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Aromatic ketone compound and organic light-emitting device thereof

A technology of organic light-emitting devices and compounds, applied in the field of organic light-emitting device materials, can solve the problems of lowering charge injection barriers, poor quantum efficiency and luminous efficiency, etc.

Active Publication Date: 2020-03-03
E RAY OPTOELECTRONICS TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, a low ΔEST can also be achieved by generating an exciplex at the contact interface with two independent charge-transporting materials. Professor J.J. Kim’s Department of South Korea used the exciplex as a common host material to prepare organic light-emitting Device, the energy level difference between the highest occupied molecular orbital (HOMO) of the charge donor and the lowest unoccupied molecular orbital (LUMO) of the charge acceptor formed, its characteristics are similar to the energy of singlet excited state and triplet excited state, so that The energy of the singlet and triplet states is completely transferred to the dopant material, which greatly reduces the charge injection barrier. However, the quantum efficiency and luminous efficiency of organic light-emitting devices through TADF or exciplex are still generally poor, and there is still room for improvement.

Method used

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  • Aromatic ketone compound and organic light-emitting device thereof
  • Aromatic ketone compound and organic light-emitting device thereof
  • Aromatic ketone compound and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0101] Synthesis Example 1: Synthesis of Compound 1-1

[0102]

[0103] A mixture of acetophenone (10 mmol) and DMF-DMA (20 mmol) was refluxed overnight. The reaction mixture was cooled and poured into water, extracted with ethyl acetate, and the organic layer of the extract was washed 3 times with brine, collected and dried over magnesium sulfate. After the solvent was removed, the crude product was purified by silica gel column chromatography with ethyl acetate / n-hexane mixture (50%) as eluent to obtain compound 1a.

[0104]

[0105]

[0106] A solution of the above-mentioned compound 1a in acetic acid / pyridine mixture (4:1) was refluxed overnight. The reaction mixture was cooled and poured into water to precipitate a solid. The solid was collected by filtration, washed thoroughly with water, and dissolved in ethyl acetate. It was washed 3 times with brine, separated and dried over magnesium sulfate. The solvent was evaporated and the crude product was purified ...

Synthetic example 2

[0108] Synthesis Example 2: Synthesis of Compound 1-2

[0109]

[0110] A mixture of m-bromoacetophenone (10 mmol) and DMF-DMA (20 mmol) was refluxed overnight. The reaction mixture was cooled and poured into water, extracted with ethyl acetate, and the organic layer of the extract was washed 3 times with brine, collected and dried over magnesium sulfate. After the solvent was removed, the crude product was purified by silica gel column chromatography with ethyl acetate / n-hexane mixture (50%) as eluent to obtain compound 2a.

[0111]

[0112] A solution of the above-mentioned compound 2a in acetic acid / pyridine mixture (4:1) was refluxed overnight. The reaction mixture was cooled and poured into water to precipitate a solid. The solid was collected by filtration, washed thoroughly with water, and dissolved in ethyl acetate. It was washed 3 times with brine, separated and dried over magnesium sulfate. The solvent was evaporated and the crude product was purified by co...

Synthetic example 3

[0114] Synthesis Example 3: Synthesis of Compound 1-3

[0115]

[0116] A mixture of p-bromoacetophenone (10 mmol) and DMF-DMA (20 mmol) was refluxed overnight. The reaction mixture was cooled and poured into water, then extracted with ethyl acetate, the organic layer of the extract was washed 3 times with brine, collected and dried over magnesium sulfate. After the solvent was removed, the crude product was purified by silica gel column chromatography with ethyl acetate / n-hexane mixture (50%) as eluent to obtain compound 2a.

[0117]

[0118] A solution of the above-mentioned compound 3a in acetic acid / pyridine mixture (4:1) was refluxed overnight. The reaction mixture was cooled and poured into water to precipitate a solid. The solid was collected by filtration, washed thoroughly with water, and dissolved in ethyl acetate. It was washed 3 times with brine, separated and dried over magnesium sulfate. The solvent was evaporated and the crude product was purified by c...

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Abstract

The invention provides an aromatic ketone compound and an organic light-emitting device thereof, wherein the aromatic ketone compound has a structure represented by a formula (I), X1 and X2 are the same or different, X1 and X2 respectively and independently represent a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C3-20 heteroarylene group containing at least one heteroatom selected from N, O and S, and a group having a structure represented by a formula (I-1), and Ar1 and Ar2 are the same or different and independently represent a substituted or unsubstituted C6-C20 arylene group.

Description

technical field [0001] The present invention relates to a material for an organic light-emitting device and an organic light-emitting device using the material, in particular to a material for an organic light-emitting device capable of producing light-emitting exciplexes and an organic light-emitting device using the material. Background technique [0002] Organic light-emitting devices (OLEDs) have the characteristics of lightness, thinness, wide viewing angle, high contrast ratio, low power consumption, high response speed, full-color and flexibility. Therefore, applications in full-color displays or portable electronic devices are highly anticipated. . [0003] A typical OLED is a multi-layer film structure formed by sequentially depositing an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode by vacuum deposition or coating. When a current is applied, the anode injects holes and the cathode injects electrons into the one or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C09K11/06H01L51/50H01L51/54
CPCC07C49/813C09K11/06C09K2211/1007H10K50/12
Inventor 黄贺隆赵登志赖振昌汪根欉洪文谊张敏忠孙杰
Owner E RAY OPTOELECTRONICS TECH
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