A compound with cyanobenzene as the core and its application in OLED devices

A compound, cyanobenzene technology, applied in the direction of electric solid-state devices, semiconductor devices, semiconductor/solid-state device manufacturing, etc., can solve efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency and other problems, to achieve the effect of strong rigidity, good industrialization prospects, and strong charge transfer effect

Active Publication Date: 2020-09-29
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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  • A compound with cyanobenzene as the core and its application in OLED devices
  • A compound with cyanobenzene as the core and its application in OLED devices
  • A compound with cyanobenzene as the core and its application in OLED devices

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] First provide the intermediate in the general formula (1) The synthetic route of is:

[0046] R 3 Expressed as a hydrogen atom, R 4 When hydrogen atoms are not represented:

[0047]

[0048] Dissolve the bromide raw material I and the amide raw material II in anhydrous toluene, add Pd after deoxygenation 2 (dba) 3 , tri-tert-butylphosphine and sodium tert-butoxide, 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, and spin the filtrate The solvent is evaporated, and the crude product is passed through a silica gel column to obtain the target compound; the molar ratio of the raw material I to the raw material II is 1:1.0~1.5, Pd 2 (dba) 3 The molar ratio to raw material I is 0.006~0.02:1, the molar ratio of tri-tert-butylphosphine to raw material I is 0.006~0.02:1, and the molar ratio of sodium tert-butoxide to raw mate...

Embodiment 2

[0066] Embodiment 2: the synthesis of compound 3:

[0067]

[0068] Dissolve 0.01mol raw material E1-1 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, TLC was used to continuously monitor the reaction process. 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 intermediate target product; Elemental analysis structure (molecular formula C 43 h 29 N 3 ): theoretical value C, 87.88; H, 4.97; N, 7.15; test value: C, 87.88; H, 4.98; N, 7.14; for 587.25.

Embodiment 3

[0069] Embodiment 3: the synthesis of compound 11:

[0070]

[0071] The preparation method of compound 11 is the same as that of Example 2, except that intermediate M1-2 is used instead of intermediate M1-1. Elemental analysis structure (molecular formula C 55 h 38 N 4 ): theoretical value C, 87.50; H, 5.07; N, 7.42; test value: C, 87.50; H, 5.06; N, 7.43. ESI-MS(m / z)(M + ): The theoretical value is 754.31, and the measured value is 754.66.

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Abstract

The invention discloses a compound with cyanobenzene as the core and its application in OLED devices. The compound uses cyanobenzene as the core and carbazole-connected triarylamine as the branch chain. The compound is not easy to crystallize between molecules, not easy to aggregate, and has good film-forming properties. The compound of the present invention is applied to an organic electroluminescent device as a light-emitting layer material, and the organic electroluminescent device using the compound of the present invention has good photoelectric performance, and can better adapt to and 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 containing cyanobenzene as the core and its application in organic light-emitting diodes. 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 positi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88H01L51/54
CPCC07D209/88H10K85/636H10K85/633H10K85/615H10K85/631H10K85/6572
Inventor 王立春张兆超李崇张小庆唐丹丹
Owner JIANGSU SUNERA TECH CO LTD
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