Bora or phosphorus heterocyclic fused ring compound containing binaphthalene ring, preparation method thereof and luminescent device

A technology of binaphthalene ring and compound is applied in the field of organic light-emitting materials, which can solve the problems of reduced external quantum efficiency of devices and complex device structure, and achieves the effects of mild conditions, high device efficiency, and high luminous efficiency.

Pending Publication Date: 2022-03-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
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Problems solved by technology

However, this D-A structure exhibits a large Stokes shift due to the obvious vibration relaxation of the excited state, and the luminescence spectrum is wide, and the half-maximum width (FWHM) is generally 70-100nm. In practical applications, filtering is usually required. sheet or construct an optical microcavity to improve the color purity, but this will lead to a decrease in the external quantum efficiency of the device or a complicated device structure

Method used

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  • Bora or phosphorus heterocyclic fused ring compound containing binaphthalene ring, preparation method thereof and luminescent device
  • Bora or phosphorus heterocyclic fused ring compound containing binaphthalene ring, preparation method thereof and luminescent device
  • Bora or phosphorus heterocyclic fused ring compound containing binaphthalene ring, preparation method thereof and luminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065]

[0066] Under argon atmosphere, 1-1 (20.0g, 52.6mmol), 1-2 (20.0g, 63.1mmol), tetrakis(triphenylphosphine) palladium (4.9g, 4.2mmol), Potassium carbonate (29.1g, 210.5mmol), 40mL water, 50mg Aliquant-336 and 200mL toluene, stirred at 120°C for 8 hours, cooled to room temperature, added 150mL ethyl acetate, and washed the organic phase 3 times with deionized water (100mL×3) , and then dried with anhydrous magnesium sulfate, and the concentrated solution obtained after removing the solvent from the organic phase was separated by silica gel column chromatography to obtain the product 1-3 (18.2 g, yield: 78%).

[0067] Elemental analysis of its structure (C 22 h 21 BBrClO 2 ): Theoretical value: C, 59.57; H, 4.77; Tested value: C, 59.63; H, 4.72.

[0068] MALDI-TOF-MS: theoretical 442.1; experimental 442.1.

[0069] Under argon atmosphere, 1-3 (15.0g, 33.8mmol), 1-4 (14.9g, 40.6mmol), tetrakis(triphenylphosphine) palladium (3.1g, 2.7mmol), Potassium carbonate (18.7...

Embodiment 2

[0079]

[0080] Under argon atmosphere, 2-1 (20.0g, 35.9mmol), 2-2 (16.5g, 79.0mmol), tris(dibenzylideneacetone) dipalladium (1.3g, 1.4mmol) were added to a 500mL three-necked flask ), tri-tert-butylphosphine tetrafluoroborate (20.8g, 71.8mmol), sodium tert-butoxide (6.9g, 71.8mmol) and 250mL of toluene, stirred at 120°C for 8 hours and cooled to room temperature, added 150mL of ethyl acetate Ester, the organic phase was washed 3 times with deionized water (100mL × 3), and then dried with anhydrous magnesium sulfate, and the concentrated solution obtained after removing the solvent from the organic phase was separated by silica gel column chromatography to obtain product 2-3 (18.2g, yield: 74%).

[0081] Elemental analysis of its structure (C 40 h 24 BrCl 2 NO): Theoretical: C, 70.09; H, 3.53; N, 2.04; Tested C, 70.12; H, 3.58; N, 2.01.

[0082] MALDI-TOF-MS: theoretical value 683.0; experimental value 683.0.

[0083] Under argon atmosphere, 2-3 (15.0g, 21.9mmol), 2-4 ...

Embodiment 3

[0090]

[0091] Under argon atmosphere, 3-1 (20.0g, 50.7mmol), 3-2 (19.3g, 60.9mmol), tetrakis(triphenylphosphine) palladium (4.7g, 4.1mmol), Potassium carbonate (28.1g, 203.0mmol), 40mL water, 50mg Aliquant-336 and 200mL toluene, stirred at 120°C for 8 hours, cooled to room temperature, added 150mL ethyl acetate, and the organic phase was washed 3 times with deionized water (100mL×3) , and then dried with anhydrous magnesium sulfate, and the concentrated solution obtained after removing the solvent from the organic phase was separated by silica gel column chromatography to obtain the product 3-3 (19.3 g, yield: 83%).

[0092] Elemental analysis of its structure (C 23 h 23 BBrClO 2 ): Theoretical value: C, 60.37; H, 5.07; Test value: C, 60.43; H, 5.02.

[0093] MALDI-TOF-MS: theoretical 456.1; experimental 456.1.

[0094] Under argon atmosphere, 3-3 (15.0g, 32.8mmol), 3-4 (14.5g, 39.3mmol), tetrakis(triphenylphosphine) palladium (3.0g, 2.6mmol), Potassium carbonate (18...

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Abstract

The invention relates to a boron-impurity or phosphorus-impurity fused ring compound containing a binaphthalene ring, a preparation method of the boron-impurity or phosphorus-impurity fused ring compound and a light-emitting device, and belongs to the technical field of organic light-emitting materials. The fused ring compound provided by the invention has a structure as shown in any one of formulas (I)-(II). According to the boron-impurity or phosphorus-impurity fused ring compound containing the binaphthalene ring provided by the invention, on one hand, the relaxation degree of an excited state structure can be reduced by utilizing a rigid framework structure of the binaphthalene ring, so that relatively narrow half-peak width is realized; on the other hand, separation of HOMO and LUMO is achieved through the resonance effect between boron atoms or phosphorus atoms and heteroatoms, and therefore small delta EST and TADF effects are achieved, and high luminous efficiency is achieved. Meanwhile, by changing the types of aromatic rings or heteroaromatic rings contained in the fused ring compound, the delayed fluorescence lifetime and the half-peak width can be further adjusted.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a bora or phosphorous heterocondensed ring compound containing a binaphthyl ring, a preparation method thereof, and a light-emitting device. Background technique [0002] Organic light-emitting devices (OLEDs) have the characteristics of rich colors, thin thickness, wide viewing angle, fast response, and flexible devices, and are considered to be the most promising next-generation flat panel display and solid-state lighting technologies. OLEDs are usually composed of ITO anode, hole injection layer (TIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) Composed of cathode and cathode, 1~2 organic layers can be omitted as needed, and the holes (Hole) injected from the positive and negative electrodes on the organic film combine with electrons (Elect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C07F9/6578C07F9/6584C09K11/06H01L51/50H01L51/54
CPCC07F5/02C07F9/6584C07F7/0816C07F9/6578C09K11/06C09K2211/104C09K2211/1055C09K2211/107C09K2211/1085C09K2211/1096C09K2211/1014C09K2211/1059H10K85/631H10K85/636H10K85/654H10K85/657H10K85/40H10K50/11
Inventor 王利祥邵世洋常宇飞吕剑虹李伟利王兴东赵磊王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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