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Thioxanthone compound and organic light emitting element having the same

A technology of organic light-emitting element and thioxanthone, applied in the field of thioxanthone compound and organic light-emitting element, can solve problems such as shallow LUMO energy level, and achieve the effect of low driving voltage and high luminous efficiency

Active Publication Date: 2013-07-03
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The thioxanthene compound disclosed in Patent Document 1 has a shallow LUMO level because it does not have a ketone skeleton

Method used

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  • Thioxanthone compound and organic light emitting element having the same
  • Thioxanthone compound and organic light emitting element having the same
  • Thioxanthone compound and organic light emitting element having the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] Synthesis of Exemplary Compound A-1

[0117]

[0118] A 200-mL recovery flask was charged with the following reactants and solvents:

[0119] F-1: 1.85g (5mmol)

[0120] F-2 (phenylboronic acid): 1.5g (12mmol)

[0121] Tetrakis(triphenylphosphine)palladium(0): 137mg (0.12mmol)

[0122] Toluene: 50mL

[0123] Ethanol: 20mL

[0124] Sodium carbonate aqueous solution (concentration: 30% by weight): 30 mL

[0125] Then, the atmosphere in the reaction system was replaced with a nitrogen atmosphere, and then, the reaction solution was stirred under reflux for 3 hours. After the reaction was completed, water was added to the reaction solution and further stirred, and deposited crystals were filtered off. Then, the crystals were successively washed with water, ethanol and acetone to obtain a crude product. Then, the crude product was heated and dissolved in toluene, and filtered hot, and then, recrystallized twice with toluene solvent to obtain purified crystals. The...

Embodiment 2

[0132] Synthesis of Exemplified Compound A-3

[0133]

[0134] A 200-mL recovery flask was charged with the following reactants and solvents:

[0135] F-1: 1.85g (5mmol)

[0136] F-3 (3-biphenylboronic acid): 2.4g (12mmol)

[0137] Tetrakis(triphenylphosphine)palladium(0): 137mg (0.12mmol)

[0138] Toluene: 50mL

[0139] Ethanol: 20mL

[0140] Sodium carbonate aqueous solution (concentration: 30% by weight): 30 mL

[0141] Then, the atmosphere in the reaction system was replaced with a nitrogen atmosphere, and then, the reaction solution was stirred under reflux for 3 hours. After the reaction was completed, water was added to the reaction solution and further stirred, and deposited crystals were filtered off. Then, the crystals were successively washed with water, ethanol and acetone to obtain a crude product. Then, the crude product was heated and dissolved in toluene, and filtered hot, and then, recrystallized twice with toluene solvent to obtain purified crystals...

Embodiment 3

[0146] Synthesis of Exemplified Compound A-5

[0147]

[0148] A 200-mL recovery flask was charged with the following reactants and solvents:

[0149] F-1: 1.85g (5mmol)

[0150] F-4: 4.3g (12mmol)

[0151] Tetrakis(triphenylphosphine)palladium(0): 137mg (0.12mmol)

[0152] Toluene: 50mL

[0153] Ethanol: 20mL

[0154] Sodium carbonate aqueous solution (concentration: 30% by weight): 30 mL

[0155] Then, the atmosphere in the reaction system was replaced with a nitrogen atmosphere, and then, the reaction solution was stirred under reflux for 3 hours. After the reaction was completed, water was added to the reaction solution and further stirred, and deposited crystals were filtered off. Then, the crystals were successively washed with water, ethanol and acetone to obtain a crude product. Then, the crude product was heated and dissolved in chlorobenzene, and filtered hot, and then, recrystallized twice with a chlorobenzene solvent to obtain purified crystals. Then, th...

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Abstract

Provided is an organic light emitting element having a high light emission efficiency and a low drive voltage. In the organic light emitting element including a positive electrode, a negative electrode and an organic compound layer disposed between the positive electrode and the negative electrode, the organic compound layer includes a thioxanthone compound represented by the following general formula [1].

Description

technical field [0001] The present invention relates to a thioxanthone compound and an organic light-emitting device comprising the thioxanthone compound. Background technique [0002] An organic light-emitting element is an electronic element having a positive electrode (anode), a negative electrode (cathode), and an organic compound layer disposed between the two electrodes. The organic light-emitting element emits light when excitons generated by recombination of holes and electrons injected from the respective electrodes in the light-emitting layer contained in the organic compound layer return to the ground state. The development of organic light-emitting devices has been remarkable in recent years, and is characterized in that the organic light-emitting devices enable the preparation of thin and lightweight organic light-emitting devices having low driving voltage, various emission wavelengths, and fast response. [0003] Organic light-emitting elements are roughly cl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/16C07D409/04C09K11/06H01L51/50H10K99/00
CPCC07D335/16C07D409/04C07D409/10C07D409/14C09K11/06H05B33/10C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092H10K85/6576H10K50/18H10K50/11H10K2101/10H10K50/16H10K59/32H10K85/626H10K85/657
Inventor 镰谷淳关真范关口武史西出洋祐齐藤章人
Owner CANON KK
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