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

Abstract

The invention relates to a hole injection material. The hole injection material comprises a compound having a structure represented by formula (I) and / or a metal complex of the compound of the formula(I); and in the formula (I), R1, R2, R3, R4, R5, R6, R7 and R8 are respectively independently selected from an electron withdrawing group, the hydrogen atom and a non-electron withdrawing group, at least one of the R1, R2, R3, R4, R5, R6, R7 and R8 is the electron withdrawing group, and n is an integer of 0-3. The hole injection material has a cross-conjugated structure, and is grafted with the electron-withdrawing group, and the electron-withdrawing group cooperates with the cross-conjugated system to expand an electron receiving area to a large range and make a large number of electrons jump to the LUMO energy level of a doped material from the HOMO energy level of a hole transport material, so that many free holes are formed in the hole transport material, thereby the conductivity of adevice is improved; and the hole injection material has good non-planar characteristics, so the a crystallization effect is prevented, and the light extraction efficiency of the device is improved.

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...

Examples

preparation example 1

[0049] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0050]

[0051] Add a-1 (406.2mg, 1mmol) and a-2 (389.82mg, 2.5mmol) to the reaction flask and stir, then add Na 2 CO 3 aqueous solution (1M, 3mL) and 20mL toluene, and finally add Pd (PPh 3 ) 4 (1.56 mg, 0.1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain a-3.

[0052] Characterization:

[0053] NMR: 13 H NMR: (2H, 75.1); (2H, 82.1); (8H, 117.2); (2H, 165.3); (2H, 178.9);

[0054] Mass spectrum: 306.04 (molecular weight).

preparation example 2

[0056] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0057]

[0058] Add b-1 (406.2mg, 1mmol) and b-2 (1129.80mg, 2.5mmol) to the reaction flask and stir, then add Na 2 CO 3 aqueous solution (1M, 3mL) and 20mL toluene, and finally add Pd (PPh 3 ) 4 (1.56 mg, 0.1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain b-3.

[0059] Characterization:

[0060] NMR: 13 H NMR: (2H, 75.1); (4H, 88.9); (2H, 114.9); (4H, 116.4); (4H, 116.5); (4H, 117.2); (2H, 141.3); (8H, 144.7) ;(8H,149.7);(2H,178.9);

[0061] Mass spectrum: 898.01 (molecular weight).

preparation example 3

[0063] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0064]

[0065] Add c-1 (529.1mg, 1mmol) and c-2 (252.92mg, 1mmol) to the reaction flask and stir, then add Cs 2 CO 3 Aqueous solution (1M, 3mL) and 20mL 1,4-dioxane, finally adding Pd(OAc) 2 (2.24 mg, 1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain c-3.

[0066] Characterization:

[0067] NMR: 13 H NMR: (2H, 71.1); (1H, 75.1); (2H, 88.9); (2H, 116.4); (2H, 116.5); (6H, 117.2); (4H, 144.7); (4H, 149.7) ;(2H,177.8);(1H,178.9);

[0068] Mass spectrum: 576.01 (molecular weight).

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...

Examples

preparation example 1

[0049] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0050]

[0051] Add a-1 (406.2mg, 1mmol) and a-2 (389.82mg, 2.5mmol) to the reaction flask and stir, then add Na 2 CO 3 aqueous solution (1M, 3mL) and 20mL toluene, and finally add Pd (PPh 3 ) 4 (1.56 mg, 0.1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain a-3.

[0052] Characterization:

[0053] NMR: 13 H NMR: (2H, 75.1); (2H, 82.1); (8H, 117.2); (2H, 165.3); (2H, 178.9);

[0054] Mass spectrum: 306.04 (molecular weight).

preparation example 2

[0056] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0057]

[0058] Add b-1 (406.2mg, 1mmol) and b-2 (1129.80mg, 2.5mmol) to the reaction flask and stir, then add Na 2 CO 3 aqueous solution (1M, 3mL) and 20mL toluene, and finally add Pd (PPh 3 ) 4 (1.56 mg, 0.1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain b-3.

[0059] Characterization:

[0060] NMR: 13 H NMR: (2H, 75.1); (4H, 88.9); (2H, 114.9); (4H, 116.4); (4H, 116.5); (4H, 117.2); (2H, 141.3); (8H, 144.7) ;(8H,149.7);(2H,178.9);

[0061] Mass spectrum: 898.01 (molecular weight).

preparation example 3

[0063] A hole-injecting material, the structure of which is The preparation method comprises the following steps:

[0064]

[0065] Add c-1 (529.1mg, 1mmol) and c-2 (252.92mg, 1mmol) to the reaction flask and stir, then add Cs 2 CO 3 Aqueous solution (1M, 3mL) and 20mL 1,4-dioxane, finally adding Pd(OAc) 2 (2.24 mg, 1% mmol). The reaction mixture was refluxed for 24h. The reaction solution was concentrated and passed through a column to obtain c-3.

[0066] Characterization:

[0067] NMR: 13 H NMR: (2H, 71.1); (1H, 75.1); (2H, 88.9); (2H, 116.4); (2H, 116.5); (6H, 117.2); (4H, 144.7); (4H, 149.7) ;(2H,177.8);(1H,178.9);

[0068] Mass spectrum: 576.01 (molecular weight).

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