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Pyridine-based five-membered-ring substituted compound and application thereof

A compound, azabenzene technology, applied in the application field of light-emitting layer materials in OLED devices, can solve the problems of efficiency roll-off, difficult exciton utilization, high fluorescence radiation efficiency, and low S1 state radiation transition rate, etc., to achieve Effects of increasing orbital overlap, avoiding agglomeration, and good industrialization prospects

Inactive 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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  • Pyridine-based five-membered-ring substituted compound and application thereof
  • Pyridine-based five-membered-ring substituted compound and application thereof
  • Pyridine-based five-membered-ring substituted compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the synthesis of compound 3:

[0058] synthetic route:

[0059]

[0060] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 2-(4-bromophenyl)-4,6-bis(2-thienyl)pyrimidine, 0.015mol intermediate A1, 0.03mol tert-butyl Sodium alkoxide, 1 x 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 99.3% and a yield of 67.5%.

[0061] Elemental analysis structure (molecular formula C 46 h 28 N 4 OS 2 ): theoretical value C, 77.07; H, 3.94; N, 7.82; O, 2.23; S, 8.95; test value: C, 77.06;

[0062] HPLC-MS: The molecular weight of the material is 716.17, and the measured molecular weight is 716.41.

Embodiment 2

[0063] Embodiment 2: the synthesis of compound 11:

[0064] synthetic route:

[0065]

[0066] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 2-(4-bromophenyl)-6-phenylpyrazine, 0.015mol intermediate B1, 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 66.7%.

[0067] Elemental analysis structure (molecular formula C 49 h 36 N 4 ): theoretical value C, 86.44; H, 5.33; N, 8.23; test value: C, 86.42; H, 5.34; N, 8.24.

[0068] HPLC-MS: The molecular weight of the material is 680.29, and the measured molecular weight is 680.52.

Embodiment 3

[0069] Embodiment 3: the synthesis of compound 19:

[0070] synthetic route:

[0071]

[0072] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-(4-bromophenyl)-6-phenylpyridazine, 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 99.1% and a yield of 65.9%.

[0073] Elemental analysis structure (molecular formula C 49 h 34 N 4 ): theoretical value C, 86.70; H, 5.05; N, 8.25; test value: C, 86.72; H, 5.04; N, 8.24.

[0074] HPLC-MS: The molecular weight of the material is 678.28, and the measured molecular weight is 678.55.

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Abstract

The invention discloses a pyridine-based five-membered-ring substituted compound and application thereof. The compound provided by the invention has the characteristics that the crystallization and the aggregation among molecules are difficult, and the compound has a favorable film-forming property. The heat stability of a material can be improved by rigid groups in the molecules of the compound provided by the invention; the compound provided by the invention is applied to OLEDs (Organic Light Emission Diodes) as a luminescent layer material; a made OLED appliance has favorable photoelectric properties, and can better meet the requirements of a panel manufacturing enterprise.

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 on an OLED 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 OLED light-emitting d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D405/14C07D409/14C07D413/14C07D401/14C07D495/04C07D487/04C07D491/048C07D403/04C07D403/10C07D491/052C07D471/04C07D491/056C07D498/04C07D497/04C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D403/04C07D403/10C07D403/14C07D405/14C07D409/14C07D413/14C07D471/04C07D487/04C07D491/048C07D491/052C07D491/056C07D495/04C07D497/04C07D498/04C09K2211/1033C09K2211/1037C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 唐丹丹徐凯李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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