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Compound based on diaryl ketone and application of compound to organic electroluminescence device

A technology of diaryl ketones and compounds, applied in electric solid devices, electrical components, luminescent materials, etc., can solve the problems of low S1 state radiation transition rate, efficiency roll-off, difficult exciton utilization and high fluorescence radiation efficiency. , to achieve good industrialization prospects, increased orbital overlap, and good fluorescence quantum efficiency.

Active Publication Date: 2016-12-14
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 of compound to organic electroluminescence device
  • Compound based on diaryl ketone and application of compound to organic electroluminescence device
  • Compound based on diaryl ketone and application of compound to organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Compound 1

[0045] The concrete synthetic route of this compound is provided now:

[0046]

[0047]In a 250ml four-necked flask, add 0.01mol 4,4'-dibromobenzophenone, 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, 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 67.00%.

[0048] Elemental analysis structure (molecular formula C 55 h 40 N 2 o 3 ): theoretical value C, 85.03; H, 5.19; N, 3.61; O, 6.18; test value: C, 84.99; H, 5.21; N, 3.70;

[0049] HPLC-MS: The molecular weight of the material is 776.30, and the measured molecular weight is 776.83.

Embodiment 2

[0050] Example 2 Compound 6

[0051] The concrete synthetic route of this compound is provided now:

[0052]

[0053] In a 250ml four-necked flask, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol 11,11-dimethyl-4a,6,11,13a-tetrahydro- 13-thia-6-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 99.0% and a yield of 69.00%.

[0054] Elemental analysis structure (molecular formula C 55 h 42 N 2 OS 2 ): theoretical value C, 81.45; H, 5.22; N, 3.45; O, 1.97; test value: C, 81.50; H, 5.21; N, 3.40;

[0055] HPLC-MS: The molecular weight of the material is 810.27, and the measured molecular weight is 810.65.

Embodiment 3

[0056] Example 3 Compound 11

[0057] The concrete synthetic route of this compound is provided now:

[0058]

[0059] In a 250ml four-necked flask, add 0.01mol 2,2'-dibromobenzophenone, 0.025mol 6,6-dimethyl-13-phenyl-11,13-dihydro -6H-11,13-diaza-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 99.5% and a yield of 72.00%.

[0060] Elemental analysis structure (molecular formula C 66 h 49 N 4 O): theoretical value C, 86.80; H, 5.44; N, 6.04; O, 1.73; tested value: C, 86.63; H, 5.29; N, 6.30;

[0061] HPLC-MS: The molecular weight of the material is 926.40, and the measured molecular weight is 926.52.

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Abstract

The invention discloses a compound based on diaryl ketone and an application of the compound to an organic electroluminescence device. The compound has the advantages that molecules are not prone to crystallization and collection, and good film forming performance is achieved; the heat stability of materials can be improved through rigid groups in the molecules. When the compound is applied to the organic electroluminescence device as a light emitting layer material, the organic electroluminescence device with the compound has good photoelectric performance 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 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): C07D519/00C07D221/18C07D241/38C07D265/38C07D279/36C07D293/10C07D403/14C07D409/14C07D405/14C07D401/14C09K11/06H01L51/54
CPCC09K11/06C07D221/18C07D241/38C07D265/38C07D279/36C07D293/10C07D401/14C07D403/14C07D405/14C07D409/14C07D519/00C09K2211/1029C09K2211/104C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092H10K85/653H10K85/655H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 李崇徐凯张兆超
Owner JIANGSU SUNERA TECH CO LTD
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