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Organic electroluminescence compound with nitrogen-containing five-membered heterocycle as core and application thereof

A five-membered heterocycle and compound technology, which is applied to the application field of organic light-emitting diodes, can solve the problems of low S1 state radiation transition rate, efficiency roll-off, difficult exciton utilization rate, and high fluorescence radiation efficiency.

Inactive Publication Date: 2017-03-01
VALIANT 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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  • Organic electroluminescence compound with nitrogen-containing five-membered heterocycle as core and application thereof
  • Organic electroluminescence compound with nitrogen-containing five-membered heterocycle as core and application thereof
  • Organic electroluminescence compound with nitrogen-containing five-membered heterocycle as core and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: the synthesis of compound 10:

[0076] synthetic route:

[0077]

[0078] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole, 0.012mol intermediate A1, 0.03mol tert-butanol Sodium, 5 x 10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; natural cooling, filtration, rotary evaporation of the filtrate, column chromatography to obtain the target product, HPLC purity 98.5%, yield 75.2%;

[0079] Elemental analysis structure (molecular formula C 42 h 26 N 4 O): theoretical value C, 83.70; H, 4.35; N, 9.30; O, 2.65; tested value: C, 83.72; H, 4.33; N, 9.31;

[0080] HPLC-MS: The molecular weight of the material is 602.68, and the measured molecular weight is 602.82.

Embodiment 2

[0081] Embodiment 2: the synthesis of compound 27:

[0082] synthetic route:

[0083]

[0084] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 3-(4-bromophenyl)-4-methyl-4,5-diphenyl-4H-pyrazole, 0.012mol intermediate B1, 0.03mol Sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, column chromatography to obtain the target product, HPLC purity 99.3%, yield 76.3%;

[0085] Elemental analysis structure (molecular formula C 50 h 33 N 3 O): theoretical value C, 86.81; H, 4.81; N, 6.07; O, 2.31; tested value: C, 86.82; H, 4.80; N, 6.05;

[0086] HPLC-MS: The molecular weight of the material is 691.82, and the measured molecular weight is 692.01.

Embodiment 3

[0087] Embodiment 3: the synthesis of compound 37:

[0088] synthetic route:

[0089]

[0090] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole, 0.012mol intermediate C1, 0.03mol tert-butanol Sodium, 5 x 10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, column chromatography to obtain the target product, HPLC purity 98.9%, yield 74.8%;

[0091] Elemental analysis structure (molecular formula C 47 h 34 N 4 O): theoretical value C, 84.15; H, 5.11; N, 8.35; O, 2.39; tested value: C, 84.14; H, 5.12; N, 8.34;

[0092] HPLC-MS: The molecular weight of the material is 670.80, and the measured molecular weight is 670.97.

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Abstract

The invention discloses an organic electroluminescence compound with nitrogen-containing five-membered heterocycle as the core and application thereof. The compound has the nitrogen-containing five-membered heterocycle as the core, is not easy to crystallize between molecules and is not easy to aggregate, and has good film forming ability. The compound, used as a luminescent layer material, is applied to organic electroluminescent devices. An organic electroluminescent device by using the compound has good photoelectric property and can better meet application requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with a nitrogen-containing five-membered heterocyclic ring as the core 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...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/10C07D403/14C07D405/14C07D413/10C07D413/14C07D417/10C07D421/10C07D471/04C07D487/04C07D491/048C07D495/04C07D491/052C07D491/044C07D491/056C07D497/04C07D498/04C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D403/10C07D403/14C07D405/14C07D413/10C07D413/14C07D417/10C07D421/10C07D471/04C07D487/04C07D491/044C07D491/048C07D491/052C07D491/056C07D495/04C07D497/04C07D498/04C09K2211/1051C09K2211/1044C09K2211/1048C09K2211/1037C09K2211/104C09K2211/1033C09K2211/1059C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1092C09K2211/1096C09K2211/1088C09K2211/1074H10K85/626H10K85/615H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 王立春唐丹丹张兆超李崇张小庆
Owner VALIANT CO LTD
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