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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 capabilities, high voltage, etc., to facilitate the transport of electrons, improve luminous efficiency and External Quantum Efficiency, Effect of Lowering Driving Voltage

Active Publication Date: 2020-04-14
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 technical field of OLED, and provides a compound with a structure represented by a chemical formula 1, wherein X1, X2 and X3 are respectively and independently selected from C and N, at least one of X1, X2 and X3 is N, L1, L2 and L3 are respectively and independently selected a single bond, C6-C30 arylene and C3-C30 heteroarylene, and Ar1 and Ar2 are respectively and independently selected from C6-C30 aryl and C2-C30 heteroaryl. According to the invention, in the compound, the iminostilbene enables the molecular structure to be arc-shaped to increase the energy band width, deepen HOMO and deepen LUMO, so that electrons can smoothly enter a light-emitting layer, and based on large polarity, a good traction effect on movement of intramolecular electrons is achieved so as to make the material have high electron mobility; and a core body formed by iminostilbene and 3,3'-biphenylene is regulated by other aryl groups and heteroaryl groups, so that the glass-transition temperature (Tg) and the thermal stability of the material can be well guaranteed. The invention further 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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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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