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Novel acridine compound and organic light-emitting devices thereof

A compound, nitrogen-anthracene technology, applied in the field of organic optoelectronic materials, can solve the problems of inability to improve and reduce luminous efficiency, and achieve the effects of improving hole mobility, good luminous efficiency, and high brightness

Inactive Publication Date: 2017-10-10
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the triplet deactivation dominates in the high-brightness region, the decrease in luminous efficiency cannot be improved under the conditions of the currently applied hole-transport materials.

Method used

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  • Novel acridine compound and organic light-emitting devices thereof
  • Novel acridine compound and organic light-emitting devices thereof
  • Novel acridine compound and organic light-emitting devices thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1. Production of Intermediate C-1

[0084]

[0085] Under the protection of nitrogen, nitrogen anthracene (18.0 g, 100 mmol) was added into the reaction vessel and dissolved with tetrahydrofuran (200 ml). Add N-bromosuccinimide (18.0 g, 101 mmol) at 0°C and stir at room temperature for 5 hours. After the reaction was terminated, the reaction was quenched with distilled water, and the organic matter was extracted with ethyl acetate. After filtering through a silica gel filter funnel, the organic solvent was concentrated and recrystallized with ethyl acetate to obtain 9-bromoazanthracene (23.2 g, 90%).

Embodiment 2

[0086] Embodiment 2. The manufacture of intermediate B-1

[0087]

[0088] 9-Bromoazephanthracene (10g, 38.74mmol) was added to a three-necked flask, THF (100mL) was added, under nitrogen protection, stirred at -78°C for 30 minutes, n-butyllithium (2.5M / 21mL) was added, reacted for 1 hour, and then Add triisopropyl borate (14 g), react at low temperature for 1 hour, and gradually return to room temperature. During post-treatment, add 2M hydrochloric acid to make the pH of the solution 4-5, statically separate the liquids, extract the aqueous layer once with ethyl acetate, combine the organic layers, and spin dry to obtain azanthracene boronic acid (4.85 g, y=55%).

Embodiment 3

[0089] Example 3. Production of Intermediate A-1

[0090]

[0091] Under nitrogen, bis(4-biphenylene)amine (19.0g, 59.1mmol), bisbromobiphenyl (18.44g, 59.1mmol), tris(dibenzylideneacetone)dipalladium (0.1g ), tri-tert-butylphosphine (15%, 0.3g), sodium tert-butoxide (1.8g), toluene (300ml), and stirred at 60°C for 12 hours. After the reaction solution was cooled, it was filtered with a silica gel filter, and after the solution was concentrated, it was subjected to column chromatography with dichloromethane and hexane to obtain (A-1) (22.21 g, yield 68%).

[0092] Intermediates A-2 to A-28 in Table 1 were prepared in the same manner as A-1.

[0093] Table 1: Preparation of intermediates A-2 to A-28

[0094]

[0095]

[0096]

[0097]

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PUM

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Abstract

The invention provides a novel acridine compound and organic light-emitting devices thereof, belongs to the technical field of organic photoelectric materials, and aims to solve the technical problems of low light-emitting efficiency, high driving voltage, short service life and low light-emitting performance of the organic photoelectric material in the prior art. Compared with the prior art, the light-emitting performance of the organic light-emitting devices based on organic electroluminescence device compounds and ink compositions can be obviously improved; the novel acridine compound is used as an excellent OLED material.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a new nitrogen anthracene compound and its application in organic light-emitting devices. Background technique [0002] An organic electroluminescent device (OLED) is a new type of flat display device, generally composed of two opposing electrodes and at least one layer of organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form electron and hole pairs, which cause light emission from organic compounds with fluorescent and phosphorescent properties. Organic electroluminescent devices have the characteristics of energy saving, fast response speed, stable color, strong environmental adaptability, no radiation, light weight, and thin thickness. With the rapid development of optoelectronic communication and multimedia fields in recent years, organic optoelect...

Claims

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Application Information

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IPC IPC(8): C07D219/02C07D401/04C07D401/12C07D405/04C07D405/12C07D405/14C07D409/04C07D409/12C07D409/14C07D417/04C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D401/04C07D401/12C07D405/04C07D405/12C07D405/14C07D409/04C07D409/12C07D409/14C07D417/04C07D471/04C09K2211/1029C09K2211/1088C09K2211/1092H10K85/622H10K85/615H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572
Inventor 蔡辉孙可一
Owner CHANGCHUN HYPERIONS TECH CO LTD
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