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Compound based on diaryl ketone and application thereof

A diaryl ketone and compound technology, applied in the field of semiconductors, 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 device life improvement and good film formation Sex and fluorescence quantum efficiency, the effect of avoiding aggregation

Active Publication Date: 2017-03-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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 diaryl ketone and application thereof
  • Compound based on diaryl ketone and application thereof
  • Compound based on diaryl ketone and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: the synthesis of compound 3

[0063] synthetic route:

[0064]

[0065] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol intermediate A, 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 98.9% and a yield of 65%.

[0066] Elemental analysis structure (molecular formula C 53 h 32 N 2 O): Theoretical value C, 89.30; H, 4.52; N, 3.93; O, 2.24; Test value: C, 89.31; H, 4.51; N, 3.92;

[0067] HPLC-MS: The molecular weight of the material is 712.83, and the measured molecular weight is 713.05.

Embodiment 2

[0068] Embodiment 2: the synthesis of compound 10

[0069] synthetic route:

[0070]

[0071] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.015mol intermediate B, 0.02mol sodium tert-butoxide, 5×10 -5 mol Pd 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; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.4% and a yield of 80%.

[0072] Elemental analysis structure (molecular formula C 37 h 24 N 2 O): theoretical value C, 86.69; H, 4.72; N, 5.46; O, 3.12; tested value: C, 86.69; H, 4.73; N, 5.47;

[0073] HPLC-MS: The molecular weight of the material is 512.60, and the measured molecular weight is 512.85.

Embodiment 3

[0074] Embodiment 3: the synthesis of compound 15

[0075] synthetic route:

[0076]

[0077] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol intermediate C, 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 65%.

[0078] Elemental analysis structure (molecular formula C 49 h 28 N 2 o 3 ): theoretical value C, 84.95; H, 4.07; N, 4.04; O, 6.93; test value: C, 84.94; H, 4.08; N, 4.03;

[0079] HPLC-MS: The molecular weight of the material is 692.76, and the measured molecular weight is 692.97.

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Abstract

The invention discloses a compound based on diaryl ketone and an application of the compound in an organic electroluminescent device. The compound has the characteristics of difficult intermolecular crystallization, difficult aggregation and good film-forming ability, and a rigid group in the molecules can increase the thermostability of a material. The compound as a luminescent layer material is used in the organic electroluminescent device, the luminescent device using the compound has good photoelectric property, and is suitable for and satisfies requirements of a panel manufacture enterprise.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing diaryl ketone 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 lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit...

Claims

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Application Information

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IPC IPC(8): C07D209/80C07D209/94C07D471/04C07D487/04C07D487/14C07D491/048C07D491/052C07D491/056C07D491/147C07D491/153C07D495/04C07D495/14C07D497/04C07D498/04C07D498/14C07D517/04C07D517/14C07D519/00H01L51/54
CPCC07D209/80C07D209/94C07D471/04C07D487/04C07D487/14C07D491/048C07D491/052C07D491/056C07D491/147C07D491/153C07D495/04C07D495/14C07D497/04C07D498/04C07D498/14C07D517/04C07D517/14C07D519/00H10K85/657H10K85/6572
Inventor 王立春张兆超李崇徐凯叶中华
Owner JIANGSU SUNERA TECH CO LTD
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