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Boron heterocyclic compound and organic light emitting display device

A light-emitting display and compound technology, applied in the field of organic electroluminescent materials, can solve the problems of short life, high cost of phosphorescent devices, poor stability, etc., and achieve the effects of increasing energy levels, weakening charge transfer, and shortening the conjugate length

Active Publication Date: 2019-01-04
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, phosphorescent devices have also been criticized for their high cost (almost several times that of fluorescent materials) and poor stability (short lifespan) due to the presence of heavy metals.

Method used

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  • Boron heterocyclic compound and organic light emitting display device
  • Boron heterocyclic compound and organic light emitting display device
  • Boron heterocyclic compound and organic light emitting display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088]

[0089] Add 10g (20.50mmol) of the compound 1,4-dibromo-2,5-diiodopyridine, 9.06g (45.11mmol) of dibromophenylboronic acid, and 5.67g (41mmol) of potassium carbonate into a three-necked flask in turn, and add 100mL of toluene solution, stir well. Nitrogen was replaced three times, and 0.1 g of palladium acetate was added under nitrogen atmosphere, and nitrogen was replaced three times after the addition. Afterwards, it was stirred for 12 h under nitrogen atmosphere. Cool to room temperature at the end of the reaction, and use 200mL saturated NaHSO 3 The reaction was quenched, and the organic phase was extracted with dichloromethane (150 mL), and the organic phase was then washed with saturated NaHSO 3 Extract twice, and finally extract once with saturated saline. The collected organic phase was added with anhydrous magnesium sulfate, stirred, filtered, and the collected filtrate was rotary evaporated to remove the solvent. The product was purified by column chro...

Embodiment 2

[0105]

[0106] Add 3.1 g (9.57 mmol) of 4-bromophenyldiphenylamine into the reaction flask, add diethyl ether (50 mL) to dissolve, and replace with nitrogen three times. Cool down to -78°C, and when the temperature reaches, control the temperature below -65°C and slowly add n-BuLi 4.21mL (2.5M, 10.52mmol) dropwise, and stir for 30min after the dropwise addition is complete. Then 3.9 g (9.57 mmol) of monomer 103 was dissolved in 60 mL of toluene, and then slowly added dropwise to the reaction liquid, and after the completion of the dropwise addition, it was naturally raised to room temperature for 6 h. After the reaction was completed, ice water (100 mL) was added to quench the reaction. Then add DCM (80mL×2) for extraction, and finally extract once with saturated brine. The collected organic phase was rotary evaporated to obtain a yellow oil. The product was purified by column chromatography (mobile phase n-hexane:dichloromethane=10:1) to obtain 2.46 g (4.30 mmol) of lig...

Embodiment 3

[0114] The chemical structure of the boron heterocyclic compound prepared in embodiment 1 and embodiment 2 is simulated by Gaussian software, and the 3D solid model obtained by simulation is shown in figure 1 . Depend on figure 1 It can be seen that both the donor and acceptor groups are almost perpendicular to the boracarbazole, and the dihedral angles are 88.15 and 62.17, respectively. The highly twisted structure is beneficial to reduce the △E ST , improve the ability to cross the reverse gap.

[0115] Similarly, the boron heterocyclic compounds M1 to M4, M1', M2' were simulated using Gaussian software, where M1' and M2' are compounds obtained by replacing the pyrazine rings in M1 and M2 molecules with benzene rings. The simulation results are shown in Table 1.

[0116] Table 1

[0117]

[0118] It can be seen from Table 1 that the HOMO of the molecules of compounds M1-M4 is about 5.1ev-5.5ev, the energy range between the singlet state and the triplet state is about ...

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Abstract

The invention provides a boron heterocyclic compound. The compound has a structure shown in a formula (I) in the description, wherein X1 or X2 is a nitrogen atom or a carbon atom, and at least one ofX1 or X2 is a nitrogen atom; L1 or L2 represents a single bond and is any one selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted acenaphthenyl, and substituted or unsubstituted aromatic heterocycle; D1 and D2 are independently selected from substitutedor unsubstituted C6-C60 aryl, substituted or unsubstituted C10-C60 fused aryl, substituted or unsubstituted C4-C60 five-membered heterocycle, substituted or unsubstituted C5-C60 six-membered heterocycle and substituted or unsubstituted diphenylamino or triphenylamino. Connection with a receptor unit is realized by a bora carbazole SP3 hybridized connecting group, the conjugate length can be shortened, energy level can be improved, and molecular thermal stability can be improved. Meanwhile, charge transfer in molecules is weakened by short-axis conjugation, and the luminescence spectrum is narrowed to a certain extent.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to a novel boron heterocyclic compound and an organic light-emitting display device containing the compound. Background technique [0002] Organic electroluminescent devices (OLEDs) can be divided into fluorescent devices and phosphorescent devices according to the type of light-emitting excitons. [0003] Compared with traditional fluorescent devices that can only emit light using singlet exciton energy (25%), phosphorescent devices have a broader application prospect because they can theoretically achieve 100% internal quantum efficiency. However, phosphorescent devices are also criticized for their high cost (almost several times that of fluorescent materials) and poor stability (short life) due to the heavy metals they contain. [0004] In the past two years, a new kind of luminescent material - Thermally Activated Delayed Fluorescence (TADF) material, using...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F5/027C09K2211/1029C09K2211/1007C09K2211/1014C09K2211/1011C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1096H10K85/624H10K85/626H10K85/615H10K85/6572H10K85/657H10K50/11Y02T90/167Y04S30/12
Inventor 潘龙鑫
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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