Boron heterocyclic compound, display panel and display device

A display panel and compound technology, applied in the field of OLED, to achieve the effects of high luminous efficiency, long service life and low operating voltage

Active Publication Date: 2022-02-25
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

TADF materials have many advantages over traditional OLED light-emitting materials, but there are few TADF materials that have been discovered so far, so it is urgent to develop new TADF materials that can be used in OLEDs

Method used

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  • Boron heterocyclic compound, display panel and display device
  • Boron heterocyclic compound, display panel and display device
  • Boron heterocyclic compound, display panel and display device

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Experimental program
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Embodiment approach

[0026] According to one embodiment of the boron heterocycle compound of the present invention, the boron heterocycle compound has a structure shown in chemical formula II:

[0027]

[0028] According to one embodiment of the boron heterocycle compound of the present invention, the boron heterocycle compound has a structure shown in chemical formula III:

[0029]

[0030] In the boron heterocyclic compound of the present invention, the two boron heterocyclic rings in the chemical structure form a spatially orthogonal structure, so that there are two donor-acceptor light-emitting units in the same molecule, which can significantly increase the oscillator strength of the light-emitting molecule and improve Luminous efficiency. The two boron heterocycles are connected by SP3 hybridization, which reduces the conjugation length of the entire molecule and effectively increases the triplet energy level of the molecule. The spatially orthogonal structure between the two boron he...

Embodiment 1

[0086] Synthesis of Compound H05

[0087]

[0088] S1 (10 mmol) was dissolved in THF (80 mL), cooled to -78°C. Using a dropping funnel, triethylsodium borohydride (10 mL, 1M THF solution) was added dropwise to the above solution for 2 h. After the dropwise addition was completed, stirring was continued for 2h. Then slowly warm to room temperature and stir overnight. The solvent was removed under high vacuum, washed with high-purity THF, and filtered to obtain a colorless solid S2 (3.6 mmol, yield 72%).

[0089] MALDI-TOF MS: C 24 h 14 B 2 f 2 : m / z calculated value: 362.1; tested value: 362.3.

[0090]

[0091] S3 (25 mmol) was dissolved in 50 mL of anhydrous THF at room temperature under nitrogen atmosphere. NaH (30 mmol) was repeatedly washed with n-hexane, and then added to the above solution. After stirring for 1 h, S2 (10 mmol) was added and stirred overnight at room temperature. The reaction was quenched by adding methanol and water. Extract with dichlor...

Embodiment 2

[0095] Synthesis of Compound H29

[0096]

[0097] S4 (12.0 mmol) was dissolved in 50 mL of anhydrous THF at room temperature under nitrogen atmosphere. NaH (15.0 mmol) was repeatedly washed with n-hexane, and then added to the above solution. After stirring for 1 h, S2 (5.0 mmol) was added and stirred overnight at room temperature. The reaction was quenched by adding methanol and water. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography using chloroform / n-hexane as the eluent, and finally purified again by sublimation to obtain solid H29 (3.8 mmol, yield 76%).

[0098] MALDI-TOF MS: C 102 h 70 B 2 N 6: m / z calculated value: 1400.6; tested value: 1400.7.

[0099] Elemental Analysis Calculated: C, 87.42; H, 5.03; B, 1.54; N, 6.00; Tested: C,...

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Abstract

The invention belongs to the field of OLED technology and provides a boron heterocyclic compound, which has the structure shown in chemical formula I, wherein X 1 and x 2 each independently selected from a single bond, ‑(R 1 )C(R 2 ) 2 ,-NR 2 、BR 3 , O atom, S atom; R 1 , R 2 and R 3 Mainly each independently selected from any one of aryl, heteroaryl, fused aryl, fused heteroaryl; D 1 and D 2 Each independently selected from hydrogen atom C12-C40 carbazolyl and its derivatives, C12-C40 diphenylamino and its derivatives, C13-C40 acridinyl and its derivatives; D 1 and D 2 respectively connected to the benzene ring of the structure shown in chemical formula I, and D 1 and D 2 are not hydrogen atoms at the same time. The boron heterocycle compound provided by the invention contains a donor-acceptor structure, has suitable HOMO and LUMO values ​​and a small ΔEst, and can bring about high brightness, low voltage, high efficiency and longer service life. The invention also provides a display panel and a display device.

Description

technical field [0001] The invention relates to the technical field of OLEDs, in particular to a novel boron heterocyclic compound, a display panel and a display device containing the compound. Background technique [0002] With the development of electronic display technology, organic light emitting devices (OLEDs) are widely used in various display devices. Especially in recent years, the demand for OLED in the smartphone industry has been increasing, and the research and application of OLED light-emitting materials have also increased. [0003] According to the light-emitting mechanism, the materials used for the OLED light-emitting layer mainly include the following four types: [0004] (1) fluorescent material; (2) phosphorescent material; (3) triplet-triplet annihilation (TTA) material 0; (4) thermally activated delayed fluorescence (TADF) material. [0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F7/10C09K11/06H01L51/54
CPCC07F5/02C07F5/027C07F7/0816C09K11/06C09K2211/1096C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1014C09K2211/1044C09K2211/1007C09K2211/1088C09K2211/1011H10K85/631H10K85/636H10K85/626H10K85/657H10K85/6574H10K85/6572
Inventor 高威张磊代文朋肖文静牛晶华冉佺安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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