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Compound, organic electroluminescent device and display device

A compound and chemical formula technology, applied in the field of organic electroluminescent devices and display devices, can solve the problems of inability to match hole transport materials, weak electron transport ability, high voltage, etc., and achieve favorable electron transport, improve luminous efficiency and External quantum efficiency, the effect of reducing the driving voltage

Active Publication Date: 2020-12-08
SHAANXI LTMS OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently commonly used electron transport materials still have weak electron transport ability and cannot match well with hole transport materials, which leads to high voltage, low efficiency, and short life in device performance testing.

Method used

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  • Compound, organic electroluminescent device and display device
  • Compound, organic electroluminescent device and display device
  • Compound, organic electroluminescent device and display device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0133] Preparation of Synthetic Example 1 Compound 2

[0134]

[0135] Under the protection of nitrogen, intermediate 1 (10.00g, 18.69mmol), 4-biphenylboronic acid (3.70g, 18.69mmol), potassium carbonate (6.46g, 46.72mmol), tetrabutylammonium bromide were successively added to the reaction flask (0.61g, 1.87mmol), toluene 80mL, ethanol 20mL, water 20mL, after the addition, start stirring, heat up to 50 ° C, then add tetrakis (triphenylphosphine) palladium (0.11g, 0.09mmol), after the addition , continue to heat up to 80°C for reflux reaction for 5h, after the reaction is completed, cool down to room temperature, extract with 80mL of toluene, wash the organic phase with 80mL of water*3 times until neutral, dry, filter, and concentrate. Recrystallize with 6 times toluene to LC>99.9%. Drying gave 7.93g of compound 2, yield: 65%. m / z=653.270[M+H] + .

Synthetic example 2

[0136] Preparation of Synthetic Example 2 Compound 13

[0137]

[0138] Under nitrogen protection, intermediate 2 (10.00g, 16.36mmol), 2-pyridineboronic acid (2.01g, 16.36mmol), potassium carbonate (5.65g, 40.91mmol), tetrabutylammonium bromide ( 0.53g, 1.64mmol), toluene 80mL, ethanol 20mL, water 20mL, after the addition, start stirring, heat up to 50°C, then add tetrakis(triphenylphosphine) palladium (0.095g, 0.082mmol), after the addition, Continue to heat up to 80°C and reflux for 3 hours. After the reaction is complete, cool down to room temperature, extract with 80 mL of toluene, wash the organic phase with 80 mL of water*3 times until neutral, dry, filter, and concentrate. Recrystallize with a mixed solvent of 4 times toluene and 2 times n-heptane to LC>99.9%. Drying gave 7.27g of compound 13, yield: 68%. m / z=654.265[M+H] + .

Synthetic example 3

[0139] Preparation of Synthetic Example 3 Compound 19

[0140]

[0141] Under nitrogen protection, intermediate 2 (10.00g, 16.36mmol), 2-naphthylboronic acid (2.81g, 16.36mmol), potassium carbonate (5.65g, 40.91mmol), tetrabutylammonium bromide ( 0.53g, 1.64mmol), toluene 80mL, ethanol 20mL, water 20mL, after the addition, start stirring, heat up to 50°C, then add tetrakis(triphenylphosphine) palladium (0.095g, 0.082mmol), after the addition, Continue to heat up to 80°C and reflux for 2 hours. After the reaction is complete, cool down to room temperature, extract with 80 mL of toluene, wash the organic phase with 80 mL of water*3 times until neutral, dry, filter, and concentrate. Recrystallized with 3 times ethyl acetate to LC>99.9%. Drying gave 6.44 g of compound 19, yield: 56%. m / z=703.286[M+H] + .

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Abstract

The invention belongs to the field of OLED technology and provides a compound having a structure shown in Chemical Formula 1: wherein, X 1 、X 2 、X 3 Each independently selected from C, N and at least one is N; L 1 , L 2 and L 3 each independently selected from single bond, C6-C30 arylene, C3-C30 heteroarylene; Ar 1 and Ar 2 Each independently selected from C6-C30 aryl, C2-C30 heteroaryl. In the compound of the present invention, the iminostilbene group makes the molecular structure arc-shaped, which can increase the energy band width, the HOMO becomes deeper, and the LUMO becomes deeper. On the one hand, it is beneficial for electrons to enter the light-emitting layer smoothly; The large polarity has a good traction effect on the movement of electrons in the molecule, so that this type of material has a high electron mobility. In addition, the core body formed by iminostilbene and 3,3'-biphenylene, regulated by other aryl and heteroaryl groups, can well ensure the glass transition temperature (Tg) and thermal stability of the material sex. The invention also provides an organic electroluminescent device and a display device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence materials, in particular to a condensed fluorene compound, an organic electroluminescence device and a display device comprising the compound. Background technique [0002] In recent years, an organic electroluminescent device (OLED, Organic electroluminescent device) as a new generation display technology has gradually entered people's field of vision. A common organic electroluminescent device is composed of an anode, a cathode, and more than one organic layer arranged between the cathode and the anode. When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the light-emitting layer, and the electrons on the anode side also move to the light-emitting layer. The two combine to form excitons in the light-emitting layer, and the excitons are excited. The ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D403/10C07D403/14C07D405/14C07D409/14C07D471/04C09K11/06H01L51/54H01L51/50
CPCC07D403/10C07D403/14C07D401/14C07D405/14C07D409/14C07D471/04C09K11/06C09K2211/1029C09K2211/1059C09K2211/1044C09K2211/1092C09K2211/1088H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/18H10K50/16
Inventor 冯震李应文杨雷
Owner SHAANXI LTMS OPTOELECTRONICS MATERIAL CO LTD
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