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Compound using cyano pyridine as core, and applications in organic electroluminescent devices

A compound, cyano nitrogen technology, applied in the application field of organic electroluminescent devices, can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc., and achieve good The effect of optoelectronic properties

Inactive Publication Date: 2019-06-21
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • Compound using cyano pyridine as core, and applications in organic electroluminescent devices
  • Compound using cyano pyridine as core, and applications in organic electroluminescent devices
  • Compound using cyano pyridine as core, and applications in organic electroluminescent devices

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] First provide the general formula (1) The synthetic route of is:

[0052]

[0053] Weigh the raw material I and dissolve it in acetic acid, cool down to 0°C with an ice-salt bath; weigh the liquid bromine and dissolve it in glacial acetic acid, slowly add it dropwise to the acetic acid solution containing the nitro compound raw material I, and stir at room temperature for 6-12 hours , take a sample point plate, show that there is no raw material I remaining, the reaction is complete, after the reaction, add aqueous sodium hydroxide solution dropwise until the solution is neutral, extract with dichloromethane, get the organic phase and filter, and the filtrate is rotary evaporated under reduced pressure until there is no fraction. Pass through a silica gel column to obtain intermediate S1; in the above reaction, the molar ratio of raw material I to liquid bromine is 1:1 to 3; 30 to 50 mL of acetic acid is used per gram of raw material I;

[0054] Weigh raw material ...

Embodiment 2

[0069] Embodiment 2: the synthesis of compound 7:

[0070]

[0071] Dissolve 0.01mol raw material E-1 and 0.012mol intermediate M1-1 in 150mL anhydrous toluene, add 0.0005mol Pd after deoxygenation 2 (dba) 3 , 0.015mol tri-tert-butylphosphine and 0.02mol sodium tert-butoxide, and reacted at 110°C for 24 hours under an inert atmosphere. During the reaction, the reaction process was continuously monitored by TLC. After the raw materials were completely reacted, cooled and filtered, the filtrate was spun Evaporate and remove solvent, thick product crosses silica gel column, obtains target product; Elemental analysis structure (molecular formula C 46 h 30 N 4 ): theoretical value C, 86.49; H, 4.73; N, 8.77; test value: C, 86.49; H, 4.73; N, 8.78; for 638.66.

Embodiment 3

[0072] Embodiment 3: the synthesis of compound 17:

[0073]

[0074] Dissolve 0.01mol of intermediate M2-2 and 0.012mol of raw material E-1 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. During the reaction process, the reaction process was continuously monitored by TLC. 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 intermediate target product ; Elemental analysis structure (molecular formula C 46 h 29 N 3 ): theoretical value C, 88.58; H, 4.69; N, 6.74; test value: C, 88.56; H, 4.69; N, 6.75; for 623.42.

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Abstract

The invention discloses a compound using cyano pyridine as a core, and applications in organic electroluminescent devices. According to the present invention, the compound uses cyano pyridine as a core, uses a carbazole fused ring group and a diarylimine group as branch chains, and has characteristics of less intermolecular crystallization, less aggregation and good film forming property; and withthe application of the compound as a light-emitting layer material in an organic electroluminescent device, the organic electroluminescent device using the compound has good photoelectric performance, and can well meet the application requirements of panel manufacturers.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with cyanoazepine as the core 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, and the positiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D403/04C07D401/10C07D403/10C07D487/04C07D491/048C09K11/06H01L51/50H01L51/54
Inventor 陈海峰张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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