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Compound with benzonitrile or thio-benzonitrile and application thereof in organic light-emitting devices

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

Active Publication Date: 2019-05-14
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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  • Compound with benzonitrile or thio-benzonitrile and application thereof in organic light-emitting devices
  • Compound with benzonitrile or thio-benzonitrile and application thereof in organic light-emitting devices
  • Compound with benzonitrile or thio-benzonitrile and application thereof in organic light-emitting devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of intermediate M:

[0049]

[0050] (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.

[0051] (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

[0059] Embodiment 2: the synthesis of compound 2:

[0060]

[0061] 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

[0062] Embodiment 3: the synthesis of compound 6:

[0063]

[0064] 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 with benzonitrile or thio-benzonitrile and application thereof in organic light-emitting devices. The compound is composed of a benzonitrile or thio-benzonitrile group, has deep HOMO (highest occupied molecular orbital) energy level and high electron migration rate, and is suitable for acting as a hole barrier material or an electron transport material. The holegroup structure contained in the compound can balance electrons and holes, so that the compound may act as a near-electron light-emitting layer main material; in addition, as the group of the compoundhas high rigidity, the compound features rarity of intermolecular crystallization or gathering, and good film-forming property. After the compound is applied as an organic light-emitting functional layer material to OLED devices, all the current efficiency, power efficiency and external quantum efficiency of the devices are greatly improved; the service lives of the devices are significantly extended.

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 Applications(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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