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Boron heterocyclic compound, display panel and display device

A technology of compound and boron heterocycle, applied in the field of organic electroluminescent materials, to achieve a high level of dipole orientation rate, improve external quantum efficiency, and reduce the effect of aggregation fluorescence quenching

Pending Publication Date: 2020-08-14
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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Synthesis of Compound P001

[0091]

[0092] X02 (4.2 mmol) was weighed and dissolved in THF (30 mL), the resulting solution was cooled to -78°C, kept stirring, and degassed for 20 min. Add nBuLi (4.4mmol, 2.5M n-hexane solution) dropwise to the above solution, and continue stirring for 2h. X01 (2 mmol) was weighed and dissolved in THF (10 mL), and the THF solution of X01 (2 mmol) was added dropwise to the reaction system through a separatory funnel, slowly warmed to room temperature, and stirred overnight. Methanol (1 mL), HCl (2 mL, 1 M) and deionized water (20 mL) were added again to the reaction system dropwise, and the reaction system was continuously stirred. The reaction system was extracted with dichloromethane (3×10mL), the organic phase was separated and collected, the organic phase was washed with saturated sodium chloride solution (30mL), and anhydrous Na 2 SO 4 The organic phase is dried. The solvent was distilled off under reduced pressure to obtain...

Embodiment 2

[0111] Synthesis of Compound P030

[0112]

[0113] X12 (4.3 mmol) was dissolved in 40 mL of anhydrous THF at room temperature under nitrogen atmosphere. NaH (5.8 mmol) was repeatedly washed with n-hexane, and then added to the above solution. After stirring for 1 h, X06 (2.0 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 P030 (1.6 mmol, yield 80%).

[0114] MALDI-TOF MS: C 74 h 48 B 2 N 2 o 2 : m / z calculated value: 1018.4; tested value: 1018.6.

[0115] Compound P030 elemental analysis calculated value: C, 87.24; H, 4.75; N...

Embodiment 3

[0117] Synthesis of compound P062

[0118]

[0119] X13 (2.2 mmol) was dissolved in 50 mL of anhydrous THF at room temperature under nitrogen atmosphere. NaH (2.9 mmol) was washed repeatedly with n-hexane, and then slowly added to the above solution. After stirring for 2 h, X10 (1.0 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 by sublimation again to obtain solid P062 (0.68 mmol, yield 68%).

[0120] MALDI-TOF MS: C 80 h 60 B 2 N 2 : m / z calculated value: 1070.5; tested value: 1070.7.

[0121] Compound P062 elemental analysis calculated value: C, 89.72; H, 5.65...

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Abstract

The invention belongs to the technical field of OLEDs and provides a compound with a structure shown as a formula I. In the formula I, X1 and X2 are independently selected from C atoms or Si atoms respectively; L1 and L2 are each independently selected from the group consisting of a covalent single bond, a substituted or unsubstituted C2-C10 alkenylidene group, a substituted or unsubstituted C2-C10 alkynylidene group, and a substituted or unsubstituted C6-C30 arylene group; R1 and R5 are respectively and independently selected from substituted or unsubstituted aryl or heteroaryl; n1 and n5 areeach independently an integer from 0 to 5; R2-R4 and R6-R8 are respectively and independently selected from a hydrogen atom, a deuterium atom, C1-C20 alkyl, C1-C20 alkoxy, and phenyl; n2, n3, n4, n6,n7 and n8 are respectively and independently integers from 0 to 4; ring A and ring B each independently represent a C4-C6 hydrocarbon ring, a C6-C20 aromatic ring, or a C4-C20 aromatic heterocyclic ring fused to the ring where X1 and X2 are located. The invention further provides a display panel and a display device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a boron heterocyclic compound that can be used as a TADF material, a display panel and a display device including 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 materials; (2) phosphorescent materials; (3) triplet-triplet annihilation (TTA) materials; (4) thermally activated delayed fluorescence (TADF) materials. [0005] For fluorescent materials, according to spin sta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/54H01L51/50
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1029C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096C09K2211/1011C09K2211/1014C09K2211/1033C09K2211/1055H10K85/626H10K85/615H10K85/322H10K85/6576H10K85/6574H10K85/657H10K85/40H10K85/6572H10K50/11
Inventor 高威冉佺牛晶华张磊代文朋肖文静
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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