Perylene double imide derivatives and preparation method and applications thereof

A technology of perylene bisimide and derivatives, which is applied in the field of organic electroluminescent materials, can solve problems such as device instability, complicated device preparation process, and influence on the color purity of red light, and achieve photothermal stability and morphological stability High, high fluorescence quantum yield, good solubility effect

Inactive Publication Date: 2010-03-03
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In doped light-emitting devices, the host and the guest emit light at the same time due to insufficient energy transfer, which seriously affects the color purity of red light; in addition, doped light-emitting devices are produced by co-evaporation or mixed solution spin coating method Therefore, the device preparation process is much more complicated than that of non-doped devices; at the same time, the phase separation between the host and guest molecules in the doped system is also the main reason for the instability of the device

Method used

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  • Perylene double imide derivatives and preparation method and applications thereof
  • Perylene double imide derivatives and preparation method and applications thereof
  • Perylene double imide derivatives and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation of embodiment 1 compound 4

[0021]

[0022] Add 1.2g (3.26mmol) 4,4'-dibromobenzophenone, 0.68g (3.26mmol) diphenylacetone, 200mg (3.59mmol) potassium hydroxide solid and 20ml absolute ethanol in a 50ml two-necked bottle, After reflux for 30 minutes, 1 (1.5 g, yield 80%) was obtained by suction filtration. 1 HNMR (400MHz, CDCl 3 )δ6.80(d, 4H, 3 J=8.4Hz), 7.1-7.3(m, 10H), 7.35(d, 4H, 3 J=8.4Hz). MS: m / z: 542 ([M+2] + ).

[0023]

[0024] Add 200mg (0.369mmol) 1, 178mg (0.811mmol) N-phenyl-1-naphthylamine, 118mg (1.84mmol) copper powder, 24.4mg (0.09mmol) 18-crown-6, 357mg ( 2.58 mmol) of potassium carbonate and 5 ml of nitrobenzene were reacted for 72 h under nitrogen protection under reflux, the solvent was removed under reduced pressure, and 2 (257 mg, yield 85%) was obtained by column chromatography. MS: m / z:: 819 ([M+H] + ).

[0025]

[0026] 135 mg (0.115 mmol) of intermediate 3 and 565 mg (0.69 mol) of 2 were refluxed in o-xylene; ...

Embodiment 2

[0027] The preparation of embodiment 2 compound 6

[0028]

[0029] 108 mg (0.09 mmol) of 3 and 548 mg (0.73 mmol) of 5 were refluxed in o-xylene for 5 days under nitrogen protection. Then it was cooled to room temperature, the solvent was removed under reduced pressure, and the target compound 6 (300 mg, 81%) was separated by column chromatography. Mp.413°C. 1 HNMR (CD 2 Cl 2 ): 8.17(s, 4H), 7.78(s, 4H), 7.44-7.38(t, 2H), 7.26-7.23(d, 4H), 7.09-7.05(d, 8H), 6.77-6.73(d, 8H ), 2.66-2.55(m, 4H), 1.03-1.00(s, 24H). 19 FNMR (CD 2 Cl 2 ): δ=-136.932~-138.826(m), -148.818~-149.007(d), -149.628(s), -150.527(s), -158.745~-159.332(m).MS(MALDI-TOF): m / z: 4039 ([M+H] + ).Elemental analysis calcd.(%)for C 192 h 58 f 80 N 2 o 8 : C, 57.07, H, 1.45, N, 0.69. Found: C, 57.01, H, 1.38, N, 0.73.

Embodiment 3

[0030] The preparation of embodiment 3 compound 8

[0031]

[0032] Add 45mg (0.038mmol) intermediate 3 and 215mg (0.228mmol) 7 in the 50ml two-necked flask, reflux in o-xylene under nitrogen protection for four days, then cool to room temperature, remove the solvent under reduced pressure, and separate by column chromatography to obtain 8 (120 mg, 65% yield). MS (MALDI-TOF): m / z: 4817 ([M+H] + ).

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Abstract

The invention relates to novel structural derivatives using perylene double imide as cores and applications to organic electroluminescent devices thereof, which belongs to the field of organic electroluminescent material preparation. The perylene double imide derivatives are characterized in that four harboring positions of 1,6,7,12- of perylene double imide derivatives are connected with charge transport functional groups with different structural types as well as different conjugate degree. The derivatives are synthesized by the following method; first 1, 6,7,12-four halogenated perylene double imide is used for synthetizing a perylene double imide with acetylene activity groups, and then Diels-Alder cycloaddition or C-N and C-C couplings react with cyclopentadiene ketone or arylamine with functional substituents so as to prepare target derivatives. The compounds have favorable thermal stability, stable format, solubility and unique electro-optical properties. The materials are usedfor preparing luminescent lights, change transport layer for the preparation of the layer on doping type electroluminescent devices, and the materials are expected to become favorable main red electroluminescent materials.

Description

technical field [0001] The invention relates to a class of perylene bisimide derivatives in the field of organic electroluminescent materials, a preparation method and application thereof. Background technique [0002] The brilliant achievements of microelectronics technology in the 20th century and the rapid development of optoelectronics technology in the 21st century make information technology face an exciting revolution. The development of the Internet and the rise of the information industry are changing the traditional way of life and social outlook of mankind. [0003] Information technology includes the collection, processing, storage, transmission and display of information. Efficient and accurate collection of information data, fast processing, high-density storage, large-capacity transmission and high-definition display constitute the main body of information technology. Among them, the display technology as the output terminal of the information system occupie...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06H01L51/54
Inventor 李久艳刘迪任辉彩陶茜
Owner DALIAN UNIV OF TECH
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