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Blue organic light emitting diode material

A light-emitting diode, an organic technology, applied in the direction of light-emitting materials, organic chemistry, electrical components, etc., can solve the problems of low external quantum efficiency, etc., and achieve the goals of improving charge injection and light-emitting stability, long-life luminous performance, and high-efficiency luminous performance Effect

Active Publication Date: 2014-07-30
冠能光电材料(深圳)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, the literature (J. Mater. Chem., 2009, 19, 1865–1871) has reported a phenanthroimidazole-based blue-light material TPIP based on symmetrical connections, which has an excellent color scale of (0.15, 0.10), but due to a single Due to electronegativity, the external quantum efficiency is less than 6%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of Compound 22

[0052] .

[0053] (1) Synthesis of intermediate M1

[0054]

[0055] In a 500 mL three-necked flask with a thermometer and a condenser tube, add 10 g (48 mmol) of phenanthrenequinone, 8.9 g (48 mmol) of p-bromobenzaldehyde, 5.38 g (57.7 mmol) of aniline, and 37.06 g (480 mmol) of ammonium acetate and 200ml glacial acetic acid, N 2 Replaced three times, raised the temperature to 130°C and refluxed the reaction overnight. The reaction was monitored by TLC plate until complete. Cool to room temperature, filter, pour the filter residue into 200ml of methanol, stir and wash twice, filter to obtain the desired product, and receive 19.8g (92%) of a tan solid. MS=448, mp=255°C, HPLC: 99.5%.

[0056] (2) Synthesis of intermediate M2

[0057] In a 250 mL three-necked flask, sequentially add intermediate M1 (9 g, 20 mmol), bis(pinacolate) diboron (7.62 g, 30 mmol), CH 3 COOK (5.9g, 60mmol), 1,4-dioxane 125 mL and S-phos (1.2g, 3mmol),...

Embodiment 2

[0069] Synthesis of compound 25

[0070] .

[0071] (1) Synthesis of intermediate M7

[0072] In a 250mL three-necked flask, add carbazole 16.72g, m-bromoiodobenzene 42.44g, cuprous iodide 1.9g, 1,2-diaminocyclohexane 3.42g, anhydrous potassium phosphate 42.4g and solvent 1 , 4-dioxane 160mL, N 2 Replaced three times, raised the temperature to reflux, and stopped after 16 hours of reaction. Cool to room temperature, filter, collect the filtrate, separate by column chromatography (dichloromethane:n-hexane=1:1-1:0), and receive 22g (69%) of the target solid product. M / Z=322.

[0073] (2) Synthesis of intermediate M8

[0074] In a 500 mL three-necked flask, intermediate M7 (20 g, 62.1 mmol), bis(pinacolate) diboron (23.6 g, 93.2 mmol), CH 3 COOK (17.5g, 178.2mmol), 1,4-dioxane 300 mL and S-phos (5.35g, 13.04mmol), N2 replacement three times, adding Pd 2 (dba) 3 (3.98g, 4.35mmol) and heated to reflux, the reaction was stopped after 24h. Cool to room temperature, f...

Embodiment 3

[0078] Synthesis of compound 26

[0079] .

[0080] (1) Synthesis of intermediate M9

[0081] In a 250mL three-necked flask, add carbazole (8.36g, 50mmol), p-bromoiodobenzene (21.22g, 75mmol), cuprous iodide (0.95g, 5mmol), 1,2-diaminocyclohexane (1.71g, 15mmol), anhydrous potassium phosphate (21.2g, 100mmol) and solvent 1,4-dioxane 160mL, N 2 Replaced three times, raised the temperature to reflux, and stopped after 16 hours of reaction. Cool to room temperature, filter, collect the filtrate, separate by column chromatography (dichloromethane:n-hexane=1:1-1:0), and receive 13.4g (83.2%) of the target solid product. M / Z=322.

[0082] (2) Synthesis of intermediate M10

[0083] In a 500 mL three-necked flask, intermediate M9 (20 g, 62.1 mmol), bis(pinacolate) diboron (23.6 g, 93.2 mmol), CH 3 COOK (17.5g, 178.2mmol), 1,4-dioxane 300 mL and S-phos (5.35g, 13.04mmol), N2 replacement three times, adding Pd 2 (dba) 3 (3.98g, 4.35mmol) and heated to reflux, the reacti...

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Abstract

The invention relates to an organic light emitting diode material which is characterized by consisting of a cathode, an anode and an organic semiconductor layer between the cathode and the anode. An organic semiconductor luminescent layer comprises an organic semiconductor compound as shown in the specification. The compound is characterized in that an aromatic hetero fused ring is connected to a benzene ring connected with phenanthroimidazole to improve charge injection and luminescent stability so as to obtain the luminescent performance which is high in stability, high in efficiency and long in service life.

Description

technical field [0001] The invention relates to an organic light-emitting material and its application in an organic light-emitting device, in particular to the application of an organic semiconductor as a light-emitting layer, which can improve luminous efficiency and prolong the working life of the device. Background technique [0002] Organic semiconductor materials are new types of optoelectronic materials. Its large-scale research originated in 1977 by Shirakawa Hideki, A. Heeger and A. McDiamid who jointly discovered doped polyacetylene with a conductive car up to copper level. Subsequently, in 1987, C. Tang of KodaK Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R. Friend and A. Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S. Forrest and M. Thomson invented a more efficient organic phosphorescent light-emitting diode PHOLED. Because organic semiconductor materials have a structure...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D403/10C07D403/14C07D405/12C07D409/12C07D409/14C07D409/10C07D495/04C09K11/06H01L51/54
CPCC09K11/06C07D235/02C07D403/10C07D403/14C07D405/12C07D409/10C07D409/12C07D409/14C07D495/04C09K2211/1092C09K2211/1088C09K2211/1044H10K85/615H10K85/622H10K85/623H10K85/631H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576
Inventor 李晓常洪海兵
Owner 冠能光电材料(深圳)有限责任公司
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