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Illuminating tetra-ligand trapezoid organic boron compound, and preparation method and application thereof

A compound and four-coordination technology, applied in the field of luminescent four-coordinate trapezoidal organoboron compound and its preparation, can solve the problems of unreported applications and few boron compounds, and achieve high carrier mobility and strong blue light emission , the effect of high thermal stability

Active Publication Date: 2017-03-22
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few boron compounds with ladder structure, and their application in electroluminescent devices has not been reported yet.

Method used

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  • Illuminating tetra-ligand trapezoid organic boron compound, and preparation method and application thereof
  • Illuminating tetra-ligand trapezoid organic boron compound, and preparation method and application thereof
  • Illuminating tetra-ligand trapezoid organic boron compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] When the structure of R is When, the preparation of compound 6a:

[0044] The synthetic route is as follows:

[0045]

[0046] Preparation of Alkynyl Compound 2:

[0047]

[0048] Take a dry reaction flask, add 1,4-dibromo-2,5-diiodobenzene (0.487g, 1mmol), trimethylethynyl silicon (0.589g, 6mmol), cuprous iodide (6mg, 0.03 mmol), tetrakistriphenylphosphopalladium (10mg, 0.1mmol), vacuumize on the double-row tube - keep nitrogen gas - vacuumize, cycle back and forth three times, and finally use nitrogen to protect the entire reaction system. Inject dry diisopropylamine (25 mL) redistilled in advance with a needle tube, and react in a closed manner at 90°C for 24 hours. Extract with water and ethyl acetate, take the organic layer, anhydrous NaSO 4 Dried, spin-dried, and passed through the column to obtain the corresponding alkynyl compound 2; 1 HNMR (400MHz, CDCl 3 )δ7.39(s,2H),0.08(s,18H),

[0049] Preparation of Compound 3 Containing Micylboron:

[0050]...

Embodiment 2

[0066] When the structure of R is When, the preparation of compound 6b:

[0067] The synthetic route is as follows:

[0068]

[0069] The preparation of the alkynyl compound 2, the phenynylsilicon compound 3 containing amygylboron and the compound 4 containing an alkyne in this example is the same as that in Example 1.

[0070] Preparation of compound 5b:

[0071]

[0072] NaN 3 (0.3575g, 5.5mmol) was dissolved in anhydrous DMSO (10mL), then benzyl bromide (0.855g, 5mmol) was added, and the reaction was stirred at 40°C for 5h. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and water (30 mL) and dichloromethane (30 mL) were added. The organic layer was washed with water (30 mL), anhydrous Na 2 SO 4 Dry and finally collect with a rotary evaporator. 1 HNMR (400MHz, CDCl 3 )δ7.36-7.33(m,4H),7.26(m,1H),2.67(m,2H).

[0073] Preparation of compound 6b:

[0074]

[0075] Weigh dimethyl borophenylacetylene (60mg, 0.17mm...

Embodiment 3

[0077] When the structure of R is When, the preparation of compound 6c:

[0078] The synthetic route is as follows:

[0079]

[0080] The preparation of the alkynyl compound 2, the phenynylsilicon compound 3 containing amygylboron and the compound 4 containing an alkyne in this example is the same as that in Example 1.

[0081] Preparation of compound 5c:

[0082]

[0083] NaN 3 (0.3575g, 5.5mmol) was dissolved in anhydrous DMSO (10mL), then bromonaphthalene (1.105g, 5mmol) was added, and the reaction was stirred at 40°C for 5h. After the reaction was complete, the reaction mixture was transferred to a separatory funnel, and water (30 mL) and dichloromethane (30 mL) were added. The organic layer was washed with water (30 mL), anhydrous Na 2 SO 4 Dry and finally collect with a rotary evaporator.

[0084] Preparation of compound 6c:

[0085]

[0086] Weigh dimethyl borophenylacetylene (60mg, 0.17mmol) and cuprous iodide (32.4mg, 0.17mmol) into a dry 100mL singl...

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Abstract

The invention discloses an illuminating tetra-ligand trapezoid organic boron compound, and a preparation method and an application thereof. The structural formula is shown in the specification, wherein the structure of R is shown in the specification and n is a positive integer from 1 to 18. The preparation method comprises the following steps: taking 1,4-dibromo-2,5-benzene diiodide as a raw material, and then performing Sonogashira coupling reaction, lithiation reaction and click chemical reaction, thereby acquiring the illuminating trapezoid organic boron compound. Under the effect of B-N ligands in molecule in the compound, a pi conjugate skeleton is effectively fixed in a plane manner, the increasing of the delocalization degree of pi electrons is benefited and the illuminating tetra-ligand trapezoid organic boron compound can be used as a potential organic photoelectric functional material. The compounding steps of the compound are simple; the compound can emit weak blue light under a solution state but can emit strong blue light under a solid state; the tetra-ligand trapezoid organic boron compound can be applied to luminescent materials, F-probes and excellent electron transmission materials.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a luminous four-coordinate trapezoidal organoboron compound and its preparation method and application. Background technique [0002] In recent years, optoelectronic functional materials with π-conjugated skeletons have attracted the research interest of many scholars at home and abroad. These materials have good applications in organic semiconductor materials and electronic devices, such as organic solar cells, organic light-emitting diodes, and organic fields. Applications in fields such as effect transistors, organic memory devices, chemical sensors, and biosensors have become international research hotspots. Compared with inorganic semiconductors, organic semiconductors have the advantages of light weight, low price, flexibility, various types, and simple preparation methods. [0003] The introduction of boron atoms (main group ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC09K11/06C07F5/02C09K2211/1044H10K85/322
Inventor 赵强秦妍妍许文娟佘鹏飞杨继光刘淑娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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