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Compound based on monosubstituent-9-fluorenone and application thereof

A compound and single substitution technology, applied in organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of low S1 state radiation transition rate, difficult exciton utilization, high fluorescence radiation efficiency, and efficiency roll-off. Achieve good industrialization prospects, improve exciton utilization rate and high fluorescence radiation efficiency, and reduce the effect of efficiency roll-off

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

[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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  • Compound based on monosubstituent-9-fluorenone and application thereof
  • Compound based on monosubstituent-9-fluorenone and application thereof
  • Compound based on monosubstituent-9-fluorenone and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Compound 26

[0052]

[0053] 250ml there-necked flask, under the atmosphere of feeding nitrogen, add 0.01mol (2.59g) 1-bromo-9-fluorenone, 0.015mol (5.23g) compound M1, 0.03mol (2.88g) sodium tert-butoxide, 10 -4 mol(0.073g)Pd(dppf)Cl 2 , 180ml of toluene, heated to reflux for 10 hours, sampling point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, the filtrate was subjected to column chromatography to obtain the target product with a purity of 99.2% and a yield of 82%;

[0054] Elemental analysis structure (molecular formula C37H22N2O2): theoretical value C,84.39; H,4.21; N,5.32; O,6.08; test value: C,84.36; H,4.22; N,5.33; O,6.09;

[0055] HPLC-MS: The theoretical molecular weight of the material is 526.17, and the actual molecular weight is 526.40.

Embodiment 2

[0056] Example 2 Compound 44

[0057]

[0058] The preparation method of compound 44 is the same as in Example 1, except that M1 is replaced by raw material M2;

[0059] Elemental analysis structure (molecular formula C29H17NOS): theoretical value C, 81.47; H, 4.01; N, 3.28; O, 3.74; S, 7.50; test value: C, 81.45; ,7.51;

[0060] HPLC-MS: The theoretical molecular weight of the material is 427.10, and the actual molecular weight is 427.35.

Embodiment 3

[0061] Example 3 Compound 56

[0062]

[0063] The preparation method of compound 56 is the same as that in Example 1, except that the raw material M3 is used to replace M1;

[0064] Elemental analysis structure (molecular formula C31H17NO3): theoretical value C,82.47; H,3.80; N,3.10; O,10.63; test value: C,82.45; H,3.79; N,3.11; O,10.65;

[0065] HPLC-MS: The theoretical molecular weight of the material is 451.12, and the actual molecular weight is 451.36.

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Abstract

The invention discloses a compound based on monosubstituent-9-fluorenone and application thereof. The compound uses monosubstituent-9-fluorenone as a mother nucleus and allows a single side to be connected with a heteroaromatic group, so crystallinity of molecules is destroyed, aggregation of molecules is prevented, and good film forming ability is obtained. The compound is used as a luminescent layer material for an organic light-emitting diode and has good photoelectric performance.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a single substituent-9-fluorenone 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 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. [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 application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D279/36C07D513/04C07D471/04C07D498/14C07D487/04C07D241/38C07D265/38C07D265/34C07D219/02C07D221/18C07D241/46C07D491/048C07D495/04C07D517/04C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D221/18C07D241/38C07D241/46C07D265/34C07D265/38C07D279/36C07D471/04C07D487/04C07D491/048C07D495/04C07D498/04C07D498/14C07D513/04C07D517/04C09K2211/1011C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1096H10K85/615H10K85/657H10K85/6572
Inventor 巨成良石宇张学衡刘英瑞
Owner JIANGSU SUNERA TECH CO LTD
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