electrons smoothly, it is necessary to use an effective electron transport material to improve electron injection and migration from the cathode, and at the same time cut off part of the hole movement.

Method used

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  • Thiophene or furan derivative and organic light emitting device using the derivative
  • Thiophene or furan derivative and organic light emitting device using the derivative
  • Thiophene or furan derivative and organic light emitting device using the derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] [Example 1] Synthesis of compound 3-1

[0056] *Synthesis of Intermediate C-1-1

[0057]

[0058] Put into thieno[3,2-b]thiophene (4.21g, 30mmol) in the reactor, under nitrogen protection, add acetic acid 30ml, chloroform 50ml in the reactor, the Br of 20mmol 2 Slowly drop into the reactor to react, then stir for 1h, then gradually add 15mmol of Br 2 , stirred for 1 h, refluxed overnight, and cooled to room temperature to obtain a solid precipitate, which was washed with deionized water and methanol successively, dried, and the obtained crude product was passed through a silica gel column to obtain compound C-1-1 (12.72 g, 93%).

[0059] *Synthesis of Compound 3-1

[0060]

[0061] Add C-1-1 (1.91g, 4.2mmol), (4-cyanophenyl) boric acid (2.5g, 18.4mmol), tetrakistriphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate ( 5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, then stirred at 120°C for 3h. After the reaction was completed,...

Embodiment 2

[0062] [Example 2] Synthesis of compound 3-21

[0063] *Synthesis of Intermediate C-21-1

[0064]

[0065] Add 30ml of DMF and thieno[3,2-b]thiophene (2.31g, 16.5mmol) into the reactor, then cool down to 0°C, add NBS (8.81g, 49.5mmol), and react in the dark for 12h. After the reaction, use NaHSO 3 After washing, the solvent in the upper layer was removed, and the organic phase of the lower layer was concentrated and purified by silica gel column to obtain compound C-21-1 (4.67 g, 95%).

[0066] *Synthesis of compound 3-21

[0067]

[0068] Add C-21-1 (2.5g, 8.4mmol), anthraceneboronic acid (3.79g, 17.07mmol), tetrakistriphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol) in the reaction vessel, Toluene 60mL, ethanol 20mL and distilled water 20mL were stirred at 120°C for 3h. After the reaction was completed, the reaction was stopped with distilled water and extracted with ethyl acetate. MgSO for organic layer 4 dry. The solvent was dist...

Embodiment 3

[0069] [Example 3] Synthesis of Compound 3-28

[0070] *Synthesis of Intermediate C-28-1

[0071]

[0072] Add C-1-1 (9.12g, 20mmol), acetic acid 500ml, toluene 200ml, Zn powder (2.62g, 40mmol) into the reactor, and slowly drop hydrochloric acid solution in the reaction process to stimulate the activity of Zn powder. After the reaction is completed, reflux After one night, then cooled to room temperature, the solution was concentrated and filtered to obtain compound C-28-1 (5.36 g, 90%). *Synthesis of intermediate C-28-2

[0073]

[0074] Add C-28-1 (2.5g, 8.4mmol), phenanthrene boric acid (3.79g, 17.07mmol), tetrakistriphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol) in the reaction vessel, Toluene 60mL, ethanol 20mL and distilled water 20mL were stirred at 120°C for 3h. After the reaction was completed, the reaction was stopped with distilled water and extracted with ethyl acetate. MgSO for organic layer 4 dry. After the solvent wa...

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Abstract

The invention discloses a thiophene or furan derivative and an organic light emitting device using the derivative, and belongs to the technical field of organic optoelectronic materials. Thiophene and [3, 2-b] thiophene, furan and [3, 2-b] furan, or thiophene and [3, 2-b] thiophene 1, 1, 4, 4-tetroxide is adopted as a main structure in the derivative, the molecular weight of materials, pi conjugacy and eletrophilicity, charge transfer capacity, photochromism and the like can be adjusted by changing the linking method of a donor, meanwhile the problem that current carriers of a unipolar luminescent material are not balanced can be effectively solved, and thus the thiophene or furan derivative has high luminescence property, electronic transmission performance, membrane stability, thermostability and triplet state energy. The organic light emitting device prepared from the thiophene or furan derivative has the advantages of being excellent in electron chemistry performance and thermostability, long in service life and the like, and has a high luminescence efficiency even on the condition of a low starting voltage.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a thiophene or furan derivative and an organic light-emitting device using the derivative. Background technique [0002] In 1987, Tang C.W and Vanslyke S.A of Kodak Company in the United States used 8-hydroxyquinoline aluminum as the light-emitting material and prepared the first organic double-layer thin-film electroluminescent device with excellent performance by using a sandwich structure, which stimulated the development of organic electroluminescent materials. After nearly 30 years of development, organic electroluminescent diode imaging has become the most promising new generation display technology, which has independent light emission, low-voltage DC drive, full curing, wide viewing angle, weight Compared with liquid crystal displays, organic electroluminescent displays do not require a backlight, have a large viewing angle, low power, and their re...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D495/04C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D493/04C07D495/04C07D519/00C09K2211/1029C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/6572Y02E10/549
Inventor 董秀芹蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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