Compound based on diaryl ketone and application thereof in organic electroluminescent devices

A technology for diaryl ketones and compounds, which is applied in the preparation of carbon-based compounds, the preparation of organic compounds, and electric solid devices, etc., can solve the problem of low S1 state radiation transition rate, efficiency roll-off, difficult exciton utilization and high fluorescence. Radiation efficiency and other issues, to achieve the effects of improving power efficiency and external quantum efficiency, increasing orbital overlap, and improving fluorescence quantum efficiency

Active Publication Date: 2017-03-01
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 based on diaryl ketone and application thereof in organic electroluminescent devices
  • Compound based on diaryl ketone and application thereof in organic electroluminescent devices
  • Compound based on diaryl ketone and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: the synthesis of compound 1

[0057] synthetic route:

[0058]

[0059]In a 250ml four-necked flask, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol 9,9-dimethyl-9H-fluorene-2-boronic acid, and 0.03mol carbonic acid under nitrogen atmosphere Sodium, 2 x 10 -4 mol Pd(PPh 3 ) 4 , 150ml of toluene, heated and refluxed for 24 hours, took a sample and spotted the plate, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.3% and a yield of 77.5%.

[0060] Elemental analysis structure (molecular formula C 43 h 34 O): Theoretical value C, 91.13; H, 6.05; O, 2.82; Test value: C, 91.15; H, 6.10; O, 2.75.

[0061] HPLC-MS: The molecular weight of the material is 566.26, and the measured molecular weight is 566.57.

Embodiment 2

[0062] Embodiment 2: the synthesis of compound 4

[0063] synthetic route:

[0064]

[0065] 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol 9-phenyl-9H-carbazole-3-boronic acid, 0.03mol sodium carbonate, 2×10 -4 mol Pd(PPh 3 ) 4 , 150ml of toluene, heated and refluxed for 24 hours, sampled and spotted, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.1% and a yield of 72.3%.

[0066] Elemental analysis structure (molecular formula C 49 h 32 N 2 O): theoretical value C, 88.53; H, 4.85; N, 4.21; O, 2.41; tested value: C, 88.61; H, 4.82; N, 4.25;

[0067] HPLC-MS: The molecular weight of the material is 664.25, and the measured molecular weight is 664.65.

Embodiment 3

[0068] Embodiment 3: the synthesis of compound 6

[0069] synthetic route:

[0070]

[0071] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol boric acid compound, 0.03mol sodium carbonate, 2×10 -4 mol Pd(PPh 3 ) 4 , 150ml of toluene, heated and refluxed for 24 hours, sampled and spotted, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.9% and a yield of 62.8%.

[0072] Elemental analysis structure (molecular formula C 65 h 38 o 3 ): theoretical value C, 90.05; H, 4.42; 0, 5.54; test value: C, 90.06; H, 4.46; 0, 5.48.

[0073] HPLC-MS: The molecular weight of the material is 866.28, and the measured molecular weight is 866.52.

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Abstract

The invention discloses a compound based on diaryl ketone and an application thereof in organic electroluminescent devices. The compound has the characters that molecules are not liable to crystallize and aggregate and the compound has excellent film forming property. In addition, rigid groups in the molecules can improve thermal stability of the material. The compound is used on the organic electroluminescent devices as a luminescent layer material. The organic electroluminescent device using the compound has excellent photoelectric performance and can satisfy application requirements of panel manufacturers better.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing diaryl ketone and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/792C07C45/68C07D209/86C07D311/96C07D405/14C07C221/00C07C225/22C07D307/91C07D405/04C07D491/107C07D471/10C07D279/22C07D417/14C07D265/38C07D219/02C07D221/20C07D333/76C07D345/00C07C211/61C07D209/88C09K11/06H01L51/54
CPCC09K11/06C07C45/68C07C49/792C07C211/61C07C221/00C07C225/22C07D209/86C07D209/88C07D219/02C07D221/20C07D265/38C07D279/22C07D307/91C07D311/96C07D333/76C07D345/00C07D405/04C07D405/14C07D417/14C07D471/10C07D491/107C09K2211/1096C09K2211/1088C09K2211/1092C09K2211/1037C09K2211/1007C09K2211/1011C09K2211/1029H10K85/626H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 王立春张兆超李崇徐凯叶中华
Owner JIANGSU SUNERA TECH CO LTD
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