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Compound taking triazine as core and organic electroluminescence device thereof

A technology of electroluminescent devices and compounds, applied in the fields of electric solid-state devices, electrical components, organic chemistry, etc., can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc. , to achieve the effect of increasing orbital overlap, good film formation and fluorescence quantum efficiency, and avoiding aggregation

Active Publication Date: 2018-04-06
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 taking triazine as core and organic electroluminescence device thereof
  • Compound taking triazine as core and organic electroluminescence device thereof
  • Compound taking triazine as core and organic electroluminescence device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The synthesis of embodiment 1 compound 3

[0062]

[0063] The concrete synthetic route of this compound is provided now:

[0064]

[0065] In a 250ml four-necked flask, add 0.01mol 3,6-dibromo-9H-carbazole and 0.03mol compound 1,1,3,3-tetramethyl-2,3-dihydro -1H-isoindole, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, naturally cooled, filtered, filtrate rotary evaporated, passed through a silica gel column to obtain intermediate A1 with a purity of 94.80% and a yield of 68.90%.

[0066] In a 250ml four-neck flask, add 0.01mol of 2-(4-bromophenyl)-4,6-diphenyl-[1,3,5]-triazine and 0.015mol of intermediate under nitrogen atmosphere 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, showing no bromide remaining,...

Embodiment 2

[0068] The synthesis of embodiment 2 compound 5

[0069]

[0070] The concrete synthetic route of this compound is provided now:

[0071]

[0072] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3,6-dibromo-9H-carbazole, 0.03mol compound 2,3-dihydro-1H-indole, 0.03mol sodium tert-butoxide , 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain intermediate A2 with a purity of 90.49% and a yield of 72.30%.

[0073] In a 250ml four-neck flask, add 0.01mol of 2-(4-bromophenyl)-4,6-diphenyl-[1,3,5]-triazine and 0.015mol of intermediate under nitrogen atmosphere A2, 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, showing no bromide remaining, the reaction ...

Embodiment 3

[0075] The synthesis of embodiment 3 compound 18

[0076]

[0077] The concrete synthetic route of this compound is provided now:

[0078]

[0079] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3,6-dibromo-9H-carbazole, 0.03mol compound 5H-dibenzazepine, 0.03mol sodium tert-butoxide, 1× 10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain intermediate A3 with a purity of 97.32% and a yield of 67.10%.

[0080] In a 250ml four-neck flask, add 0.01mol of 2-(4-bromophenyl)-4,6-diphenyl-[1,3,5]-triazine and 0.015mol of intermediate under nitrogen atmosphere A3, 0.03mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, showing no bromide remaining, the reaction was c...

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Abstract

The invention relates to a compound taking triazine as a core and application thereof on an organic electroluminescence device thereof. The compound takes the triazine as the core, and has the characteristics of being difficult to crystallize among molecules, difficult to gather and excellent in film-forming property. When the compound disclosed by the invention is used as a luminous layer material of the organic electroluminescence device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved. Meanwhile, the compound has a very obvious effect of prolonging the life of the device.

Description

technical field [0001] The invention relates to a compound with triazine as the core and its application in organic electroluminescent devices and its application as a light-emitting layer material in organic light-emitting diodes, belonging to the field of semiconductor materials. 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D471/04C07D405/14H01L51/50H01L51/54
CPCC07D401/14C07D403/14C07D405/14C07D471/04H10K85/654H10K85/6574H10K85/6572H10K50/121
Inventor 徐凯李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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