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Organic compound taking pyridine as core and application thereof to OLED

An organic compound, azabenzene technology, applied in the application field of organic electroluminescent devices, can solve the problems of low S1 state radiation transition rate, difficult exciton utilization rate, high fluorescence radiation efficiency, efficiency roll-off and the like

Active Publication Date: 2017-02-15
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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  • Organic compound taking pyridine as core and application thereof to OLED
  • Organic compound taking pyridine as core and application thereof to OLED
  • Organic compound taking pyridine as core and application thereof to OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1: the synthesis of compound 1:

[0072] synthetic route:

[0073]

[0074] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4-bromo-2,6-di(2-thienyl)pyridine, 0.015mol intermediate A1, 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 99.1% and a yield of 68.4%.

[0075] Elemental analysis structure (molecular formula C 41 h 25 N 3 OS 2 ): theoretical value C, 76.97; H, 3.94; N, 6.57; O, 2.50; S, 10.02; test value: C, 76.98;

[0076] HPLC-MS: The molecular weight of the material is 639.14, and the measured molecular weight is 639.37.

Embodiment 2

[0077] Embodiment 2: the synthesis of compound 4:

[0078] synthetic route:

[0079]

[0080] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 2,5-dibromopyrazine, 0.025mol intermediate B1, 0.04mol sodium tert-butoxide, 2×10 -4 mol Pd 2 (dba) 3 , 2×10 -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 63.7%.

[0081] Elemental analysis structure (molecular formula C 60 h 36 N 6 o 2 ): theoretical value C, 82.55; H, 4.16; N, 9.63; O, 3.67; test value: C, 82.53; H, 4.17; N, 9.64;

[0082] HPLC-MS: The molecular weight of the material is 872.29, and the measured molecular weight is 872.51.

Embodiment 3

[0083] Embodiment 3: the synthesis of compound 12:

[0084] synthetic route:

[0085]

[0086] In a 250ml four-necked flask, under nitrogen atmosphere, add 0.01mol 2-(4-bromophenyl)-5-phenylpyrazine, 0.015mol intermediate C1, 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 point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, silica gel column, the target product was obtained with a purity of 98.7% and a yield of 65.6%.

[0087] Elemental analysis structure (molecular formula C 49 h 34 N 4 O): Theoretical value C, 84.70; H, 4.93; N, 8.06; O, 2.30; Test value: C, 84.72; H, 4.92; N, 8.05;

[0088] HPLC-MS: The molecular weight of the material is 694.27, and the measured molecular weight is 694.49.

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Abstract

The invention discloses an organic compound taking pyridine as a core and application thereof to OLED. The organic compound has the characteristics that the molecules are not easy to crystallize and aggregate, and have good film-forming property. The rigid group in the compound molecule can improve the heat stability of materials. When the compound serving as a luminescent layer material is applied to OLED, manufactured OLED devices have good photoelectric property and can properly meet the requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with azabenzene as the core and its application as a light-emitting layer material in an organic electroluminescent device. 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 ends of the...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D403/14C07D401/04C07D401/14C07D405/14C07D417/14C07D491/048C07D487/04C07D513/04C07D413/04C07D498/04C07D491/052C07D471/04C07D403/04C07D498/06C07D471/06C07D487/06C07D409/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/04C07D401/14C07D403/04C07D403/14C07D405/14C07D409/14C07D413/04C07D413/14C07D417/14C07D471/04C07D471/06C07D487/04C07D487/06C07D491/048C07D491/052C07D498/04C07D498/06C07D513/04C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1044H10K85/636H10K85/633H10K85/653H10K85/655H10K85/656H10K85/615H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 唐丹丹李崇张兆超叶中华张小庆
Owner JIANGSU SUNERA TECH CO LTD
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