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Red light emitting material based on aza-beta diketone boron difluoride central core, preparation method and application thereof, and organic electroluminescent device

A boron difluoride and diketone technology, which is applied in the field of organic electroluminescence devices, can solve the problems of low fluorescence quantum yield of red light materials, difficulty in realizing deep red light emission, restricting the application of red light materials, etc., so as to improve the luminescence Efficiency, realizing commercial application, and the effect of simple operation steps

Pending Publication Date: 2022-07-08
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the small energy gap difference of red light materials, the ground state and excited state vibrations are easy to overlap, and non-radiative transitions are prone to occur during molecular deexcitation, resulting in low fluorescence quantum yield of red light materials.
Secondly, the molecules of red light materials generally have a long conjugated structure. In the thin film state, the distance between molecules is reduced, and the strong π-π interaction is not conducive to the light emission of the material, which reduces the luminous efficiency of the device and limits the red light. Application of Optical Materials in OLED Devices
Therefore, there are few types of red light materials with high luminous efficiency, and it is difficult to achieve deep red light emission in the light emitting region with an orange-red light emission color.

Method used

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  • Red light emitting material based on aza-beta diketone boron difluoride central core, preparation method and application thereof, and organic electroluminescent device
  • Red light emitting material based on aza-beta diketone boron difluoride central core, preparation method and application thereof, and organic electroluminescent device
  • Red light emitting material based on aza-beta diketone boron difluoride central core, preparation method and application thereof, and organic electroluminescent device

Examples

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preparation example Construction

[0043] The present invention provides the preparation method of the red light material described in the above scheme, comprising the following steps:

[0044] (1) Put R 1 H, amide solvent, 4-fluorobenzamide and potassium tert-butoxide are mixed, carry out the first nucleophilic substitution reaction, obtain the compound of the structure shown in formula C;

[0045] (2) mixing the compound of the structure shown in the formula C, methyl p-halogenated benzoate, a polar solvent and sodium cyanide, and carrying out the second nucleophilic substitution reaction to obtain the compound of the structure shown in the formula D;

[0046] (3) the compound of the structure shown in the formula D, boron trifluoride ether, piperidine and the chlorinated alkane solvent are mixed, carry out Knoevenagel condensation reaction, obtain the compound of the structure shown in the formula E;

[0047] (4) The compound of the structure represented by the formula E, R 2 H, tris(dibenzylideneacetone)d...

Embodiment 1

[0089] This embodiment provides a red light material based on the central core of aza-β-diketone boron difluoride, which has the structure shown in the following formula I-1:

[0090]

[0091] (1). The synthetic method of compound triphenylamine benzamide (C):

[0092]

[0093] Diphenylamine (16.7 g, 100 mmol) was dissolved in N,N-dimethylformamide (100 mL), to which were added 4-fluorobenzamide (13.9 g, 100 mmol) and potassium tert-butoxide (5.6 g, 50 mmol) ), vacuumed and passed nitrogen for three times, heated to 110°C, and stirred for 24 hours. Cool to room temperature, add the reactant to 400 mL of water, a white solid will be precipitated, use CH 2 Cl 2 Extraction was followed by washing with saturated NaCl solution, drying over anhydrous magnesium sulfate, and filtration to obtain the organic phase. The organic solvent was evaporated under reduced pressure, and the obtained crude product was purified by column chromatography (petroleum ether:ethyl acetate=12:1 ...

Embodiment 2

[0104] This embodiment provides a red light material based on the central core of aza-β-diketone boron difluoride, which has the structure shown in the following formula I-2:

[0105]

[0106] The only difference from Example 1 is that diphenylamine in step (1) and step (4) is replaced with carbazole to obtain azafluoroboron dipyrrole red light compound I-2 (18.75g, 31.08mmol, 60% yield). Structural Characterization Data: 1 HNMR (600MHz, CDCl 3 )δ8.43-8.40(m, 4H), 8.20(dd, J=8.4, 1.2Hz, 2H), 8.16-8.14(m, 2H), 7.86-7.82(m, 4H), 7.73(t, J= 7.4Hz, 2H), 7.61-7.58(m, 2H), 7.54(d, J=8.2Hz, 2H), 7.47-7.44(m, 2H), 7.37-7.33(m, 2H), 7.27(s, 2H) ); the molecular ion mass determined by mass spectrometry was: 603.20 (calculated value: 603.19).

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Abstract

The invention provides a red light emitting material based on an aza-beta diketone boron difluoride central core, a preparation method and application thereof, and an organic electroluminescent device, and belongs to the technical field of electroluminescent materials. The red light emitting material based on the aza-beta-diketone boron difluoride central core provided by the invention has high electroluminescent efficiency, and can realize dark red light emitting. In addition, according to the preparation method of the red light material provided by the invention, the initial raw materials are easy to obtain, the reaction conditions are mild, the operation steps are simple, the preparation cost is reduced, the compound has good solubility, 100 mg of compound can be dissolved in per 1 mL of solvent, and the preparation method of the red light material is beneficial to wet-process large-area device preparation and commercial application realization.

Description

technical field [0001] The invention relates to the technical field of electroluminescent materials, in particular to a red light material based on the central nucleus of aza-betadiketone boron difluoride, a preparation method and application thereof, and an organic electroluminescent device. Background technique [0002] Organic light-emitting diode (OLED) is an emerging flat panel display. Compared with traditional displays, it has the advantages of fast response, low energy consumption, self-luminescence, wide color gamut, ultrathin, With the advantages of flexibility and the ability to make large-size panels, it is the most ideal and promising new type of display in the future. [0003] OLED is a carrier dual-injection light-emitting device. The light-emitting mechanism is: driven by an external electric field, electrons and holes are injected into the organic light-emitting layer from the cathode and the anode, respectively, and recombine in the organic light-emitting l...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/022C09K11/06C09K2211/1029C09K2211/1037C09K2211/104H10K85/656H10K85/631H10K85/657H10K85/6572H10K50/11Y02B20/00
Inventor 曹辰辉税新凤庞玉东
Owner 安徽秀朗新材料科技有限公司
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