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Naphthalimide azacyclo-luminescent material and application thereof

A luminescent material, naphthalimide technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low efficiency and poor stability of luminescent materials, achieve good thermal stability, improved luminescence performance, good The effect of the application foreground

Active Publication Date: 2021-03-09
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a naphthalimide aza-heterocyclic luminescent material and its application, the purpose of which is to synthesize the naphthalimide-aza-heterocyclic luminescent material by adopting a simple and feasible synthesis scheme and apply it to organic electroluminescence Devices, solving the technical problems of low efficiency and poor stability of luminescent materials in the prior art

Method used

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  • Naphthalimide azacyclo-luminescent material and application thereof
  • Naphthalimide azacyclo-luminescent material and application thereof
  • Naphthalimide azacyclo-luminescent material and application thereof

Examples

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Effect test

Embodiment 1

[0052] Naphthalimide azacyclic luminescent material 1(3,4-bis(4-(diphenylamino)phenyl)-7H benzo[de]benzo[4,5]imidazo[ 2,1-a]isoquinolin-7-one) can be synthesized by the following method.

[0053]

[0054] (1) In a dry 500ml two-necked flask, add 1,4,5,8-naphthalene tetracarboxylic anhydride (10.03g, 37.3mmol), then add 350ml of water and stir to dissolve, then add potassium hydroxide (10.51g, 186.4 mmol), the solution was heated to 85°C, liquid bromine (4.7ml, 93.2mmol) was slowly added dropwise, heated and stirred for 1 hour, and after the reaction solution was cooled to room temperature, 20ml of hydrochloric acid was slowly added. After a large amount of solid was precipitated, it was suction-filtered, and the crude product was washed alternately with water and methanol three times to obtain intermediate 1-1 (4,5-dibromo-1,8-naphthalene dicarboxylic anhydride), with a yield of 91%.

[0055] (2) Add intermediate 1-1 (1.77g, 5mmol), phenylenediamine (0.54g, 5mmol), and 100...

Embodiment 2

[0058] The same preparation method as in Example 1, the difference is that the phenylenediamine in the reaction step (2) is replaced by 4',5'-diamino-[1,1':2',1'-triphenyl] -4,4'-dicarbonitrile, and finally the target product 3(4,4'-(3,4-bis(4-(diphenylamino)phenyl)-7-oxo-7H-benzo[de ]benzo[4,5]imidazo[2,1-a]isoquinoline-10,11-diyl)dibenzonitrile), the yield was 59%. MS(MALDI-TOF):m / z[M(H) + ] 960.076. Elemental analysis results (%): C 85.01; H 4.29; N 8.85; O 1.56.

Embodiment 3

[0060] The naphthalimide azacyclic luminescent material 13(10,11-bis(4-(diphenylamino)phenyl)-7H benzo[de]benzo[4,5]imidazo[ 2,1-a]isoquinolin-7-one) can be synthesized by the following method.

[0061]

[0062] (4) Add 4,5-dibromobenzene-1,2-diamine (1.33g, 5mmol), 1,8-naphthalene dicarboxylic anhydride (0.99g, 5mmol), and 100ml acetic acid solution in a dry 250ml single-necked flask , heated to reflux and stirred for 8 hours. After the reaction is complete, the intermediate 3-1(10,11-dibromo-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinoline-7- ketone), yield 80%.

[0063] (5) Intermediate 3-1 (1.27g, 3mmol), triphenylamine 4-boronate (2.43g, 8.4mmol), tetrakistriphenylphosphine palladium (0.34g, 0.3mmol), potassium carbonate (3.31g, 24mmol ), 12ml of water, 18ml of toluene, and 5ml of ethanol were sequentially added into a 100ml two-necked flask, stirred rapidly and passed a large amount of nitrogen for 10-15 minutes, and heated to reflux under nitrogen protection for 3...

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Abstract

The invention discloses a naphthalimide azacyclo-luminescent material and application thereof. The general structural formula of the naphthalimide azacyclo-luminescent material is descried in the descriptions of the invention. The naphthalimide azacyclo-luminescent material provided by the invention has hybrid local charge transfer state performance; triplet excitons can be effectively utilized through high-energy-state reverse inter-gap jump, so that the electroluminescent performance of a device is improved; meanwhile, the naphthalimide azacyclo-luminescent material provided by the inventionis high in conjugation degree, high in rigidity, high in radiation transition rate and high in luminous efficiency; with the types of aryl and substituent groups changed, the light emitting efficiency and light color of the material can be adjusted, and the material can be used as a guest material and a host material and can be applied to the field of organic electronic display.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a naphthalimide azacyclic luminescent material and its application. Background technique [0002] Since Kodak first reported Organic Light Emitting Diode (OLED) in 1987, through the continuous synthesis of new materials and optimized device structures, relevant research has made major breakthroughs, and has been used in the next generation of flat-panel displays and lighting sources. It shows great industrialization prospect. During the working process of OLED, electrons and holes recombine to generate excitons. Devices based on fluorescent materials can only use 25% of singlet excitons in theory. If the other 75% of triplet excitons can be used, the fluorescence can be greatly improved. The luminous efficiency of the material. In 1998, Forrest, Thompson and Ma used the strong spin-orbit coupling effect of h...

Claims

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Application Information

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IPC IPC(8): C07D471/06C07D471/16C09K11/06C07D471/22H01L51/54
CPCC07D471/06C07D471/16C09K11/06C07D471/22C09K2211/1029C09K2211/1074C09K2211/1092C09K2211/1088C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1007C09K2211/1011H10K85/653H10K85/655H10K85/654H10K85/657H10K85/6576H10K85/6574H10K85/6572
Inventor 杨楚罗周长江
Owner SHENZHEN UNIV
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