Carbazole Derivatives and Their Applications in Electroluminescent Devices

An electroluminescent device, a carbazole-based technology, applied in the field of organic electroluminescent materials, can solve the problems of efficiency stability not perfectly meeting the requirements of industrialization, unbalanced carrier transport matching ability, etc.

Active Publication Date: 2021-07-06
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, carbazole is a strong electron donor unit, which leads to the fact that most of the host materials of carbazole derivatives are p-type host materials, which makes the carrier transport matching ability unbalanced, resulting in the exciton quenching effect in the device. strong
Therefore, although the efficiency of traditional blue organic light-emitting diodes has been greatly improved, compared with other light colors, it does not perfectly meet the requirements of industrialization in terms of efficiency and stability.

Method used

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  • Carbazole Derivatives and Their Applications in Electroluminescent Devices
  • Carbazole Derivatives and Their Applications in Electroluminescent Devices
  • Carbazole Derivatives and Their Applications in Electroluminescent Devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]

[0055] 2-iodobenzonitrile (5g, 21.8mmol), (4-chlorophenyl) boronic acid (4.08g, 26.16mmol), K 2 CO 3 (12.03g, 87.2mmol) and tetrakis (triphenylphosphine) palladium Pd (PPh 3 ) 4 (254mg, 0.22mmol) was dissolved in a mixture of 1,4-dioxane and water (200ml, 1,4-dioxane / water=10 / 1, v / v). The resulting solution was heated at 90 °C overnight. After cooling to room temperature, the solution was mixed with 200 mL of water and the desired product was extracted with dichloromethane. The organic layers were collected and evaporated under reduced pressure. The resulting crude product was purified by column chromatography using petroleum ether / dichloromethane (PE / DCM, 3 / 1, V / V) as eluent to give 4'-chloro-[1,1'-biphenyl]- 2-Carbonitrile as a white solid (4.57 g, 98%), which 1 H-NMR test results such as figure 1 shown.

Embodiment 2

[0057]

[0058] 3,6-dibromo-9H-carbazole (2g, 6.15mmol), phenylboronic acid (1.80g, 14.76mmol), K 2 CO 3 (3.4g, 24.6mmol) and tetrakis(triphenylphosphine)palladium Pd(PPh 3 ) 4 (208 mg, 0.18 mmol) was dissolved in a mixture of 1,4-dioxane and water (100 mL, 1,4-dioxane / water=10 / 1, v / v). The resulting solution was heated at 90 °C overnight. After cooling to room temperature, the solution was mixed with 200 mL of water and the desired product was extracted with dichloromethane. The organic layers were collected and evaporated under reduced pressure. The resulting crude product was purified by column chromatography using petroleum ether / dichloromethane (PE / DCM, 2 / 1, V / V) as eluent to give 3,6-diphenyl-9H-carbazole as a white solid (1.69g, 86%), which 1 H-NMR test results such as figure 2 shown.

Embodiment 3

[0060]

[0061] 3,6-diphenyl-9H-carbazole (1g, 3.13mmol), 4'-chloro-[1,1'-biphenyl]-2-carbonitrile (805mg, 3.76mmol), Pd 2 (dba) 3 (147 mg, 0.16 mmol), s-Phos (193 mg, 0.47 mmol) and t-BuONa (1.2 g, 12.52 mmol) in 100 mL of toluene were heated at 110° C. overnight under argon. After cooling to room temperature, the mixture was extracted with dichloromethane. The resulting organic extract was dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane (PE / DCM, 1 / 1, V / V) as eluent to obtain BPCN-Cz2Ph as a white solid (1.24 g, 80%), Figure 4-5 respectively its 1 H-NMR and 13 C-NMR spectrum, its 1 H-NMR and 13 The corresponding results of C-NMR are as follows:

[0062] BPCN-Cz2Ph: 1 H NMR (600MHz, DMSO) δ8.77 (s, 2H), 8.04 (d, J = 7.8Hz, 1H), 7.93 (d, J = 7.8Hz, 2H), 7.90–7.85 (m, 3H), 7.83 (d, J=8.1Hz, 5H), 7.80(d, J=11.6Hz, 2H), 7.66(t, J=7.6Hz, 1H), 7.57(d, J=8.6H...

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Abstract

The present invention discloses carbazole derivatives as shown in formula (1)-(3): the present invention also discloses that the above-mentioned carbazole derivatives are used as host materials in OLED organic light-emitting layers or in the preparation of electroluminescent devices Applications. The above-mentioned carbazole derivatives have a high triplet state and exhibit bipolar transport properties at the same time, and the carrier mobility is high, and the electron-hole matching is more balanced, which is conducive to the formation of excitons. It is used in organic electroluminescent blue light devices Excellent performance, low voltage, high efficiency.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a carbazole derivative and its application in electroluminescent devices. Background technique [0002] Organic light emitting diodes (OLEDs) have been widely used in display and lighting fields. Based on the three primary colors of blue, green and red, full-color display and white lighting can be realized. However, among the three primary colors, the efficiency and stability of blue light restrict the development of organic light-emitting diodes. At present, both blue thermally delayed fluorescent materials and phosphorescent materials themselves have a large triplet energy level, which determines that a host material with a larger triplet energy level is required to achieve sufficient energy transmission. The triplet energy level of an organic molecule is related to the conjugate length of the molecule. In order to obtain a larger triplet energy level, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86H01L51/50H01L51/54
CPCC07D209/86H10K85/6572H10K50/11
Inventor 廖良生张园览冉佺樊健
Owner SUZHOU UNIV
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