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Organic electroluminescent compound, organic electroluminescence device and application thereof

A technology of luminescence and compounds, applied in the field of organic electroluminescence compounds, can solve the problems of high driving voltage, unsatisfactory luminous efficiency, and low luminous efficiency of light-emitting devices, and achieve low driving voltage, high luminous efficiency, and thermal stability good sex effect

Active Publication Date: 2018-06-01
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 electroluminescent compound, organic electroluminescence device and application thereof
  • Organic electroluminescent compound, organic electroluminescence device and application thereof
  • Organic electroluminescent compound, organic electroluminescence device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The synthesis of embodiment 1 compound (58)

[0051] (1) Synthesis of Intermediate-1

[0052] [Reaction 1]

[0053]

[0054] 20.4g (100mmol, 1.0eq.) 5-phenyl-2-thienyl boronic acid and 27.3g (110mmol, 1.1eq.) 4-bromo-4'-aminobiphenyl were added to a 2L three-necked flask, Add 1000ml of toluene and 100ml of ethanol to dissolve, pass nitrogen gas for 15 minutes, then add 150ml of 2M containing 41.5g (300mmol, 3.0eq.) K 2 CO 3 Aqueous solution, finally add 2.3g Pd(PPh 3 ) 4 (2mol%). The temperature was raised to 110° C., and the reaction was completed overnight. Add activated carbon for adsorption, filter with suction, spin off the solvent, dry, and recrystallize with toluene and ethanol to obtain 26.5 g of Intermediate-1 with a yield of 81%.

[0055] (2) Synthesis of Intermediate-2

[0056] [Reaction 2]

[0057]

[0058] Add 26.5g (81mmol, 1.1eq.) intermediate-1 and 23.8g (73.6mmol, 1.0eq.) 4-(4-bromophenyl)-dibenzo Furan, then add dry and degassed 1000ml ...

Embodiment 2

[0082] The synthesis of embodiment 2 compound (76)

[0083] (1) Synthesis of Intermediate-7

[0084] [Reaction 8]

[0085]

[0086] In a dry 2L three-necked flask, put 24.4g (100mmol, 1.0eq.) of 4-phenyldibenzofuran into it, dissolve it in 300ml of dry tetrahydrofuran, pass nitrogen gas, drop to -10°C, and add dropwise 44ml of 2.5M ( 110mmol, 1.1eq.) of LDA, after the dropwise addition, continue to stir at this temperature for 1 hour, add 38.1g (150mmol, 1.5eq.) of iodine in batches, remove the cooling environment, and continue to react overnight for 17 hours. At the end, add 4M HCl solution dropwise, stir for 1 hour, let stand, separate layers, wash the upper organic phase with water 3 times, extract the lower organic phase with dichloromethane, wash 3 times, combine the organic phases, dry, spin off the solvent, layer Purified by column analysis to obtain 32.6g of Intermediate-7 with a yield of 88%.

[0087] (2) Synthesis of Intermediate-8

[0088] [reaction formula 9...

Embodiment 3

[0122] The synthesis of embodiment 3 compound (99)

[0123] (1) Synthesis of Intermediate-15

[0124] [Equation 17]

[0125]

[0126]Add 17.2g (100mmol, 1.0eq.) of p-bromoaniline and 23.3g (110mmol, 1.1eq.) of dibenzofuran-4-boronic acid into a 2L three-necked flask, add 800ml of toluene and 80ml of ethanol to dissolve, and blow nitrogen 15 minutes, then add 150ml 2M containing 41.5g (300mmol, 3.0eq.) K 2 CO 3 Aqueous solution, finally add 2.3g Pd(PPh 3 ) 4 (2mol%). The temperature was raised to 100° C., and the reaction was completed overnight. Add activated carbon for adsorption, filter with suction, spin off the solvent, dry, and recrystallize with toluene and ethanol to obtain 21g of Intermediate-15 with a yield of 81%.

[0127] (2) Synthesis of Intermediate-16

[0128] [Equation 18]

[0129]

[0130] In a dry 2L three-necked flask, put 21g (81mmol, 1.0eq.) of the intermediate-15 obtained in Reaction Formula 17, dissolve it in 200ml of dry tetrahydrofuran, b...

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Abstract

The invention provides an organic electroluminescent compound, an organic electroluminescence device and application thereof. The structure of the organic electroluminescent compound is described in the description, wherein R1 and R4 are respectively independent hydrogen, heavy hydrogen, linear or branched chain alkyls of C1-C20, and or one of phenyl, anilino, diphenylamino, 2-phenyl-3-amino-pyridyl, 3-amino-dipyridyl, 2-phenyl-1-naphthylamine, 2-amino-dinaphthyl, 2-phenyl-1-amino-phenanthryl, 3-amino-diphenanthryl, 2-phenyl-1-amino-anthranyl, 2-amino-dianthranyl, phenanthridinyl, biphenyl, pyridyl, pyrimidinyl or triazinyl; R2 and R3 are respectively independent hydrogen, heavy hydrogen, linear or branched chain alkyls of C1-C20, or phenyl, pyridyl, naphthyl, phenanthryl, anthryl, phenanthridine, biphenyl, pyridyl, pyrimidinyl and triazinyl; l, m, n and o are integers of 0-4.

Description

technical field [0001] It relates to an organic electroluminescence compound, an organic electroluminescence device and applications thereof. technical background [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 has been actively researched worldwide since its excellent display performance as a self-emitting device, and it is easy to manufacture because of its simple device mechanism, enabling the manufacture of ultra-thin and ultra-light monitor. In the most common OLED device structure, it usually includes the following types of organic materials: hole injection materials, hole transport materials, electron transport materials, and various light-emitting materials (dye or doped guest materials) and corresponding host materials, etc. . [0003...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/14C09K11/06H01L51/54
CPCC09K11/06C07D407/14C09K2211/1007C09K2211/1011C09K2211/1044C09K2211/1055C09K2211/1088C09K2211/1092H10K85/624H10K85/626H10K85/636H10K85/655H10K85/615H10K85/631H10K85/654H10K85/6574H10K85/6572
Inventor 金振禹钱超王晓维戴培培
Owner NANJING TOPTO MATERIALS CO LTD
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