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A compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices

An electroluminescent device, thiocyanobenzene technology, applied to compounds containing cyanobenzene or thiocyanobenzene, the application field of organic electroluminescent devices, can solve different problems, and achieve difficult aggregation, high glass melting temperature and thermal stability, and the effect of not being easy to crystallize

Active Publication Date: 2021-03-30
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • A compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices
  • A compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices
  • A compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the synthesis of intermediate M:

[0048]

[0049] (1) Dissolve raw material B and raw material C in a mixed solution of toluene and ethanol, add Pd(PPh 3 ) 4 and K 2 CO 3 , react at 95-110°C for 10-24 hours under an inert atmosphere, monitor the reaction process with TLC during the reaction process, cool and filter the raw materials after the reaction is complete, spin the filtrate to remove the solvent, and pass the crude product through a silica gel column to obtain Intermediate S; the consumption of described toluene and ethanol is to use 30~50mL toluene and 5~10mL ethanol per gram of raw material C, the molar ratio of raw material B and raw material C is (1~1.5):1, Pd(PPh 3 ) 4 The molar ratio with raw material C is (0.006~0.02):1, K 2 CO 3 The molar ratio with raw material C is (1.5~2):1.

[0050] (2) Under the protection of nitrogen, weigh the intermediate S and dissolve it in tetrahydrofuran, cool to -78°C, then add 1.6mol / L tetrahydrofur...

Embodiment 2

[0058] Embodiment 2: the synthesis of compound 2:

[0059]

[0060] In a 250mL three-necked flask, 0.01mol raw material A-1 and 0.012mol raw material B-3 were dissolved in 150mL of toluene and ethanol (V 甲苯 :V 乙醇 =5:1) In the mixed solution, add 0.0002mol Pd(PPh 3 ) 4 and 0.02mol K 2 CO 3 , reacted at 110°C for 24 hours under an inert atmosphere, and continuously monitored the reaction process with TLC during the reaction process. After the raw materials were completely reacted, cooled and filtered, the filtrate was rotary evaporated to remove the solvent, and the crude product was passed through a silica gel column to obtain the target product; element Analytical structure (molecular formula C 44 h 27 NS): theoretical value C,87.82; H,4.52; N,2.33; S,5.33; test value: C,87.82; H,4.52; N,2.34; S,5.32; ): The theoretical value is 601.19, and the measured value is 601.47.

Embodiment 3

[0061] Embodiment 3: the synthesis of compound 6:

[0062]

[0063] In a 250mL three-necked flask, 0.01mol raw material A-2 and 0.012mol raw material B-3 were dissolved in 150mL of toluene and ethanol (V 甲苯 :V 乙醇 =5:1) In the mixed solution, add 0.0002mol Pd(PPh 3 ) 4 and 0.02mol K 2 CO 3 , reacted at 110°C for 24 hours under an inert atmosphere, and continuously monitored the reaction process with TLC during the reaction process. After the raw materials were completely reacted, cooled and filtered, the filtrate was rotary evaporated to remove the solvent, and the crude product was passed through a silica gel column to obtain the target product; element Analytical structure (molecular formula C 44 h 27 NOS): theoretical value C, 85.55; H, 4.41; N, 2.27; S, 5.19; test value: C, 85.55; ): The theoretical value is 617.18, and the measured value is 617.48.

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Abstract

The invention discloses a compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices. The compound is composed of cyanobenzene or thiocyanobenzene group and has deep HOMO energy level and high electron mobility, suitable for application as hole blocking materials or electron transport materials; the structure containing hole groups in the present invention can balance the electrons and holes of the material, so that the material can be used as the host material of the electron-biased light-emitting layer; In addition, the compound group of the present invention has strong rigidity, and has the characteristics of not being easy to crystallize and aggregate between molecules, and having good film-forming properties. After being used as an organic electroluminescent functional layer material in an OLED device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the device life is significantly improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing cyanobenzene or thiocyanobenzene and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30C07C331/08C07D311/96C09K11/06H01L51/50H01L51/54
CPCC07C253/30C07C255/50C07C331/08C07D219/00C07D265/38C07D279/00C07D311/96C07D401/14C07D413/14C07D417/14C07D471/04C09K11/06H10K50/11
Inventor 陈海峰张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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