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Organic electroluminescence luminescent compound, organic electroluminescence luminescent device and application thereof

A technology of luminescence and compounds, which is applied in the field of organic electroluminescent compounds, can solve the problems of high driving voltage, low luminous efficiency of light-emitting devices, and unsatisfactory luminous efficiency, and achieve the effect of reducing driving voltage and improving luminous efficiency

Inactive Publication Date: 2018-06-05
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these materials have advantages in light-emitting properties, the luminous efficiency of organic electroluminescent devices is directly proportional to the current efficiency and inversely proportional to the driving voltage. At present, light-emitting devices using existing organic materials require higher driving voltages, resulting in The luminous efficiency of electroluminescent devices is low, and the luminous efficiency is still unsatisfactory

Method used

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  • Organic electroluminescence luminescent compound, organic electroluminescence luminescent device and application thereof
  • Organic electroluminescence luminescent compound, organic electroluminescence luminescent device and application thereof
  • Organic electroluminescence luminescent compound, organic electroluminescence luminescent device and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The synthesis of embodiment 1 compound (55)

[0060] (1) Synthesis of Intermediate A

[0061] [Reaction 1]

[0062]

[0063] Put 19.5g (100mmol, 1.0eq.) of acridone and 20.4g of iodobenzene (100mmol, 1.0eq.) into a dry 2L three-necked flask, then add dry and degassed 800ml of toluene as a solvent, and nitrogen for 15 minutes . Then add 28.8g (300mmol.3.0eq.) sodium tert-butoxide, 1.8g (2%mol) catalyst Pd 2 (dba) 3 and 8.1ml (4%mol) P(t-bu) 3 Toluene solution (m / v, 10%). The temperature was raised to 100° C., and the reaction was carried out overnight for 5 hours. After the reaction is finished, cool to room temperature, add activated carbon for adsorption, filter with suction, spin off the solvent, and recrystallize with toluene and ethanol to obtain 22.5 g of intermediate A with a yield of 83%.

[0064] (2) Synthesis of Intermediate B

[0065] [Reaction 2]

[0066]

[0067] Put 22.5g (83mmol, 1.0eq.) of intermediate A into a 1L three-neck flask, use 400m...

Embodiment 2

[0086] The synthesis of embodiment 2 compound (72)

[0087] (1) Synthesis of Intermediate F

[0088] [Reaction 6]

[0089]

[0090] Put 19.5g (100mmol, 1.0eq.) of acridone and 20.4g of iodobenzene (100mmol, 1.0eq.) into a dry 2L three-necked flask, then add dry and degassed 800ml of toluene as a solvent, and nitrogen for 15 minutes . Then add 28.8g (300mmol) sodium tert-butoxide, 1.8g (2%mol) catalyst Pd 2 (dba) 3 and 8.1ml (4%mol) P(t-bu) 3 Toluene solution (m / v, 10%). The temperature was raised to 100° C., and the reaction was carried out overnight for 5 hours. After the reaction was completed, cool to room temperature, add activated carbon for adsorption, filter with suction, spin off the solvent, and recrystallize with toluene and ethanol to obtain 22.5 g of intermediate F with a yield of 83%.

[0091] (2) Synthesis of Intermediate G

[0092] [Reaction 7]

[0093]

[0094] Put 22.5g (83mmol) of intermediate F into a 1L three-neck flask, use 400ml of DMF as s...

Embodiment 3

[0117] The synthesis of embodiment 3 compound (97)

[0118] (1) Synthesis of Intermediate L

[0119] [Equation 13]

[0120]

[0121] 28.3g (100mmol, 1.0eq.) m-bromoiodobenzene and 20.6g o-bromoaniline (120mmol, 1.2eq.) were dropped into a dry 3L three-necked flask, and then dried and degassed 1000ml toluene was added as a solvent. Nitrogen for 15 minutes. Then 2.9 g (15% mol) of cuprous iodide, 5.9 g (30% mol) of 1,10-phenanthroline and 63.7 g (300 mol, 3 eq.) of potassium phosphate were added. The temperature was raised to 110°C, and the reaction was carried out for 18 hours. After the reaction was completed, it was cooled to room temperature, filtered with suction, the solvent was spun off, and recrystallized with toluene and ethanol to obtain 28.1 g of intermediate L with a yield of 86%.

[0122] (2) Synthesis of Intermediate M

[0123] [Equation 14]

[0124]

[0125] Put 28.1g (86mmol) of intermediate L and 17.9g (86mmol) of anthraquinone into a 2L three-neck f...

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PUM

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Abstract

The invention provides an organic electroluminescence luminescent compound, an organic electroluminescence luminescent device and application thereof. The organic electroluminescence luminescent compound has the following structure: (the formula is shown in the description), wherein R1, R2 and R4 are hydrogen, C1-C20 linear-chain or branched-chain alkyl, phenyl, pyridyl, naphthyl, phenanthryl, anthryl, phenanthridinyl, biphenylyl, pyrimidyl or tirazinyl respectively and independently; R3 is C1-C10 alkyl or C6-C30 aryl; R5 is hydrogen, deuterium, halogen, C1-C20 linear-chain or branched-chain alkyl or C6-C30 aryl; R6 and R7 are hydrogen, deuterium, C1-C20 linear-chain or branched-chain alkyl, phenyl, pyridyl, naphthyl, phenanthryl, anthryl, phenanthridinyl, biphenylyl, pyrimidyl or tirazinyl respectively and independently; X is carbon or nitrogen independently; I is an integer of 0 to 4; m and n are 0 or 1 respectively and independently. The organic electroluminescence luminescent compound provided by the invention can effectively reduce the working voltage of devices, improve the light-emitting efficiency of the devices and prolong the service life.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to an organic electroluminescent compound, an organic electroluminescent device and applications thereof. Background technique [0002] With the continuous advancement of OLED technology in the two major fields of lighting and display, people are paying more attention to the research of high-efficiency organic materials that affect the performance of OLED devices. As a novel flat display technology, OLED display has been actively researched all over the world since it exhibited its excellent display performance as a self-emitting device. At the same time, because the device structure is simple and easy to manufacture, it can also be used to manufacture ultra-thin and ultra-light displays. In the most common OLED device structure, the following types of organic materials are usually included: hole injection materials, hole transport materials, electron transport materials, and v...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D401/12C07D221/20C07D405/12C07D405/14C07D401/14C07D471/10C07D209/86C07C211/58C07D307/79C07D213/74C07F7/10C07D307/91C07D405/10C07C211/61C07D307/87C07D401/06C07D251/24C07D239/26C07D221/12C07D401/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/58C07C211/61C07D209/86C07D213/74C07D221/12C07D221/20C07D239/26C07D251/24C07D307/79C07D307/87C07D307/91C07D401/04C07D401/06C07D401/10C07D401/12C07D401/14C07D405/10C07D405/12C07D405/14C07D471/10C07F7/0812C07F7/0814C09K2211/1029C09K2211/1022C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1059C09K2211/1044C09K2211/1088H10K85/624H10K85/636H10K85/633H10K85/615H10K85/654H10K85/6574H10K85/6572H10K50/11
Inventor 金振禹钱超王晓维戴培培
Owner NANJING TOPTO MATERIALS CO LTD
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