9,10-anthraquinone based compound and application thereof in organic electroluminescent devices

A technology of light-emitting devices and compounds, applied to organic electroluminescent devices, in the field of compounds containing 9,10-anthraquinone, which can solve the problems of efficiency roll-off, low S1 state radiative transition rate, difficult exciton utilization and Problems such as high fluorescence radiation efficiency, to achieve the effect of increasing orbital overlap, good industrialization prospects, and avoiding aggregation

Active Publication Date: 2017-08-18
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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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  • 9,10-anthraquinone based compound and application thereof in organic electroluminescent devices
  • 9,10-anthraquinone based compound and application thereof in organic electroluminescent devices
  • 9,10-anthraquinone based compound and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Compound 1

[0045]

[0046]In a 250ml four-necked flask, add 0.01mol 2,6-dibromo-4a,9a-dihydro-anthraquinone, 0.025mol 6,6-dimethyl-6,11-dihydro -13-Oxa-11-aza-indole[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, 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 97.2% and a yield of 75.00%.

[0047] Elemental analysis structure (molecular formula C 56 h 40 N 2 o 4 ): theoretical value C, 83.56; H, 5.01; N, 3.48; 0, 7.95; test value: C, 83.65;

[0048] HPLC-MS: The molecular weight of the material is 804.30, and the measured molecular weight is 804.96.

Embodiment 2

[0049] Example 2 Compound 5

[0050]

[0051] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 1,5-dibromo-4a,9a-dihydro-anthraquinone, 0.025mol 6,6,13,13-tetramethyl-11, 13-Dihydro-11-aza-indo[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, 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 99.2% and a yield of 72.00%.

[0052] Elemental analysis structure (molecular formula C 62 h 52 N 2 o 2 ): theoretical value C, 86.88; H, 6.12; N, 3.27; O, 3.73; test value: C, 86.93; H, 6.11; N, 3.20;

[0053] HPLC-MS: The molecular weight of the material is 856.40, and the measured molecular weight is 857.10.

Embodiment 3

[0054] Example 3 Compound 6

[0055]

[0056] In a 250ml four-neck flask, add 0.01mol 2,6-bis-(4'-bromobiphenyl-3-yl)-4a,9a-dihydro-anthraquinone, 0.025mol 11H- 6,13-Dioxa-11-aza-indole[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, 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 99.5% and a yield of 68.00%.

[0057] Elemental analysis structure (molecular formula C 74 h 44 N 2 o 6 ): theoretical value C, 84.07; H, 4.20; N, 2.65; 0, 9.08; test value: C, 84.21;

[0058] HPLC-MS: The molecular weight of the material is 1056.32, and the measured molecular weight is 1056.80.

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PUM

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Abstract

The invention discloses a 9,10-anthraquinone based compound and an application thereof in organic electroluminescent devices. According to the compound disclosed by the invention, 9,10-anthraquinone serves as a parent core, two sides are connected with two aromatic heterocyclic groups, thus, the crystallinity of molecules is destroyed, the aggregation of the molecules is avoided, and the film forming property is good; and the compound disclosed by the invention is applied to the organic electroluminescent devices as a luminescent layer material, and the organic electroluminescent devices using the compound disclosed by the invention have good photoelectric properties and can better adapt to and meet the application requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing 9,10-anthraquinone and its application as a light-emitting layer material in an organic electroluminescence device. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products. [0003] 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 purpose 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, the positive and negative charges in the functional material film layer of the organic layer are acted by the electric field,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D491/048C07D471/04C07D487/04C07D221/18C07D498/04C07D513/04C07D265/34C07D495/04C07D241/38C07D487/06C09K11/06H01L51/54
CPCC09K11/06C07D221/18C07D241/38C07D265/34C07D471/04C07D487/04C07D487/06C07D491/048C07D495/04C07D498/04C07D513/04C07D519/00C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1044H10K85/6572H10K85/657
Inventor 李崇徐凯张兆超
Owner JIANGSU SUNERA TECH CO LTD
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