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Thermally activated delayed fluorescence luminescent material containing nitrogen hetero helicene parent nucleus and applications of thermally activated delayed fluorescence luminescent material in electroluminescent devices

An electroluminescent device, a technology of thermal activation delay, applied in the direction of luminescent materials, electric solid devices, electrical components, etc., to achieve the effects of flexible derivation methods, simple synthesis, and high color purity

Active Publication Date: 2020-02-28
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on thermally activated delayed fluorescent materials with chirality

Method used

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  • Thermally activated delayed fluorescence luminescent material containing nitrogen hetero helicene parent nucleus and applications of thermally activated delayed fluorescence luminescent material in electroluminescent devices
  • Thermally activated delayed fluorescence luminescent material containing nitrogen hetero helicene parent nucleus and applications of thermally activated delayed fluorescence luminescent material in electroluminescent devices
  • Thermally activated delayed fluorescence luminescent material containing nitrogen hetero helicene parent nucleus and applications of thermally activated delayed fluorescence luminescent material in electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Among the w-1 compounds shown in the present invention, when R 1 =R 2 =R 3 When =H, it is compound 3 of the following formula; in w-2 compound, when R 1 =R 2 =R 3 When =H, it is compound 4 of the following formula. The preparation of compound 3 and 4 can be synthesized according to following reaction, and its synthetic route is as follows:

[0044]

[0045] Preparation of compound 1

[0046] Phenothiazine (1.75 g, 8.78 mmol), methyl 2-iodobenzoate (2.3 g, 8.78 mmol), cuprous iodide (167 mg, 0.88 mmol) and potassium carbonate (1.21 g, 8.78 mmol) were added to di In chlorobenzene (30mL), react at 190°C for 24h 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 2.44g of white solid , yield 83.2%.

[0047] MS(EI):m / z 333.1[M + ]. Elemental analysis, theory:: C, 72.05; H, 4.54; N, 4.20; O, 9.60; S, 9.62; actua...

Embodiment 2

[0057] In w-6, when R 1 =R 2 =H, , it is compound 9 of the following formula; when R 1 =R 2 =H, , it is compound 10 of the following formula.

[0058] The preparation method of compound 9, 10 can be prepared according to the following reaction formula and its synthetic route is as follows:

[0059]

[0060] Compounds 5-8 were operated as in Example 1.

[0061] Preparation of compound 9

[0062] Add compound 8 (0.41g, 1mmol), 10H-phenothiazine (0.2g, 1mmol), tris(dibenzylideneacetone) dipalladium (92mg, 0.1mmol), potassium carbonate (0.28 g, 2mol) and tri-tert-butylphosphine (10% toluene solution, 1.4mL), under nitrogen protection, heated to reflux and stirred for 24h. Cool to room temperature, filter, wash the filter residue with dichloromethane, collect the filtrate, distill off the solvent under reduced pressure, and the residue is an eluent with a mixed solvent of petroleum ether (PE) and dichloromethane (DCM) (PE:DCM=5: 1, V:V), separated by column chromatogr...

Embodiment 3

[0066] In the shown w-3 core compound provided by the present invention, when R 1 =R 2 =R 3 When =H, it is compound 13 in the following formula. In the shown w-4 core compound provided by the present invention, when R 1 =R 2 =R 3 When =H, it is compound 14 in the following formula. Compounds 13 and 14 can be prepared according to the following reaction formula. :

[0067]

[0068] Preparation of Compound 11

[0069] Phenothiazine (13.15g, 0.066mol), diethyl 2,5-dibromoterephthalate (11.4g, 0.03mol), cuprous iodide (570 mg, 3mmol) and potassium carbonate (9.11g, 0.0668mol) was added to dichlorobenzene (150mL), reacted at 190°C under nitrogen protection for 24h, cooled, filtered, washed the solid with dichloromethane, and the filtrate was concentrated and then chromatographed on a silica gel column (petroleum ether: dichloromethane = 2:1 ) to obtain brown solid 11.34g, yield 61.3%.

[0070] MS(EI):m / z 616.1[M + ]. Elemental Analysis, Theory: C, 70.11; H, 4.58; N, ...

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Abstract

The invention provides a thermally activated delayed fluorescence luminescent material constructed based on a nitrogen-containing hetero-helicene mother nucleus and applications of the thermally activated delayed fluorescence luminescent material in electroluminescent devices. The invention has the obvious characteristics that: 1) sulfonyl and carbonyl are very good acceptor units in TADF materials, but no sulfonyl and carbonyl double acceptor units exist in one TADF molecule at the same time; the helicene containing heteroatoms has a relatively large helical curvature; 2) directly construction of an MR-TADF material by utilizing the nitrogen hetero helicene parent nucleus is realized; 3) a TICT-TADF material is constructed by taking the nitrogen hetero helicene parent nucleus as a receptor unit, and hanging a donor unit at the periphery; and 4) the novel TADF (including MR-TADF and TICT-TADF) material can cover emission regions such as blue light, green light, red light-near infraredlight and even single-molecule white light. The nitrogen-containing hetero-helicene parent nucleus has the advantages of novel receptor, different TADF construction modes, wide color gamut and the like.

Description

technical field [0001] The present invention relates to multiple resonance-induced thermally activated delayed fluorescence (MR-TADF) materials and molecular twist-charge transfer induced thermally activated delayed fluorescence (TICT-TADF) materials constructed by novel nitrogen-containing helichelicene cores, and their The application in electroluminescence devices belongs to the field of organic light-emitting materials. Background technique [0002] Thermally activated delayed fluorescence (TADF) materials are considered to be the third generation of organic light-emitting materials after fluorescent materials and phosphorescent materials due to their theoretical internal quantum efficiency of 100%, which can be compared with noble metal complex phosphorescent materials. [1] . TADF materials can also form exciplexes with TADF properties through intermolecular interactions [2-3] . [0003] The relatively large helical curvature of nitrogen-containing helicenes lays the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/06C07D513/22C09K11/06H01L51/50H01L51/54
CPCC07D513/06C07D513/22C09K11/06C09K2211/1037C09K2211/1051H10K85/657H10K50/11Y02B20/00
Inventor 朱卫国吴秀刚刘邓辉王亚飞刘煜朱梦冰
Owner CHANGZHOU UNIV
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