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Bicarbazole derivatives and organic light emitting device thereof

An organic light-emitting device and biscarbazole technology, applied in the field of biscarbazole derivatives and organic light-emitting devices

Inactive Publication Date: 2018-03-02
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally speaking, the direction of OLED in the future is to develop high-efficiency, high-brightness, good-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many problems

Method used

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  • Bicarbazole derivatives and organic light emitting device thereof
  • Bicarbazole derivatives and organic light emitting device thereof
  • Bicarbazole derivatives and organic light emitting device thereof

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preparation example Construction

[0039] The preparation method of the biscarbazole derivatives of the present invention can be obtained through the following reactions.

[0040]

[0041] The biscarbazole derivatives represented by the formula (I) of the present invention can be prepared by Suzuki coupling reaction and Ullmann reaction, using conventional reaction conditions well known to those skilled in the art. The present invention has no special limitation on the sources of the raw materials used in the above-mentioned various reactions, and can be prepared by using commercially available product raw materials or using preparation methods well known to those skilled in the art.

[0042] The present invention also provides an organic light-emitting device, comprising an anode, a cathode, and several organic functional layers between the anode and the cathode, and the organic functional layers at least contain the biscarbazole derivatives.

[0043] The above-mentioned organic functional layer at least in...

Embodiment 1

[0046] Embodiment 1: the preparation of compound 1

[0047] Preparation of intermediate 1-A:

[0048]

[0049]Weigh compound 1-a (30.6g, 251mmol), compound 1-b (90.81g, 251mmol), tetrakistriphenylphosphine palladium (11g, 10mmol) and potassium carbonate (84.2g, 609mmol), the reaction The product was dissolved in a solvent of toluene (1L) / EtOH (200mL) / distilled water (200mL), heated at 90°C for 2 hours, and after several layers of vacuum distillation, it was ground with methanol, and the obtained solid was dissolved in dichloromethane and filtered through silica gel. , triturated with dichloromethane and hexane to give compound 1-c (62.65, 80%).

[0050] Compound 1-c (11.73g, 37.6mmol) was dissolved in tetrahydrofuran (140mL), and a hexane solvent and 2.5M n-butyllithium (18mL, 45.1mmol) were added dropwise at -78°C, followed by stirring for 1 hour. After slowly adding trimethyl borate (13 mL, 56.4 mmol) dropwise, stirred for 2 h. Then 2M hydrochloric acid was added dropw...

Embodiment 2

[0063] Embodiment 2: the preparation of compound 3

[0064] Preparation of Intermediate 3-B:

[0065]

[0066] Weigh intermediate 1-A (13.21g, 41mmol), compound 3-g (8.41g, 41mmol), cuprous iodide (3.9g, 20.5mmol), ethylenediamine (1.4mL, 20.5mmol) and cesium carbonate (40g, 123mmol), and added to toluene (250mL) in the above order, and stirred at reflux. The intermediate 3-B (13.59 g, 83%) was obtained by extraction with ethyl acetate, vacuum distillation, dichloromethane and hexane column.

[0067] Mass Spectrum m / z: 398.03 (calculated: 398.04). Theoretical element content (%)C 23 h 15 BrN 2 : C, 69.19; H, 3.79; Br, 20.01, N, 7.02. Measured element content (%): C, 69.20; H, 3.79; Br, 20.01, N, 7.01. The above results confirmed that the obtained product was the target product.

[0068] Preparation of compound 3:

[0069]

[0070] Compound 3-B (15.01 g, 37.6 mmol) was dissolved in tetrahydrofuran (140 mL), and a hexane solvent and 2.5M n-butyllithium (18 mL, 45....

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Abstract

The invention provides bicarbazole derivatives and an organic light emitting device thereof, and belongs to the technical field of organic light emitting materials. The bicarbazole derivatives solve technical problems in the prior art that luminous performance is poor, for example, luminous efficiency is low, and service life is short. According to the invention, 3 and 3' positions of two carbazole structures are connected to form a bicarbazole structure, charge carrier injection balance is improved through adjusting groups of R1, R2, Ar1, and Ar2, and the recombination ratio of electrons andelectron holes in a luminous layer is improved. The bicarbazole derivatives provided by the invention can be used for the organic light emitting device, and especially used as host materials of a luminescent layer in the organic light-emitting device to exhibit the advantages of higher luminous efficiency and obviously-increased service life; and the organic light emitting device provided by the invention is superior to a current common OLED (organic light emitting diode) device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a biscarbazole derivative and an organic light-emitting device thereof. Background technique [0002] Organic light emitting diode (Organic Light Emitting Diode, OLED) technology is a new generation of display technology that began in the 1980s from Kodak Corporation of the United States. Its principle is to use ITO transparent electrodes and metal electrodes as the anode and cathode of the device respectively. Driven by voltage, electrons and holes are injected from the cathode and anode into the electron and hole transport layers respectively, and the electrons and holes migrate to the light-emitting layer through the electron and hole transport layers respectively and meet in the light-emitting layer to form excitons and make The luminescent molecules are excited to emit visible light. [0003] OLED display technology is currently widely used in mobile...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D401/14C07D403/14C07D405/14C07D409/14C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/86C07D401/14C07D403/14C07D405/14C07D409/14C07D519/00C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1029H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 蔡辉王雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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