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Hole injection material, hole injection layer comprising same, and OLED display panel

A technology of hole injection material and hole injection layer, which is applied in chemical instruments and methods, preparation of organic compounds, electrical components, etc., can solve problems such as hole injection performance needs to be improved, compound reduction potential is weak, etc., and achieve strong interaction effect, increase electrical conductivity, and good thermal stability

Active Publication Date: 2019-12-31
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reduction potential of its compound is weak, and the hole injection performance needs to be improved.

Method used

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  • Hole injection material, hole injection layer comprising same, and OLED display panel
  • Hole injection material, hole injection layer comprising same, and OLED display panel
  • Hole injection material, hole injection layer comprising same, and OLED display panel

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0064] a compound A preparation method comprising the steps of:

[0065]

[0066] Potassium tert-butoxide (112.21mg, 1mmol), a-1 (306.09mg, 1mmol) and 10mLTHF were added to the reaction flask, and a-2 was generated after stirring at room temperature for 6 hours, and the product was directly used in the next step without purification Then add dioxomalononitrile (80mg, 1mmol) and stir for 1 hour, then add potassium fluoride (58.10mg, 1mmol) and tetrabutyllithium fluoride (261.46mg, 1mmol) and continue to stir for 1 hour; Reaction solution Concentrate and column to give a-3.

[0067] Characterization:

[0068] NMR: 13 H NMR: (1H, 73.1); (2H, 117.2); (2H, 118.4); (2H, 136.8); (2H, 143.9); (1H, 176.7);

[0069] Mass spectrum: 224 (molecular weight)

[0070] The LUMO energy level of the compound of Preparation Example 1 was 5.38 eV.

preparation example 2

[0072] a compound

[0073]

[0074] A preparation method comprising the steps of:

[0075]

[0076] Potassium tert-butoxide (112.21mg, 1mmol), a-1 (306.09mg, 1mmol) and 10mLTHF were added to the reaction flask, and a-2 was generated after stirring at room temperature for 6 hours, and the product was directly entered into the next step without purification . Add oxo(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)propionitrile (270.99 mg, 1 mmol) and stir for 1 hour, followed by potassium fluoride (58.10 mg, 1 mmol) and Tetrabutyllithium fluoride (261.46 mg, 1 mmol) was stirred for an additional 1 hour. The reaction solution was concentrated and passed through a column to obtain a-3.

[0077] Characterization:

[0078] NMR: 13 H NMR: (1H, 97.7); (1H, 102.7); (1H, 107.4); (1H, 115.4); (1H, 117.2); (1H, 118.4); (2H, 136.8); (1H, 97.7) ;(2H,118.4);(2H,143.0);(2H,143.9);(2H,144.3),(1H,151.5);

[0079] Mass spectrum: 414.99 (molecular weight).

[0080] The LUMO energy lev...

preparation example 3

[0082] a compound

[0083]

[0084] A preparation method comprising the steps of:

[0085]

[0086] Add c-1 (229.93mg, 1mmol) and 10mL cyclohexane to the reaction flask, then add n-butyllithium (32.03mg, 0.5mmol) dropwise to the reaction system to obtain intermediate c-2, and finally the reaction system continues Stir for 6 hours. The reaction solution was concentrated and passed through a column to obtain c-3.

[0087] Characterization:

[0088] NMR: 13 H NMR: (4H, 118.4); (2H, 132.3); (4H, 136.8); (4H, 143.9);

[0089] Mass spectrum: 319.99 (molecular weight).

[0090] The LUMO energy level of the compound of Preparation Example 3 was 5.20 eV.

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Abstract

The present invention relates to a hole injection material. The hole injection material comprises a compound having a structure represented by formula (I) and / or a compound having a structure represented by formula (II). The hole injection material has a cross-conjugated structure, holes are formed by grafting using an electron withdrawing group, and the holes are matched with the pi bond of the cross-conjugated structure to make the holes exist in a large area to form free holes, so a high hole extraction rate is obtained, and the conductivity of a device is improved; and the electron withdrawing group and the cross-conjugated structure are combined, so that the hole injection material has a good thermal stability.

Description

technical field [0001] The invention belongs to the field of preparation of organic light-emitting diodes, and in particular relates to a hole injection material, a hole injection layer containing it, an OLED display panel and electronic equipment. Background technique [0002] An OLED display is a display made of organic light-emitting diodes. Due to its self-illumination, high contrast ratio, thin thickness, fast response speed, flexible panel, and simple structure, it is considered to be the next generation of flat-panel display technology. The structure of OLED devices is generally: cathode (Cathode) / electron injection layer (EIL) / electron transport layer (ETL) / light emitting layer (EML) / hole transport layer (HTL) / hole injection layer (HIL) / anode ( Anode). Energy level matching is very important for organic electroluminescent devices. The general structure of OLED devices mostly uses ITO as the anode, but its work function is relatively high, and the energy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C17/269C07C255/35C07C25/22C07C255/51H01L51/54H01L51/50
CPCC07C255/35C07C25/22C07C255/51C07C2602/04C07C2602/20C07C2603/08H10K85/60H10K85/615H10K50/17
Inventor 俞云海杨红领鄢亮亮
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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