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Compound for organic optoelectronic device, organic light emitting diode and display device

A technology of optoelectronic devices and compounds, applied in organic chemistry, electroluminescent light sources, luminescent materials, etc., can solve problems such as unsatisfactory development and achieve excellent life expectancy

Active Publication Date: 2012-07-11
CHEIL IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of organic material layer-forming materials for organic light-emitting diodes has so far been far from satisfactory, and new materials are still required

Method used

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  • Compound for organic optoelectronic device, organic light emitting diode and display device
  • Compound for organic optoelectronic device, organic light emitting diode and display device
  • Compound for organic optoelectronic device, organic light emitting diode and display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0143] (Preparation of Compounds for Organic Optoelectronic Devices)

[0144] Synthesis of intermediates

[0145] Synthesis of Intermediate M-1

[0146] [Reaction Scheme 1]

[0147]

[0148] In a nitrogen atmosphere, 30 g (141.5 mmol) of (4-dibenzofuryl) boronic acid, 37.1 g (148.6 mmol) of methyl-2-bromo-5-chlorobenzoate and 8.2 g (7.1 mmol) Tetrakis(triphenylphosphine)palladium was put into a flask and dissolved in 550ml of toluene, and 353.8ml of aqueous solution in which 104.2g (707.51mmol) of potassium carbonate was dissolved was added thereto. The mixture was stirred for 12 hours. When the reaction was complete, the resulting product was extracted with ethyl acetate. The extract was dried over magnesium sulfate and filtered, then concentrated under reduced pressure. The concentrated product was purified by silica gel column chromatography using n-hexane / dichloromethane mixed in a volume ratio of 7:3 to obtain 38.2 g (yield: 80%) of the desired compound, interme...

Embodiment 1

[0329] Embodiment 1: the preparation of compound C-1

[0330] [Reaction Scheme 43]

[0331]

[0332] Dissolve 5.0 g (15.68 mmol) of Intermediate M-3, 5.04 g (15.68 mmol) of Intermediate A, 4.52 g (47.95 mmol) of sodium tert-butoxide and 0.1 g (0.47 mmol) of tri-tert-butylphosphine In 200ml of toluene, and add 0.27g (0.47mmol) of Pd(dba) to it 2 . The mixture was refluxed and stirred under nitrogen atmosphere for 12 hours. When the reaction was complete, the reactant was extracted with toluene and distilled water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography using n-hexane / dichloromethane mixed in a volume ratio of 2:1 to obtain 7.8 g (yield: 82.3%) of the desired compound C-1 as a white solid.

[0333] Calculated: C, 89.52; H, 5.51; N, 2.32; O, 2.65

[0334] Analytical values: C, 89.51; H, 5.52; N, 2.32; O, 2.65

Embodiment 2

[0335] Embodiment 2: the preparation of compound C-31

[0336] [Reaction Scheme 44]

[0337]

[0338] Dissolve 5.0 g (15.68 mmol) of Intermediate M-3, 4.63 g (15.68 mmol) of Intermediate B, 4.52 g (47.95 mmol) of sodium tert-butoxide and 0.1 g (0.47 mmol) of tri-tert-butylphosphine In 200ml of toluene, and add 0.27g (0.47mmol) of Pd(dba) to it 2 . The mixture was refluxed and stirred under nitrogen atmosphere for 12 hours. When the reaction was complete, the reactant was extracted with toluene and distilled water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography using n-hexane / dichloromethane mixed in a volume ratio of 2:1 to obtain 7.3 g (yield: 80.5%) of the desired compound C-31 as a white solid.

[0339] Calculated: C, 89.40; H, 5.41; N, 2.42; O, 2.77

[0340] Analytical values: C, 89.42; H, 5.39; N, 2.42; O, 2.77

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Abstract

The present invention relates to a compound for an organic optoelectronic device, organic light emitting diode and display device. The compound for an organic optoelectronic device may be represented by the following Chemical Formulas 1 to 4 and have excellent electrochemical and thermal stability and thus, provide an organic photoelectric device with excellent life-span characteristics and high luminous efficiency at a low driving voltage. The above Chemical Formulas 1 to 4 are the same as described in the specification.

Description

technical field [0001] The present invention discloses compounds for organic optoelectronic devices, organic light-emitting diodes comprising the compounds and displays comprising the organic light-emitting diodes, which can provide devices with good lifetime, efficiency, electrochemical stability and thermal stability Organic optoelectronic devices. Background technique [0002] Broadly speaking, an organic optoelectronic device is a device that converts light energy into electrical energy, or vice versa. [0003] Organic photoelectric devices may be classified as follows according to their driving principles. The first type of organic photoelectric device is an electronic device that is driven by: generating excitons within an organic material layer by photons from an external light source; separating the above-mentioned excitons into electrons and holes; and transferring the electrons and holes to different electrodes as an electric current source (voltage source). [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93C07D333/78C07D405/12C07D409/12C07D409/14C07D491/048C07D495/04H01L51/46H01L27/32H10K99/00
CPCC09B57/008C09K2211/1092C09K2211/1029H01L51/5056C07D333/50H01L51/0061H01L51/006C07D307/93C07D405/12C07D409/12C07D409/14C07D495/04C09B57/00H05B33/22H01L51/0074C07D491/04C09K11/06H01L51/0071H01L51/0073C09K2211/1088Y02E10/549H10K85/636H10K85/633H10K85/657H10K85/6576H10K85/6574H10K50/15H10K50/00
Inventor 李庚美郑成显柳东完李承珉李炫揆蔡美荣许达灏洪振硕
Owner CHEIL IND INC
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