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A kind of naphthalene[1,2]imidazole bipolar conjugated compound and its preparation and application

A conjugated compound, bipolar technology, applied in the field of luminescent materials, can solve the problems of low device current efficiency and quantum efficiency, difficult to achieve carrier balance, difficult to obtain blue light emission, etc., and achieve good solubility and film formation. The effect of properties, novel structure, and molecular weight determination

Active Publication Date: 2018-01-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the classic blue organic fluorescent materials in the past can be divided into n-type molecules or p-type molecules from the molecular structure. They are either electron-dominated or hole-dominated in the device work, so it is difficult to realize the carrier balance, resulting in low device current efficiency and quantum efficiency
And the simple design Donor-Acceptor (D-A) type molecule, although it is possible to realize bipolar transport, achieve the purpose of balancing the charge carriers, but due to the intramolecular charge transfer between the electron-donating unit and the electrophilic unit, the compound’s The band gap narrows, resulting in a red shift of the luminescence peak, making it difficult to obtain ideal blue luminescence

Method used

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  • A kind of naphthalene[1,2]imidazole bipolar conjugated compound and its preparation and application
  • A kind of naphthalene[1,2]imidazole bipolar conjugated compound and its preparation and application
  • A kind of naphthalene[1,2]imidazole bipolar conjugated compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) The preparation of 1-nitronaphthalene-2-trifluoromethanesulfonate, the reaction formula is as follows:

[0031]

[0032] In a 1-liter single-necked flask, add 1-nitro-2-naphthol (0.20mol, 37.8g) into 500ml of dichloromethane and stir to dissolve, add 50ml of triethylamine and cool to 0°C, then slowly drop Add trifluoromethanesulfonic anhydride (0.25 mol, 70.5 g). After the dropwise addition, it was naturally raised to room temperature and reacted for 10 hours. The mixture was then poured into 1 L of water, and the product was extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, remove the solvent after separation, and separate and purify with silica gel column to obtain a white solid (59.1 g, yield 92%).

[0033] (2) The preparation of 1-nitro-N-benzene-2-naphthylamine, the reaction formula is as follows:

[0034]

[0035] In a 250 ml three-necked flask, 1-nitronaphthalene-2-trifluoromethanesulfonate (50mmol, 16.1g) was ad...

Embodiment 2

[0046] (1)~(4) are with embodiment 1;

[0047] (5) Preparation of compound 1-1-2, the reaction formula is as follows:

[0048]

[0049] Add 2-(4-bromobenzene)-3-benzene-3-H-naphthalene[1,2]imidazole (5mmol, 2.0g) and N,N-diphenyl- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7mmol, 2.6g), 30ml of toluene and 15ml of tetrahydrofuran were added 20 milliliters of aqueous sodium carbonate solution with a weight concentration of 10%, 50 milligrams of tetrakis(triphenylphosphine) palladium, stirred and reacted under reflux for 24 hours, after cooling, the mixed solution was poured into 200 milliliters of water, and the product was extracted with dichloromethane . The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation. The yellow solid was separated and purified by silica gel chromatography, and then dried and sublimed under vacuum to obtain a high-purity product (1.7 g, yield 61%).

Embodiment 3

[0051] (1)~(4) are with embodiment 1;

[0052] (5) The preparation of compound 1-1-3, the reaction formula is as follows:

[0053]

[0054] Add 2-(4-bromobenzene)-3-benzene-3-H-naphthalene[1,2]imidazole (5mmol, 2.0g) and N,N-diphenyl- 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-biphenyl-4-amine (7mmol, 3.1g), 30ml Toluene and 15 milliliters of tetrahydrofuran, add 20 milliliters of weight concentration again and be 10% sodium carbonate aqueous solution, 50 milligrams of tetrakis(triphenylphosphine) palladiums, stir and react under reflux for 24 hours, after cooling, pour the mixed solution into 200 milliliters water and extract the product with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation. The green solid was separated and purified by silica gel chromatography, and then dried and sublimed under vacuum to obtain a high-purity product (1.9 g, yield 59%).

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Abstract

The invention belongs to the technical field of luminescent materials, and discloses a naphtho[1,2]imidazole bipolar conjugated compound as well as its preparation and application. The compound has the general structural formula shown in (1) or (2), wherein R1 and R2 are the same or different conjugated units with electron-donating properties. The preparation method is as follows: react o-nitronaphthol with trifluoromethanesulfonic anhydride, then react with the conjugated unit substituted by amino group, then reduce the nitro group to amino group, and then condense the amino group with the conjugated unit substituted by acid chloride or aldehyde group reaction, and finally through Suzuki coupling, Buchwald-Hartwig coupling or copper-catalyzed amination reaction of halogenated aromatic hydrocarbons to react with active conjugated units to obtain naphthalene[1,2]imidazole bipolar conjugated compounds. The compound of the present invention is beneficial to realize better carrier balance, thereby obtaining high device efficiency.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to a naphtho[1,2]imidazole bipolar conjugated compound and its preparation and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. Over the past two decades, OLED devices employing novel emitters, especially organic-heavy metal complex phosphorescent emitters, have achieved considerable success. However, due to the difficulty in obtaining wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/54
CPCC09K11/06C07D235/02C07D403/10C07D403/14C09K2211/1044H10K85/6572
Inventor 苏仕健刘明
Owner SOUTH CHINA UNIV OF TECH
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