Nitrogen-containing heterocyclic compound, application thereof and organic light-emitting device

A nitrogen heterocyclic compound and heterocyclic compound technology, which is applied in the field of organic electroluminescent materials, can solve the problem of unbalanced electron and hole transport, severe triplet-polaron annihilation, and low crossover rate between inverse systems, etc. question

Active Publication Date: 2019-11-15
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 m

Method used

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  • Nitrogen-containing heterocyclic compound, application thereof and organic light-emitting device
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  • Nitrogen-containing heterocyclic compound, application thereof and organic light-emitting device

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 invention relates to a nitrogen-containing heterocyclic compound. The heterocyclic compound has a structure shown in the following formula (1). The nitrogen-containing heterocyclic compound comprises asymmetric carboline groups and carbazole groups, so that molecules have excellent hole and electron transmission performance at the same time; meanwhile, bridged N heterocyclic rings and electron-withdrawing groups such as triazine, phenylcyano, pyrazine, pyridylcyano and the like are introduced into the molecular structure, so that improvement of the molecular electron transmission capability is facilitated. The nitrogen-containing heterocyclic compound has excellent bipolar transmission capacity, and can widen a charge composite area and reduce efficiency roll-off. Through introductionof different carboline groups and through change of relative substitution positions of carbazole groups and/or carboline groups, the energy level of the compound can be regulated and controlled, so that materials with different energy levels are screened, and selection and collocation of device materials are facilitated.

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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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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