Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof

An electroluminescent device, an organic technology, applied in chemical instruments and methods, electrical solid-state devices, semiconductor/solid-state device manufacturing, etc., can solve problems such as low maximum brightness, low efficiency, unbalanced electron and hole concentrations in the light-emitting layer, etc. , to achieve the effect of improving performance and efficiency

Active Publication Date: 2013-04-10
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

[0004] However, the existing carbazole-based host materials are mainly based on hole transport, resulting in an unbalanced concentration of electrons and holes in the light-emitting layer, resulting in poor performance and low efficiency of the device, especially in such carbazole-based host materials. For devices made of medium-doped blue light-emitting materials with low efficiency, the maximum power efficiency is lower than 15ml / W, and the maximum brightness is lower than 10000cd / m 2

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  • Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof
  • Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof
  • Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof

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preparation example Construction

[0055] The present invention does not have special limitation to the preparation method of CzBPO, preferably comprises the following steps:

[0056] Using 4,4'-dibromobiphenyl and carbazole as raw materials, potassium carbonate and CuI as catalysts, 1,3-dimethyl-2-imidazolidinone (DMI) as reaction medium, and argon as protection Gas, react under the condition of 100°C-250°C to obtain N-(4'-bromobiphenyl)-N-carbazole;

[0057] With N-(4′-bromobiphenyl)-N-carbazole and diphenylphosphorous chloride (Ph 2 PCl) as raw material, with tetrahydrofuran (THF) as the reaction medium, with n-BuLi as the initiator, react under room temperature conditions, the reaction product obtained with H 2 o 2 Oxidation gives the product.

[0058] The product is subjected to nuclear magnetic resonance analysis, and its proton nuclear magnetic resonance spectrum proves that the product is indeed CzBPO having the structure of formula (I-a).

[0059] According to the present invention, when Ar 1 Pref...

Embodiment 1

[0095] Add 75mmol (23g) 4,4'-dibromobiphenyl, 50mmol (8.3g) carbazole, 100mmol (14g) potassium carbonate, 10mmol (2.0g) CuI and 10mL 1,3-dimethyl-2 - Imidazolidinone (DMI), under the protection of argon, heated to 190 ° C for 20 hours; after cooling, the reaction mixture was dissolved in dichloromethane, washed three times with water, dried with anhydrous sodium sulfate, then filtered, concentrated, silica gel Obtain 7.9gN-(4'-bromobiphenyl)-N-carbazole after column separation, productive rate 40.2%, through characterization analysis, confirm that this product is N-(4'-bromobiphenyl)-N-carbazole azole. 1 H NMR (300MHz, CDCl 3 )[ppm]: δ8.16(d, J=7.8Hz, 2H), 7.78(d, J=8.7Hz, 2H), 7.62-7.66(m, 4H), 7.55(d, J=8.7Hz, 2H ), 7.40-7.48 (m, 4H), 7.31 (td, J=7.2, 1.5Hz, 2H);

[0096] Add 3mmol (1.2g) N-(4′-bromobiphenyl)-N-carbazole and 50mL dry tetrahydrofuran (THF) into the dry reaction flask, and cool to -78 ℃, add 4.5mmol n-BuLi (1.8mL 2.5M n-hexane solution) into the reaction f...

Embodiment 2

[0101] Add 200mmol (4.8g) of magnesium chips and a small amount of iodine to the dry reaction flask, add 10mL of dry THF under the protection of argon, slowly add 150mL of THF solution containing 200mmol (47.2g) of p-dibromobenzene, and react at 50°C for 4 hours , add 90mmol (16.1g) phenyl phosphorus dichloride (PhPCl 2 ), continue to react for 24 hours. Slowly add 20mL H 2 o 2 After stirring for 2 hours, the reaction mixture was poured into water, extracted with dichloromethane, washed three times with water, dried with anhydrous sodium carbonate, filtered, concentrated, and separated on a silica gel column to obtain 22.6g of bis(4-bromophenyl)phenylphosphine , The yield was 57.7%. After characterization and analysis, it was confirmed that the product was indeed bis(4-bromophenyl)phenylphosphine. 1 H NMR (300MHz, CDCl 3 )[ppm]: δ7.58-7.68 (m, 7H), 7.48-7.55 (m, 6H).

[0102] Add 0.5mmol (0.22g) bis(4-bromophenyl) phenylphosphine, 3mmol (0.50g) carbazole, 3mmol (0.29g) t-...

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Abstract

The invention provides a carbazole compound which is at least provided with phosphorylase and a bridging unit with pi-conjugate character; the invention further provides an organic electroluminescence device, comprising a substrate, a first electrode layer is arranged on the substrate, at least one or multiple the organic electroluminescence layers are arranged on the first electrode layer, and asecond electrode layer is arranged on the organic electroluminescence layer; the organic electroluminescence layer contains carbazole compound with phosphorus oxide group; the invention further provides a preparation method of the organic electroluminescence device, comprising the following steps: the first electrode is formed on the substrate, at least one or multiple the organic electroluminescence layers are formed on the first electrode, and the e organic electroluminescence layer comprises the carbazole compound with phosphorus oxide group in the technical proposal, and the second electrode is formed on the organic electroluminescence layer; in the invention, the phosphorus oxide group is led in the carbazole compound, so as to lead the carbazole compound to have twin pole carrier transportation capacity.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a carbazole compound, an organic electroluminescent device containing the carbazole compound and a preparation method thereof. Background technique [0002] An organic electroluminescence device is a self-luminous device that, when charges are injected between an electron injection electrode (first electrode) and a hole injection electrode (second electrode), the electrons and holes combine and then annihilate, thus producing bright. Organic electroluminescent devices have the characteristics of low voltage, high brightness, wide viewing angle, fast response, and good temperature adaptability, and are widely used in digital cameras, mobile phones, MP3 and other electronic product displays. [0003] Organic electroluminescent materials are generally singlet fluorescent dyes or triplet phosphorescent dyes, but such materials have a strong concentration quenchin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/572C07F9/6558C07F9/6561H01L51/54H01L51/56
Inventor 王利祥丁军桥吕剑虹赵磊孟彬
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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