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Thermally activated delayed fluorescent material constructed based on nitrogen-containing heteroaromatic ring derivative and carbonyl and application of thermally activated delayed fluorescent material

A technology of thermally activated delay and fluorescent materials, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low oscillator strength, low luminous quantum efficiency, large half-peak width, etc., and achieve easy adjustment and high luminous efficiency , the effect of small half-peak width

Active Publication Date: 2022-01-28
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This also leads to a smaller oscillator strength of the molecule, a relatively low luminous quantum efficiency of the molecule, and a larger half-peak width

Method used

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  • Thermally activated delayed fluorescent material constructed based on nitrogen-containing heteroaromatic ring derivative and carbonyl and application of thermally activated delayed fluorescent material
  • Thermally activated delayed fluorescent material constructed based on nitrogen-containing heteroaromatic ring derivative and carbonyl and application of thermally activated delayed fluorescent material
  • Thermally activated delayed fluorescent material constructed based on nitrogen-containing heteroaromatic ring derivative and carbonyl and application of thermally activated delayed fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In formula (1) provided by the present invention, when R 1 is tert-butyl, R 2 and R 3 for H, for When, be following formula compound 2, its synthetic route is as follows:

[0023]

[0024] Synthesis of compound 1:

[0025] Tert-butylcarbazole (13.43g, 48mmol), tert-butyl iodobenzene (15.00g, 58mmol), cuprous iodide (0.91g, 4.8mmol), o-phenanthroline (1.73g, 9.6mmol), carbonic acid Potassium (19.87g, 14.4mmol) and 18-crown-6 (1.90g, 7.2mmol) were added to dioxane (60ml), and reacted overnight at 110°C under nitrogen protection. Cool, spin dry, extract with dichloromethane / water, dry the organic phase with anhydrous sodium sulfate, concentrate and then silica gel column chromatography (petroleum ether:dichloromethane=5:1) to obtain 17.91g of white solid, yield 90.68% . 1 H NMR (500MHz, CDCl 3 )δ8.14(d, J=1.7Hz, 2H), 7.57(d, J=8.5Hz, 2H), 7.48–7.42(m, 4H), 7.35(d, J=8.6Hz, 2H), 1.46( s,18H),1.41(s,9H). 13 C NMR (101MHz, CDCl 3 )δ149.91, 142.61, 139.39, 135....

Embodiment 2

[0029] In formula (1) provided by the present invention, when R 1 , R 2 and R 3 for H, respectively When, be following formula compound 5,8,11, its synthetic route is as follows:

[0030]

[0031] Synthesis of compound 3:

[0032] Acridine (4.18g, 20mmol), methyl 2-iodobenzoate (5.76g, 22mmol), cuprous iodide (381mg, 2mmol), copper (1.3mg, 20mmol) and potassium carbonate (3.03g, 22mmol) Add it into dichlorobenzene (30 mL), and react at 190° C. for 24 h under the protection of nitrogen. Cool, filter, wash the solid with dichloromethane, concentrate the filtrate, and perform silica gel column chromatography (petroleum ether:dichloromethane=2:1) ​​to obtain 5.89 g of a light green solid with a yield of 85.8%. 1 H NMR (400MHz, CDCl 3 )δ8.20–8.14(m,1H),7.76(td,J=7.7,1.5Hz,1H),7.63–7.56(m,1H),7.45(dd,J=7.5,1.5Hz,2H),7.34 (d,J=7.8Hz,1H),6.97–6.85(m,4H),6.05(d,J=9.1Hz,2H),3.54(s,3H),1.71(d,J=22.8Hz,6H) . 13C NMR (126MHz, CDCl 3 )δ165.95, 140.70, 140.43, 134.58, 133.4...

Embodiment 3

[0052] Compounds 2, 5, 8, and 11 were dissolved in toluene to form 10 -5 M solution, test the UV-Vis absorption spectrum of its solution. Depend on figure 1 It can be seen that there are roughly two absorption peaks in the UV-Vis absorption spectra of these three types of compounds in solution: the absorption peak at the short wavelength (325nm) is mainly attributed to the π-π* transition absorption of the molecule; the long wavelength (400-410nm) The absorption peak of is attributed to the intramolecular charge transfer (ICT) transition from the donor unit to the acceptor unit.

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Abstract

The invention belongs to the field of organic light-emitting materials, and particularly discloses a thermally activated delayed fluorescent material constructed based on a nitrogen-containing heteroaromatic ring derivative and carbonyl and application of the thermally activated delayed fluorescent material. The material has the remarkable characteristics that: (1) a push-pull electron effect exists between nitrogen atoms and carbonyl, so that the material can be directly used for constructing a multi-resonance thermally activated delayed fluorescent material; and (2) the half-peak width and the luminescence peak value of the molecule can be regulated and controlled through the intensity of the electron donating group, so that blue-green-red light emission regions are covered; and (3) the material can also be used as an acceptor parent nucleus, and a donor unit (one of carbazolyl, substituted carbazolyl, phenothiazinyl, substituted phenothiazinyl, phenazinyl, substituted phenazinyl, acridine and substituted acridinyl) is hung in the periphery to construct a TICT-TADF material.

Description

technical field [0001] The invention belongs to the field of organic luminescent materials, and mainly relates to a class of nitrogen-containing heteroaromatic ring derivatives and carbonyl-structured heat-activated delayed fluorescent materials, which have the characteristics of narrow half-width emission and adjustable emission wavelength with the intensity of electron-donating groups , and use it as a guest in organic electroluminescent devices to obtain high-performance organic electroluminescent diodes. Background technique [0002] Thermally activated delayed fluorescent materials can theoretically achieve 100% internal quantum efficiency, breaking the theoretical limit of 5% external quantum efficiency of traditional fluorescent devices, and can be comparable to noble metal phosphorescent complex devices. Then the third generation of organic electroluminescent diode materials. However, traditional thermally activated delayed fluorescence (TADF) molecules reduce the o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D498/06C07D513/06C09K11/06H01L51/50H01L51/54
CPCC07D471/06C07D498/06C07D513/06C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037H10K85/6572H10K85/657H10K50/12
Inventor 朱卫国黄经纬吴秀刚王赛孙静
Owner CHANGZHOU UNIV
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