Boron-containing compound, preparation method thereof and application of boron-containing compound

A technology of boron compounds and compounds, applied in the field of boron-containing organic light-emitting materials and their preparation, can solve problems such as restricting the application of TADF materials, affecting the color purity of materials, and increasing molecular charge transfer, so as to achieve short-wavelength light emission and good color purity , weaken the effect of luminous red shift

Active Publication Date: 2019-03-12
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the molecular design idea widely used in TADF materials is to connect the donor unit (D) and the acceptor unit (A), let the HOMO be distributed on the D segment, and the LUMO be distributed on the A segment, and then let the molecule realize the TADF characteristics, but Such a design increases the charge transfer within the molecule, and the emission spectrum of TADF molecules will be wider than that of traditional fluorescent materials, which will affect the color purity of the luminescence of the material and restrict the further application of TADF materials.

Method used

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  • Boron-containing compound, preparation method thereof and application of boron-containing compound
  • Boron-containing compound, preparation method thereof and application of boron-containing compound
  • Boron-containing compound, preparation method thereof and application of boron-containing compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] This embodiment provides a boron-containing compound, which has the structure shown in the following formula C-1:

[0049]

[0050] The synthetic route of the boron-containing compound shown in formula C-1 is as follows:

[0051]

[0052] The preparation method of the boron-containing compound shown in formula C-1 specifically comprises the following steps:

[0053] Under the protection of nitrogen, add 4.6g (20mmol) of compound M-2, 500mL of diethyl ether, dropwise add 18.75mL of n-butyl lithium (1.6M, 30mmol) at -78°C, react at low temperature for 30min, and slowly warm up to room temperature for 0.5 h, cooled to -78°C again and added 300mL of compound M-1 (3.3g, 10mmol) in toluene solution dropwise, slowly rose to room temperature and reacted for 10h, added aqueous ammonium chloride to quench the reaction, extracted with dichloromethane, and spun The solvent was evaporated and passed through a silica gel column to obtain 3.6 g of solid compound C-1 (yield 76%)...

Embodiment 2

[0056] This embodiment provides a boron-containing compound, which has the structure shown in the following formula C-3:

[0057]

[0058] The synthetic route of the boron-containing compound shown in formula C-3 is as follows:

[0059]

[0060] The preparation method of the boron-containing compound shown in formula C-3 specifically comprises the following steps:

[0061] Under the protection of nitrogen, add 2.3g (10mmol) of compound M-2, 500mL of diethyl ether, dropwise add 6.25mL of n-butyllithium (1.6M, 10mmol) at -78°C, react at low temperature for 30min, and slowly warm up to room temperature for 0.5 , cooled to -78°C again and added 300mL of compound M-1 (3.3g, 10mmol) toluene solution dropwise, slowly rose to room temperature and reacted for 10h, added ammonium chloride aqueous solution to quench the reaction, extracted with dichloromethane, and rotary evaporated Remove the solvent and dry to obtain the crude product of compound M-3;

[0062] Under the protect...

Embodiment 3

[0065] This embodiment provides a boron-containing compound, which has the structure shown in the following formula C-2:

[0066]

[0067] The difference between the preparation steps of the boron-containing compound shown in formula C-2 and the preparation step of the boron-containing compound shown in C-1 provided in Example 1 is only:

[0068] Compound M-2 in Example 1 was replaced by a compound represented by the following formula A-1. Yield 69%,

[0069]

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Abstract

The invention discloses a boron-containing compound with a structure as shown in a formula (I). Boron atoms have empty P orbits, can interact with pi electron cloud of peripheral aryl and further display good luminescent properties. The boron-containing compound has the luminescent properties of TADF (thermally activated delayed fluorescence), the TADF properties of molecules are regulated by molecular structure optimization, so that the molecules acquire small delta EST (expressed sequence tags), efficient anti-intersystem crossing of exciters from T1 to S1 can be realized, and internal quantum efficiency approximate to 100% is realized. Besides, by the aid of molecular design of weak D-A structures, intramolecular charge transfer of D-A structure molecules is effectively inhibited, and narrow luminescent spectra are acquired while efficient luminescence is realized. The invention further discloses an organic light-emitting device, and at least one functional layer contains the boron-containing compound.

Description

technical field [0001] The invention relates to the field of display technology, and specifically relates to a boron-containing organic luminescent material and its preparation method and application. Background technique [0002] Organic electroluminescent (OEL) devices (hereinafter referred to as "OEL" devices) have a series of advantages such as self-luminescence, high contrast, wide color gamut, wide viewing angle, and fast response. In 1963, Pope et al. first discovered the phenomenon of electroluminescence of organic compounds [JChemPhys,38:2042]. In 1987, C.T.Tang et al. first invented the OEL device, and realized low-voltage, high-brightness luminescence [ApplPhysLett,1987,51: 913]. [0003] Current OEL devices generally include opposite cathodes and anodes and one or more organic layers sandwiched between the two electrodes. Electrons and holes are respectively injected into the organic layer from the cathode and the anode, and finally recombine in the organic lig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC09K11/06C07F5/02C09K2211/1096C09K2211/1011C09K2211/1007H10K85/649
Inventor 孙华朱文明陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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