Benzo[c]phenanthrene derivative with electron donor-acceptor structure and application thereof and electroluminescent device

An electron donor and derivative technology, applied in the fields of electric solid device, semiconductor device, semiconductor/solid state device manufacturing, etc., can solve the problems of concentration quenching, difficult to achieve light color, high turn-on voltage, and achieve good thermal stability. Effect

Inactive Publication Date: 2016-04-20
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, more blue-light dopants such as perylene derivatives TBP (J.Shi, C.W.Tang, Anthracene Derivatives for Stable Blue-Emitting Organic Electroluminescence Devices. Applied Physics Letters 2002, 80 (17): 3201-3203.), but because the perylene ring is hard and planar, it is easy to lead to concentration quenching, the doping concentration is very low
Diarylamine styrene derivatives DSA-Ph (M.-T.Lee, H.-H.Chen, C.-H.Liao, et al., StableStyrylamine-DopedBlueOrganicElectroluminescentDeviceBasedon2-Methyl-9,10-Di(2- Naphthyl)Anthracene.AppliedPhysicsLetters2004,85(15):3301-3303), th

Method used

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  • Benzo[c]phenanthrene derivative with electron donor-acceptor structure and application thereof and electroluminescent device
  • Benzo[c]phenanthrene derivative with electron donor-acceptor structure and application thereof and electroluminescent device
  • Benzo[c]phenanthrene derivative with electron donor-acceptor structure and application thereof and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 9 described in the present invention can be synthesized by the following method.

[0034]

[0035] Add 4-bromodibenzofuran (30g, 121.5mmol), phenylboronic acid (15.6g, 127.6mmol), tetrakistriphenylphosphine palladium (0.7g, 0.61mmol), potassium carbonate (41g, 297.1mmol) into a 1000ml three-necked flask mmol), toluene 300ml, ethanol 150ml, water 150ml, reacted at 80°C for 12h under nitrogen protection. TLC showed the reaction was complete. Spin off the toluene and ethanol, extract the aqueous phase with dichloromethane (200ml×3), combine the organic phases, dry over anhydrous sodium sulfate, concentrate, and distill under reduced pressure to obtain the product 4-phenyldibenzofuran (24.4g, 82% yield )

[0036]

[0037] Add 4-phenyldibenzofuran (22g, 90.2mmol) and 300ml of anhydrous tetrahydrofuran into a 500ml three-necked flask, replace the air, protect with nitrogen, lower the temperature to -78°C with liquid nitrogen and ethanol, and slowly add n-bu...

Embodiment 2

[0042] Example 2: 9 is used as a light-emitting layer to prepare a device.

[0043] This example demonstrates the performance verification of an electroluminescent device fabricated with 9 as a guest luminescent material. The ITO (Indium Tin Oxide) glass was ultrasonically cleaned in detergent and deionized water for 30 minutes sequentially. Then vacuum dry for 2 hours (105°C), then put the ITO (indium tin oxide) glass into the plasma reactor for 5 minutes of oxygen plasma treatment, transfer it to the vacuum chamber to prepare organic films and metal electrodes, and then use the method of vacuum evaporation Preparation of a layer of 10nm hole injection material molybdenum trioxide followed by evaporation of 80nm thick hole injection material: 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC) , and then continue on the hole transport layer by vacuum evaporation a layer of 12nm material 9,10-bis(2-naphthyl)-2-methylanthracene; 2-methyl-9,10-bis(naphthalene -2-yl) anth...

Embodiment 3

[0045] Example 3: 21 described in the present invention can be synthesized by the following method.

[0046]

[0047] Add 4-bromodibenzofuran (30g, 121.5mmol), phenylboronic acid (15.6g, 127.6mmol), tetrakistriphenylphosphine palladium (0.7g, 0.61mmol), potassium carbonate (41g, 297.1mmol) into a 1000ml three-necked flask mmol), toluene 300ml, ethanol 150ml, water 150ml, reacted at 80°C for 12h under nitrogen protection. TLC showed the reaction was complete. Spin off the toluene and ethanol, extract the aqueous phase with dichloromethane (200ml×3), combine the organic phases, dry over anhydrous sodium sulfate, concentrate, and distill under reduced pressure to obtain the product 4-phenyldibenzofuran (24.4g, 82% yield )

[0048]

[0049] Add 4-phenyldibenzofuran (22g, 90.2mmol) and 300ml of anhydrous tetrahydrofuran into a 500ml three-necked flask, replace the air, protect with nitrogen, lower the temperature to -78°C with liquid nitrogen and ethanol, and slowly add n-b...

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PUM

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Abstract

The invention belongs to the field of photoelectric material application science and technology, and particularly relates to a benzo[c]phenanthrene derivative with an electron donor-acceptor structure and application thereof and an electroluminescent device. The derivative takes benzo[c]phenanthrene as a core, and by linking different aromatic amine groups to different sites of the benzo[c]phenanthrene in a key mode or changing a bridged structure, an efficient fluorescence material with the double polarity is formed. The material has the advantages that the stability and conjugacy of large aromatic rings of the benzophenanthrene are utilized, distribution of electron clouds on the molecules is adjusted through the periphery groups, and therefore luminescent property can be effectively adjusted.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and specifically relates to derivatives of benzo[c]phenanthrenes with an electron donor-acceptor structure, their application and electroluminescent devices. Background technique [0002] The 21st century is an era of knowledge economy with the information industry as the core, and its notable features are the digitization and networking of information and the construction of information superhighways. Since 1987, American Kodak Company (PopeM., Kallmann.H.P., Magnante.P., Electroluminescence in Organic Crystals. The Journal of Chemical Physics 1963, 38 (8): 2042-2043) and Cambridge University in 1990 respectively launched organic and polymer electroluminescence materials and devices. Since then, international competition for "modern flat panel display technology" has been aroused worldwide in the fields of material science and information technology. [0003] OLED fu...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D307/91C07D333/76C07D209/88C07D209/86C07D235/18C07F7/08C09K11/06H01L51/54
CPCC09K11/06C07C211/61C07D209/86C07D209/88C07D235/18C07D307/91C07D333/76C07F7/081C09K2211/1044C09K2211/1092C09K2211/1088C09K2211/1014C09K2211/1029C09K2211/1011H10K85/622H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6574H10K85/40H10K85/6572
Inventor 穆广园王磊
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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