Nitrogen-containing heterocyclic compounds and their applications and organic electroluminescent devices

A nitrogen heterocyclic compound and electroluminescent device technology, applied in the field of nitrogen-containing heterocyclic compounds and organic electroluminescent devices, can solve the mismatch of hole transport capability and electron transport capability, affect the luminous efficiency of electroluminescent devices, and three-wire The problem of serious state-polaron annihilation, etc., achieves the effect of excellent hole and electron transport performance, excellent bipolar transport ability, and easy selection and matching.

Active Publication Date: 2022-03-29
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the current thermally activated delayed fluorescence (TADF) materials have a mismatch between the hole transport ability and the electron transport ability, and the reverse intersystem crossing rate (k RISC ) is low, triplet-polaron annihilation (TPA) is more serious, etc.
[0005] In addition, in organic electroluminescent materials, its hole transport ability is often better than electron transport ability, which leads to unbalanced electron and hole transport and affects the luminous efficiency of electroluminescent devices.

Method used

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  • Nitrogen-containing heterocyclic compounds and their applications and organic electroluminescent devices
  • Nitrogen-containing heterocyclic compounds and their applications and organic electroluminescent devices
  • Nitrogen-containing heterocyclic compounds and their applications and organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0079] Preparation of intermediate M1:

[0080] Add 13.5g (70mmol, 1eq) of 2,5-difluorobromobenzene, 35.4g (140mmol, 2eq) of diboronic acid pinacol ester, and 68g (697mmol, 20%eq), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride 6.1g (8.4mmol, 12%eq), solvent dioxane 1000mL, add and replace nitrogen 3 times. The temperature of the oil bath was raised to 100° C., and the reaction was carried out overnight. (PE:EA=10:1, product Rf=0.5, 2,5-difluorobromobenzene Rf=1.0)

[0081] The reaction solution was lowered to room temperature, extracted with ethyl acetate, the upper layer was taken, the reaction solution was spin-dried, and PE:EA=30:1 was subjected to column chromatography to obtain a white solid, intermediate M1, 13g.

[0082] Preparation of intermediate M2:

[0083] Add toluene 500mL, intermediate M1 20g (83.3mmol, 1.2eq), 4-bromoisophthalonitrile 14.3g (70mmol, 1eq), sodium carbonate aqueous solution (sodium carbonate 22.3g, 210mmol, 3eq, water 105mL, 2M),...

Embodiment 2

[0181] Example 2 The organic electroluminescence performance of the OLED using the compound P28 of the present invention as a dye is better than that of the OLED organic electroluminescence performance using A129 as a dye in Comparative Example 1, and P28 obtains higher current efficiency and lower drive Voltage; This shows that the introduction of asymmetric carbazolecarboline groups into dyes to prepare organic electroluminescent devices can significantly reduce the driving voltage and improve the luminous efficiency.

[0182] At the same time, the organic electroluminescent performance of the OLED using the compound P66 of the present invention as the dye in Example 5 is better than that of the OLED using A130 as the dye in Comparative Example 2. P66 also obtained higher current efficiency and lower The driving voltage; this shows that the carboline group and the bridged pyridine group are introduced into the molecule, which can significantly reduce the driving voltage and i...

Embodiment 9

[0211] Example 9 The organic electroluminescent performance of the OLED using the compound P8 of the present invention as the main body is better than that of the OLED organic electroluminescent performance using CBP as the main body in Comparative Example 3, and the device in Example 9 has obtained higher current efficiency And lower driving voltage; This shows that the material based on asymmetric carbazolecarboline group is used as the main body to prepare organic electroluminescent devices, which can also obviously reduce the driving voltage and improve the advantages of luminous efficiency.

[0212] At the same time, the organic electroluminescence performance of the OLED using the compound P82 of the present invention as the dye in Example 11 is better than that of the OLED organic electroluminescence performance using P8 as the main body in Example 9. P82 has obtained higher current efficiency and lower Driving voltage; this shows that when the host material uses bridged...

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Abstract

The disclosure relates to a nitrogen-containing heterocyclic compound, which has a structure shown in the following formula (1): The nitrogen-containing heterocyclic compound of the present disclosure includes an asymmetric carboline group and a carbazole group, so that the molecule At the same time, it has excellent hole and electron transport properties; at the same time, bridged N heterocycles and electron-withdrawing groups such as triazine, benzocyano, pyrazine, and pyridine cyano are introduced into the molecular structure, which contributes to the molecular electron transport ability. improvement. The nitrogen-containing heterocyclic compound has excellent bipolar transport ability, can broaden the charge recombination area, and reduce the efficiency roll-off; and through the introduction of different kinds of carboline groups, as well as the The change of the relative substitution position can regulate the energy level of the compound, so that materials with different energy levels can be screened, and it is easy to select and match device materials.

Description

technical field [0001] The present disclosure relates to the field of organic electroluminescent materials, in particular, to a nitrogen-containing heterocyclic compound, its application and an organic electroluminescent device. Background technique [0002] The research on organic electroluminescent materials and devices began in the 1960s. According to different luminescent principles, organic electroluminescence can be divided into two categories: electroluminescence and electrophosphorescence. The triplet excitons of fluorescent materials are subject to spin prohibition, and can only return to the ground state in a non-radiative form to generate photons, resulting in the internal quantum efficiency of electroluminescence being limited to within 25%. Electrophosphorescence can make full use of the energy of singlet excitons and triplet excitons, so theoretically the internal quantum efficiency of phosphorescent devices can reach 100%. In 1998, Ma et al. of Hong Kong Uni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC07D471/04C09K11/06C09K2211/1029C09K2211/1044C09K2211/1007C09K2211/1059H10K85/615H10K85/654H10K85/6572
Inventor 李国孟高文正魏金贝代志宏
Owner BEIJING ETERNAL MATERIAL TECH
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